1-877-778-6066

View All Beach Homes by Island Real Estate of Anna Maria Island, Inc

Island Real Estate Vacation Rentals has many different options, so we mean it when we say “Vacation YOUR Way”! There are over 200 hand-picked properties available for your vacation – by selecting “View All” you are now able to scroll through all choices in order to better locate your perfect “peace” of paradise. On this page, a small thumbnail photo of each rental will give you an idea of what the property looks like. On the other side you will find the number of bedrooms and how many guests the property sleeps. You will also see Island Real Estate’s proprietary Star Rating for the property. 5 star is high luxury with every amenity imaginable while 2 star is an average, clean, comfortable vacation rental.

With just one click you may read what previous guests have had to say about any property – these are always the very best testimonials (we hope to list one from you after you stay with us!).

Like what you see and want more information? Click on the photo and be taken to a page specifically for the property. Available to review is a more detailed description, locate the rental on a Google map, check the rates, watch a virtual tour and confirm availability.

After looking through all the information, you may email the property to a friend, family member or traveling companion by choosing the “email property” button. You may also create a “favorites” page and save to look again later or compare with others you like as well.

No matter what, you may ALWAYS call us toll free and our experienced vacation specialists will help you find the perfect vacation spot. Enjoy and let us make your experience fun!

SeaBreeze Sands-202 38th
** Enjoy 20% off a new reservation made within 30 days of arrival!  Ask for the "Last Minute Special"!!  **

Seabreeze Sands offers over 2500 sq ft of Anna Maria Island style luxury - you'll never want to go back to hotel living again. (3) Bedroom, (3.5) Bathroom, accomodates up to (6) people: 1 King, 1 Queen, 2 Twins. Private heated pool, free wireless, sorry no pets allowed, less than two blocks to the beach.
 


Palm Isle 3201
** Fantastic Value - Flexible Arrival Dates - Last Minute Discounts **

 

 

Captivating and cute cottage-style ground level condos perfect for your relaxing island getaway. (2) Bedroom, (2) Bathroom, accommodates up to (8) people: 1 King, 1 Queen, 1 Sleeper Sofa, 1 Air Mattress. Heated pool, free wireless, sorry no pets allowed, across the road from the beach access.


Southern Comfort on HolmesBlvd
Get comfortable in your own corner of island life by enjoying a week of Southern Comfort in Holmes Beach, FL. Nothing soothes your sunburn quite like a luxury vacation rental to come home to! (3) Bedroom, (2.5) Bathroom, accomodates up to (86) people: 1 King, 1 Queen, 2 Twins, 1 Sleeper Sofa. Private heated pool, free wireless, pet friendly (with deposit), less than two blocks to the beach

Sea Glass - 126A 51st St
** SEPTEMBER 2014 WEEKLY SPECIAL $999.00 per week (no other discounts would apply) **

Sophisticated designer decor with enough fun personality to make it a dreamy spot for your next Florida family holiday.  (3) Bedroom, (2) Bathroom, accommodates up to (8) people: 1 King, 1 Queen, 2 Twins, 1 Sleeper Sofa. Private heated pool, free wireless internet, sorry no pets, less than two blocks to the beach.


Turtle Cove West
Both sides of this charming vacation duplex are decorated in a palette of warm tropical colors and Old Florida style in Holmes Beach, FL. (2) Bedroom, (1) Bath, accomodates to (4) people: 1 Queen, 2 Twin. Heated pool, free wireless, sorry no pets allowed, less than two blocks to the beach. 

303B 61st St-East Wind
Elegant and tropical poolside paradise holiday rental. (4) Bedroom, (3.5) Bath, accommodates to (11) people: (1) King, (2) Queens, (1) Twin, (1) Double, (1) Queen Sleeper Sofa. Heated pool, free wireless internet, sorry no pets allowed, about two and a half blocks to the beach.

Palm Gables - 106 36th St
All the comfort and amenities of home, with all the decadence of a hotel at this charming luxury rental.  (3) Bedroom, (2) Bathroom, accommodates up to (6) people: 1 King, 2 Queens. Free wireless, sorry no pets allowed, DIRECT gulf front.

Sandy Point Unit 207
Lovely Island holiday condo in Sandy Pointe condominiums. The condo backs up to a 30+ acre reserve! (2) Bedroom, (2) Bath, accommodates (4) people: 1 Queen, 2 Twins. Community, heated pool, free wireless internet.

525 Key Royale Drive
Escape to the quiet and coveted neighborhood known as Key Royale - it's where everyone on Anna Maria Island wants to be. (3) Bedrooms, (3) Bath, accommodates up to (6) people: 1 King, 1 Queen, 2 Twins. Private heated pool, sorry not pets allowed, free wireless, canal-front location.

La Casa Leann
Some of the most popular vacation rentals on Anna Maria Island can be found at La Casa Costeria. And the reason is blissfully simple – because they’re the crème de la crème. (3) Bedroom, (2.5) Bathroom, accommodates up to (6) people: 1 King, 1 Queen, 2 Twin, 1 Air Mattress. Heated pool with spa, free wireless, sorry no pets allowed, gulf front location.

PBC 944 Sandpiper
Tasteful, spacious and beautifully decorated, vacation villa in a private gated community less than two miles from the beach in Bradenton, FL.  (2) Bedroom, (2) Bath, accommodates up to (4) people: 1 Queen, 2 Twins. Heated pool, free wireless, sorry no pets.

Blue Manatee Retreat-214 69th
Coastal and bright tropical vacation home for your idyllic holiday. (3) Bedroom, (3) Bath, accommodates (8) people: 1 King, 2 Queens, 1 Queen Sleeper sofa. Private heated & caged pool, free wireless internet, less than two blocks to the beach.

4808A Gulf Drive
Chic, beachy and at-home feel, tropical island getaway vacation home. (3) Bedroom, (2.5) Bath, accommodates up to (8) people: 1 King, 1 Queen, 2 Twin, 1 Port-a-Crib. Private heated pool, free wireless internet, pets welcome with fee, less than two blocks to the beach.

No Bad Days-7100 Holmes
Wash away the sand, salt, and stress with a luxurious vacation at this vacation home where a bad day simply isn't allowed. (4) Bedroom, (3) Bathroom, accommodates up to (10) people: 2 King, 1 Queen, 2 Twin, 1 Sleeper Sofa. Private heated pool with spa, free wireless, sorry no pets allowed, less than two blocks to the beach.

Casa Sierra 203 A 36th ST
Immaculate Mediterranean style condo. (2) Bedroom, (2) Bath, accommodates (6) people: 1 King, 2 Twins, 1 Queen Sleeper sofa. Shared heated pool, free wireless internet, pet friendly with fee, seashell throw to the beach access.

120 White Avenue
Luxurious and idyllic vacation retreat - a dreamy pick for weddings or any other celebration in paradise. (4) Bedrooms, (2) Bath, accommodates up to (14) people: 1 King, 2 Queen, 4 Twin, 3 air mattresses. Private heated pool with waterfall and outdoor kitchen, free wireless, pet friendly with fee, only a few houses to the beach.

Palm Isle 3210
Captivating and cute cottage-style ground level condos perfect for your relaxing island getaway. (1) Bedroom, (1) Bathroom, accommodates up to (4) people: 1 King, 1 Sleeper sofa. Heated pool, free wireless, sorry no pets allowed, across the road from the beach access.

Addie-Sea Palma Sola Condo
Freshly updated, light and bright holiday rental. (1) Bedroom, (1) Bathroom: 1 Queen bed.  Free wireless internet, canal front, two community heated pools, sorry no pets, three month minimum.

Casa Calienta-217 Pine Ave
Impeccable and luxurious, tasteful island vacation home. (2) Bedroom, (2) Bathroom, accommodates up to (6) people: 1 King, 1 Queen, 1 Queen Sleeper Sofa. Private heated pool, tiki hut, free wireless, sorry no pets, less than two blocks to the beach.

North Beach Village Unit 50
Refresh, renew, and relax among lush landscaping for privacy at this vacation condo. (3) Bedroom, (2.5) Bath, accommodates (6) people: 1 King, 1 Queen, 2 Twins.  Community heated pool, free wireless internet, sorry no pets, less than two blocks to the beach access.

Garden Cottage-420 Spring Ave
Quaint cottage in historic Anna Maria. (2) Bedrooms, (2) Bath, accommodates up to (6) people: 1 Queen, 2 Full. Free wireless, pet friendly (up to 25lbs) with fee.

Shell House -215 Fir Ave
Let yourself be charmed by the Old Florida style and state of mind at this ground level vacation home. Heated lagoon style pool.(2) Bedrooms, (2) Bathrooms, accomodates up to (4) guests. 1 King, 2 Twins. Free wireless, pets welcome (with deposit), less than two blocks from the beach.

PBC 518 Sanderling Circle
Enjoy a week of rest and re-cooperation in the Perico Bay Club in Bradenton, FL.  (2) Bedrooms, (2) Bath, accommodates up to (6) people: 1 Queen, 1 Double, 1 Sleeper Sofa. Pool, free wireless, sorry no pets allowed. Free domestic long distance calling.

Beach Escape 4105 5th Ave
In certain parts of the world, the Mediterranean is a byword for family vacations in the sun, relaxing, and taking a break from the stresses and strains of modern life.

Sandy Pants - 133 White Ave
The only thing that makes a week in paradise better is if you're spending it in the sort of laid back luxury found at this vacation rental called Sandy Pants. (2) Bedroom, (1.5) Bathroom, accommodates up to (5) people; 1 King, 1 Twin, 1 Double, 1 Sleeper Sofa. Private heated pool, free wireless, sorry no pets allowed, one block to the beach.

Sunset Beach Unit 204
Sundrenched days and sweet dreams are waiting for you at the Sunset Beach condominium complex right on the world famous, white sands of Anna Maria Island. (2) Bedrooms, (2) Bath, accommodates up to (4) people: 2 Queen. Heated pool, free wireless, sorry no pets allowed, gulf front location.

Tiffany Place 213
Don't miss a single sunset from your balcony at this gulf front vacation condo in Holmes Beach, FL.  (2) Bedroom, (2) Bath, accomodates up to (6) people: 1 King, 2 Twin, 1 Bunk Bed. Heated pool, free wireless, sorry no pets allowed, less than two blocks to the beach.

Water's Edge 105 South
If you're looking for a charming vacation rental to spend your next visit to Anna Maria Island, you might just be looking for something in the Water's Edge condominium complex. You'll be right in the heart of Holmes Beach! (1) Bedroom, (1.5) Bath, accomodates to (4) people: 1 King, 1 Queen Murphy Bed. Heated pool, free wireless, sorry no pets allowed, gulf front location. 

Beachcomber-3020 Ave F
A beach lover's paradise.  (2) Bedroom, (1.5) Bath, accommodates up to (6): 2 Kings, 1 Sleeper Sofa. Free wireless, sorry no pets allowed, DIRECT gulf front.

124 50th AMI Beach House
Glamorous, luxury-style island getaway. (5) Bedrooms, (4.5) Bath, accommodates up to (14) people: 2 King, 1 Queen, 4 Twin, 2 Sleeper Sofas. Private heated pool with spa, outdoor kitchen & life-size chess game, free wireless internet, sorry no pets allowed, less than two blocks to the beach.

408 80th Street
No need for frills when this vacation home is less than two blocks from the Gulf of Mexico with a private pool. (3) Bedroom, (3) Bath, accommodates up to (6) people: 2 Queen, 2 Twin. Private heated pool, free wireless, pets welcome with fee.

Mangrove Cottage-105 Mangrove
Charming and quaint "old Florida" style vacation cottage. (2) Bedrooms, (2) Bath, accommodates up to (5) people: 1 King, 2 Twin, 1 Trundle. Private heated pool, free wireless, pets welcome with fee, only a couple houses to the beach access.

209 69th A
"Old Florida" chic elevated duplex perfect place to getaway for your holiday. (2) Bedrooms, (2) Bath, accommodates up to (6) people: 1 King, 2 Twin, 1 Queen Sleeper Sofa. Shared heated pool, free wireless internet, pet friendly with fee, less than two blocks to the beach.

Bermuda Bay Club 26 - 1437
Excellent beach getaway for your island sojourn. (3) Bedroom, (2.5) Bath, accommodates (8) people: 2 Queens, 2 Twins, 1 Queen Sleeper Sofa. Heated pool with spa, free wireless, sorry no pets allowed, less than two blocks from the beach.

Coquina Sands - 100A 52nd St
This whimsical vacation beach house offers you the ultimate Anna Maria Island experience complete with panoramas of the Gulf of Mexico in Holmes Beach, FL.  (3) Bedroom, (3) Bath, accommodates up to (6) people: 1 King, 1 Queen, 2 Twins. Private pool with spa (heat in spa only), free wireless internet, sorry no pets allowed, less a block to the beach.

Old Bridge Village
** Remodeled July 2014, check out the new layout! ** Vacation in style at new LOWER RATES!  SPECIAL - $2500 for 2 weeks **

Glamour meets good times when you spend a week of holiday at this vacation condo home. (2) Bedroom, (2.5) Bathroom, accommodates up to (6) people: 1 King, 1 Queen, 1 Sleeper Sofa. Heated pool, free wireless, sorry no pets allowed, less than two blocks from the beach.


SeaDreams - 721 North Shore Dr
Direct Gulf front 2014 SUMMER SPECIALS!   August 31st to September 27th just $1549 per week rental fee!

Enjoy fantastic sunsets and views of the aqua blue waters of the Gulf of Mexico from this Anna Maria City vacation rental. All your Sea Dreams can come true with a week of holiday here. (4) Bedroom, (3) Bathroom, accomodates up to (10) people: 2 King, 1 Queen, 4 Bunk Beds. Free wireless, sorry no pets allowed, gulf front location.


Palm Isle 3205
Captivating and cute cottage-style ground level condos perfect for your relaxing island getaway. (1) Bedroom, (1) Bathroom, accommodates up to (2) people: 1 King, Sleeper sofa. Heated pool, free wireless, sorry no pets allowed, across the road from the beach access.

6407A Gulf Drive, Downstairs
Charming, cozy and beachy; perfect for your ideal holiday getaway. (2) Bedroom, (2) Bath, accommodates up to (5) people: 1 King, 2 Twin, 1 Air Mattress. Shared heated pool, free wireless internet, sorry no pets allowed, across the road from the beach access.

Serenity Now 6820 Gulf Dr.
Welcome to West Winds Condo located at 6820 Gulf Drive, Holmes Beach, FL. This updated 2 bedroom 2 bathroom condo and accommodates up to 6 guests. It is located in a quiet, small, Gulf front condo complex West of Gulf Dr.

Hidden Cove Unit 2
Breath-taking panoramic views of the sparkling Gulf of Mexico and sugar sand beaches.  (2) Bedrooms, (2.5) Bathroom, accommodates up to (6) people: 1 King, 2 Twins and loft. Community pool, free wireless, sorry no pets, gulf front location.

Hideaway - 304 74th St
This charming duplex makes for a stylish and comfortable seasonal vacation getaway. (2) Bedrooms, (2) Bathroom, accommodates up to (6) people: 1 King, 2 Twins, 1 Sleeper Sofa. Private heated pool, free wireless, pets welcome with fee.

303Aand303B 61st St-Gulf Winds
Enjoy this set of elevated vacation homes with two private lagoon style perfect for large family getaways. (8) Bedroom, (7) Bath, accommodates up to (23) people: 3 King, 3 Queen, 5 Twins 1 Double & 2 Sleeper Sofas. Two private heated pools, free wireless internet, sorry no pets allowed, about two and a half blocks to the beach.

My Sisters Beach House
Immaculate, stunning and spacious multi-level holiday island rental. (5) Bedroom, (4) Bathroom, accommodates up to (12) people: 4 Kings, 2 Twins, 1 Queen Sleeper, 1 Twin Sleeper. Private heated pool with foot bridge leading to spa, free wireless, sorry no pets, canal front with large dock.

Anna Maria Island Club Unit 18
Bright, beachy and breezy direct gulf front seasonal rental. (2) Bedroom, (2) Bath, accommodates up to (6) people: 1 King, 2 Twins, 1 Sleeper sofa. Shared heated pool and spa, free wireless internet, elevator, sorry no pets.

414 B Magnolia
Chic and cozy vacation rental nestled right between the Tampa Bay and the Gulf of Mexico.   (2) Bedroom, (1) Bath, accommodates up to (6) people: 1 Queen, 2 Twin, 1 Sleeper Sofa. Private heated pool, free wireless, sorry no pets allowed, less than three blocks to both the Bay and Gulf.

Gulfpath - 104A 29th St
You'll be bronzed, barefoot, and blissful after a week at this island vacation home. (3) Bedroom, (2) Bathroom, accommodates up to (8) people: 2 Queens, 2 Twins, 1 Sleeper Sofa, 1 Portable Crib. Free wireless, sorry no pets, only 100 steps to the beach access.

Blue Lagoon
Find the perfect vacation cottage for your trip to Holmes Beach, FL.  With a total of 10 bedrooms available, Blue Lagoon can accommodate as much as 28 guests or as few as just the 2 of you.

Windshore-206 B 73rd St
Windshore is an ALL NEW beautifully renovated duplex only a SHORT walk to the beach. This property showcases designer quality furnishings and is fully equipped.

Blue Lagoon 1 - Coquina
Cute and cozy cottage perfect for your tropical island holiday.(1) Bedroom, (1.5) Bath, accommodates up to (4) people: 1 King, 1 Sleeper Sofa. Shared heated large lagoon-style pool, free wireless, pet friendly with fee, less than two blocks to the beach.

202 78th Street
Custom, spacious and bright elevated vacation home. (2) Bedrooms plus loft, (2) Bath, accommodates up to (6) people: 1 King, 1 Queen, 2 Twin, 1 Futon. Free wireless internet, pet friendly (25lbs or less) with fee, no pool but you’re less than two blocks from the beach.

Tortuga-212 81st St
** SPECIAL newly listed property!  Enjoy introductory rates before the word gets out about this great home.  Plus 20% off last minute reservations! **

 

 

 

 

Slow down and get yourself on island time with a week at this ground level duplex in Holmes Beach, FL. (3) Bedrooms, (2) Bathrooms, accomodates up to (6) guests. 2 King, 2 Twins. Private heated pool, free wireless, sorry no pets allowed.  Note, this property has a Friday-Friday schedule.  Please call our office if you would like to request an exception.


Runaway Bay Unit 279
** Now through October 31, 2014, all NEW reservations just $500 per week! **

 

Great get away on beautiful Anna Maria Island. This condo in a fabulous bay front complex. (1) Bedroom, (1) Bath, accommodates (4) people: 1 King, 1 Sleeper sofa. Community heated pool, free wireless internet, less than two blocks to the beach.


Dragonfly Breeze - 140 50th St
Spacious and bright private custom built home in the heart of the island. (3) Bedroom, (2) Bathroom, accommodates up to (6) people: 1 King, 2 Queen. Private heated salt water pool, free wireless, sorry no pets, less than two blocks from the beach.

25 Seaside Court
Coastal and cozy vacation villa. (2) Bedrooms, (2) Bathrooms, accommodates up to (4) guests. 1 Queen, 2 Twins. Highspeed internet, pets welcome with fee, bay front location with boat access, not far from the beach. 

Appletini - 308W 58th St
Beautifully renovated tropical paradise for your holiday getaway. (2) Bedroom, (2) Bathroom, accommodates up to (7) people: 1 King, 1 Double, 1 Sleeper Sofa. Private heated pool, free wireless internet, pet friendly (up to 25lbs) with fee, less than two blocks from the beach.

Palm Isle 3204
** Fantastic Value - Flexible Arrival Dates - Last Minute Discounts **

 

Captivating and cute cottage-style ground level condos perfect for your relaxing island getaway. (2) Bedroom, (1) Bathroom, accommodates up to (6) people: 1 Queen, Set of short bunk beds, 1 Sleeper Sofa. Heated pool, free wireless, sorry no pets allowed, across the road from the beach access.


Bermuda Bay Club 12 - 1461
Chic and tropical townhome-style seasonal rental. (3) Bedroom, (2.5) Bath, accommodates (6) people: 1 King, 4 Twins, 1 Queen Sleeper Sofa. Community heated pool with spa, free wireless, sorry no pets allowed, less than two blocks from the beach.

Fun In The Sun - 302 62nd St
Memorable and magical tropical island home with beautiful pool oasis. (3) Bedrooms, (2) Bath, accommodates up to (6) people: 1 King, 1 Queen, 2 Twins. Private heated pool, free wireless, sorry no pets, less than two blocks to the beach.

Casa Morado-147 50th St
This gorgeous multi-level home is truly a tropical paradise. (4) Bedroom, (3.5) Bath, accommodates (8) people: 1 King, 1 Queen, 2 Twins, 1 set of Bunks with Double and Twin. Private heated pool, free wireless internet, sorry no pets, less than two blocks to the beach with no main streets to cross.

Holly Hideaway-730 Holly Road
With a breezy wooden patio outside, a cozy brick fireplace inside, and Florida gulf coast style throughout, you'll never want to spend a holiday on Anna Maria Island anywhere else. (2) Bedrooms, (2) Bathroom, accommodates up to (4) people: 1 King, 1 Queen, 1 Double Sleeper sofa,  Private heated pool, free wireless, pets are welcome (dogs only, up to 25lbs) with fee.

Blue Heron Beach House
** 2014 Fall Weeks now just $1400 - call and book your fall getaway before the owner comes to his senses! **

 

Adorable and quaint old-Florida style seasonal vacation cottage. (4) Bedroom, (2) Bath, accommodates (10) people: 2 Kings, 2 Twins, 1 Bunk Bed, 2 Queen Sleeper Sofas. Private heated pool, free wireless, only 6-7 houses to the beach with no streets to cross.


Gulf View Townhomes Unit 4
Quiet and cozy retreat in a centrally located, small, town-home style condo complex. (2) Bedrooms, (2.5) Bath, accommodates up to (6) people: 1 Queen, 2 Twins, 1 Sleeper Sofa. Shared heated pool, free wireless, sorry no pets, about a block to the beach access.

606 Key Royale Dr.
Vacation home in a private community with ample amenities – all on a small island linked to Anna Maria Island in Holmes Beach, FL. (3) Bedroom, (3) Bath, accommodates up to (8) people. 2 Queen, 2 Twin, 1 Sleeper Sofa. Private heated pool, sorry no pets allowed, canal front location. 

Palm Isle 3209
Captivating and cute cottage-style ground level condos perfect for your relaxing island getaway. (2) Bedroom, (2) Bathroom, accommodates up to (6) people: 2 Kings, 1 Sleeper sofa, 1 Air Mattress. Heated pool, free wireless, sorry no pets allowed, across the road from the beach access.

303A 61st St-West Wind
Elegant and tropical poolside paradise holiday rental. (4) Bedroom, (3.5) Bath, accommodates to (12) people: (2) Kings, (1) Queen, (4) Twin Bunks, (1) Queen Sleeper Sofa. Heated pool, free wireless internet, sorry no pets allowed, about two and a half blocks to the beach.

Palm Isle 3208
Captivating and cute cottage-style ground level condos perfect for your relaxing island getaway. (2) Bedroom, (1) Bathroom, accommodates up to (6) people: 1 King, 1 Queen, 1 Sleeper sofa. Heated pool, free wireless, sorry no pets allowed, across the road from the beach access.

North Beach Village Unit 58
Refresh, renew, and relax among lush landscaping for privacy at this vacation condo. (3) Bedroom, (3) Bath, accommodates (6) people: 2 Queens, 2 Twins.  Community heated pool, free wireless internet, sorry no pets, less than two blocks to the beach access.

West Bay Point 234
Old Florida but still fabulous and updated, this holiday condo in West Bay Point and Moorings offers a quiet slice of paradise to calll your own. (2) Bedroom, (2) Bath, accomodates to (4) people: 1 King, 1 Queen. Heated pool, free wireless, sorry no pets allowed. 

Beach House on 5th Ave
In certain parts of the world, the Mediterranean is a byword for family vacations in the sun, relaxing, and taking a break from the stresses and strains of modern life.

North Beach Village Unit 72
Refresh, renew, and relax among lush landscaping for privacy at this vacation condo. (3) Bedroom, (2.5) Bath, accommodates (6) people: 1 Queen, 4 Twins.  Community heated pool, free wireless internet, sorry no pets, less than two blocks to the beach access.

La Casa Wendt
Some of the most popular vacation rentals on Anna Maria Island can be found at La Casa Costeria. And the reason is blissfully simple – because they’re the crème de la crème. (2) Bedroom + den, (2.5) Bathroom, accommodates up to (6) people: 1 King, 1 Queen, 1 Sleeper Sofa. Heated pool with spa, free wireless, sorry no pets allowed, gulf front location.

Runaway Bay Unit 272
Great get away on beautiful Anna Maria Island. This condo in a fabulous bay front complex. (2) Bedroom, (2) Bath, accommodates (6) people: 1 Queen, 2 Twins, 1 Double Sleeper sofa. Community heated pool, free wireless internet, less than two blocks to the beach.

Bermuda Bay Club 24 - 1473
Light & bright tropical townhome-style seasonal rental. (3) Bedroom, (2.5) Bath, accommodates (6) people: 1 King, 1 Queen, 2 Twins. Community heated pool with spa, free wireless, sorry no pets allowed, less than two blocks from the beach.

Cayman Cay Unit 207
Happy memories and sweet dreams provided by this adorable condo.  (2) Bedroom, (2) Bathroom, accommodates up to (4) people: 1 King, 2 Twin, 1 Sleeper Sofa. Heated pool, free wireless, sorry no pets, less than two block to the beaches.

North Shore Cottage-871 NShore
Old Florida-style living at this charming split level vacation cottage on the coveted north end of Anna Maria City. (3) Bedroom, (2) Bathroom, accommodates up to (8) people: 2 Queens, 2 Twins, 1 Sleeper sofa. Pets are welcome with fee, less than two blocks from the beach, near City Pier.

Starfish Beach Unit 1
Kingfisher Cottage at Starfish Beach isn’t just a place to stay – it’s your means to a truly tranquil state of mind. (2) Bedroom, (2) Bathroom, accomodates up to (6) people: 2 Queen, 1 Sleeper Sofa. Heated pool, free wireless, pet friendly (with deposit)
 

Anna Maria Island Club Unit 17
Luxurious, light and bright tropically decorated  direct gulf front seasonal rental. (2) Bedroom, (2) Bath, accommodates up to (4) people: 1 King, 2 Twins. Shared heated pool and spa, free wireless internet, elevator, sorry no pets.

Flip Flops Forever-201 73rd St
Beautiful beachy escape makes for a peaceful and homely seasonal island rental. (5) Bedroom, (3) Bathroom, accommodates up to (12) people: 1 King, 3 Queen, 2 Twin, 1 Trundle, 1 Infant-sized Bed. Private heated pool, free wireless, pets are welcome (dogs only) with fee, across the road from the beach access with gulf views from master bedroom.

Bungawillow - 116 Willow
Peaceful and homely cottage-style duplex for a soothing vacation.  (1) Bedrooms, (1) Bath, accommodates up to (4) people: 1 Queen, 1 Sleeper Sofa. Free wireless, sorry no pets allowed, only a half of a block to the beach.

Sea la vie - 101 31st St
Ideal for small families and honeymooners, this cozy little cottage is private and perfectly located directly on the Gulf of Mexico. (2) Bedroom, (1) Bathroom, accommodates up to (5) people: 1 Queen, 1 Twin, 1 Sleeper Sofa. Free wireless, sorry no pets allowed, gulf front location.

Fountainhead 5
Coastal, clean and bright centrally located seasonal vacation condo. (2) Bedroom, (2) Bath, accommodates (6) people: 1 Queen, 2 Twins, 1 Sleeper sofa. Shared heated pool, free wireless internet, pets are welcome with fee, less than two blocks to the beach.

Almost Gulf Front-203 69th St
A dream come true holiday oasis perfect for large families. (6) Bedrooms, (4.5) Bath, accommodates up to (16) people: 4 King, 1 Queen, 2 Twin, 2 Sleeper Sofa. Private heated pool with spa, outdoor kitchen, free wireless, pet friendly with fee, less than two blocks to the beach.

Anna Maria AHHHH
Immaculate and chic direct gulf front seasonal rental. (2) Bedroom, (2) Bath, accommodates up to (6) people: 1 King, 1 Queen, 1 Twin, 1 Sleeper sofa. Shared heated pool and spa, free wireless internet, elevator, sorry no pets.

Rest a Shore - 838 South Bay
This effervescent luxury rental is a balance of modern comfort and casual beach living, and it all sits against an endless backdrop of the bay and pool deck. (4) Bedroom, (3.5) Bathroom, accommodates up to (8) people: 1 King, 1 Queen, 4 Twins. Private heated pool with spa, free wireless, sorry no pets allowed, bay front location.

316 Hardin A
Soothing and tropical villa-style duplex. (2) Bedrooms, (1) Bath, accommodates up to (4) people: 1 King, 1 Sleeper Sofa. Free wireless internet, pet friendly with fee, about two and a half blocks to the beach.

Water's Edge 209 South
If you're looking for a charming vacation rental to spend your next visit to Anna Maria Island, you might just be looking for something in the Water's Edge condominium complex. You'll be right in the heart of Holmes Beach! (2) Bedroom, (2) Bath, accomodates to (4) people: 1 King, 1 Queen. Heated pool, free wireless, sorry no pets allowed, gulf front location. 

Sundance-744 North Shore Dr
No flips flops required to walk to the beach from this luxury vacation home in Anna Maria City, FL. (3) Bedroom, (2) Bath, accomodates up to (6) people: 2 King, 2 Twin. Private heated pool, free wireless, sorry no pets allowed, less than two blocks to the beach.

Starfish Beach Unit 2
*** COMPLETELY RENOVATED June 2014!  All new furniture, paint, appliances, patio, etc.  Be one of the first to enjoy the new improved Starfish 2 ***

Starfish Beach are one of Anna Maria Island's most coveted condominium complexes. From the moment you arrive, you’ll feel like this vacation cottage is an oasis all your own. (2) Bedroom, (2) Bathroom, accomodates up to (4) people: 2 Queen. Heated pool, pet friendly (with deposit).


Anna Maria Island Club Unit 40
Idyllic and beachy direct gulf front seasonal rental. (2) Bedroom, (2) Bath, accommodates up to (4) people: 1 King, 2 Twins. Shared heated pool and spa, free wireless internet, elevator, sorry no pets.

Palm Isle 3215
Captivating and cute cottage-style ground level condos perfect for your relaxing island getaway. (1) Bedroom, (1.5) Bathroom, accommodates up to (4) people: 1 King, 1 Sleeper sofa. Heated pool, free wireless, sorry no pets allowed, across the road from the beach access.

Water's Edge 104 South
If you're looking for a charming vacation rental to spend your next visit to Anna Maria Island, you might just be looking for something in the Water's Edge condominium complex. You'll be right in the heart of Holmes Beach! (2) Bedroom, (2) Bath, accomodates to (4) people: 1 King, 2 Twin. Heated pool, free wireless, sorry no pets allowed, gulf front location. 

Key Lime Cottage West-202 73rd
Coastal and vibrant private duplex for your relaxing seasonal getaway. (3) Bedroom, (2) Bath, accommodates up to (6) people: 2 Queens, 2 Twins.  Pets are welcome with fee, free wireless internet, private heated pool, less than two blocks to the beach.

Palm Isle 3211
Captivating and cute cottage-style ground level condos perfect for your relaxing island getaway. (1) Bedroom, (1.5) Bathroom, accommodates up to (2) people: 1 King, 1 Sleeper sofa. Heated pool, free wireless, sorry no pets allowed, across the road from the beach access.

Sunset Beach Unit 106
DIRECT GULF FRONT condo! Sundrenched days and sweet dreams are waiting for you at the Sunset Beach condominium complex right on the world famous, white sands of Anna Maria Island. (2) Bedrooms, (2) Bath, accommodates up to (6) people: 1 Queen, 2 Twins, 1 Sleeper Sofa. Heated pool, free wireless, sorry no pets allowed, gulf front location.

Casa Varadero-619 Gladstone
Quiet, gorgeous upscale location in Key Royale perfect for a delightful holiday getaway. (4) Bedroom, (3) Bath, accommodates up to (8) people: 2 Kings, 2 Queens.  Heated spa, free wireless internet, sorry no pets, canal access for boat lovers.

North Beach Village Unit 27
Refresh, renew, and relax among lush landscaping for privacy at this vacation condo. (3) Bedroom, (2.5) Bath, accommodates (8) people: 2 Queens, 2 Twins, 1 Queen Sleeper Sofa.  Community heated pool, free wireless internet, sorry no pets, less than two blocks to the beach access.

Sandy's Getaway-122 Peppertree
Enjoy the leisurely pace of Old Florida with a week of holiday at this charming vacation home. (3) Bedroom, (2) Bathroom, accommodates up to (9) people: 2 Queens, 1 Twin, 1 Trundle Bed, 2 Sleeper Sofa. Free wireless, pets are welcome (dogs only please) with fee, one block to the beach.

Palm Cottage 2916 Avenue E
Enjoy the privacy and shade from lush vegetation surrounding this darling vacation bungalow. (4) Bedrooms, (2) Bath, accommodates up to (8) people: 1 King, 2 Queen, 2 Twin (trundle).  Private heated pool, free wireless, sorry no pets allowed, less than two blocks to the beach.

Dolphin - 706 Rose B
Welcome to the Dolphin located at 706 Rose unit B. This quaint 2 bedroom 1 bath duplex located on a quiet street on the north end of beautiful Anna Maria Island awaits

North Beach Village Unit 55
Refresh, renew, and relax among lush landscaping for privacy at this vacation condo. (3) Bedroom, (2.5) Bath, accommodates (6) people: 2 Queens, 2 Twins.  Community heated pool, free wireless internet, sorry no pets, less than two blocks to the beach access.

316 Hardin Ave
Light and bright seasonal rental, perfect for multi-family getaways.  (3) Bedroom, (2) Bath, accommodates up to (8) people: 1 King, 1 Queen, 2 Twin, 1 Sleeper Sofa. Free wireless internet, pet friendly with fee, about two and a half blocks to the beach.

414 A Magnolia
Chic and cozy vacation rental nestled right between the Tampa Bay and the Gulf of Mexico.   (2) Bedroom, (1) Bath, accommodates up to (6) people: 1 Queen, 2 Twin, 1 Sleeper Sofa. Free wireless, sorry no pets allowed, less than three blocks to both the Bay and Gulf.

LaRaya-801 Jacaranda
Updated, beachy and spacious private home in the historic city of Anna Maria. (3) Bedroom, (2) Bath, accommodates (6) people: 1 King, 2 Queens. Private heated pool, pets are welcome with fee, free wireless internet, less than two blocks to the beach.

Down by the Sea-268 Gladiolus
Lush, tropical setting with a heated salt water pool. Lovingly and locally decorated to make you feel right at home. (3) Bedroom, (2) Bath, accommodates up to (6) people: 1 King, 1 Queen, 2 Twin. Private heated salt water pool, free wireless, pet friendly (under 25lbs) with fee, less than two blocks to the beach.

Key Lime Cottages 202-204 73rd
202 & 204 73rd ST welcomes you to this recently re-done and updated island duplex. Just steps from the Gulf of Mexico and the pure white sandy beaches of Anna Maria. (6) Bedroom, (4) Bath, accommodates (12) people: 4 Queens, 4 Times.  Two heated pools, free wireless internet, pets are welcome with pet fee, less than two blocks to the beach.

Coquina Beach Club 205
Sunsets, shimmering gulf waters, and sand between your toes are all waiting for you at this fabulous and recently renovated vacation condo in Bradenton Beach.  (2) Bedroom, (2) Bathroom, accommodates up to (4) people: 1 King, 2 Twin. Heated pool, free wireless, sorry no pets allowed, gulf front location.

Gulf Shores Unit 205
The breath-taking panoramic Gulf views is what this vacation rental is all about. (3) Bedrooms, (2) Bath, accommodates up to (8) people: 1 King, 1 Double, 1 Queen, 1 Sleeper Sofa. Free wireless, sorry no pets, DIRECT gulf front location.

Island Pearl - 204 76th St
August 2014 Weekly special of $1,699.00 and September 2014 Weekly special of $1,499.00. Non holiday weeks and no other discounts would apply.

Beautiful light, bright and beachy relaxing seasonal rental. (4) Bedroom, (4) Bathroom, accommodates up to (8) people: 2 Kings, 1 Queen, 2 Twins. Private heated pool with spa, free wireless, sorry no pets allowed, less than two blocks to the beach.


619 Rose - Dream Maker
Everything about this Bean Point area home is special, from the unique architecture and design, the one of a kind "egg lights" over the dining table, porcelain tile floors, chef's kitchen, vaulted ceilings with elegant overhead palm fans and a very unique floor plan offer the perfect balance between privacy and comfort.  (3) Bedroom, (3) Bath, accommodates up to (6) people: 2 Queens and 2 Twins.  Free wireless internet, private heated pool, sorry no pets allowed, less than two blocks to the beach. 

La Vie en Rose 616 Rose St
Sunny and relaxing seasonal vacation rental in historic Anna Maria. (3) Bedroom, (2) Bath, accommodates (6) people: 1 Queen, 2 Twins, 1 Futon.  Pets are welcome with fee, free wireless internet, private heated pool, less than two blocks to the beach.

Island Jewel-632 Emerald Lane
A home-away-from-home in the coveted Key Royale neighborhood; perfectly situated at the end of a quiet cul-de-sac just one house from Bimini Bay. (3) Bedrooms, (2.5) Bathroom, accommodates up to (8) people: 1 King, 4 Twins, 1 Queen Air Mattress. Private heated pool, free wireless, sorry no pets, canal front location.

Sunfish - 104 55th St
Holiday rental condo for the discriminating vacationer only in Holmes Beach, FL. (3) Bedrooms, (2.5) Bath, up to (6) people: 1 King, 1 Queen, 1 Sleeper Sofa. Heated pool, free wireless, pets welcome (with deposit).  West of Gulf Drive.

Peony House-405 Spring Ave
Peony house is an elevated vacation home with that same bright and inviting quality as the blossom it's named for. (4) bedrooms, (3) bathrooms, accommodates up to (10) guests: 1 King, 1 Queen, 2 Twins, 1 Full. Free wireless, sorry no pets allowed.

Starfish Beach Unit 3
Star Fish Beach 3 - Anna Maria Island's premier upscale development offers this vacation rental condo for the discriminating vacationer only. Starfish Beach are one of Anna Maria Island's most coveted condominium complexes. From the moment you arrive, you’ll feel like this vacation cottage is an oasis all your own. (2) Bedroom, (2) Bathroom, accomodates up to (4) people: 2 Queen. Heated pool, pet friendly (with deposit).

Pisces Playground-205 73rd St
Military Discount:  This owner is offering a 15% military discount.

 

This vacation duplex is open, airy, and waiting to welcome you into paradise. (2) Bedroom + loft, (2) Bathroom, accommodates up to (6) people: 1 Queen, 3 Twins, 1 Trundle. Free wireless, sorry no pets allowed, less than two blocks from the beach.


Star Fish Cottage-209 Palm Ave
When a starfish wants to get away, it's more than happy to just detach an arm and take time to recuperate. This elevated coastal cottage might be worth giving up an

Shoreline Terrace-901 NShore
Come sunset, there’s no better place to be than the sundrenched patio of this vacation rental. Cook up the day’s catch on the propane grill and experience love at first sunset. (3) Bedroom, (3) Bathroom, accomodates up to (6-8) people: 2 King 1 Full, 2 Twins. Free wireless, sorry no pets allowed, gulf front location.
 

306 B 56th St
Coastal and beachy multi-level home with a serene and relaxing pool oasis. (3) Bedrooms, (2) Bath, accommodates up to (6) people: 1 King, 1 Queen, 2 Twins, 1 Sleeper Sofa. Private heated pool, free wireless internet, sorry no pets allowed, less than two blocks to the beach.

Coral Reef - 215 64th St
Spacious, private vacation home that offers peeks of the gulf and backyard tiki bar.(5) Bedroom, (3.5) Bath, accommodates up to (10) people: 2 King, 1 Queen, 2 Twin, 1 Sleeper Sofa. Private heated pool, free wireless, pet friendly (with deposit), less than two blocks to the beach.

Sand Dollar Cottage-738NShore
This charming bungalow offers a peaceful place to getaway from it all on the quiet north end of Anna Maria Island. (2) Bedroom, (1) Bathroom, accommodates up to (4) people; 1 Queen, 2 Twin. Free wireless, pet friendly with deposit, less than two blocks to the beach.

Long Board-131WWhite
Elegant and chic duplex ready for your tropical escape. (3) Bedrooms, (2.5) Bath, accommodates up to (9) people: 2 King,  2 Twin Bunk Beds, 1 Trundle Bed, 1 Air Mattress. Shared heated pool, free wireless, pet friendly with fee, only a few houses to the beach.

Hidden Cove Unit 1
Breath-taking panoramic views of the sparkling Gulf of Mexico and sugar sand beaches.  (2) Bedrooms, (2.5) Bathroom, accommodates up to (4) people: 1 King, 2 Twins. Community pool, free wireless, sorry no pets, gulf front location.

La Casa Poulos
Some of the most popular vacation rentals on Anna Maria Island can be found at La Casa Costeria. And the reason is blissfully simple – because they’re the crème de la crème. (3) Bedroom, (3) Bathroom, accommodates up to (8) people: 1 King, 1 Queen, 2 Twin, 1 Air Mattress. Heated pool with spa, free wireless, sorry no pets allowed, gulf front location.

Island Oasis - 111 81st St
Magical and stunning vacation rental with an enviable backyard that includes a wet bar and pool oasis. (5) Bedroom, (3.5) Bath, accommodates up to (12) people: 4 King, 2 Sleeper Sofa. Private heated pool with spa, free wireless, sorry no pets, less than two blocks to the beach.

6407B Gulf Dr, Upstairs
Charming, cozy and beachy; perfect for your ideal holiday getaway. (2) Bedroom, (2) Bath, accommodates up to (6) people: 1 King, 2 Twin, 2 Air Mattresses. Shared heated pool, free wireless internet, sorry no pets allowed, across the road from the beach access.

Las Palmas-120 Park Avenue
Spacious, stunning and captivating private island home perfect for a soothing holiday getaway. (3) Bedroom, (2) Bath, accommodates (6) people: 2 Queens, 2 Twins. Private heated pool, sorry no pets, free wireless internet, one block to the beach access.

Heron-Dolphin 706 Rose
Welcome to the Dolphin/Heron located at 706 Rose Street .This quaint duplex with each unit having 2 bedroom 1 bath and located on a quiet street on the north end of

Shore Birds-514 68th St
The perfect vacation home for the family of water loving anglers. Shore Birds is a luxury vacation rental complete with its own dock. (2) Bedroom, (2) Bathroom, accomodates up to (4) people: 1 Queen, 1 Full. Private heated pool, free wireless, pet friendly (small dogs only, with $500 deposit), canal front location.
 

4002 6th Avenue
Chic, Mediterranean-style tropical paradise sojourn. (3) Bedrooms, (3) Bath, accommodates up to (6) people: 2 Queen, 2 Twins. Private heated pool, free wireless internet, just one block to the beach.

Dolphin Watch - 12108 Gulf Dr
Absolutely adorable, charming, colorful and relaxing small island vacation home. (2) Bedrooms, (1) Bath, accommodates up to (6) people: 1 Queen, 2 Twin, 1 Sleeper Sofa. Free wireless, pet friendly with fee, gulf front location.

The Palms - 810 NShore Dr
This well constructed, well cared for extra large Anna Maria City holiday home boasts beach access to Bean Point!  (5) Bedrooms, (3.5) Bath, accommodates up to (10) people: 1 King, 3 Queen, 2 Twins. Free wireless, sorry no pets allowed, just a short walk across the street to Bean Point!   

A Sassy Seahorse 264 Gladiolus
Soothing, immaculately clean and whimsically decorated, professionally landscaped, and boasts one of the larger pools and larger backyards on the Island. The spa is accented by iridescent glass. The 20' tall tiki hut that houses the bar and seating for six. (2) Bedroom, (2) Bath, accommodates up to (6) people: 1 King, 2 Twins and 1 Full futon.  Free wireless internet, private heated pool, about two blocks to the beach.

Blue Waters-230 Willow
New to the rental market in June 2014, gorgeous luxury Mediterranean-style villa in peaceful surroundings. (4) Bedroom, (4) Bath, accommodates (8) people: 1 King, 2 Queens, 2 Twins. Fabulous outdoor & indoor living areas, gourmet kitchen, private office, heated swimming pool with spa, private dock and boat lift, full size billiards table and large screen outdoor TV are just a few of the highlights. Minutes from beach & Pine Avenue.

Jackie's Cottage-209 N Harbor
** Weekly special from 9/6/14 to 11/21/14 of only $1,200 per week.  No other discounts would apply. **

Captivating canal front private family vacation home with community boat dock.  (4) Bedroom, (3) Bathroom, accommodates up to (8) people: 2 Kings, 4 Twins, 1 Sleeper. Private solar heated pool, free wireless, sorry no pets allowed, less than two blocks to the beach and canal front.


Sangria Sunrise 506 SoBay Blvd
Directly on beautiful Tampa Bay and views of the Sunshine Bridge makes this the picture perfect vacation rental. "Sangria Sunrise" Cottage is a 3 bedroom 3 bathroom

Manna-Tee Beach House-6301B
Get yourself on island time with a holiday at this three story, key lime colored vacation rental. (3) Bedroom, (2.5) Bathroom, accommodates up to (8) people: 1 King, 1 Queen, 2 Twin, 1 Sleeper Sofa. Private heated pool, free wireless,  less than two blocks to the beach.

Willow Cottage - 108 Willow
Bright vacation bungalow with sundrenched, private pool deck in Anna Maria City, FL. (3) Bedrooms, (2) Bath, accommodates up to (8) people: 1 King, 1 Queen, 2 Twins & Queen sleeper sofa Private heated pool, free wireless, pets under 25lbs. are welcome, 3rd house away from the beach.

Bradenton Beach Club
Luxurious DIRECT gulf front Mediterranean-style condominium for a delightful island escape. (2) Bedrooms, (2) Bath, accommodates up to (4) people: 1 King, 2 Twin. Shared heated pool, free wireless, sorry no pets, gulf front location. 

Coastal Sands-213 70th St
Cool and coastal beachy vacation rental home. (3) Bathroom, (2) Bath, accommodates up to (8) people: 1 King, 1 Queen, 2 Twins, 1 Queen Sleeper Sofa.  Private heated pool, free wireless, pets welcome with fee, less than two blocks to the beach.

Playa Casanas North-3222 Gulf
Perfect for multifamily vacations, rent one or both sides of this vacation rental duplex directly on the sparkling white, quartz sands of Holmes Beach, FL. (2) Bedroom, (1) Bathroom, accommodates up to (4-6) people: 1 Queen, 2 Twins, 1 Sleeper Sofa. Free wireless, sorry no pets allowed, gulf front location.

411 63rd St
Light and bright vacation villa with community boat ramp available for an idyllic holiday getaway.  (2) Bedroom, (2) Bath, accommodates up to (4) people: 1 King, 2 Twin. Free wireless internet, sorry no pets allowed.

Casa di Rose-6250 Holmes Blvd
Refresh, renew, and relax among lush landscaping for privacy at this vacation condo. (3) Bedrooms, (2.5) Bath, accommodates up to (8) people: 2 Queens, 2 Twins, 1 Twin Sleeper Sofa and 1 Twin cot. Free wireless, pet friendly with fee, less than two blocks to the beach.

La Casa O'Bar
Some of the most popular vacation rentals on Anna Maria Island can be found at La Casa Costeria. And the reason is blissfully simple – because they’re the crème de la crème. (3) Bedroom, (2.5) Bathroom, accommodates up to (6) people: 1 King, 2 Queen, 2 Twin. Heated pool with spa, free wireless, sorry no pets allowed, gulf front location.

Sweet Retreat Cottage-748 NoSh
Enjoy a week or a month of seaside serenity at this indulgent vacation cottage in Anna Maria City, FL. (3) Bedrooms, (2) Bath, accommodates up to (8) people: 1 King, 1 Queen, 2 Twins, 1 Sleeper Sofa. Private heated pool, free wireless, sorry no pets allowed, less than two blocks to the beach. Beach access is right across the street.

West Bay Point 12
A chic and charming vacation condo in the desired Westbay Point and Moorings complex. You'll love every minute of a Holmes Beach holiday at this property. (2) Bedroom, (1.5) Bath, accomodates to (6) people: 1 Queen, 2 Twin, 1 Sleeper Sofa. Heated pool, free wireless, sorry no pets allowed. 

Allegria by the Sea-309 64thST
Bright and beachy custom built holiday rental with tropical pool paradise. (4) Bedroom, (2.5) Bath, accommodates up to (10) people: 1 King, 2 Queens, 3 Twins, 1 Futon. Private heated pool, free wireless internet, sorry no pets, less than two blocks to the beach.

Almost Heaven-205 72nd St
Charming retreat seasonal rental. (3) Bedroom, (2) Bath, accommodates up to (8) people: 1 King, 1 Queen, Set of twin bunks. Private heated pool, free wireless internet, sorry no pets, less than two blocks to the beach.

506 Key Royale Drive
Spacious and sunny vacation home. (3) Bedroom, (2.5) Bath, accommodates up to (6) people: 1 King, 4 Twin. Private heated and caged pool, free wireless internet, pet friendly with fee, canal front with boat access.

Vista Grande 3 Penthouse
This exclusive penthouse is the crown jewel of Vista Grande - experience over the top decadence without sacrificing any of Anna Maria Island's friendly beachtown charm. (3) Bedroom, (3) Bath, accomodates to (6) people: 1 King, 1 Queen, 2 Twin. Heated pool, free wireless, sorry no pets allowed, gulf front location. 

Key Lime Cottage East-204 73rd
Coastal and vibrant private duplex for your relaxing seasonal getaway. (3) Bedroom, (2) Bath, accommodates up to (6) people: 2 Queens, 2 Twins.  Pets are welcome with fee, free wireless internet, private heated pool, less than two blocks to the beach.

Runaway Bay Unit 256
Great get away on beautiful Anna Maria Island. This condo in a fabulous bay front complex. (1) Bedroom, (1) Bath, accommodates (2) people: 1 King. Community heated pool, free wireless internet, less than two blocks to the beach.

Palm Isle 3207
Captivating and cute cottage-style ground level condos perfect for your relaxing island getaway. (1) Bedroom, (1) Bathroom, accommodates up to (3) people: 1 King, Sleeper sofa. Heated pool, free wireless, sorry no pets allowed, across the road from the beach access.

Grande Haven-804 No Shore Dr.
Grande Haven is a spectacular example of high architecture, fine design and custom finishing at its best. This home was designed by the award winning Gene Leedy,

Blue Lagoon 3 - Egret
** Summer Savings!  $875 per week on all new reservations for arrivals now through October 31, 2014 **

Charming, light and bright cottage for your perfect island getaway. (2) Bedrooms, (2) Bathrooms, accommodates up to (6) people: 1 Queen, 2 Twins, 1 Sleeper Sofa. Shared heated large lagoon-style pool, free wireless, pets welcome with fee, less than two blocks to the beach.


316 Hardin B
Soothing and tropical villa-style duplex. (1) Bedrooms, (1) Bath, accommodates up to (4) people: 1 Queen, 2 Twins. Free wireless internet, pet friendly with fee, about two and a half blocks to the beach.

Harmony House-779 Jacaranda Rd
Blissfulness and relaxation will surround your vacation days in this private cottage in historic Anna Maria.  (3) Bedrooms, (2) Bathroom, accommodates up to (8) people: 1 King, 1 Full, 2 Twins, 1 Full Sleeper Sofa. Private heated pool (small), free wireless, sorry no pets, less than two blocks to the beach.

Blue Lagoon 5 - Sandpiper
Chic and breezy cottage-style seasonal rental condo. (2) Bedrooms, (2) Bathrooms, accommodates up to (6) people: 1 King, 2 Twins, 1 Sleeper Sofa. Large lagoon-style shared heated pool, free wireless, pets welcome with fee, less than two blocks to the beach.

5200 Gulf Dr Unit 401S
A magical sunset oasis.  (2) Bedroom, (2) Bath, accommodates up to (4) people; 2 Kings, free wireless internet, community heated pool, DIRECT beach front condo.

Water's Edge 106 North
There are seven miles of pristine, powder soft sands on Anna Maria Island and you can spend a week on them with a holiday to Water's Edge Condominiums. (2) Bedroom, (1.5) Bathroom, accomodates up to (6) people: 1 Queen, 2 Twin, 1 Sleeper Sofa. Heated pool, free wireless, sorry no pets allowed, gulf front location.

Living The Dream 703 So Bay
BRAND NEW to our rental program! Gorgeous canal front vacation home with immaculate decor. (4) Bedroom, (3) Bath, accommodates (8) people: 2 Kings, 2 XL Twins, 2 Twins. Private heated pool, boat access, free wireless internet, sorry no pets, across the street from the bay beach access.

620 Rose Street
No-frills  vacation cottage with a shady oasis for you to enjoy in the backyard -- (3) Bedroom, (2) Bathroom, accommodates up to (7) people: 2 Queens and 2 Twins, 1 Futon. Free wireless, sorry no pets allowed. 

Sunfish - 102 55th St
Holiday rental condo for the discriminating vacationer only in Holmes Beach, FL. (3) Bedrooms, (2.5) Bath, accommodates up to (6) people: 1 King, 1 Queen, 2 Twins. Heated pool, free wireless, pets welcome (dogs only, with deposit).  West of Gulf Drive.

Beachy Villa Vista-116 45th
Immaculate and beachy, multi-level island vacation home.  (5) Bed: (4.5) Bath, accommodates up to (12) people: 1 King, 2 Queens, 2 Twins, 2 bunks, 1 Queen Sleeper. Private heated pool, peaks of Gulf, free wireless internet, pets are welcome with fee, only a couple houses to the beach.

516 68th St
A coastal oasis holiday rental and a boat lover’s paradise.  (4) Bedroom, (4) Bath, accommodates up to (8) people: 1 King, 1 Queen, 2 Twin, 1 Trundle Bed. Private heated & caged pool, free wireless internet, pets welcome (up to 25 lbs.) with fee.  NOTE:  This home welcomes vacations with a month & bi-weekly minimum stay.

Bikini Bottom-213 Periwinkle
Idyllic seasonal vacation cottage with your own personal poolside oasis.  (3) Bedroom, (2) Bath, accommodates up to (10) people: 2 Kings, 4 Twins, 1 Queen Sleeper Sofa. Private heated pool & spa, free wireless, sorry no pets allowed, easy walk to beach access.

Blue Lagoon 4 - Loggerhead
Spacious and sunny vacation villa. (3) Bedrooms, (3.5) Bath, accommodates up to (6) people: 2 King, 1 Queen. Shared large lagoon-style heated pool, free wireless, pet friendly with fee, less than two blocks to the beach.

Katie's Beach Bungalow
Elevated, Old Florida style vacation house right across from the Gulf of Mexico. (2) Bedrooms, (2) Bath, accommodates up to (4) people: 1 King, 1 Queen. Free wireless, pets welcome (with deposit), less than two blocks to the beach.

Tarpon Key-308 55th St
You'll never forget the peeks of the gulf and sunset vistas from your balcony at this Holmes Beach vacation rental. (3) Bedroom, (2.5) Bathroom, accomodates up to (6) people; 2 Queen, 2 Twin. Free wireless, Dogs under 25lbs welcome!

Blue Lagoon 2 - Sand Dollar
Beautiful, bright and beachy holiday rental cottage. (2) Bedrooms, (2) Bathrooms, accommodates up to (6) people: 1 King, 1 Queen, 1 Sleeper Sofa. Shared heated large lagoon-style pool, free wireless, pets welcome with fee, less than two blocks to the beach.

Sea Grape Lane - 103 Seagrape
The perfect vintage vacation cottage tucked away for privacy under the shade of actual sea grapes and directly on the Gulf of Mexico. (2) Bedroom, (1) Bathroom, accomodates up to (6) people: 1 King, 1 Queen,1 Twin, 1 Trundle. Free wireless, sorry no pets allowed, DIRECT gulf front location.

Water's Edge 103 North
If you're looking for a charming vacation rental to spend your next visit to Anna Maria Island, you might just be looking for something in the Water's Edge condominium complex. You'll be right in the heart of Holmes Beach! (3) Bedroom, (3) Bath, accomodates to (6) people: 1 Queen, 2 Twin, 1 Sleeper Sofa. Heated pool, free wireless, sorry no pets allowed, gulf front location. 

Vista Grande 1
Nothing but gulf front decadence is waiting at this luxury holiday rental for the most discriminating of vacationers. (3) Bedroom, (3) Bath, accomodates to (6) people: 1 King, 1 Queen, 2 Twin. Heated pool, free wireless, sorry no pets allowed, gulf front location. 

All Decked Out-509 SoBay Blvd
A whimsical multi-level home for your idyllic sojourn.  (5) Bedroom, (2.5) Bath, accommodates up to (10) people: 2 Kings, 1 Queen, 2 Twins, 2 Doubles. Private heated pool, amazing bay views, free wireless internet, pets welcome with fee.

Sea Palm Cottage-3008 Avenue E
**  Summer of Savings!  Rent one week, get the second for FREE!  14 days of sunshine and paradise for the price of 7!  Now through November 2014, new reservations only **
 
"Old Florida" style, charming vacation cottage. (3) Bedroom, (2) Bathroom, accommodates up to (7) people: 2 Queens, 1 Twin, 1 Twin Air Mattress. Free wireless, sorry no pets allowed, short stroll to the beach.

Paradise Found-5802 DePalmas
Sweet dreams and soothing, tropical decor at this peaceful vacation rental home. (3) Bedroom, (3) Bathroom, accommodates up to (6) people: 1 King, 1 Queen, 2 Twin. Heated pool, Free wireless, sorry no pets allowed, less than two blocks from the beach.

6300 Flotilla Dr Unit 81
Sports buffs spend your holiday at this vacation condo with community features such as tennis courts and your own practice putting green in Holmes Beach, FL.(2) Bedroom, (2) Bath, accommodates up to (4) people. 1 King, 2 Twin. Heated pool, sorry no pets allowed, free wireless. 

Wind Song-114 48th ST
Welcome to Wind Song. Fantastic brand new luxury home just two houses from the beach at 114 48th St., Holmes Beach on Anna Maria Island. (4) Bed: (3) Bath: Accommodates up to (8) people.

Casa Campoamor 11107 Gulf Dr.
"Old Florida" beach cottage. (3) Bed: (2 ) Bath, accommodates up to (6) people: 2 Kings, 1 Queen. free wireless internet, sorry no pets, steps to the beach access.

Coral Escape - 132 50th St
Luxurious custom built multi-level tropical oasis and pool paradise. (6) Bedroom, (4.5) Bath, accommodates up to (14) people: 3 Kings, 2 Queens, 1 Bunk Bed, 1 Sleeper Sofa. Private heated pool, free wireless, sorry no pets, less than a block to the beach.

Mango Breeze - 141 50th St
Mango Breeze will leave you refreshed, renewed, and relaxed. (4) Bedroom, (3.5) Bathroom, accommodates up to (8) people: 2 King, 1 Queen, 2 Twin. Private heated pool, free wireless, pet friendly (dogs up to 25 lbs only) with fee, less than two blocks to the beach.

901 Waterside Lane
Perico Bay Club vacation condo with floor to ceiling windows overlooking a gorgeous mangrove nature preserve in Bradenton, FL.(2) Bedroom, (2) Bath, accommodates up to (6) people: 1 King, 1 Queen, 1 Sleeper Sofa. Heated pool, free wireless, sorry no pets allowed. 

Anna Maria Island Club Unit 21
Light and bright direct gulf front seasonal rental. (2) Bedroom, (2) Bath, accommodates up to (4) people: 2 Kings,  Shared heated pool and spa, free wireless internet, elevator, sorry no pets.

 

 

 

 

 

 


Pretty Palms-203 Periwinkle
Updated furnishings and fixtures inside with a backyard paradise outside. (3) Bedrooms, (2) Bath, accommodates up to (6) people: 2 Queen, 2 Twin. Private heated pool, free wireless, sorry no pets allowed, less than two blocks to the beach.

Plum Cottage 322 64th St
Ground level vacation villa just a short stroll to the beach and features a garden area with lagoon style heated pool - the perfect place to relax! (2) Bedroom, (2) Bathroom, accommodates up to (6) people: 1 Queen, 2 Twins, 1 Sleeper Sofa. Private heated pool, free wireless, less than two blocks to the beach.

Promise Kept 206 76 ST
** SEPTEMBER 2014 SPECIAL of $899.00 per week (no other discount would apply) **

 

Modern and captivating island home perfect for your holiday getaway. (3) Bedroom, (2) Bath, accommodates (6) people: 1 King, 2 Queens. Private, heated pool, free wireless internet, less than two blocks to the beach.


PBC 908 Waterside Lane
Tasteful, spacious, vacation villa in a private gated community less than two miles from the beach in Bradenton, FL.  (2) Bedroom, (2) Bath, accommodates up to (4) people: 1 King, 1 Queen. Heated pool, free wireless, pet friendly (with deposit).

202 66th St E
Perfect bright and beachy duplex for your idyllic island getaway. (2) Bedrooms, (2) Bathrooms, accommodates up to (6) guests: 1 King, 1 Queen, 1 sleeper sofa. Shared heated pool with waterfall, free wireless, sorry no pets allowed, one block from the beach access.

Gulf Shores Unit 203
The breath-taking panoramic Gulf views is what this vacation rental is all about. (3) Bedrooms, (2) Bath, accommodates up to (6) people: 1 King, 2 Twins, 1 Sleeper Sofa. Free wireless, sorry no pets, DIRECT gulf front location.

Sun Ray - 305B 65th St
This vacation duplex is a warm, welcoming spot for your next holiday in Holmes Beach. Rent one or both sides and soak up the Florida sunshine with your whole family. (2) Bedroom, (2) Bathroom, accomodates up to (4) people: 1 Queen, 2 Twin. Private heated pool, free wireless, sorry no pets allowed.

La Casa Denton
Some of the most popular vacation rentals on Anna Maria Island can be found at La Casa Costeria. And the reason is blissfully simple – because they’re the crème de la crème. (2) Bedroom + den, (2.5) Bathroom, accommodates up to (6) people: 1 King, 1 Queen, 2 Twins. Heated pool with spa, free wireless, sorry no pets allowed, gulf front location.

Grant's View - 412 S Bay Blvd
Immaculate panoramic views of the Tampa Bay make for an unforgettable holiday sojourn. (2) Bedrooms, (2) Bath, accommodates up to (6-8) people: 1 King, 1 Queen, 2 Twins. Free wireless, pets welcome (up to 15lbs) with deposit.

Turtle Nest - 305A 65th St
Cozy and oh-so-comfy vacation rental across the street from the world-famous white sand beaches of Anna Maria Island and the Florida gulfcoast. (2) Bedroom, (2) Bath, accomodates to (4) people: 1 Queen, 2 Twin. Private heated pool, free wireless, sorry no pets allowed. 

Imperial House D-23
A quiet vacation condo for 55+ visitors that will put you right in the heart of all your favorite ways to unwind. (2) Bedrooms, (1) Bathroom, accomodates up to (4) people: 1 Queen, 1 Double. Heated pool, sorry no pets allowed, less than two blocks to the beach and bayfront

Playa Casanas South-3222 Gulf
Perfect for multifamily vacations, rent one or both sides of this vacation rental duplex directly on the sparkling white, quartz sands of Holmes Beach, FL. (2) Bedroom, (1) Bathroom, accommodates up to (4-6) people: 1 Queen, 2 Twins, 1 Sleeper Sofa. Free wireless, sorry no pets allowed, gulf front location.

West Bay Cove 214
Charming and spotless condo located at West Bay Cove - one of the most popular spots for a quiet Anna Maria Island vacation. (1) Bedroom, (1) Bath, accomodates to (4) people: 1 Queen, 1 Queen Sleeper Sofa. Heated pool, free wireless, sorry no pets allowed. 

Misty Beach-5802 Imperiore Ave
Bright and beachy island home for a peaceful island getaway. (2) Bedroom, (2) Bathroom, accommodates up to (4) people: 1 King, 1 Queen. Private heated pool, free wireless, pet friendly (up to 25lbs) with fee, less than two blocks to the beach.  

Sea's the Day - 207 Coconut
A soothing vacation cottage like the one at 207 Coconut will make you forget all about hotel living. (2) Bedroom, (2) Bathroom, accomodates up to (7) people: 1 Queen, 2 Twin, 1 Sleeper Sofa. Private heated pool, free wireless, pet friendly, washer-n-dryer (with deposit), less than two blocks to the beach.
 

Lazy Daze 512 74th ST
Bay Palms canal home perfect for boat lovers. (3) Bedroom, (2) Bath, accommodates (6) people: 1 King, 1 Queen, 1 Double. Private heated pool, sorry no pets, free wireless internet, boat access right from your backyard.

Holly Jewel-727 Holly Road
Beautiful upscale seasonal home in tranquil neighborhood. (3) Bedroom, (2.5) Bath, accommodates up to (6) people: 1 King, 1 Queen, 2 Twins. Free wireless internet, canal front with boat access.

Turtle Cove East
Both sides of this charming vacation duplex are decorated in a palette of warm tropical colors and Old Florida style in Holmes Beach, FL. (2) Bedroom, (1) Bath, accomodates to (4) people: 1 Queen, 2 Twin. Heated pool, free wireless, sorry no pets allowed, less than two blocks to the beach. 

Palm Isle 3206
Captivating and cute cottage-style ground level condos perfect for your relaxing island getaway. (2) Bedroom, (1) Bathroom, accommodates up to (6) people: 1 Queen, Set of short bunk beds, 1 Sleeper Sofa. Heated pool, free wireless, sorry no pets allowed, across the road from the beach access.

Bridgeport 501 Gulf Dr N 304
Vibrant and relaxing condominium with beautiful views of the inter-coastal. (2) Bedroom, (2) Bath, accommodates (4) people: 1 King, 2 Twins.  Community heated pool, elevator, free wireless internet, sorry no pets.

Peaceful Palms-7302 Palm Dr
Enjoy a week of serenity by taking your next Florida holiday to this cozy vacation rental. (2) Bedroom, (1) Bathroom, accommodates up to (6) people: 1 Queen, 2 Twins, 1 Futon. Free wireless, pet friendly (up to 25lbs, with deposit).

Water's Edge 205 South
If you're looking for a charming vacation rental to spend your next visit to Anna Maria Island, you might just be looking for something in the Water's Edge condominium complex. You'll be right in the heart of Holmes Beach! (1) Bedroom, (1.5) Bath, accomodates to (4) people: 1 Queen, 1 Sleeper Sofa. Heated pool, free wireless, sorry no pets allowed, gulf front location. 

Paradise Pointe 411 Poinsettia
Paradise Pointe located in the quiet north end of beautiful Anna Maria awaits the vacationer in you. This picture perfect ground level three bedroom two bathroom vacation

Hidden Cove Unit 3
Breath-taking panoramic views of the sparkling Gulf of Mexico and sugar sand beaches.  (2) Bedrooms, (2.5) Bathroom, accommodates up to (4) people: 1 King, 2 Twins. Community pool, free wireless, sorry no pets, gulf front location.

Starfish Beach Unit 4
Starfish Beach Cottage #4 is a totally renovated vacation condo offering you a retreat wit hthe best of Anna Maria Island life and luxury. (2) Bedroom, (2) Bathroom, accomodates up to (6) people: 1 King, 1 Queen, 1 Sleeper Sofa. Heated pool, free wireless, pet friendly (up to 25lbs, with deposit).

200 66th St W
Perfect bright and beachy duplex for your idyllic island getaway. (3) Bedrooms, (2) Bathrooms, accommodates up to (6) guests: 1 King, 1 Queen, 2 Twins. Shared heated pool with waterfall, free wireless, sorry no pets allowed, one block from the beach access.

Sunset Villa 3- 1001 Gulf Dr
Sunset Villa is waiting for you! Located directly across the street from the some of gulfcoast Florida's best beaches. (2) Bedrooms, (1.5) Bath, accommodates up to (6) people: 1 King, 2 Twins, 1 Sleeper Sofa. Heated pool, free wireless and sorry no pets allowed. Direct Gulf views and the beach is right across the street. 

Beach House Resort 4
Cute and cozy holiday rental with stunning views of the gulf. (1) Bedroom, (1) Bath, accommodates up to (4) people: 1 Queen, 1 Sleeper Sofa. Free wireless internet, heated spa, pet friendly (small only) with fee, DIRECT gulf front.

Short Board-131EWhite
Cozy and chic duplex ready for your tropical escape. (2) Bedrooms, (2) Bath, accommodates up to (6) people: 1 King, 2 Twin, 1 Sleeper Sofa. Shared heated pool, free wireless, pet friendly with fee, only a few houses to the beach.

Au Soleil - 717 Jacaranda Rd
Spacious and elegant home idyllic for your holiday sojourn. (4) Bedroom, (3) Bath, accommodates up to (10) people: 1 King, 2 Queen, 2 Twin, 1 Murphy Bed. Private pool with spa, free wireless, pets welcome (under 25lbs) with fee, less than two blocks to the beach.  

Beach View 5 - 3704 6th Ave
Bright and breezy seasonal condo rental. (2) Bedroom, (2) Bath, accommodates up to (6) people. 1 King, 2 Twins, 1  Queen Sleeper. Free wireless, sorry no pets, shared heated pool, less than two blocks to the beach.  

La Casa LaMar
Some of the most popular vacation rentals on Anna Maria Island can be found at La Casa Costeria. And the reason is blissfully simple – because they’re the crème de la crème. (2) Bedroom + den, (2) Bathroom, accommodates up to (5) people: 1 King, 2 Twin, 1 Sleeper Sofa. Heated pool with spa, free wireless, sorry no pets allowed, gulf front location.

Sea 'Esta - 890 North Shore
Easy access to the beach and historic Rod N Reel Pier is available at this vivid luxury rental home in Anna Maria City. (2) Bedroom, (2) Bathroom, accommodates up to (6) people: 1 King, 1 Queen, 1 Sleeper Sofa. Free wireless, pet friendly (up to 25 lbs) with fee, less than two blocks to the beach.

Fountain Head 2
Coastal, clean and bright centrally located seasonal vacation condo. (2) Bedroom, (2) Bath, accommodates (4) people: 1 Queen, 2 Twins. Shared heated pool, free wireless internet, sorry no pets, less than two blocks to the beach.

Seaside Beach House 105
Ideal for small families and honeymooners, this cozy little cabin is private and perfectly located (2) Bedroom, (1.5) Bathroom, accomodates up to (4) people: 1 King, 2 Twin. Heated pool, free wireless, sorry no pets allowed, gulf front location.
 

Cabana - 104B 29th St
Delightful little beach bungalow. (1) Bedroom, (1) Bathroom, accommodates up to (3) people: 1 Queen, 1 Sleeper Sofa. Free wireless, sorry no pets allowed, 100 steps to the beach access.

200-202 66th St House
Light and bright coastal duplex-style home perfect for larger groups. (5) Bedrooms, (4) Bathrooms, accommodates up to (12) guests: 2 King, 2 Queen, 2 Twins, 1 Sleeper Sofa. Heated pool shared for both sides to access, free wireless, sorry no pets allowed, one block from the beach access.

Sea Pirate Unit 2- 3303 Gulf
Tranquil ground level condo. (2) Bedroom, (1) Bathroom, accommodates up to (4) people: 1 Queen, 2 Twins. Shared heated pool, free wireless, sorry no pets allowed, across the street from the beach.

305 B 62nd Street
No-frills, laid back duplex for a quiet and relaxing island getaway. (2) Bedrooms, (2) Bath, accommodates up to (6) people: (2) Queen, (1) Queen Sleeper Sofas. Free wireless internet, pet friendly with fee, about two blocks to the beach.

L'Plage 6430
Luxury at its finest with this stand-alone, spacious condo in all its elegance. (4) Bedroom, (4) Bathroom, accommodates up to (8) people: 1 King, 1 Queen, 2 Twins, 1 Sleeper Sofa. Heated pool with spa, free wireless, sorry no pets allowed, gulf front complex yet this unit has limited views.

Little Miss Magic-116 81st St
**Now until  September 30th 2014 $869.00  (No other discounts would apply) **

Brand NEW, charming and cute vacation oasis.  (3) Bedrooms, (2) Bath, accommodates up to (6) people: 2 Queens, 2 Twins.  Private, heated pool, free wireless internet, sorry no pets allowed, only a few houses to the beach.


Safari Suite - 1105 Gulf Dr S
A vibrant vacation condo such as Safari Suite comes around once in a lifetime! See for yourself with a week of island life. (1) Bedroom, (1) Bathroom, accommodates up to (4) people; 1 King, 1 Sleeper Sofa. Pet friendly with fee, across the road from the beach.

SeaShell-Sunsets-105 78th
A custom-built luxury vacation rental with a tropical paradise right out in your own backyard! 4) Bedroom, (4.5) Bathroom, accomodates up to (10) people: 2 King, 4 Twin Beds, 2 Trundle. Private heated pool with spa, free wireless, sorry no pets allowed.
 

Palm Cay Unit 8 3000 Gulf Dr
Adorable vacation condo with peeks of the Gulf of Mexico from your front porch!  (1) Bedroom, (1) Bathroom, accommodates up to (4) people: 1 King, Sleeper.  Shared heated pool, free wireless, sorry no pets allowed, less than two blocks from the beach.

About a Mermaid 621 Emerald Ln
Beautifully Designed & Decorated vacation rental home in Holmes Beach, FL. Just a few blocks from Bimini Bay on KeyRoyale Street. Private Pool, Dock, Direct Intracoastal Access!

Hidden Cove Unit 6
Breath-taking panoramic views of the sparkling Gulf of Mexico and sugar sand beaches.  (2) Bedrooms, (2.5) Bathroom, accommodates up to (4) people: 1 King, 2 Twins. Community pool, free wireless, sorry no pets, gulf front location.

Tina's Piece of Paradise
A vacation home like Tina's Piece of Paradise is just the place to make fabulous family memories in Florida! A high chair and Pack & Play are also available for the littlest vacationers. (4) Bedrooms, (3) Bath, accommodates up to (14) people: 3 King, 1 Bunk Bed, 2 Sleeper Sofa, 1 Air Mattress. Private heated pool, free wireless, sorry no pets allowed.  

Beach Retreat-208A 72nd St
Coastal and spacious vacation paradise seasonal rental  (4) Bedroom, (2.5) Baths, accommodates up to (8) people: 1 King, 1 Queen, 2 Twin, 1T with Trundle that can convert into King. Heated private pool, free wireless, a short block and a half from the beach.

Maple Cottage-120 Maple
Charming and relaxing vacation cottage. (3) Bedrooms, (2) Bathrooms, accommodates up to (8) guests. 1 King, 1 Queen, 2 Twins, 1 Sleeper Sofa. free wireless internet, sorry no pets, one block to the beach access.

Playa Casanas Family
Perfect for multifamily vacations, rent one or both sides of this vacation rental duplex directly on the sparkling white, quartz sands of Holmes Beach, FL. (4) Bedroom, (2) Bathroom, accommodates up to (8 - 10) people: 2 Queen, 4 Twins, 2 Sleeper Sofa. Free wireless, sorry no pets allowed, gulf front location.

HoneyWood House 243 Willow
Captivating, beachy and relaxing private home on a quiet cul-de-sac street perfect for your tranquil island getaway. (2) Bedroom, (2) Bath, accommodates up to (6) people: 1 King, 1 Queen, 1 Twin Futon. Private heated pool and spa, free wireless internet, sorry no pets, less than two blocks to the beach.

Captains House-208 Haverkos
Vibrant, colorful and delightful seasonal rental. (3) Bedroom, (2.5) Bath, accommodates (8) people: 2 Queens, 2 Twins, Queen Sleeper sofa. Private heated pool, free wireless internet, sorry no pets, not far from the beach access.

Coco Cabana 309 58th ST Unit A
Designer quality interior and tropical oasis feel make this duplex an ideal location for your island getaway. (3) Bedroom, (2) Bath, accommodates (8) people:2 Kings, 2 Twins, 1 Queen Sleeper sofa.  Private heated pool, free wireless internet, pets are welcome with a fee, about three blocks to the beach.

Sandy Point Unit 208
Lovely Island holiday condo in Sandy Pointe condominiums. The condo backs up to a 30+ acre reserve! (2) Bedroom, (2) Bath, accommodates (6) people: 1 King, 2 Twins, 1 Queen Sleeper sofa. Community, heated pool, free wireless internet, pets welcome with fee.

Blue Wave Villas-207W 75th St
Cozy, comfortable, but above all classy vacation duplex. (2) Bedrooms, (1) Bath, accommodates up to (4) people: 1 King, 2 Twin. Private heated pool, free wireless, sorry no pets allowed, less than two blocks to the beach.

Gulf Breeze-203E 69th St
** Some 2014 late summer and fall weeks as low as $2250! **

 

You'll never forget the views from this luxury vacation rental - a sweeping vista of the Gulf of Mexico and its shimmering quartz sand beaches. It will be love at first sunset! (6) Bedrooms, (4.5) Bath, accommodates up to (16) people: 3 King, 1 Queen, 2 Twins, 1 Full, 2 Sleeper Sofa. Private heated pool with spa, free wireless, pet friendly with fee, less than two blocks to the beach.


Plum Cottage 324 64th St
Enjoy plenty of island flavors as you’ll be close to some of our favorite local dining, shopping, and water activities while staying at this quaint vacation cottage. (3) Bedroom, (2) Bathroom, accommodates up to (6) people: 1 King, 1 Queen, 2 Twins. Private heated pool, free wireless, sorry no pets allowed, less than two blocks to the beach.

208 Periwinkle Plaza
Newly renovated, elegant oasis escape with a screened in patio. (3) Bedrooms, (2.5) Bath, accommodates up to (8) people: 1 King, 1 Queen, 2 Twin, 1 Double Sleeper Sofa. Private heated pool, free wireless internet, sorry no pets allowed, boat access, less than two blocks to the beach.

Villa de la Playa-3603A 4th
** SPECIAL: 10% DISCOUNT ON ALL BOOKINGS MADE WITHIN 45 DAYS OF ARRIVAL **

 

 

The whole family can get away from it all on the top floor of this condo building located less than two blocks from the Gulf of Mexico beaches. (2) Bedroom, (1) Bath, accomodates to (6) people: 1 King, 2 Queen. Private heated pool, free wireless, pet friendly (dogs only, with deposit), less than two blocks to the beach. 


Nautilus 7100 Gulf 105
Cute and cozy gulf front vacation rental. (2) Bedroom, (2) Bath, accommodates (4) people: 1 King, 2 Twins. Community heated pool, free wireless internet, sorry no pets, gulf front complex.

Water's Edge 209 North
If you're looking for a charming vacation rental to spend your next visit to Anna Maria Island, you might just be looking for something in the Water's Edge condominium complex. You'll be right in the heart of Holmes Beach! (2) Bedroom, (2) Bath, accomodates to (6) people: 1 King, 2 Twin, 1 Sleeper Sofa. Heated pool, free wireless, sorry no pets allowed, gulf front location. 

Sandy Point Unit 206
Lovely Island holiday condo in Sandy Pointe condominiums. The condo backs up to a 30+ acre reserve! (2) Bedroom, (2) Bath, accommodates (4) people: 1 King, 2 Twins. Community, heated pool, free wireless internet.

North Beach Village Unit 63
Refresh, renew, and relax among lush landscaping for privacy at this vacation condo. (2) Bedroom, (2.5) Bath, accommodates (6) people: 1 King, 2 Twins, 1 Queen Sleeper sofa.  Community heated pool, free wireless internet, pet friendly with fee, less than two blocks to the beach access.

Minnie Cottage - 125 47th St
Vacation in style and comfort in this coastal cottage with in-pool tiki bar and umbrella. (3) Bedroom, (3) Bathroom, accommodates up to (8) people: 2 King, 1 Queen, 1 Sleeper Sofa. Private heated pool, free wireless, sorry no pets allowed, less than two blocks to the beach.

Gulf View Unit 101
Spend a week living in a postcard right on the diamond white shores of Bradenton Beach. (2) Bedrooms, (2) Bath, accommodates up to (4) people: 1 King, 2 Twins. Free wireless, sorry no pets, gulf front location.

 

 

 


 


209 69th B
Renovated island chic elevated duplex perfect getaway for your holiday. (2) Bedrooms, (2) Bath, accommodates up to (6) people: 1 King, 2 Twin, 1 Queen Sleeper Sofa. Shared heated pool, free wireless internet, sorry no pets, less than two blocks to the beach.

Blue Wave Villas-207E 75th St
Cozy, comfortable, but above all classy vacation duplex. (2) Bedrooms, (1) Bath, accommodates up to (4) people: 1 King, 2 Twin. Private heated pool, free wireless, sorry no pets allowed, less than two blocks to the beach.

Heron - 706 Rose A
Welcome to the Heron located at 706 Rose unit A. This quaint 2 bedroom 1 bath duplex located on a quiet street on the north end of beautiful Anna Maria Island awaits the

Casa Del Sol - 310 Clark Lane
Stunning tropical paradise for a relaxing island getaway (4) Bedrooms, (3.5) Bath, accommodates up to (10) people: 2 Kings, 1 Queen, 2 Twins, 1 Queen Sleeper Sofa. Private heated pool paradise, free wireless, pet friendly (less than 25lbs) with fee, less than two blocks to the beach.

Beach Blanket Bungalow-206Lake
Welcome to  206 LakeView Drive located on the northern end of beautiful Anna Maria Island. This private and lovely three bedroom and 2  bath vacation rental

Palm Isle 3203
Captivating and cute cottage-style ground level condos perfect for your relaxing island getaway. (2) Bedroom, (2) Bathroom, accommodates up to (8) people: 1 King, 1 Queen, 1 Sleeper Sofa, 1 Air Mattress. Heated pool, free wireless, sorry no pets allowed, across the road from the beach access.

The Seashell Cottage
This fabulous little beach cottage is a getaway worth writing home about. Enjoy a week of small town serenity in Anna Maria City. (2) Bedrooms, (2) Bath, accommodates up to (6) people: 1 King, 2 Twins, 1 Sleeper Sofa. Free wireless, Small dogs only, less than two blocks to the beach. 

Pelican Landing AMI-306 55th
September  2014 Weekly Special of $1,599.00 non-holiday weeks and no other discounts would apply.

Fabulous and modern island home with designer kitchen. (3) Bedroom, (2) Bathroom, accommodates up to (8) people: 1 King, 1 Queen, 2 Twins, 1 Sleeper Sofa. Private heated pool, free wireless, sorry no pets allowed, less than two blocks from the beach.


Heron Heaven-5613 Gulf
Modern, custom built seasonal vacation home with sensational sunset views from a large, elevated deck. (2) Bedroom, (2) Bath, accommodates up to (6) people: 1 King, 1 Queen, 2 Twins, 1 Queen Sleeper Sofa. Free wireless, sorry no pets allowed, seashell throw from the beach access.

Check Availability
In the UK: 0 800 883 0462   |   Admin Login