Top 7 Anna Maria Island Thanksgiving Beach Rentals

Another Fall is here and there couldn’t be a more perfect time for Anna Maria Island Thanksgiving beach rentals!

Anna Maria Island Thanksgiving Beach Rentals

Anna Maria Island Thanksgiving Beach Rentals

Here is our list of the top seven beach rentals to visit with family and friends while we all give thanks. We have picked a variety of rentals from one bedroom all the way up to six bedrooms, so you’ll find something here for any size group. Take a look and see what Anna Maria Island Thanksgiving beach rentals fit your vacation plans!

Villa 4 – Sleeps 4 

Villa 4 is a great one bedroom home a short walk from gulf beaches in the city of Bradenton Beach. This cozy five unit complex offers a heated pool, bbq grills and is just a few blocks from Historic Bridge Street.

Bradenton Beach rental villa 4
Villa 4 in Bradenton Beach – one bedroom.

Comes with a full kitchen too! Reserve your stay at Villa 4 November 18-25 for $1,119.60 – all in.

Bradenton Beach rental
Kitchen at Villa 4.

Turtle Nest – Sleeps 6

This is a comfortable two bedroom duplex with a private heated pool about two blocks from the beach.

Holmes Beach rental
Turtle Nest Holmes Beach – one bedroom.

At Turtle Nest you’ll find a nice relaxing spot to enjoy the beach with family. Find a lovely balcony, outdoor shower and plenty of comfortable seats around the pool. Reserve Turtle Nest November 18-25 for $1,377.20 – all in.

 Beach Rental Holmes Beach
Kitchen at Turtle Nest

Sweet Retreat Cottage – Sleeps 8

Sweet Retreat is a vibrant three bedroom beach house just across the street from coveted north-end beaches. Not only is this location amazing, but well-appointed too! The stylish blue and white kitchen here will make preparing that Turkey feast a pleasure, and find enough seating for everyone.

Holmes beach cottage rental
Sweet Retreat Cottage Anna Maria – three bedroom.

The backyard has a private heated pool with waterfall feature for the perfect family getaway! Reserve November 18-25 for $2,682.00 – all in.

Sweet Retreat Cottage Anna Maria
Kitchen at Sweet Retreat

Living the Dream – Sleeps 8

Living the Dream is a true luxury beach rental with four bedrooms in the city of Anna Maria. This house was updated recently with amenities you don’t find everyday. Enjoy the canal front beach patch next to the heated pool and outdoor lounge complete with a flat screen T.V and bar.

Living the dream
Living the Dream Anna Maria – four bedroom.

The beach is just short walk away along with Pine Avenue! You’ll love this high-end kitchen perfect for Thanksgiving meals! Reserve November 18-25 for $4,787.60 – all in.

Living the dream anna maria beach rental
Kitchen at Living the Dream

Pineapple Cottage – Sleeps 8

Pineapple Cottage is a great old Florida rental in the city of Anna Maria with a sophisticated beachy style. This four bedroom home is just a short walk to both gulf and bay beaches.

Pineapple Cottage Anna Maria
Pineapple Cottage Anna Maria – 4 bedroom

Find a whimsical feel throughout, but with high-end touches like stainless steel appliances and a heated pool and spa! Relax in the backyard like you have found your own private oasis. Reserve November 18-25 for  $3,415.60 – all in.

Pineapple Cottage Anna Maria rental
Kitchen at Pineapple Cottage

Au Soleil – Sleeps 10

This unique rental is great for larger groups with a spacious floor plan and five bedrooms. Thanksgiving was made for gathering together all your friends and family to give thanks, and this is the spot!

Anna Maria
Au Soleil Anna Maria – five bedroom.

While Au Soleil has great amenities it’s also just across the street from north-end beaches. Enjoy the heated pool and spa, covered outdoor lounge and both indoor and outdoor seating areas. Reserve November 18-25 for $3,314.80 – all in.

Au Soleil Anna Maria
Kitchen at Au Soleil

Coral Escape – Sleeps 12

Coral Escape is the ultimate big family Thanksgiving beach rental and it has EVERYTHING! From location to amenities this home is a gem. Inside you’ll find 6 bedrooms to comfortably sleep your group, and a kitchen fit for preparing that huge Thanksgiving dinner.

Coral Escape
Coral Escape Holmes Beach – 6 bedroom.

The backyard has a heated pool and spa along with covered lounge, bar and flat screen television. Your family will have a blast! Reserve November 18-25 for $5,151.60 – all in.

Coral Escape
Kitchen at Coral Escape

 

Anna Maria Island Thanksgiving Beach Rentals are the perfect thing your family and friends need this year! Book your stay now!

Top 10 Fall Anna Maria Island Beach Rentals 2017

Here are 10 Fall Anna Maria Island beach rentals to help you get ready for the change of season. Summer was hot this year, but these rentals will help cool you down! Check out our list and get to planning your Fall vacation now!

Top 10 Fall Anna Maria Island Beach Rentals 2017

Top 10 Fall Anna Maria Island Beach Rentals 2017

Our list includes rentals across Anna Maria Island’s three cities and is organized by number of bedrooms. Find both luxury and budget rentals to fit any group!

Runaway Bay Club – Sleeps 2

This lovely one bedroom unit is the perfect couples getaway by the beach. Enjoy the heated community pool, short walk to the beach and a bay viewing dock too! You’ll be close to shopping, dining and free trolley stops.

Holmes Beach Vacation Rental
Fall 2017 base rates start at $500/week – Holme Beach.

Water’s Edge 105 South – Sleeps 4

You’ll be steps from the beach when you visit Water’s Edge. Sleep four guests with one bedroom and 1.5 baths. The community pool looks over the gulf and makes a wonderful spot to relax island style. The luxury rental you’ve been searching for!

Fall Beach rentals Anna Maria Island
Fall 2017 base rates start at $1400/week – Holmes Beach

Sea Esta – Sleeps 5

Sea Esta was just completely remodeled Summer 2017, and is on the coveted north end of Anna Maria Island. This beach renal has it all! Find two stylish bedrooms along with fun new amenities too! Walk to Rod & Reel Pier and secluded Bean Point beaches.

Anna Maria Fall beach rentals
Fall 2017 base rates start at $950/week.

North Beach Village 55 – Sleeps 6

The North Beach Village complex is a quiet Holmes Beach community just a couple blocks from gulf beaches. This three bedroom unit is spacious and offers lovely balconies for to enjoy fresh salt breezes. The central location of this town house makes everything close by!

North Beach Village Holmes Beach rental
Fall 2017 base rates start at $950/week – Holmes Beach

Sugar Plum Hideaway West – Sleeps 6

Less than a block from the beach, this three bedroom unit will have you feeling relaxed in paradise. Find a fun style and updated amenities. Sugar Plum Hideaway West offers a heated shared pool, and welcomes pets up to 25 pounds with fee.

Anna Maria beach rental
Fall 2017 base rates start at $1400/week – Holmes Beach

Rest Assured – Sleeps 6

Rest Assured is a comfortable single family home with a heated caged pool, three bedrooms and three bathrooms. Everyone will have plenty of space to spread out here like your own private beach resort! The beach is less than two blocks away making this an excellent location.

Anna Maria Island Fall Rental
Fall 2017 base rates start at $2200/week – Holmes Beach

Sandy’s Getaway – Sleeps 8

This raised single family home is less than a block from gulf beaches with no major roads to cross. Beach trips were never this easy! Find three bedrooms, two bathrooms and two sleeper sofas to comfortably accommodate all eight guests. Dogs welcome with pet fee!

Anna Maria Fall vacation rental
Fall 2017 base rates start at $950/week – Anna Maria

Playa Casanas Family Home – Sleeps 8

The Playa Casanas Family Home is a direct beach front duplex in central Holmes Beach. Each unit sleeps 4 guests with a combined total of four bedrooms and two bathrooms. This is a great spot for a no-frills trip to beach! Spend all day in the sun, or walk to shopping and dining!

Direct gulf front rental Anna Maria Island
Fall 2017 base rates start at $2100/week – Holmes Beach

Beachy Blue – Sleeps 8

This is a luxury rental your family will adore! The style and amenities are high-end, accommodating and all just a short walk to gulf beaches. With four bedrooms you’ll have tons of space for eight guests. The backyard offers a private heated pool and spa along with a covered lounge area for ultimate relaxation.

Luxury Holmes Beach Rental
Fall 2017 base rates start at $2150/week – Holmes Beach

Coral Escape – Sleeps 12

Coral Escape is an amazing location for those large family beach getaways. Six bedrooms and four bathrooms allow for your group to feel comfortable in paradise. Just a block from the beach, this home has a fantastic heated pool and spa in the backyard. Enjoy the covered outdoor lounge with pool table, barbecue and flat screen television.

Fall vacation rental holmes beach florida
Fall 2017 base rates start at $2500/week – Holmes Beach.

Enjoy these Fall Anna Maria Island beach rentals for the perfect Florida vacation this year!

 

14 Things Locals Always Have to Explain to Anna Maria Island Vacationers

There are things locals always have to explain to Anna Maria Island vacationers. While you may be an expert at the island life, chances are at one time you were new to the scene.

14 Things Locals Always Have to Explain to Anna Maria Island Vacationers

Anna Maria Island is a quirky little island that both locals and vacationers love. Here are 14 things you may, or may not, have know about this place we call paradise.

Things Locals Always Have to Explain to Anna Maria Island Vacationers

1. Three cities

Anna Maria Island might only be seven miles long, but we have three distinct cities. The north end is called Anna Maria or the city of Anna Maria. In the middle we have Holmes Beach, and to the south Bradenton Beach. Each has it’s own vibe, but all are beautiful.

2. Sunblock

Sunblock is crucial, and you need to put it on BEFORE you get to the beach. Lather SPF on at least 20 minutes before you plan on being in the sun. REAPPLY every 2 hours. Yes you can get sunburned while in the water. The sun also reflects off the surface of the water and sand, so under an umbrella doesn’t make you safe from damaging rays. Higher SPF’s are better protection, and spray on sunblock, though convenient, typically isn’t as effective. Also, drink lots of water.

3. Wildlife

Please mind the wildlife and NEVER FEED THE GULLS. Don’t let the kids chase birds, stay away from turtle nests, and call Wildlife Inc. if you find injured or sick animals. Not only does Anna Maria Island have nesting sea turtles, but we have two species of tortoise. If you find a turtle on the beach and it doesn’t have flippers then leave it on the beach. It’s likely a box turtle or Gopher tortoise. They live in the dunes not the water. From May to October DO NOT leave anything on the beach, fill in holes and flatten sand castles. Be sure all beach facing lights are off, so nesting turtles and hatchlings don’t become disoriented.

4. Bugs

Bugs happen. They just do. Invest in a bottle of deet spray if you are a mosquito magnet. Even the cleanest homes, shops and restaurants will have the occasional pest. Welcome to Florida! Luckily Florida also has Lizards, Geckos and a unique wildlife food chain to help keep bugs in check. Here is a link to the Manatee County Mosquito Control Schedule.

5. Where is the…

Before you come to the island, take a look at a map. You’ll notice there is really only one main road that runs the length of the island. It does change names, Gulf Drive, East Bay, Marina Drive, and isn’t necessarily straight, but it is the main drag. Often tourists wonder about getting lost, and ask how to get places. Getting around is extremely simple once you catch your bearings. The free trolley is a great way to get a feel for the area. Often if you are unsure where your destination is the trolley driver can help. Island Real Estate does offer local maps too!

6. Gators don’t like the beach

Yes, Florida is home to some crazy prehistoric, bite your arm off, big scary Alligators. However, salt water is not the natural habitat of the gator, and none have been spotted on AMI in decades. Ask any Anna Maria Island native and they’ll laugh at the idea of a gator on the beach. If you plan on visiting any fresh or brackish water (a mix of salt and fresh) that is an entirely different story. Any non-salt body of water is fair game for gators. Even if you don’t see “do not swim” signs near fresh water, it’s probably best to avoid getting in or near it.

7. Respect the Gulf of Mexico

While visiting the beach always check for the color coded swimming condition signs. The gulf is a powerful body of water. On a rough day even the strongest adult swimmers can be quickly caught up. Always use extreme caution, look for rip tide warning signage, swim with a buddy, and never allow children to swim without an adult. If your group has inexperienced swimmers consider avoiding the very northern beaches where under currents are strongest. Always respect the power of the gulf.

8. Locals

Yes, people do live on Anna Maria Island year round, and no they are not all fat, happy, tan retirees.

Anna Maria Island is a unique community. We have our own elementary school, people work full time jobs, and no our houses are not completely filled with tons of sand. Okay, maybe our houses have a little bit of sand though… The island community is unlike anywhere else in Florida. If you are looking to make the island your full time home contact an Island Real Estate Sales Agent!

9. Weather

Don’t even try to figure out EXACTLY what the weather is going to be like for your stay.

Trying to figure out the rain is like herding gators. Pointless and stressful. Visitors love to ask locals what they think the rain will be like. Nobody likes a vacation ruined by rain, but there isn’t one solid answer.

Predictions change regularly, but some trends are constant. Florida is a sub-tropical climate so we get rain all seasons of the year. During the summer months we have rain roll in around 4-5pm, almost daily, for an hour and then it clears before sunset. Late summer is usually the wettest. Winter is mild. Spring and Fall are warm and sometimes hot.

Hurricane season lasts from June 1st through November 30th. If you get travel insurance for your trip you’ll be covered for evacuations due to named storms. The great thing about modern weather tracking is the ability to closely monitor large storms. In the rare event that the island needs to be evacuated you’ll have ample time to do so.

10. Don’t collect live shells.

Shells play an important roll to local ecosystems. Collecting living shells is not only illegal without permit, but ethically in poor judgement. You must hold a saltwater fishing license to collect any living shell including Sand Dollars, Starfish, Whelks, Conchs, Urchin and many others. Bag limits are 2 per person per a day.

People love to collect Sand Dollars, but be sure they are white in color as these ones are already dead. Living Sand Dollars will be more of a gray color. It is okay to gently touch them but please put them right back.

While beach combing is relaxing and fun please don’t over collect dead shells. Limit yourself to less than a quart size container. Even dead shells play an important roll in the gulf. If you take all the dead shells where will hermit crabs live?

11. Pick it up!

Don’t leave any trash on the beach. Millions of sea and shore birds around the world die every year due to ingesting plastics and garbage. Sea life can become entangled too. Trash on the beach isn’t just dangerous, but unsightly. If you do see trash, do your part to help, and pick it up!

12. Stingray Shuffle

The Stingray shuffle might sound like a funny dance move, but it is a sure way to avoid a ray run-in. Stingrays are extremely non-aggressive animals but they carry a unique defense mechanism. By simply shuffling your feet you can avoid a painful trip to the beach.

13. Where to park.

Parking can be limited on Anna Maria Island, but we have a few suggestions. First, if you can avoid driving and use alternatives such as the Trolley, Uber and local shuttles you won’t have to deal with parking. Here is our guide to alternative transportation.

Also be sure to read our Anna Maria Parking Guide to help you find less popular parking areas and avoid getting a ticket too!

14. Anna Maria Island Vacation Rentals

Anna Maria Island vacation rentals are absolutely fantastic! AMI offers a huge selection of rentals and none are too far from the beach! Typically rentals are offered Saturday to Saturday and ALL beach rentals have a 3 night minimum. Book your next stay today!

Now you can enjoy your next Anna Maria Island vacation in the know. You won’t even have to ask the things locals always have to explain to Anna Maria Island vacationers!

Top 5 Anna Maria Island Memorial Day Beach Rental

An Anna Maria Island Memorial Day Beach Rental is an excellent way to celebrate with family and friends while enjoying the holiday! Memorial day is a time to not only reflect on those who lost their life defending America, but to enjoy the company of the ones you love.

Anna Maria Island Memorial Day Beach Rental
Anna Maria Island is the perfect place to enjoy a Memorial Day Beach Vacation with your family!

Anna Maria Island Memorial Day Beach Rental

Here is our list of the top 5 beach rentals to reserve for this years holiday! There’s no place better to gather with family and friends than Anna Maria Island!

Villa 1 – Sleeps 4

Villa 1 is a quaint one bedroom condo just a short walk from gulf beaches, free trolley stops, shopping and dining. This small four unit condo building offers a community heated pool and grills too. Great for small families or even a couples getaway, this spot is premium.

Villa 1 Bradenton Beach
Villa 1 – Bradenton Beach – Week 5/27-6/3 Base rate $850.

Starfish Beach 3 – Sleeps 6

Starfish Beach 3 is a great two bedroom cottage style condo just a block from gulf beaches. During your stay you’ll love relaxing on the sand or swimming in the heated community pool. This home is well-equipped with everything your family will need for the perfect week in paradise.

Starfish Beach 3 Holmes Beach
Starfish Beach 3 – Holmes Beach – Week 5/27-6/3 Base rate $1300.

Water Colors – Sleeps 8

If your family is looking for luxury then Water Colors is the spot for you! Everything about this four bedroom home is high-end. From the Anna Maria location to the decor and amenities you’re sure to be impressed. Enjoy roof top views of the gulf in addition to a lovely heated pool and spa. Pets up to 25 pounds welcome with pet fee.

Water Colors Anna Maria vacation rental
Water Colors – Anna Maria – Week 5/27-6/3 Base rate $4900.

Sunset Glow – Sleeps 10

Sunset Glow is a well-appointed family home with five bedrooms. Its just two blocks from gulf beaches and also nearby to free trolley stops. The backyard is great for a family get together with a propane grill, sun deck, covered lounge area, and a heated pool and spa. Dogs up to 50 pounds welcome with pet fee.

Sunset Glow Holmes Beach rental
Sunset Glow – Holmes Beach – Week 5/27-6/3 Base rate $4000

Almost Gulf Front – Sleeps 12

Your family will love spending time at Almost Gulf Front. This six bedroom home is less than two blocks to gulf beaches and offers a laid back tropical style. The spacious open floor plan is great for gathering your group all in one spot. In the backyard you’ll find a heated pool and salt spa. The covered lounge area has a fun Tiki bar vibe perfect for grilling up a Memorial Day Feast!

Almost Gulf front beach rental
Almost Gulf Front – Holmes Beach – Week 5/27-6/3 Base rate $4500.

 

Enjoy a fun filled holiday with one of these great Anna Maria Island Memorial Dayt beach rentals from IslandReal.com!

Easter 2017 – Anna Maria Island Beach Rental SPECIALS!

Anna Maria Island Beach Rental Specials are a fantastic way to gather the family for the holiday. You won’t have to break the bank while enjoying Easter on Anna Maria Island!

Easter Special

Anna Maria Island Beach Rental SPECIALS!

Island Real Estate has some terrific specials going on. All of these deals cover Easter week from April 15-22. Most of these are 25% off your base rental fee, but some are offering 40%. Additionally, some of these beach rentals are also offering discounts now through May. Check out the list below, or head over to our Sunshine Special Page for more details on current promotions.

You’ll find a variety of homes to pick from to perfectly suite your vacation crew. These 8 beach rentals are spread across the island and include bungalows, villas and large single family homes too. You’ll find occupancy accommodating for groups as small as 6 all the way up to 14!

Peruse these deals and click on the name of the homes to view the full listing. This list is organized by occupancy from smallest to largest.

Key Lime Cottages East and West – 25% off

The Key Lime Cottage is a duplex accommodating 6 guests in each with 6 bedrooms and 4 baths total. Rent a single side or both for a fun island getaway. Both side have separate heated pools, and are less than 2 blocks to gulf beaches.

Anna Maria Island Beach Rental SPECIALS
Key Lime Cottages in Holmes Beach.

Blue Heron Beach House – 25% off

This 4 bedroom 2 bath bungalow is just a short walk to the beach with no major roads to cross! Blue Heron Beach House is great for families with a bunk bed, 2 twins and 2 king beds. You’ll love the heated lagoon style pool.

Blue Heron Beach House
Blue Heron Beach Housein the city of Anna Maria

Living the Dream – 25% off

Living the Dream is a gorgeous canal front luxury rental sleeping 8 guests. Recently updated, you’ll find an amazing outdoor bar and lounge, heated pool and your very own private patch of sand too! 4 bedroom 3 bath just a short walk to Tampa Bay beaches.

Easter beach rental
Living the Dream in the city of Anna Maria

Beachy Villa Vista – 25% off

This rental is less than a block from gulf beaches with well-appointed amenities. You’ll find everything for a luxury vacation for a large group or family. Enjoy the heated pool and spa and great outdoor entertainment area too.

Beachy Villa Vista
Beachy Villa Vista in Holmes Beach

Gulf Breeze – 40% off

Gulf Breeze is less than 2 blocks to gulf beaches and offers a great spot to relax in style. Enjoy the heated pool and spa with a lovely waterfall feature. The backyard pool table and entertainment area will have your entire family enjoying island life. Sleeps 12 with 6 bedrooms and 4.5 baths.

Gulf Breeze
Gulf Breeze in Holmes Beach

Coral Escape – 30% off

Coral Escape accommodates up to 12 guests comfortably with 6 bedrooms and 4 baths. You’ll be just a short walk to gulf beaches and free trolley stops. Enjoy the heated pool and spa plus pets welcome with pet fee.

Coral Escape
Coral Escape in Holmes Beach.

AMI Beach House – 25% off

This great beach house is well-appointed for a perfect vacation. You’ll love relaxing by the heated pool and spa, or walk over to the free trolley stops for sightseeing. No detail was overlooked in this home. Sleeps 12 with 6 bedrooms and 4.5 baths.

AMI Beach House
AMI Beach House in Holmes Beach

Waterfront Retreat – 25% off

Waterfront Retreat was made for entertaining a large group! This lovely canal front rental is just a short walk to Tampa Bay beaches. Enjoy the large kitchen, and bar over looking the canal. Sleeps 14 with 6 bedrooms 3 full baths and 2 half baths.

Waterfront Retreat
Waterfront Retreat in the city of Anna Maria.

5 Romantic Anna Maria Island Beach Rentals for 2017

Here is our list of five romantic Anna Maria Island beach rentals to visit this year. While Valentines day is still months away, these rentals are great for a romantic getaway anytime.

Romantic Anna Maria Island Beach Rentals

Sugaree

Sugaree is a stylish elevated duplex in Holmes Beach just a short walk to the beach. This is the perfect spot for a romantic island vacation. You’ll enjoy the private heated pool, outdoor space and updated amenities.

Romantic Anna Maria Island Beach Rentals
Sugaree in Holmes Beach – Gold Rated.

Sleep up to six guests at Sugaree! Not only is this rental close to the beach, but it’s also near the quiet Holmes Beach town center.

Holmes Beach Rental
Everything is updated in this rental with fantastic amenities.

Cayman Bay

Cayman Bay is a lovely canal front rental just a short walk to Tampa Bay beaches. You’ll absolutely adore the master suite at Cayman Bay! Here you’ll find a private balcony with canal views, fireplace, wet bar and a stunning master bathroom. while this home offers spacious accommodations for up to eight you’ll feel like you have your own private getaway in the large master suite.

Romantic Anna Maria Island beach rentals
Cayman Bay in Anna Maria – Gold Rated.

Enjoy the heated pool and spa in this gorgeous backyard. Guests have access to the boat dock, and the canal leads out to Bimini Bay and also Tampa Bay.

romantic vacation rental
Enjoy a one of a kind Master suite at Cayman Bay.

 

Sangria Sunrise

When you visit Sangria Sunrise you’ll have your very own strip of beach with amazing sunrise views. This is truly a romantic Florida vacation spot with the beach right at your feet. You’ll enjoy water views from the master bedroom too.

romantic beach vacation destination
Sangria Sunrise in Anna Maria – Silver Rated.

This Anna Maria beach rental sleeps up to seven guests with three bedrooms. You’ll be close to Pine Avenue shopping and dining while you visit Sangria Sunrise!

beach vacation rentals
Enjoy a romantic beach vacation at Sangria Sunrise.

Bradenton Beach Club B

Bradenton Beach Club B has everything you’ll want for a romantic beach front vacation. During your stay you’ll have spectacular views in a well-appointed condominium in an amazing location.

Romantic Bradenton Beach Rentals
Bradenton Beach Club B in Bradenton Beach – Gold Rated.

This direct gulf front beach rental sleeps up to six guests with 2 bedrooms. Also enjoy the heated pool over looking the gulf of mexico and powder fine sand.

Romantic Anna Maria Island vacation rentals
Bradenton Beach Club B has a great coastal style and location.

Vitamin Sea

Vitamin Sea offers fantastic updated amenities and is just a block to the beach! You’ll love this destination for a romantic beach getaway. Enjoy the updated style, vibrant decor, and plenty of space for your entire group to spread out.

Romantic Anna Maria Island beach rentals
Vitamin Sea in Holmes Beach – Gold Rated.

While you visit, you’ll fall in love with the view from the private master suite balcony.

Holmes Beach rental Anna Maria Island
You’ll find a well-appointed master bedroom during your stay at Vitamin Sea.

 

Enjoy a romantic paradise vacation with your special someone when you visit these great Anna Maria Island beach rentals.

Best Anna Maria Island Roof Top View Rentals

Anna Maria Island roof top view rentals are great when looking to see the beach without paying gulf front prices! It’s always amazing when you can simply head to the roof for sunshine or nightly sunsets.

Anna Maria Island Roof Top View Rentals

Here is our list of the best Anna Maria Island beach rentals with roof top views!

Seashell Sunsets

While this Platinum rental offers stunning gulf views from the roof, it’s also less than a block to the beach! Access the spiral staircase leading to the roof from the upper living level balcony.

Anna Maria Island Roof Top View Rentals
Seashell Sunset in Holmes Beach.

Seashell Sunsets offers four bedrooms with accommodations for up to eight guests. This recently built beach rental also has a heated pool and spa along with a modern style.

Anna Maria Island Beach Rental
Seashell Sunsets

Palm Isle Village 3210

Palm Isle Village is among the island’s most popular cottage beach rental complexes. This Holmes Beach rental is just across the street from gulf beaches and offers a roof top view.

Holmes Beach roof top view rental
Palm Isle Village 3210

Gold rated, Palm Isle 3210 sleeps up to four guests with one bedroom. Enjoy the community heated pool and a central island location too.

Holmes Beach Rental
Palm Isle Village 3210

Island Oasis

Island Oasis is a great platinum beach rental with roof top views of the Gulf of Mexico. This Holmes Beach rental sleeps 10 guests with five bedrooms.

Anna Maria Island Gulf view Beach Rental
Island Oasis

While visiting enjoy the heated pool and spa, outdoor kitchen lounge and pool table too.

Anna Maria Island Roof Top View Rentals
Island Oasis

 

Heron Heaven

While the deck at Heron Heaven only offers partial roof top views, it’s still good enough to make the list! This lovely outdoor space is just off the living room and offers plenty of seats for relaxing beach side.

beach rental with a view
Heron Heaven

This spacious two bedroom is just across the street from gulf beaches, and offers a great old Florida style. Find the nearest beach access just steps away!

Anna Maria Island Beach Rental
Heron Heaven

 

Water Colors

When you visit Water Colors you are sure to fall in love with roof top island views.

Anna Maria Island beach rental with a view
Water Colors

This platinum Anna Maria rental has all the amenities you could ever want! Enjoy the heated pool/spa and a gorgeous sophisticated beach style. Sleep up to eight guests with four bedrooms.

Anna Maria vacation rental
Water Colors

Sideways

Sideways is truly a gem, and a unique find for it’s Bradenton Beach location. Accommodating up to six guest this two bedroom, two bathroom home is gold rated.

Bradenton Beach roof top beach rental
Sideways

While you visit this great rental you’ll be just a short walk to gulf beaches, shopping, dining and free trolley stops. You will absolutely love the heated pool and spa during your stay!

Bradenton Beach rental roof top view
Sideways

 

Anna Maria Island Mediterranean Style Vacation

Island Real Estate has what you need for an Anna Maria Island Mediterranean style vacation! Why travel across the world for beautiful beaches when they are waiting right here on the Florida Gulf Coast?

Anna Maria Island Mediterranean Style Vacation for Less

A Mediterranean vacation is full of relaxation, blue seas, and beautiful sunshine. The countries around the Mediterranean offer great sight seeing and interesting history too. All of these things are on Anna Maria Island! An exotic destination, with perfect weather and fun leisure activities is waiting for you. All you need is the quintessential Mediterranean style beach rental to set the tone for your Anna Maria Island vacation. Best of all, you won’t break the bank during your coastal siesta to Anna Maria Island!

Mediterranean Style Beach Rentals

Under the Tuscan Sun

This beach rental is about two-three blocks from gulf beaches, and one of the island’s most popular public accesses. Under the Tuscan Sun offers 3 bedrooms and 3 bathrooms with plenty of space for up to 9 guests. Not only will you be close to the beach, but you’ll be able to walk to shops, restaurants and free trolley stops! Enjoy the private heated pool too.

Anna Maria Island Mediterranean style vacation beach rental
Under the Tuscan Sun 4005 5th Avenue in Holmes Beach.

Beach Escape

Beach Escape is three blocks from Gulf beaches and also centrally located to Anna Maria Island activities and attractions. This 3 bedroom, 3 bath rental offers accommodations for up to 8 guests. Inside you’ll find an updated style with the cool blues and whites characteristic of Mediterranean decor. Enjoy the heated pool and spa, or open air balconies at this fantastic Anna Maria Island beach rental!

Anna Maria Island Vacation Rental
Beach Escape 4105 5th Avenue in Holmes Beach

Blue Waters

Located in Anna Maria, Blue Waters is a platinum rated rental on direct canal front. This 4 bedroom, 4 bath home sleeps 8 guests, and is a few blocks from coveted Anna Maria gulf beaches. You’ll find luxury amenities including a large heated pool and spa, boat dock and a lovely Mediterranean style. You’ll truly love this one of a kind destination.

Anna Maria vacation rental
Blue Waters 230 Willow in Anna Maria.

Casa Sierra Rentals

Casa Sierra is a small 4 unit condo complex just a short two blocks from gulf beaches. These great Mediterranean style condos offer 2 bedrooms and 2 baths with accommodations for up to 6 guests. These rentals are relaxed, however, they do have all the great amenities that come with their gold rating. Enjoy the community heated pool along with a fabulous location too. Casa Sierra Unit 205 A, Unit 205 B, Unit 203 A.

Holmes Beach rental Anna Maria Island
Casa Sierra Complex located on 36th Street in Holmes Beach.

L’Plage

The L’Plage complex is on direct gulf front in Holmes Beach. This luxury condo offers everything you’ll need for the perfect Mediterranean style holiday. Enjoy the community heated pool and spa just steps from the powder white sands of the Gulf of Mexico. Inside this unit you’ll find 3 bedrooms and 3 baths with room for up to 8 guests too!

Anna Maria Island Luxury beach rental
L’Plage 6420 Gulf Drive unit 3 in Holmes Beach

Beach House on 5th

Beach House on 5th is a great spot for up to 10 guests! This 3 bedroom 3 bath rental is less than 3 blocks to gulf beaches, shopping, dining and free trolley stops too. You’ll love the heated pool and the fun coastal decor in this Mediterranean style home.

Mediterranean style Anna Maria Island beach rental
Beach House on 5th 4107 5th Avenue in Holmes Beach

Vista Grande

You’ll enjoy direct gulf front views when you spend a holiday at Vista Grande. This lovely platinum rated villa sleeps 6 guests with 3 bedrooms and 3 bathrooms. Not only does this beach rental have million dollar views, but also luxurious amenities fit for a Mediterranean style vacation.

Anna Maria Island beach villa
Vista Grande 5622 Gulf Drive in Holmes Beach

The Oasis

Perfect for a family getaway, The Oasis has accommodations for up to 6 guests with 3 bedrooms and 3 bathrooms. You’ll be 3 blocks from pristine Gulf of Mexico beaches, and centrally located on Anna Maria Island. Enjoy the heated pool during your stay!

Anna Maria Island Holmes Beach Rental
The Oasis 4004 6th Avenue in Holmes Beach.

La Casa Costiera 

The La Casa Costiera is a gorgeous luxury condo complex right on the Gulf of Mexico. Here you’ll find many well-appointed rentals to pick from. These units sleep 6 or 8 guests, and each has unique tropical decor. They have 3 bedrooms and either 2, 2.5 or 3 bathroom. Enjoy the heated pool and spa or relax all day long on the beach.

La Casa Costiera Anna Maria Island luxury beach rental
La Casa Costiera 7318 Gulf Drive in Holmes Beach

Cayman Bay

This canal front Anna Maria rental is just a short walk to Tampa Bay beaches. You’ll love the fantastic style and amenities at Cayman Bay. Sleep up to 8 guests with 4 bedrooms and 4 bathrooms. Each of the bedrooms at this home have a great luxury feel. Enjoy the beautiful backyard with a heated pool and spa. Dock your boat in the canal too!

Anna Maria beach rental
Cayman Bay 505 Magnolia Avenue in Anna Maria.

Top 15 Anna Maria Island Beach Cottage Rentals

Anna Maria Island beach cottage rentals are the perfect way to experience this old Florida vacation destination. There aren’t many places like the island anymore. You won’t find any high rises, big night clubs or chain store outlets in this quaint coastal getaway. Such a charming gulf island, a beautiful vacation cottage is the perfect match.

Anna Maria Island Beach Cottage Rentals

Here is a list of 15 of the best Anna Maria Island beach cottage rentals for you to try out! All offer a little something different. Additionally, these range from old to new, and from bronze to platinum rated. Arranged by city location in Anna Maria, Holmes Beach or Bradenton Beach, these great cottages also span the entire island.

Anna Maria beach cottage rentals

Sea Song is a direct gulf front cottage. Updated in December 2015, the beach is your backyard! Sleep up to six in this two bedroom home with beautiful beach views and amenities. Gold rated.

Anna Maria Island beach cottage rentals
Sea Song 103 Sea Grape Lane.

The Seashell Cottage is just down the street from gulf beaches, and is within walking distance to Pine Avenue shopping and dining. This quaint cottage also sleeps six guests with two bedrooms. Silver rated.

Anna Maria Beach cottage rental
The Seashell Cottage 118 Palmetto Avenue.

Fish House is really something special! Sleep eight guests with three bedrooms. Enjoy high end luxury mixed with an old fish camp feel. Heated pool and spa too! Gold rated.

Anna Maria cottage vacation rental
Fish House 231 Oak Avenue.

Dolphin Watch is similarly a great beach front cottage. Furthermore, this home sleeps six with two bedrooms, and beach views. Gold rated.

Anna Maria beach rental.
Dolphin Watch 12108 Gulf Drive.

Blue Bayou is a stylish updated cottage. Sleeps six with three bedrooms on direct canal front. Undoubtedly a beautiful location with heated pool and spa! Platinum rated.

Anna Maria Rental Cottage
Blue Bayou 229 Chilson Avenue

Hacienda Del Mar is in fact one of the larger cottage beach rentals offered on the list. Sleep eight guests with four bedrooms. Also on direct gulf front, and recently updated. Gold rated.

beach rental Anna Maria
Hacienda Del Mar 765 North Shore Drive.

Holmes Beach cottage rentals

Minnie Cottage is surely the ideal Holmes Beach cottage. Also sleeps eight guests, but with three bedrooms. This raised cottage has a heated pool and is a newer home. Platinum rated.

Holmes beach cottage rental
Minnie Cottage 125 47th Street.

Blue Lagoon 6 Osprey is a popular cottage. In contrast to others, this cottage is located in a small complex. Sleeps four with two bedrooms, and just a short walk to the beach. Gold rated.

Beach Cottage rental Holmes Beach
Blue Lagoon 6 – Osprey – 215 67th Street.

Beach Comber is great for a no frills cottage. That is to say, this rental offers all the basics, but with the addition of direct gulf views. Also sleeps six with two bedrooms. Bronze rated.

Anna Maria Island vacation rental Holmes Beach
Beach Comber 3020 Avenue F.

Captains House is a funky Florida cottage. To clarify, this home has a retro feel that is super fun. Sleep eight with three bedrooms, and also a loft style with two living levels. Bronze rated.

Beach house rentals anna maria island
Captains House 208 Haverkos.

Misty Beach has an updated beach style, and sleeps six guests with two bedrooms. This cottage offers a heated pool too! Gold rated.

Vacation cottage Holmes Beach
Misty Beach 5802 Imperiore Avenue.

Pelican Landing AMI is a spacious cottage with three bedrooms for up to eight guests. This great home also has a fun backyard Tiki hut and heated pool. Gold rated.

Rental cottage Holmes Beach
Pelican Landing AMI 306 55th Street.

Jackie’s Cottage is an updated canal front cottage with a heated pool. Manatees frequent this canal too! Sleep eight guests with four bedrooms. Gold rated.

Anna Maria Island cottage rental Holmes Beach
Jackie’s Cottage 209 North Harbor Drive.

Bradenton Beach cottage rental

A Pirate’s Cove is a 1950’s cottage updated with modern coastal charm and amenities. Heated pool, and also just a block from gulf beaches. Sleep six with two bedrooms. Gold rated.

Bradenton Beach cottage rental Anna Maria Isalnd
A Pirate’s Cove 2109 Avenue C.

Katie’s Beach Bungalow is a short walk to gulf beaches, and has a heated pool and spa! Sleep four guests with two bedrooms. Bronze rated.

Cottage rental Anna Maria Island
Katie’s Beach Bungalow 108 8th Street South.

Enjoy the perfect Old Florida paradise getaway by the beach with one of these charming Anna Maria Island beach cottage rentals. Visit IslandReal.com today to reserve your stay.

Summer’s End Beach House Rentals Anna Maria Island

It’s not too late to enjoy end of summer beach house rentals Anna Maria Island style! Pumpkin spice latte is back on the Starbucks menu, kids are in school again, and Fall is less than a month away. Now is the time to plan that last minute summer getaway!

Summer Beach House Rentals Anna Maria Island in September

September is a fantastic time of year to visit Anna Maria Island. This is the off season, so the beaches are far less busy. During a September visit you’ll also notice there are fewer cars on the streets. The entire Island has a different vibe in the late summer. People are a little calmer as locals enjoy the respite from busy high season.

End of Summer beach Scene

Anna Maria Island beaches are as beautiful as ever in the late summer. The weather is hot and rainy during September in Florida, however, beaches are still very nice. Lots of rain may make the water a tad less blue than the normal, but it also cools the water temperature down. Gulf beaches are bathtub like in July and August, so a little rain makes them more refreshing.

End of Summer Island Activities

When you visit the island at the end of summer you may notice a few of the island’s restaurants are closed. This is when operators make improvements, and also have a little summer vacation before seasons starts again. However, there are still plenty of places to dine that are open year round. Closures are typically no more than a week long, or even just a few days.

Summer is also an excellent time to visit activities off island. With less congested roads, getting on and off the island is much easier in late summer. This is a fantastic time to drive down to Sarasota, or head into Bradenton to try new activities. You will find museums, shopping and sightseeing in both Sarasota and Bradenton.

Summer’s End Beach House Rentals Anna Maria Island have lowest rates.

The end of summer is one of the most affordable times to visit Anna Maria Island. September is when many beach houses lower their rates. These lower rates continue through to mid December when visitors from the north start to come down again. These lower rates don’t always include Labor Day weekend as this is the last busy weekend of the season. Rates for beach house rentals typically fluctuate to coincide with demand or popular seasons.

Direct Beach House Rentals Anna Maria Island

September is also the perfect time of year to reserve a direct beach front rental!

Hidden Cove is a fantastic direct gulf Front beach rental Anna Maria Island style. This is a great example of the type of rentals available in September.

Beach house rentals Anna Maria Island
Beach House Rentals Anna Maria Island style! Click on the image to learn more about this great condo!

Hidden Cove unit 1 offers accommodations for up to four guests with two bedrooms and two and half bathrooms. During your stay, enjoy direct gulf views from the master bedroom and main living space. You will love spending time on the open balcony watching sunsets, and relaxing. The quiet Hidden Cove complex also offers a community pool, and is located near free trolley stops, shopping and dining.

Beach House Rentals Anna Maria Island Florida
Click on the image to reserve Hidden Cove unit 1 for your next Beach house rental Anna Maria Island Holmes Beach.

Island Real Estate has the largest selection of Anna Maria Island beach rentals you’ll find in the area! When searching for a summer’s end beach rental be sure to check out the Sunshine Specials page for great deals.

Enjoy an Anna Maria Island paradise vacation and reserve the perfect beach rental today at IslandReal.com!