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Pet Friendly

Island Real Estate has about 60 pet friendly properties available for those traveling with pets. Please note that there is an additional damage deposit of $250-$500 depending on size of and number of pets vacationing with you. Half of this deposit will be returned to you within 14 days of departure, pending no damage. The causeway (located on Manatee Avenue between Bradenton and the island) and Robinson Preserve are both great spots for your dog to enjoy the warm waters as the island beaches do not welcome pets. Florida has a strict leash law so don’t forget yours!
Your search has found 73 homes
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Showing homes 1 - 25 of 73

Southern Comfort on HolmesBlvd

Holmes Beach 8 3 bedrooms
2.5 baths
$1,080 -
$2,225
Gold

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


Plum Cottage 324 64th St

Holmes Beach 6 3 bedrooms
2 baths
$880 -
$1,978
Gold

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, 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.


La Vie en Rose 616 Rose St

Anna Maria 6 3 bedrooms
2 baths
$1,113 -
$2,219
Silver

Welcome to "La Vie en Rose"" located at 616 Rose Street on the northern end of beautiful Anna Maria Island. This lovely three bedroom and two bath vacation rental with heated pool 


Beachy Villa Vista-116 45th

Holmes Beach 12 5 bedrooms
4.5 baths
$2,100 -
$7,350
Platinum

Welcome to Beachy Villa Vista! Gulf Peeks from this New Luxury Home located at 116 45th Street, Holmes Beach, Anna Maria Island, FL-- (5) Bed: (4.5) Bath: Accommodates up to 12 people and Pet Friendly.


Coco Cabana 309 58th ST Unit A

Holmes Beach 8 3 bedrooms
2 baths
$1,253 -
$2,100
Gold

This property showcases designer quality furnishings and is fully equipped with all the most updated features. This vacation rental is close to shopping,dining and hop


Sunfish - 104 55th St

Holmes Beach 6 2 bedrooms
2 baths
$770 -
$1,764
Gold

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.


Blue Lagoon 5 - Sandpiper

Holmes Beach 6 2 bedrooms
2 baths
$770 -
$1,848
Silver

Blue Lagoon has one of the most charming community pools around - you're sure to make new friends next to waterfall or under the shade of a tiki hut. (2) Bedrooms, (2) Bathrooms, accomodates up to (6) people: 1 King, 2 Twins, 1 Sleeper Sofa. Heated pool, free wireless, pets welcome (with deposit), less than two blocks to the beach.


Starfish Beach Unit 2

Holmes Beach 4 2 bedrooms
2 baths
$900 -
$1,483
Gold

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).


Grant's View - 412 S Bay Blvd

Anna Maria 8 2 bedrooms
2 baths
$897 -
$2,219
Bronze

You're in a prime location for dolphin watching at this Anna Maria City vacation home right on Tampa Bay. (2) Bedrooms, (2) Bath, accomodates up to (6-8) people: 1 King, 2 Twins, 1 Sleeper Sofa. Free wireless, pets welcome (up to 15lbs, with deposit).


Blue Lagoon 3 - Egret

Holmes Beach 6 2 bedrooms
2 baths
$770 -
$1,764
Silver

Get away from it all with a week at Blue Lagoon - one of the most popular spots to have your Anna Maria Island vacation. (2) Bedrooms, (2) Bathrooms, accomodates up to (6) people: 1 Queen, 2 Twins, 1 Sleeper Sofa. Heated pool, free wireless, pets welcome (with deposit), less than two blocks to the beach.


Casa di Rose-6250 Holmes Blvd

Holmes Beach 8 3 bedrooms
2.5 baths
$715 -
$1,607
Silver

Refresh, renew, and relax among lush landscaping for privacy at this vacation condo in Holmes Beach, FL. (3) Bedrooms, (2.5) Bath, accommodates up to (8) people: 2 Queen, 2 Twin, 1 Sleeper Sofa and Chair. Free wireless, pet friendly (with owner approval and deposit), less than two blocks to the beach.


Almost Gulf Front-203 69th St

Holmes Beach 16 6 bedrooms
4.5 baths
$1,900 -
$7,210
Platinum

Something for everyone in this bright, spacious luxury rental in Holmes Beach, FL. (6) Bedrooms, (4.5) Bath, accommodates up to (16) people: 4 King, 1 Queen, 2 Twin, 2 Sleeper Sofa. Private heated pool with spa, free wireless, pet friendly (with deposit), less than two blocks to the beach.


Au Soleil - 717 Jacaranda Rd

Anna Maria 10 4 bedrooms
3 baths
$1,855 -
$2,940
Gold

You'll certainly be feeling sunny after a week of holiday at this luxury vacation rental on Anna Maria Island, FL. (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 deposit), less than two blocks to the beach.  


Coral Reef - 215 64th St

Holmes Beach 10 5 bedrooms
3.5 baths
$2,205 -
$4,326
Platinum

Spacious, private vacation home that offers peeks of the gulf and backyard tiki bar in Holmes Beach, FL. (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.


Holly Hideaway-730 Holly Road

Anna Maria 4 2 bedrooms
2 baths
$938 -
$2,098
Silver

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, accomodates up to (4) people: 1 King, 1 Queen,  Private heated pool, free wireless, pets welcome (dogs only, up to 25lbs with deposit).


Hideaway - 304 74th St

Holmes Beach 6 2 bedrooms
2 baths
$1,000 -
$1,470
Gold

A perfect blend of Anna Maria Island's tiny beach town charm, stylish and comfortable taste with room for the whole family!  (2) Bedrooms, (2) Bathroom, accomodates up to (6) people: 1 King, 2 Twins, 1 Sleeper Sofa. Private heated pool, free wireless, pets welcome (with a deposit).


Blue Lagoon 2 - Sand Dollar

Holmes Beach 6 2 bedrooms
2 baths
$770 -
$1,764
Silver

Get away from it all with a week at Blue Lagoon - one of the most popular spots to have your Anna Maria Island vacation. (2) Bedrooms, (2) Bathrooms, accomodates up to (6) people: 1 King, 1 Queen, 1 Sleeper Sofa. Heated pool, free wireless, pets welcome (with deposit), less than two blocks to the beach.


316 Hardin B

Anna Maria 4 1 bedroom
1 bath
$400 -
$989
Silver

Decorated with Key West style and sensibility, this vacation cottage is a short walk from the gulf in Holmes Beach, FL. (1) Bedrooms, (1) Bath, accomodates up to (4) people: 1 Queen, 2 Twins. Free wireless, pet friendly (with deposit).


Sea's the Day - 207 Coconut

Anna Maria 7 2 bedrooms
2 baths
$825 -
$1,890
Gold

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.  


Mango Breeze - 141 50th St

Holmes Beach 8 4 bedrooms
3.5 baths
$1,442 -
$3,276
Platinum

A weeklong holiday at this vacation cottage, lovingly called Mango Breeze, will leave you refreshed, renewed, and relaxed. (4) Bedroom, (3.5) Bathroom, accomodates up to (8) people: 2 King, 1 Queen, 2 Twin. Private heated pool, free wireless, pet friendly (dogs up to 25 lbs only, with deposit), less than two blocks to the beach.


Casa Del Sol - 310 Clark Lane

Holmes Beach 10 4 bedrooms
3.5 baths
$1,575 -
$3,605
Platinum

This vacation townhome has some truly special touches such as a private veranda off the master bedroom in Holmes Beach, FL. (4) Bedrooms, (3.5) Bath, accommodates up to (10) people: 2 King, 1 Queen, 2 Twin, 1 Sleeper Sofa. Free wireless, pet friendly (less than 25lbs, with deposit), less than two blocks to the beach.


Blue Lagoon 1 - Coquina

Holmes Beach 4 1 bedroom
1.5 baths
$900 -
$1,298
Silver

Cozy vacation cottage perfect for honeymooners in Holmes Beach, FL. Our sunsets are the most romantic around! (1) Bedroom, (1.5) Bath, accomodates up to (4) people: 1 King, 1 Sleeper Sofa. Heated pool, free wireless, pet friendly (with deposit), less than two blocks to the beach.


North Shore Cottage-871 NShore

Anna Maria 8 3 bedrooms
2 baths
$550 -
$1,386
Bronze

Enjoy a week of Old Florida-style living at this charming split level vacation cottage on the coveted north end of Anna Maria City. (3) Bedroom, (2) Bathroom, accomodates up to (8) people: 2 Queen, 2 Twin, 1 Sleeper Sofa. Pet friendly (dogs only, with a deposit), less than two blocks from the beach. 


506 Key Royale Drive

Holmes Beach 6 3 bedrooms
2.5 baths
$1,236 -
$1,273
Bronze

Spacious and sunny vacation home on the canal in Holmes Beach, FL. (3) Bedroom, (2.5) Bath, accomodates up to (6) people: 1 King, 4 Twin. Private heated pool, free wireless, pet friendly (with deposit).


Starfish Beach Unit 4

Holmes Beach 6 2 bedrooms
2 baths
$900 -
$1,483
Gold

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).


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Showing homes 1 - 25 of 73
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