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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 76 homes
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Showing homes 1 - 25 of 76

Sandy Point Unit 208

Holmes Beach 6 2 bedrooms
2 baths
$495 -
$1,112
Bronze

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.


Mango Breeze - 141 50th St

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

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.


Blue Lagoon 5 - Sandpiper

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

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.


316 Hardin Ave

Anna Maria 8 3 bedrooms
2 baths
$893 -
$2,209
Silver

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.


Short Board-131EWhite

Holmes Beach 6 2 bedrooms
2 baths
$700 -
$1,617
Gold

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.


Gulf Breeze-203E 69th St

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

** 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.


25 Seaside Court

Holmes Beach 4 2 bedrooms
2 baths
$630 -
$1,298
Silver

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. 


Misty Beach-5802 Imperiore Ave

Holmes Beach 4 2 bedrooms
2 baths
$1,197 -
$2,473
Gold

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.  


Safari Suite - 1105 Gulf Dr S

Bradenton Beach 4 1 bedroom
1 bath
$550 -
$1,386
Silver

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.


About a Mermaid 621 Emerald Ln

Holmes Beach 6 3 bedrooms
3 baths
$1,225 -
$1,890
Not Rated

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!


Peaceful Palms-7302 Palm Dr

Holmes Beach 6 2 bedrooms
1 bath
$400 -
$960
Bronze

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).


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.(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.


Villa de la Playa-3603A 4th

Holmes Beach 6 3 bedrooms
3 baths
$1,715 -
$2,870
Platinum

** 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. 


120 White Avenue

Anna Maria 14 4 bedrooms
2 baths
$1,470 -
$3,675
Silver

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.


North Shore Cottage-871 NShore

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

Old Florida-style living at this charming split level vacation cottage with direct bay access 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.


Key Lime Cottage East-204 73rd

Holmes Beach 6 3 bedrooms
2 baths
$1,078 -
$2,380
Gold

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.


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, 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.


Starfish Beach Unit 1

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

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)  


316 Hardin B

Anna Maria 4 1 bedroom
1 bath
$420 -
$1,041
Silver

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.


Down by the Sea-268 Gladiolus

Anna Maria 6 3 bedrooms
2 baths
$960 -
$2,016
Silver

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.


Appletini - 308W 58th St

Holmes Beach 7 2 bedrooms
2 baths
$999 -
$1,983
Gold

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.


Blue Manatee Retreat-214 69th

Holmes Beach 8 3 bedrooms
3 baths
$1,240 -
$2,448
Gold

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.


Blue Lagoon 4 - Loggerhead

Holmes Beach 6 3 bedrooms
3.5 baths
$1,200 -
$1,759
Silver

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.


All Decked Out-509 SoBay Blvd

Anna Maria 10 5 bedrooms
2.5 baths
$1,540 -
$4,950
Silver

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.


Heron - 706 Rose A

Anna Maria 4 2 bedrooms
1 bath
$1,000 -
$1,610
Bronze

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


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