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Welcome to your Anna Maria Island escape "Pineapple Paradise"! New to the vacation rental market, this beautifully designed 4-bedroom, 5-bathroom home in Holmes Beach is just two blocks from the beach—perfect for families and groups ready to enjoy sun, sand, and relaxation."Pineapple Paradise" is a spacious two-level home offers plenty of room to s
Pineapple Paradise
Home- 4
- 5
- Pool
- No Pets
- Sleeps 8
- 103 Views
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When you visit Anna Maria Island vacation rental “Hop, Skip and a Beach” you are sure to have an amazing Florida getaway! Sleep up to eight guests in luxury and style. This four-bedroom rental with game room with heated pool and spa is just a short walk from the best beaches you’ll find on the gulf coast.When you enter “Hop, Skip and a Beach” you’l
Hop Skip and a Beach
Home- 4
- 4
- Pool
- No Pets
- Sleeps 8
- 40 Views
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Welcome to “Blue Water Escape” – Your Island Retreat in Holmes Beach!Experience laid-back island living just steps from the sugar-sand shores of Anna Maria Island at this inviting vacation home. “Blue Water Escape” is a bright, beachy getaway perfect for up to six guests, offering three bedrooms, two bathrooms, and everything you need for a relaxin
Blue Water Getaway
Home- 3
- 2
- Pool
- No Pets
- Sleeps 6
- 11 Views
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Discover the revitalized charm of Coconuts Beach Resort 101, a newly remodeled ground-level condo located in the heart of Holmes Beach on Anna Maria Island. This one-bedroom, one-bathroom retreat has been given a complete makeover, offering a clean, modern aesthetic with inviting coastal touches. Comfortably accommodating up to four guests, this po
Coconuts 101
Condominium- 1
- 1
- Pool
- No Pets
- Sleeps 4
- 54 Views
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Experience Island Living at Waters Edge 208S, an exquisite, newly remodeled condo located just a short stroll from the serene shores of Anna Maria Island. Whether you're drawn to the beach for sunbathing, water sports, or peaceful relaxation, this charming property has it all. With easy beach access, a shared heated pool, and local shops and restau
Waters Edge 208S
Condominium- 2
- 2
- Pool
- No Pets
- Sleeps 6
- 15 Views
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After you stay at the "Sea Pirate 2" you’ll want to make it your vacation destination year after year! This two bedroom one bathroom Holmes Beach vacation rental home sleeps four guests with one king bed, and two twin beds. "Sea Pirate 2" offers a fun and fresh island feel with exciting colors and endless style. Find everything for the perfect beac
Sea Pirate 2
Condominium- 2
- 1
- Pool
- No Pets
- Sleeps 4
- 24 Views
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This beautiful Holmes Beach get-away is sure to make your stay on Anna Maria Island a memorable one. “Water’s Edge 204S” is a beach side condo with views of the tropical garden are just outside your window as well as peeks of the beach and Gulf of Mexico. Unit 204S is updated, with a gorgeous kitchen, spacious living area, and a dining area that ca
Waters Edge 204S
Condominium- 2
- 2
- Pool
- No Pets
- Sleeps 4
- 10 Views
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“Palms Beach West” on Gulf Drive is where Anna Maria Island vacations become lifetime memories! This beautiful Holmes Beach vacation rental home provides accommodations for up to 6 guests including 3 Bedrooms, 2 Bathrooms with 1 King bed, 1 Queen bed, and 2 Twin beds. <br /><br />Located a short walk away from a pristine gulf beach access 3700 bloc
Palms Beach West
Multi-Family- 3
- 2
- Pool
- No Pets
- Sleeps 6
- 28 Views
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DISCLOSURE!!: There is currently an ongoing disagreement regarding the beach access path on 78th Street. In the meantime, we ask that you use the beach access trail that is located on 77th street, directly behind the home you will be staying in.You can access it by walking through the side yard of this home. There is no need to walk all the way up
Flirty Flamingo
Home- 2
- 2
- No Pets
- Sleeps 4
- 5 Views
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Fun and tastefully decorated recently remodeled, “Aquarius” is the ideal place for a fabulous Anna Maria Island vacation getaway for up to eight guests. Situated just a short walk from beautiful gulf beaches, when you visit this vibrant vacation rental you’ll leave with memories that last a lifetime.Offering four bedrooms and two and a half bathroo
Aquarius
Home- 4
- 3
- Pool
- Dogs Allowed
- Sleeps 8
- 20 Views
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Blue Lagoon 3 “Egret” has everything you’ll need for a fun Anna Maria Island paradise vacation. This two bedroom and two bathroom Key West style Holmes Beach vacation rental condo offers accommodations for up to six guests with one king bed, two twin beds and a queen sleeper sofa. <br /><br />When you arrive at Blue Lagoon 3 “Egret” you are greete
Blue Lagoon 3
Condominium- 2
- 2
- Pool
- Dogs Allowed
- Sleeps 6
- 29 Views
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Gulf View Cottage is a charming, recently renovated home with a rooftop deck offering sweeping views of the Gulf. Relax and enjoy the private, heated pool while experiencing the ultimate Florida vacation!As you arrive at Gulf View Cottage, you'll notice its unique shape, spacious driveway, and beautiful tropical plants in the front yard. Step insid
Gulf View Cottage
Home- 3
- 3 Full Baths , 1 Half Baths
- Pool
- No Pets
- Sleeps 6
- 39 Views
