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Experience the island life at Fairwinds, a luxury vacation rental on Anna Maria Island that blends comfort, fun, and style. This family-friendly beach home offers four bedrooms, three and a half bathrooms, and a tropical outdoor oasis just a short stroll from the Gulf of Mexico’s turquoise waters.Relax in your private heated pool with swim-up bar t
Fairwinds
Home- 4
- 3 Full Baths , 1 Half Baths
- Pool
- No Pets
- Sleeps 8
- 5 Views
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Welcome to Jacaranda Beach House, a beautifully refreshed vacation retreat tucked away in Anna Maria Island’s desirable North End. Just three homes from the sugar-white sands and a short walk to the island’s northernmost point, this home places you moments from the natural beauty of Bean Point and the charm of Pine Avenue’s boutiques and eateries.D
Jacaranda Beach House
Home- 3
- 3
- Pool
- No Pets
- Sleeps 6
- 34 Views
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With stunning direct gulf front views, the stylish “Gulf Place 23” is a fine example of a luxury island vacation getaway. Comfortably rooming up to 6 guests this 2 bedroom 2 bathroom Holmes Beach vacation rental condominium offers one king bed, two twin beds and a queen sleeper sofa in a beautiful coastal inspired atmosphere. <br /><br />Situated o
Gulf Place #23
Condominium- 2
- 2
- Pool
- No Pets
- Sleeps 6
- 23 Views
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GONE COASTAL at FOUNTAINHEAD CONDOMINIUMS - Accommodating up to four guests for a fun laid back beach vacation, Fountainhead Unit 2 offers the perfect two bedroom, two bathroom getaway for you and your family. Centrally located on Anna Maria Island, Fountainhead Unit 2 is near everything for an entertaining stay including gulf beaches, free trolley
Fountainhead 2 - Gone Coastal
Condominium- 2
- 2
- Pool
- No Pets
- Sleeps 4
- 13 Views
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This three bedroom three and a half bath villa is located just a few blocks from the white sandy beaches of Anna Maria Island. This spacious vacation home offers an open floor plan, perfect for all family and friends to gather for laughter and wonderful memories. This dreamy vacation home has a remodeled kitchen features such as granite countertops
Blue Lagoon 4
Condominium- 3
- 3 Full Baths , 1 Half Baths
- Pool
- No Pets
- Sleeps 6
- 35 Views
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NEWLY RENOVATED - LESS THAN A 5MIN WALK TO THE GULF BEACHES - Find the perfect Anna Maria Island vacation spot at “Starfish Beach Cottage 2”! This newly renovated duplex is comfortable, stylish and close to the beach too! When you visit “Starfish Beach Cottage 2” you’ll find everything you’ll need for up to four guests. Inside this Holmes Beach ren
Starfish Beach 2
Condominium- 2
- 2
- Pool
- Dogs Allowed
- Sleeps 4
- 42 Views
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Experience relaxed waterfront living at this beautifully renovated bayfront home in the prestigious Key Royale neighborhood of Anna Maria Island. This charming ground-level 2-bedroom, 2-bath vacation rental combines modern coastal design with peaceful island ambiance, offering everything needed for an unforgettable monthly getaway.Perfectly positio
By the Bay
Home- 2
- 2
- Pool
- No Pets
- Sleeps 4
- 5 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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Experience the Tropical beach paradise vacation of a lifetime when you stay at Holmes Beach vacation rental condominium “Vista Grande Sul Mar”. This gorgeous beach front condo, located within the Vista Grande complex, rooms up to 6 guests with 1 king bed, 1 queen bed and 2 twin beds in this 3 bedroom 3 bathroom spacious vacation destination.<br /><
Vista Grande 1 Sul Mare
Condominium- 3
- 3
- Pool
- No Pets
- Sleeps 6
- 22 Views
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Enjoy a week in tropical island luxury when you visit the beautiful “Gulfview Townhomes Unit 4"! The perfect Anna Maria Island vacation rental condominium, “Gulfview Townhomes Unit 4" is a refreshing departure from the ordinary Florida holiday. Sleeping up to six guests just a short walk to pristine gulf beaches, this Holmes Beach vacation rental i
Gulfview Townhomes 4
Condominium- 2
- 2 Full Baths , 1 Half Baths
- Pool
- No Pets
- Sleeps 6
- 5 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
