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“Palm Isle 3211” is the perfect Anna Maria Island beach rental for a cozy couple’s getaway, or even a casual vacation for up to four guests. This one bedroom villa beach rental offers a premium location near beaches, shopping and dining. Enjoy a well-appointed unit with nice updates and a laid back feel.<br /><br /> When you visit “Palm Isle 3211”
Palm Isle Village 3211
Condominium- 1
- 1 Full Baths , 1 Half Baths
- Pool
- Dogs Allowed
- Sleeps 4
- 34 Views
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“Pirate’s Cove” is a great island oasis to enjoy during your stay, the perfect cove for your vacation getaway. One of the only "Any Day" arrival properties on the island.*Disclaimer: Please note that the stovetop currently has a minor issue—two of the five burners are not functioning. We are actively addressing this and expect it to be resolved sho
Pirates Cove
Home- 7
- 7 Full Baths , 1 Half Baths
- Pool
- No Pets
- Sleeps 10
- 34 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
- 25 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
- 33 Views
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“115 South Beach Village” is the perfect Anna Maria Island vacation home to make a fun and memorable beach vacation destination! This pastel pink 3 bedroom, 2.5 bathroom, town house style vacation rental rooms up to 6 guests with 1 king bed, 1 queen bed and 2 twin beds. <br /><br />Stroll across the street to enjoy the best white sandy beaches the
South Beach Village 115
Condominium- 3
- 2 Full Baths , 1 Half Baths
- Pool
- Dogs Allowed
- Sleeps 6
- 47 Views
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“Promise kept” is located in Holmes Beach on Anna Maria Island. This property has been renovated to feature some of the original characteristics of the vintage home. One stay here, and your promise will be kept to return again and again. Now dog friendly with 1 dog up to 25lbs.<br /><br />This beautiful ground level home has 3 bedrooms and 2 bathr
Promise Kept
Home- 3
- 2
- Pool
- No Pets
- Sleeps 6
- 30 Views
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Inside this Holmes Beach vacation rental you’ll find a well-appointed condominium to kick your feet up in island style. The living room offers a flat screen television, comfortable furniture and the dining area seating four. In the kitchen you’ll find all the basics including a dishwasher. Off the kitchen there is a private balcony.Accommodating up
Casa Sierra 205B
Condominium- 2
- 2
- Pool
- Dogs Allowed
- Sleeps 6
- 7 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
- 38 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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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
- 3 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
- 11 Views
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*Please Note: Exterior painting and roofing projects are scheduled between Sept 22–Dec 31, 2025. Work may cause noise or limited access to decks. Schedule may vary due to weather.*With stunning direct gulf front views, the stylish “Water's Edge 209S” is a fine example of a luxury island vacation getaway. Comfortably rooming up to 4 guests this 2 be
Waters Edge 209S
Condominium- 2
- 2
- Pool
- No Pets
- Sleeps 4
- 15 Views
