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“Summer Breeze” is one of the premier homes on the island. The perfect home for an Anna Maria Island getaway. With tropical landscaping, updated inside and out, and this rental home is stunning on all fronts. Elevated, high-end tropical décor, and pristine floors, “Summer Breeze” is love at first sight. Five large bedrooms, a spacious layout, this
Summer Breeze
Home- 5
- 4
- Pool
- Dogs Allowed
- Sleeps 14
- 60 Views
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Island Living Meets Coastal LuxuryWelcome to Gulf Shores Unit 205, your private island oasis on Anna Maria Island accessed by stairs only (no elevator). This 3-bedroom, 2-bathroom gulf-front condo sits directly on the pristine sands of Holmes Beach, offering top-floor panoramic views of the shimmering Gulf.Designed with bright, island-style décor,
Gulf Shores 205
Condominium- 3
- 2
- No Pets
- Sleeps 6
- 42 Views
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Anna Maria Island vacation rental home “EverLasting Sunsets A and B” is a fabulous ground level duplex perfect for any family getaway. Enjoy 3 bedrooms and 2 bathrooms with 2 king beds and 1 queen bed providing everyone space for a comfortable vacation.<br /><br />With separate units “EverLasting Sunsets A&B” is a great way to vacation with fam
EverLasting Sunsets AB
Home- 3
- 3
- Pool
- No Pets
- Sleeps 8
- 11 Views
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“Hideaway” is a fantastic Anna Maria Island vacation rental in Holmes Beach offering space for up to six guests just a few blocks from the beach! <br /><br />During your stay you’ll find everything you need for a laid back island getaway. Inside this Holmes Beach rental you’ll enjoy updated decor with a coastal flair. <br /><br />The main living sp
Hideaway
Multi-Family- 2
- 2
- Pool
- No Pets
- Sleeps 6
- 21 Views
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This Anna Maria Island vacation Bungalow is perfect for a party of six. “Harrington Bungalow 6” is a three bedroom and two bathroom ground level home. This newly renovated property is only a short walk to the beautiful beach access. All this and more with a brand new private heated pool.<br /><br />You will be welcomed with the elegant and cozy de
Harrington Bungalow 6
Home- 3
- 2
- Pool
- No Pets
- Sleeps 6
- 19 Views
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Nestled into a gorgeous resort style setting, Anna Maria Island vacation rental home “Blue Lagoon 6 – Osprey” is a fun vacation destination with endless character. Accommodating up to 4 guests this 2 bedroom 2 bathroom vacation rental home offers 1 king bed, 1 queen bed and all the amenities of a beachy home away from home. <br /><br />Inside “Blue
Blue Lagoon 6
Condominium- 2
- 2
- Pool
- Dogs Allowed
- Sleeps 4
- 47 Views
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Discover coastal living at its finest with this stunning 3-bedroom, 3-bathroom bayfront home located at “Royale View” 631 Key Royale Dr, Holmes Beach, FL. Newly remodeled and ideally situated directly on the water, this single-level retreat offers unparalleled access to ocean activities and breathtaking bay views.Perfect for both relaxation and en
Royale View
Home- 3
- 3
- Pool
- Dogs Allowed
- Sleeps 6
- 33 Views
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Everything you expect from a relaxing stay can be found at this Anna Maria Island vacation rental condominium. If you’ve never experienced Gulf of Mexico beaches you are in for a real treat. Enjoy powder white sand, crisp blue water, gorgeous sunsets and great beach combing all waiting right outside your door! If you visit in the winter months, enj
Buena Vista 3
Condominium- 4
- 3 Full Baths , 1 Half Baths
- Pool
- No Pets
- Sleeps 8
- 57 Views
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BG’s Bungalow is your quintessential “Key West style” home that is located on the beautiful North End of Anna Maria Island where guests can enjoy the world-renowned beaches that are just across the street! This home offers guests a true island-experience with its tall ceilings, beachy decor, and amount of outdoor space. This bedroom has 4 bedrooms,
BGs Bungalow
Home- 4
- 4
- Pool
- No Pets
- Sleeps 8
- 47 Views
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"ENDLESS BAY VIEWS - 2 Bedroom, 2 Bathroom (Sleeps 4) – “West Bay Point 88” – 6400 Flotilla Drive unit 88 in Holmes Beach.Discover your perfect Anna Maria Island retreat at "West Bay Point 88" – a vacation rental with 2 bedrooms and 2 bathrooms in Holmes Beach, comfortably accommodating up to 4 guests. Nestled in the tranquil corner of Anna Maria I
WBPT 88
Condominium- 2
- 2
- Pool
- Dogs Allowed
- Sleeps 4
- 52 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
- 28 Views
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Check out Coquina Sands in Holmes Beach on Anna Maria Island! This newly updated townhome style vacation rental with private pool is a beautifully decorated 3 bedroom 3.5 bathroom home that comfortably sleeps 6.Renovated in April 2024, all bedrooms are conveniently located on the main entry level and offer a king bed in the master, a queen bed in t
Coquina Sands
Multi-Family- 3
- 3 Full Baths , 1 Half Baths
- Pool
- Dogs Allowed
- Sleeps 6
- 18 Views
