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The perfect spot for a memorable island vacation! This ground level vacation rental offers a gorgeous heated pool with a fabulous outdoor common area including gazebo, tropical landscaping, dining areas and plenty of lounge chairs for relaxing. There is also a putting green, custom cornhole and a bocce ball pitch. If you want to enjoy the outdoors,
Casa Sierra 205A
Condominium- 2
- 2
- Pool
- Dogs Allowed
- 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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Experience the best of island living at Elm Street Retreat, a stunning Anna Maria Island vacation rental located just steps from the Gulf’s pristine beaches. Nestled in the heart of Anna Maria City, this elegant coastal home offers easy beach access, walkability to Pine Avenue, and private amenities designed for relaxation and comfort.This 3-bedroo
Elm Street Retreat
Home- 3
- 3
- Pool
- No Pets
- Sleeps 6
- 29 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
- 30 Views
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Newly Updated - New bathrooms and updates completed in February of 2023!! Four minutes from the beach, located in the heart of Holmes Beach, and a private oasis on Anna Maria Island. All this and more makes “Forget Me Knot” the ideal place to stay during your island vacation. From the secluded and private placement to its closeness to the beach as
Forget Me Knot
Home- 3
- 3
- Pool
- No Pets
- Sleeps 6
- 17 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
- 27 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
- 19 Views
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Spend your Anna Maria Island vacation in five star luxury when you visit “Fernweh”. This new Holmes Beach vacation rental offers both a stylish and relaxing destination for up to eight guests. If you experience wanderlust “Fernweh” is truly the place for you with a fabulous location, gorgeous floor plan, beautiful aesthetic and sophisticated island
Fernweh
Home- 4
- 4
- Pool
- No Pets
- Sleeps 8
- 26 Views
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Discover your perfect island escape at Coconuts Beach Resort Unit 108! A completely renovated, ground-floor condo situated directly on the shores of the Gulf in the heart of Holmes Beach on Anna Maria Island. This modern, one-bedroom, one-bath vacation rental offers a fresh and inviting coastal retreat, just steps from the sand.Thoughtfully redesig
Coconuts 108
Condominium- 1
- 1
- Pool
- No Pets
- Sleeps 4
- 19 Views
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“Sea Glass” is a lovely ground level 3 bedroom 2 bathroom duplex style Holmes Beach vacation rental home suited for up to 6 vacationers. Plenty of space for everyone, this rental home has 1 king bed, 1 queen bed, a Twin over Full Bunk, a Twin bed, and a queen sleeper sofa. Spacious, but not too big, “Sea Glass” is sophistication without pretension.
Sea Glass
Multi-Family- 3
- 2
- Pool
- No Pets
- Sleeps 6
- 41 Views
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Relax and unwind in the luxurious Anna Maria Island vacation rental home “Beach Pearl”. This five star rental has everything experienced vacationers look for in a home from the perfect location to well-appointed amenities. Just a block and a half from the powder sand beaches of Anna Maria City, “Beach Pearl” is the quintessential Anna Maria Island
Beach Pearl
Home- 3
- 2
- Pool
- No Pets
- Sleeps 6
- 36 Views
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This recently built single-family home is situated on a serene and picturesque street, just 6 houses away (ONLY STEPS) from the beach access path!On the ground floor, the home features a 1 car garage and provides access to the stunning pool and patio areas within the beautifully landscaped backyard. The residence boasts a dazzling, spacious heated
Sea Glass on Park
Home- 4
- 3 Full Baths , 1 Half Baths
- Pool
- No Pets
- Sleeps 8
- 30 Views
