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Vacation Rentals in Holmes Beach, FL

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    Travellers to Holmes Beach are booking March dates now. Secure your vacation rental today, and have the perfect trip.
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    About this property
    Relax in casual luxury and comfort at North Beach Village unit 69 , Holmes Beach, FL, a newly refurbished island beach town house on beautiful Anna Maria Island. This large and spacious three bedroom and two and a half bath town home located in North Beach Village complex and is just a few... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. Hidden Cove is a slightly ironic name for these vacation condominiums – they’re some of the most popular properties we offer! It must have something to do... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. Enjoy spacious Florida glamour with a week at this three bedroom, three bath vacation townhome. Outfitted with lighthearted colors on the wall and... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.   Hidden Cove is a slightly ironic name for these Holmes Beach vacation condominiums. They’re some of the most popular places to stay on Anna Maria Island!... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. Welcome to Sun Ray just a short walk to the Gulf of Mexico and the sugar sand beaches of Holmes Beach. This vacation rental duplex has everything to offer... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.   Breath-taking panoramic views of the sparkling Gulf of Mexico and sugar sand beaches.  (2) Bedrooms, (2.5) Bathroom, accommodates up to (4) people: 1... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. Accommodating up to six guests for a fun laid back beach vacation, Casa Sierra 205 B offers the perfect two bedroom, two bathroom getaway for you and your... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    1 / 29
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. Recently updated, find the casual and relaxing Anna Maria Island paradise getaway you’ve dreamt of at North Beach Village 55. This three bedroom two and a... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. It was Holly Golightly, as played by the immortal Audrey Hepburn, that once looked off into the distance and sighed, “Calms me down right away. The... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. Located on gulf front property, “Sun Plaza West” is a beautiful beach side Holmes Beach vacation rental home perfect for 4 guests! Well equipped with... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. 2 Bedroom, 2.5 Bath (Sleeps 6) - “North Beach Village” - 6250 Holmes Boulevard unit 63 in Holmes Beach. You will love spending time with friends and... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    This newly decorated and refurbished condo is the answer to your dreams this fall. This 2 bedroom 1.5 bath condo is 300 steps to the beautiful white sands and crystal blue waters of Anna Maria Island. The condo is completely turn-key ready--nothing to bring but your swimsuit and toothbrush. Condo... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. Direct gulf front two bedroom and two bath condo in desirable Water's Edge complex which is the best place for a holiday rental. Enjoy the large heated... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    West Bay Point Moorings 42 - Condo 2 Bedroom/ 2 Bath , maximum occupancy of 6 people. Relax and enjoy the tranquility of West Bay Cove with its community of waterfowl, splashing dolphins and slow moving pleasure boats while taking in the panoramic view of Tampa Bay. Your vantage point for these... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Come and stay in Holmes Beach at this contemporary, custom, elevated, single family home with spectacular Bimini Bay frontage. This magnificent home has all the bay-front views you would ever want from almost every room. This home was remodeled in 2013 to include a great open floor plan with 3,676... View all property information
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    Holmes Beach, Anna Maria Island
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    Please note these Check-in Day Requirements for this property: Jan 31 - Dec 31 : Saturday check-in required, Saturday check-out required. The decor inside of 5613 Gulf Drive is tasteful and with a nod to old Florida sensibilities. The gulf coast themed artwork echoes natural beauty found all... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. This two bedroom, two bath Direct gulf frontvacation condo gives room for four guest to enjoy the Gulf waves crash in the distance while a little bit closer... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. Tranquil ground level condo. (2) Bedroom, (1) Bathroom, accommodates up to (4) people: 1 Queen, 2 Twins. Shared heated pool, free wireless, no pets allowed,... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Once you open the door to Gulf View 201, you will begin to relax. This two-bedroom, two-bath vacation rental condo will encourage you to have a fabulous vacation on Anna Maria Island. The breathtaking view of the sparkling Gulf of Mexico water through floor to ceiling windows in the open living... View all property information
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    Holmes Beach, Anna Maria Island
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. 4 Bedroom, 3 Bath (sleeps 8) - 'Jackie's Cottage' - 209 N. Harbor Drive, Holmes Beach Manatee Heaven! – Watch the manatees play from the private boat... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. Welcome to Gulf Shores Condominiums! We more than know how to live a life of luxury, but simplicity is what we really covet. What will really stick with you... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.   Create lasting memories at this island oasis just steps from eight continuous miles of uncrowded sugar-sand beach. Relax, unwind, and immerse yourself in... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. Enjoy the large heated pool and just steps to the Gulf of Mexico. Whether you stay a week or a month this is the perfect condo for a winter retreat, vacation... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. The quintessential Florida beach side condo, you’ll love your Anna Maria Island vacation when you stay at West Winds 6828. This fun and tropical inspired... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. Fountain Head 2 is located at the Fountain Head Condo Complex and just a short walk from the gorgeous beaches and azure blue water of the Gulf of Mexico.... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Casa Del Mar is a 4 bedroom, 2.5 bath chic Key West style island home with a brand new heated swimming pool located in northern Holmes Beach. Designer decorated from top to bottom. Close to shopping, restaurants, and the trolley stop. Come and enjoy the island life at its very best! Sleeps upto 6-8... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. When you arrive at Anna Maria Island vacation rental home “Mermaid Crossing” you are greeted with true island style and luxury. This three bedroom three bath... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Only 2 houses away from the beautiful white sandy beaches of Anna Maria Island. This newly constructed Holmes Beach 2 bedrooms and 1- 1/2 bathroom house is over 2000 square foot with a heated private saltwater pool. Open floor plan, flat screen TV's, and two balconies overlooking the beach are... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. This home was completely remodeled from the ground up, so everything is new. The designer decor is sophisticated, yet fun and perfect for the island... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. The cottages at Palm Isle Village are some of the finest and most favored vacation properties on Anna Maria Island. We are always very proud to recommend them... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. 3 Bedroom, 2.5 Bath (Sleeps 8) - “North Beach Village” - 6250 Holmes Boulevard unit 27 in Holmes Beach. For a relaxing and fun Anna Maria Island vacation... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. Fall in love with Anna Maria Island paradise when you stay at the luxury Holmes Beach vacation rental town home “North Beach Village 50”! This spacious... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. 3207 Gulf Drive at Palm Isle Village in Holmes Beach, Florida is located in one of Anna Maria Island's favorite and finest condominium resorts.  It offers a... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. Bedroom, 1.5 Bath (sleeps 5) - "Sandy Pants" - 133 White Avenue, Anna Maria Remodel January 2015! Be the first to see all the new decor, appliances, etc.... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. Turtle Cove is a little home away from home in paradise! This updated oasis is a peaceful and sunny stroll from the Gulf of Mexico and our flour soft, sugar... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. 2 Bedroom, 1 Bath (sleeps 4-6) - 'Playa Casanas North' - 3222 Gulf Drive unit B in Holmes Beach. Welcome to the direct gulf front vacation you’ve been... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. Turtle Cove is a little home away from home in paradise! This updated oasis is a peaceful and sunny stroll from the Gulf of Mexico and our flour soft, sugar... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. Anna Maria Island still maintains an old Florida feel, with peaceful beaches and glowing sunsets, while offering a diverse choice of restaurants and... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.   The Captains House welcomes you! Living at the beach is like living anywhere else except it's better in almost every way imaginable! Experience it for... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. The right company can be a retreat all in themselves. So when you’re looking for an escape in Anna Maria Island with someone special, consider a week spent... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. Adorable vacation condo with peeks of the Gulf of Mexico from your front porch!  (1) Bedroom, (1) Bathroom, accomodates up to (4) people: 1 King, Sleeper. ... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. The Nautilus Complex is directly on the Gulf of Mexico and has the best beaches on the West coast of Florida. Unit 105 is a ground level 2 bedroom 2... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.   Southern Comfort is a luxury three bedroom vacation home less than two blocks from the beach. (3) Bedroom, (2.5) Bathroom, accomodates up to (8) people: 1... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    1 Bedroom, 2 Bathrooms, Sleeps 6 | Quick View
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    Welcome to Seychelles 902! If you are looking for a Panama City Beach vacation rental that offers you incredible views of the world's most beautiful beach, our 1 bedroom, 2 bath vacation rental condo that sleeps up to 6 is just the spot for you and your family because it is perfect for the whole... View all property information
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    Holmes Beach, Anna Maria Island 32408
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. perfect for vacations with kids thanks to a charming set of bunk beds in the guest bedroom.  (2) Bedroom, (1) Bathroom, accommodates up to (6) people: 1... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. On Anna Maria Island, you hear a lot about visitors experiencing love at first sunset. By the time sun is setting on your first day, most people are hooked.... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required. Key Lime Cottage East, 3 bedroom 2 bath new duplex with private heated pool.  Sleeps up to 6. Key Lime Cottage East welcomes you to this recently re-done... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217