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Vacation Rentals in Holmes Beach, FL

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    Travellers to Holmes Beach are booking July dates now. Secure your vacation rental today, and have the perfect trip.
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    6 Bedrooms / 3 Bathrooms / Sleeps 12
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    Mermaids Crossing 207 69th Unit B Holmes Beach, Fl. 34217 Mermaids Crossing is a cute-as-a-button newly renovated, ground level 3 bedroom and 2 bathroom private duplex that offers a private heated pool, lush tropical landscaping, fantastic furnishings and so much more! Centrally located on the... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    La Plage Unit # 5 6422 Gulf Drive Holmes Beach, Fl. 34217 An exquisite example of Mediterranean architecture nestled right on the sands of the Gulf of Mexico, this brand new beachfront enclave will exceed all your expectations. Relax in the tropical splendor of this brand new ultra-luxurious... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    Welcome to Castaway Cottage on Anna Maria Island. This completely remodeled duplex is comprised of two stunning new beach homes that are close to the beach and in a quiet residential neighborhood. The Castaway Cottage side includes a private heated pool (not shared), hot/cold outdoor shower, lush... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    The Reef's Edge 3302 Gulf Dr. Apt 103 Holmes Beach, Fl. 34217 The Reef's Edge is a luxury 3 bedroom, 2 bathroom direct beachfront condo and is one of a select group of just five direct beachfront condos that makes up this exclusive property. It get's it name from the natural reef that is... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    Calypso Cottage 515 42nd St. Holmes Beach, Fl. 34217 Calypso Cottage is a stylish Mediterranean beach villa with all the finishing touches of what you would expect from an exquisite Anna Maria vacation home. Only a 5 minute stroll to the beach, the focal point has to be the brand new elaborate... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Overlooking stunning turquoise waters of Anna Maria Island is the Mainsail Beach Inn offering guests a superb island experience. This ideally located resort offers 12 upscale vacation rentals, all with beachfront access, and some with a Gulf view. Our community vacation rental amenities include... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms / 2 Bathrooms / Sleeps 10
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    About this property
    Island Life 108 78th St. Holmes Beach, Fl. 34217 The name says it all. Just a stone's throw away from the sugar white sand beaches of the Gulf of Mexico. You almost don't even need to leave the front yard to enjoy a full sunset! This ground level home has 3 bedrooms and 2 bathrooms. The home... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    Island Retreat 4805 2nd Avenue Holmes Beach, FL 34217 Key West meets Anna Maria Island in a dream vacation home. Island Retreat combines the best of both worlds, oozing a traditional south Florida style outside, with shaded balconies and intricate wooden architecture, with unrivalled, modern... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    5 Bedrooms / 4 Bathrooms / Sleeps 12
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    Bayfront Paradise 238 South Harbor Dr. Holmes Beach, Fl 34217 Bayfront Paradise is an absolutely stunning custom luxury home that is tucked away on a quiet residential street with the most amazing Bay views. As soon as you enter the property you are immediately immersed in the relaxing isle... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Island Paradise #6 3708 Gulf Drive #6 Holmes Beach, Fl. 34217 Island Paradise is just that- the best view on Anna Maria Island. Panoramic views of the beautiful blue waters of the Gulf of Mexico and the white sand beaches. And don't forget the legendary sunsets. It simply does not get any better... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    Newly built and beautiful is this professionally decorated 3 bedroom/3 bath home with private heated pool, swim-up tiki bar, and stone-scaped waterfall! Amazingly appointed with designer finishes throughout to the 'Island-tune' of travertine, custom hardwood floors, wainscoted walls, vaulted... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Villa Sand Dollar 113 75th Street Holmes Beach, Fl. 34217 Newly remodeled and a perfect location! This Island retreat offers 3 bedrooms, 2 1/2 baths and is a very short walk to the Gulf beach. The home sits West of Gulf Dr, only 5 houses in from the beach and about a 30 second walk!... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    Sea Place 215 66th St. Holmes Beach, Fl. 34217 WOW- look at the reduced pricing on this one! This is a ground level island bungalow with 3 bedrooms and 2 full baths. Recently professionally re-decorated in a tasteful tropical island style, it also has a brand new heated pool to enjoy. One of... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    About this property
    Island Paradise #4 3708 Gulf Drive #4 Holmes Beach, Fl 34217 Island Living at its best! The best view on Anna Maria Island. Panoramic views of the beautiful blue waters of the Gulf of Mexico and the white sand beaches. And don't forget the legendary sunsets. This is as good as it gets!... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    About this property
    Seabreeze Cottage 5009 2nd Avenue Holmes Beach FL. 34217 This gorgeous property is nestled in a quiet residential neighborhood West of Gulf Dr, just over one block to the beach access. Seabreeze Cottage is just a one to two minute stroll to the beach. This pretty 3 bedroom/3 bathroom property... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    3 Bedroom/2 Bath Villa, with its own Backyard, PRIVATE Heated pool, and only 75 yards to the beach! Beautiful new granite countertops, stainless appliances, and tile throughout. King Master bedroom with TV, Queen Bedroom w/ TV, Full/Twin bunk in the third bedroom with TV, and a full size Sleeper... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Newly decorated 3 bedroom, 2 bath townhouse located in central Holmes Beach just a half block from the beach. Sleeps up to 8 people. Amenities Include: Full kitchen, dishes, cook ware, utensils, dishwasher, microwave, blender, toaster, coffee maker, linens, washer/dryer, central air... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    5 Bedrooms / 3 Bathrooms / Sleeps 12
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    About this property
    Mojito Splash 304 65th St. Holmes Beach, Fl. 34217 This beautiful 5 bedroom, 3.5 bathroom Island style home is perfect for all your vacation needs. It is only a short 2-3 minute walk to the white sand beaches of the Gulf of Mexico. It also is a very short walk to the free trolley stop which... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    Huge 4 bedroom/3.5 bath home, just a short block to the beach(just over 100 yards), and a couple houses to the free Island trolley! Beautiful back yard with Heated Pool. Large Master Suite upstairs with private deck Sleeps up to 10. 2830 sq. ft. 210 67th 4 Bedroom/3.5 Bath/House $2325 Weekly... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    Gulf Sound is a gulf side, ground level tri-plex located at 2814 Gulf Drive in the southern end of Holmes Beach. This two bedroom one bath unit is fully equipped with everything you need for your stay. Each unit has been updated and is comfortably furnished. It's quiet, yet close to shopping,... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Hawaiian Hideaway 206 81st Street Unit A Holmes Beach, Fl 34217 Hawaiian Hideaway is a brand new ground level private duplex! A true gem of a home with a private heated pool and tropical landscaping throughout the backyard area for privacy. Centrally located, this property is close to it all -... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Coral Cottage 6700 Holmes Blvd. Unit B (South Unit) Holmes Beach, Fl. 34217 This is a brand new renovation, ground level 2 bedroom, 2 bathroom bungalow which includes its own private heated pool nestled in lush tropical landscaping. It is only a short 2-3 minute stroll over to the pristine Anna... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    About this property
    Two bedroom, two bath condo in the quiet, four-unit complex of Seabreeze! Clean and Comfortable! Nicely appointed kitchen with Stainless Steel Applicances. Conveniently located for shopping, restaurants, and the beach, yet tucked back into a quiet area! Just a block to Skinny's for the Best Burger... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    5 Bedrooms / 4 Bathrooms / Sleeps 14
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    About this property
    Sunset Landing 4804 Gulf Dr. Holmes Beach, Fl. 34217 Sunset Landing is a brand new 5 bedroom+ bonus room, 4.5 bathroom vacation home sitting West of Gulf Dr. and an easy 2 minute walk to the beach. Professionally decorated, this fabulous vacation home has it all! Granite counters, travertine... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    La Plage 9 is the cream of the crop. Direct Gulf Front, high-floor views make this one of the most spectacular luxury condos on all of Anna Maria Island. What you get on the inside is no less outstanding. The deep cherry wood island style furniture is the finest around. Granite counter tops, crown... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    About this property
    La Plage Unit # 7 6424 Gulf Dr. Unit #7 Holmes Beach, Fl. 34217 La Plage, unit # 7, it just does not get any better than this direct Gulf front, 3rd floor corner unit. Located in the prestigious La Plage condominium complex, this unit has it all. These luxury Mediterranean style condos are... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Gulf Shores #106 5616 Gulf Drive #106 Holmes Beach, FL 34217 Enjoy the beautiful, unobstructed views of the Gulf of Mexico from your living room, kitchen or dining room in this lovely Gulf front condo in Holmes Beach. Offering 2 bedrooms and 2 baths, this very spacious direct gulf front condo is... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms / 1 Bathroom / Sleeps 6
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    About this property
    Sea Pirate 1 has been recently renovated throughout and is conveniently located close to shops and restaurants; and most of all; less than 100 feet from the beach. There are eight units total in the complex with a heated pool with easy access to the beach. Amenities Include: Full kitchen, dishes,... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    Sunset Beach 302 74th St. Holmes Beach, Fl. 34217 This cute island bungalow is just perfect for your laid-back Anna Maria retreat! Newly updated throughout, this 2 bedroom, 2 bathroom beach cottage is just a short 2-3 minute stroll over to the fabulous Gulf beaches. There is a private heated... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    1 Bedroom / 1 Bathroom / Sleeps 4
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    About this property
    Island Hideaway 6504 Holmes Blvd. Holmes Beach, Fl. 34217 Island Hideaway is just as its name says- a beautiful, tastefully decorated, luxury one bedroom, one bathroom 'hideaway' offering a secluded and private heated pool! It is only a short 2 minute stroll over to the beautiful white sand... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms / 1 Bathroom / Sleeps 5
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    About this property
    Welcome to the Groovy Gecko Cottage on Anna Maria Island. This completely remodeled duplex is comprised of two stunning new beach homes that are close to the beach and in a quiet residential neighborhood. The Groovy Gecko Cottage side includes a private heated pool (not shared), hot/cold outdoor... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    The Beachfront 3302 Gulf Drive, Unit 101 Holmes Beach, FL 34217 This three bedroom, two bathroom direct Gulf front vacation property is one of a select group of just five beachfront condos, close to Bradenton Beach and the old fishing village of Cortez. Walk out on to your own beachfront... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    5 Bedrooms / 3 Bathrooms / Sleeps 12
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    • Pets allowed
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    About this property
    Gulf View Cottage 113 36th St. Holmes Beach, Fl. 34217 Gulf View Cottage has just completed a major renovation and is ready for rental. It has all new bedrooms, bathrooms, kitchen, private heated pool, 2 decks and much more! It is only a short 1 minute stroll over to the beach and there are no... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
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    $309
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Shared Outdoor Pool...
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    • x
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    About this property
    Coastal Sunset 3302 Gulf Dr. Unit 201 Holmes Beach, Fl. 34217 Looking for luxury- you found it! Wow, what can you say about this gorgeous, custom direct Gulf front condo. The views you can take in from most parts of the top floor corner unit are breathtaking. Kitchen, living room, bedroom and... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
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    $211
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    3 Bedrooms / 2 Bathrooms / Sleeps 9
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    • Dishwasher
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    • x
    • x
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    • x
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    About this property
    Starfish 105 79th Street Holmes Beach, Fl 34217 Location, location, location! This home is literally just steps to the beach- about a 30 second walk! It sits one house in, at the end of a dead-end, very quiet street. It just does not get much more convenient than this. It has 3 bedrooms and... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
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    $284
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    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    Riki Tiki 110 46th Street Holmes Beach, Fl 34217 Riki Tiki is a beautiful beach house that is only 3 houses away from the stunning Gulf of Mexico. Offering a fantastic location, private heated pool, lots of amenities including a gourmet and fully stocked kitchen and much more! The sleeping... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
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    $318
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • ?
    About this property
    Just steps from the beach and breathtaking views of the Gulf of Mexico from almost every room you may never want to leave this two-bedroom, two-bath Anna Maria Island vacation rental. Starfish Villa is located in Holmes Beach, and with 1100 square feet this family-friendly home gives you a... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
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    $174
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Grill
    • Pool
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    About this property
    2 Bedroom/1 Bath Duplex, with a HEATED POOL, and only 75 yards to the beach! Connecting door to make it a 4 Bedroom/2 Bath. Great location close to trolley stop. Sleeps up to 4 each side! 798 Sq. ft.. 203 71st St. east HB 2 Bedroom/I Bath duplex Heated pool 75 yards to the beach... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
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    $216
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    2 Bedrooms / 1 Bathroom / Sleeps 5
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    • Grill
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • x
    • ?
    About this property
    Welcome to the Loggerhead Beach House on Anna Maria Island. This completely remodeled duplex is comprised of two stunning new beach homes that are close to the beach and in a quiet residential neighborhood. The Loggerhead Beach House side includes a private heated pool (not shared), hot/cold... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
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    $247
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Pets allowed
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    • x
    • x
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    About this property
    Quiet Palms 215 81st St. Holmes Beach, FL. 34217 The name says it all! Quiet palms resides on a docile street on Holmes Beach, just a few minutes walk from the white sandy beaches. This 3 bedroom, 2.5 bathroom Florida vacation home offers a lovely serene atmosphere. The very private backyard... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 63128
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    $158
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    • ?
    About this property
    Sun-Day West is the picture-perfect name for this two-bedroom, two-bath, elevated duplex. Located in Holmes Beach on Anna Maria Island, this vacation rental features a large, west-facing balcony that allows for plenty of sunshine in the afternoon and shade in the morning for that early cup of... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
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    $495
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    1 / 29
    6 Bedrooms / 4 Bathrooms / Sleeps 16
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    • Pets allowed
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    • x
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    About this property
    Conch House 307 B 66th St. Holmes Beach, Fl. 34217 Conch House is a brand new construction, luxury island home with 6 bedrooms and 4.5 bathrooms. The pool area is an oasis of luxury, including a 6' water-slide, a unique enclosed 'grotto' spa, lush tropical landscaping, a pool side bar with TV... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    From
    $711
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    1 / 8
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Safe
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    This beautifully decorated unit is right across the street from the beach with 2 bedrooms and 1 bathroom. Sea Pirate has all brand new furniture, ceramic tile floors, and new kitchen and bathroom & a partial Gulf view. There are eight units total in the complex with a heated pool and easy access to... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
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    $152
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
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    • x
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    About this property
    Beach Isle 304 58th st. Holmes Beach, Fl. 34217 This newly constructed private 2/2 home is perfect for your island vacation getaway! Lounge by your tropical private, heated pool or on our white sandy beaches, the choice is yours with this versatile home! Centrally located to local restaurants... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
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    $371
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    6 Bedrooms / 6 Bathrooms / Sleeps 16
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    • Internet Access
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    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
    • x
    • ?
    About this property
    Hemingway House 4103 4th Avenue Holmes Beach, Fl 34217 Hemingway House is a gorgeous, brand new elevated Island house that is tucked away on a quiet residential street and only a short one minute stroll to the Gulf beaches. This 6 bedroom and 6.5 bathroom luxury home is equipped with a private... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
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    $155
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • x
    • x
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    About this property
    Seaside Gardens 460 63rd Street Holmes Beach, Fl 34217 This lovely canal front, ground level, attached bungalow offers fantastic views and amenities! Enjoy the shared deep water dock right off of your backyard, community tennis courts, private ping-pong table, board games and so much more! This... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217
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    $371
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
    • x
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    About this property
    Casa on the Beach 404 South Bay Boulevard Anna Maria, Fl 34216 Newly renovated!- Casa on the Beach is a gorgeous 'Old Florida' styled elevated cottage that faces the Bay with its own private beach area. Enjoy breathtaking views of the water and Skyway Bridge right from the privacy of your own... View all property information
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    Location Information
    Holmes Beach, Anna Maria Island 34217