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Holiday Rentals in Holmes Beach

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    Travellers to Holmes Beach are booking December dates now. Secure your holiday rental today, and have the perfect trip.
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Stunning 6 Bed 5 Bath Heated Pool Spa Water Slide1 / 46
    (1)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    Whoever said “you can’t have it all” never spent a week in this property.  This elevated, Mediterranean style private single family home is ideal for vacationers who appreciate both luxury and local flavor. Up to six people can stay at this property, located in the heart of Holmes Beach with easy...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Luxury Beach Vacation Rental on Anna Maria Island1 / 11
    (139)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    "Island Garden Villas is the most enchanting spot on Anna Maria Island." Imagine yourself surrounded by lush tropical gardens with the soft sounds of water trickling in the nearby fountain. Our six luxurious villas are beautifully decorated and just steps from the spectacular Gulf beaches....
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The Lake by the Beach at 6806 Palm Drive offers the best of both worlds! This beautiful two bedroom, two bath home is situated on a spring fed lake yet it's only three blocks to the beach. New renovations include a brand new family room addition with easy access to the beautiful pool! A unique...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Fountain Head Condominiums sit only a few properties to the azure blue waters of the Gulf of Mexico. All you need do is get comfortably into the island frame of mind. (2) Bedroom, (2) Bath, accommodates (6) people: 1 Queen, 2 Twins, 1 Sleeper sofa. Recent renovations include new tile floors,...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    A SHORE THING1 / 38
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
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    A Shore Thing will surely please the entire family and have you wanting to return for years to come. The heated pool is nestled amongst native palms and outfitted with a built-in tiki umbrella where you can relax away the day. The spacious, open concept, vaulted ceiling, living area along with...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Anna Maria Island's chic upscale development offers this ground level, vacation cottage at called Sunfish Cottage! Every detail has been taken care of with our guest's relaxation in mind. It starts with three bedrooms, two and a half bathrooms all with premium, professionally laundered linens to...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Enjoy spacious Florida glamour with a week at this three bedroom, three bath vacation townhome. Outfitted with lighthearted colors on the wall and designer quality furnishing, you can enjoy all the luxury of hotel living without having to sacrifice any of the intimacy or privacy of home. The whole...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    The Anna Cabana Beach House is an adorable two bedroom, two bath home located at 3709 Gulf Drive in Holmes Beach. This quaint home has a large open deck with a great view of the beach. Watch the sunsets or enjoy the tropical landscaping on the large deck facing the Gulf. Numerous fruit trees and...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    Shore Leave is a 1 bedroom, 1 bath private cottage located on the West side of Gulf Drive just across the street from the beach. It has a large backyard, refinished tarazzo floors, and some new furnishings. Amenities Include: Small kitchen, dishes, cook ware, utensils, microwave, toaster,coffee...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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 family. Centrally located on Anna Maria Island, Casa Sierra 205 B is near everything for an entertaining stay including gulf beaches, free...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Wash away the sand, salt, and stress with a luxurious vacation at this vacation home where a bad day simply isn't allowed. (4) Bedroom, (3) Bathroom, accomodates up to (10) people: 2 King, 1 Queen, 2 Twin, 1 Sleeper Sofa. Private heated pool with spa, free wireless, sorry no pets allowed, less than...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    The large heated pool and nestled right in the sands of the Gulf of Mexico beaches. Enjoy a sunset right on your direct gulf front enclosed lanai. This unit accepts a one month stay or longer. (2) Bedroom, (2) Bath, accommodates up to (4) people 2 Kings. There are so many island activities at...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    It’ll be hard to miss the style, taste, and indulgence waiting for you at this three story, Holmes Beach vacation home. From the moment you pull into the driveway and spot that distinctive and invigorating coral color we love so much in Florida, you’ll know a week of cushy comfort and relaxation is...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    When a starfish needs to get away, it is more than prepared to detach an arm in order to do that. Don’t let yourself get that stressed! Stay for a week in Starfish Beach Cottages and feel all your cares and worries just fall away. From the moment you arrive, you’ll feel like this vacation cottage...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    SUN DAZE1 / 27
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    About this property
    Adorable and Updated 2 BR/2BA villa with a private heated pool. This villa is located on a quiet residential street, just a short walk to the beautiful beach, with no busy streets to cross to get there, and easily walkable to the 'downtown' Holmes Beach area for shopping and restaurants and more!...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    ISLAND GIRL NORTH1 / 37
    (5)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Smoking allowed
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    COMPLETELY REMODELED 2 bedroom/ 2 bath duplex unit. Tastefully furnished and decorated, you will feel right at home. A plush King bed in one bedroom and twin beds in the other. It's just over a block to the beach, and a block to the free Island trolley! Elevated, with one car garage underneath...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Welcome to West Winds Condo. This updated 2 bedroom 2 bathroom condo comfortably accommodates up to 6 guests.  (2) Bedroom, (2) Bath, accommodates up to (6) guests: 1 King, 2 Twins, 1 Sleeper. It is located in a quiet, small, Gulf front condo complex West of Gulf Drive, on beautiful Anna Maria...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    SIMPLY CHIC1 / 38
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
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    Beautiful, Brand New, Ground Level 4 bedroom/3 bath home, just a short block to the beach. Beautiful back yard with Heated Pool surrounded by a large paver deck and beautiful outdoor dining and gas grill area by pool. Open Living/Family/Dining Room area for everyone to gather, and attention to...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    Enjoy a laid back tropical paradise vacation when you visit Anna Maria Island vacation rental “Catchin’ Rays”. Just a short block to Gulf of Mexico beaches, “Catchin’ Rays” is the perfect beach vacation destination for up to eight guests. This easy going home offers everything you and your...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    ISLAND GIRL WEST1 / 36
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    COMPLETELY REMODELED 2 bedroom/ 2 bath duplex unit. Tastefully furnished and decorated, you will feel right at home. A plush King bed in one bedroom and queen bed in the other. It's just over a block to the beach, and a block to the free Island trolley! Elevated, with one car garage underneath...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Smoking allowed
    About this property
    The Absolutely Perfect Beach House, located at 3009 Avenue F in Holmes Beach is just that – absolutely perfect! This spectacular four bedroom, three and one half bath gulf front home with an extra media room. It has its own private beach and heated pool has just been built. This beautiful home is...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Experience the best of Holmes Beach from this magnificent 2-bedroom, 1.5-bathroom condo. Offering an abundance of amenities, a cozy interior, and a convenient location near the best attractions that Holmes Beach has to offer, this abode is the perfect place to create lifelong memories with your...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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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...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Experience a glamorous Anna Maria Island vacation rental home when you stay at 623 Ivanhoe Lane. Nestled in between the fifth hole of Key Royale Golf course and Bimini Bay 623 Ivanhoe Lane is in the most coveted area of Holmes Beach. This Luxury ground level, 3 bedroom, 3 bathroom Anna Maria Island...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Key Lime Cottages 202 & 204  welcomes you to this recently re-done and updated island duplex. Just steps from the Gulf of Mexico and the pure white sandy beaches of Anna Maria. (6) Bedroom, (4) Bath, accommodates (12) people: 4 Queens, 4 Times.  Two heated pools, free wireless internet, pets are...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Smoking allowed
    About this property
    Seaside Beach House #201 located at 102 68th Street in Holmes Beach is a direct Gulf front complex with a heated pool at beachside. It’s one of the nicest complexes on Anna Maria Island. This "hidden away" property is located on a quiet side street in the northern end of Holmes Beach. The beach...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Island Jewel welcomes you! This is a renovated and designer decorated vacation home in the highly coveted Key Royale neighborhood perfectly situated at the end of a quiet cul-de-sac just one house from Bimini Bay with southern exposure. You’ll be surrounded by the verdant Florida landscape and...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    (3) Bedroom, (3) Bath (Sleeps 6) – “LaMedeira”- 305 64th St unit A in Holmes Beach. “LaMedeira” is a stylish Anna Maria Island vacation rental home sure to make your dream getaway luxurious and memorable! No details were overlooked in the design of the sleek and comfortable blue white and...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Relax and unwind in the casually luxurious Anna Maria Island vacation rental home “Sapphire Beach House”. This four star rental has everything experienced vacationers look for in a home from the perfect location to well-appointed amenities. Just two blocks from the powder sand beaches of...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The perfect condominium with direct views of the pristine Gulf of Mexico, you’ll want to vacation at “La Casa LaMar” year after year. This ground level 3 bedroom 2 bathroom condominium comfortably sleeps 5 guests with 1 king bed, 2 twin beds and 1 sleeper sofa. Fall into a sense of peace at...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Private Outdoor Pool (Heated)
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    AquaBella is a delightful architecturally designed canal front home that offers 3 bedrooms and 2 full bathrooms. This U-shaped home was constructed to take full advantage of the many tranquil views of the deep water canal and lush tropical landscaping. As you sit with your morning tea or coffee...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    About this property
    Remodeled cottage with a private, tropically landscaped backyard, heated pool, paver deck, and propane grill! Fig Leaf is just steps to the free Island Trolley and a mere 3 blocks to the gorgeous white sand beaches of Anna Maria. Also in close proximity is the family-friendly Ugly Grouper bar and...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    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 family during your Anna Maria Island getaway when you spend a week at North Beach Village 63! This two bedroom, two and a half bathroom townhome...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    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 atmosphere. The new kitchen with granite counters, and beautiful stainless steel appliances is equipped with everything you need to make your meals...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Welcome to Seaglass!! This home was completely remodelled from the ground up, so everything is new. The designer decor is sophisticated, yet fun and perfect for the island atmosphere.  The new kitchen with granite counters, and beautiful stainless steel appliances is equipped with indoor and...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
    • Satellite TV
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    Carissa Coastal Beach Cottage has just been updated with everything you need for your stay, and has a Great Location, only 150+/- steps to the Sugary White Sand Beach! Carissa Cottage has "beachy" decor, nice size living room space with large sofa sleeper and two additional comfy chairs, Flat...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
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    Smoking allowed
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    Visit AMI Beach Home, a marvelous custom-built ground floor vacation rental home just a few steps from the white sandy beaches of Anna Maria. 4 spacious Bedrooms, 3.5 Bathrooms, accommodates up to 8 people, 3 King beds, 2 Twin beds, 1 Queen sleeper sofa in living room. Enter the luxurious...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Smoking allowed
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    Stunning canal front Anna Maria Island vacation rental home “3 Oars” is the perfect destination for your next luxury getaway! With everything you expect from a fun and relaxing vacation, “3 Oars” has it all! Spaciously accommodating up to eight guests with four bedrooms and four bathrooms no...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    When a starfish needs to get away, it is more than prepared to detach an arm in order to do that. Don’t let yourself get that stressed! Stay for a week in Starfish Beach Cottages and feel all your cares and worries just fall away. From the moment you arrive, you’ll feel like this vacation cottage...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    (4) Bedroom, (4) Bath (Sleeps 8) – “Beachy Blue”- 129 52nd St in Holmes Beach. “Beachy Blue” is a magnificent Anna Maria Island vacation home that will make your vacation feel truly luxurious! This spacious rental home offers accommodations for up to 8 guests including 4 roomy bedrooms with 1...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    • Washer
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    • Private Outdoor Pool (Heated)
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    • Wi-Fi
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    • Satellite TV
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    Pet friendly
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    Smoking allowed
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    Eye-popping Peach Bellini is a newly renovated, small-dog friendly, 2 Bedroom/2 Bath Villa. Whether you relax in the private heated pool nestled in a lush tropical landscaped setting or take a short 2-3 minute stroll to the sugar white sand beaches this bunglaow and its conveinient location will...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Welcome to Blue Lagoon!  This complex has one of the best community pools on the island!  Large, tropical pool with a 10' waterfall right outside your back door! Dogs under 50lbs are welcome with a pet fee. The lovely upgraded kitchen offers granite countertops, stainless steel appliances and...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Fantastic private "Coastal Cottage" vacation home just a few houses to the white sandy beaches of Anna Maria Island and the Gulf of Mexico. Enjoy the large heated pool with large tiki umbrella in pool bar area all in a tropical paradise setting! Enjoy the feel of this cottage for your next holiday...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Terrace
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    Kid friendly
    Smoking allowed
    About this property
    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. “Sandy Pants” is a chic multilevel Anna Maria vacation rental home with coastal flair and everything you need for the perfect Island...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Smoking allowed
    About this property
    Find everything that makes a fun beach getaway on Anna Maria Island memorable when you stay at Holmes Beach vacation rental home 6313 North Beach Village. This three bedroom townhouse style vacation rental sleeps up to five guests, and is just a short walk to beautiful gulf beaches. Nestled a...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Enjoy your own slice of island life with a week at 25 Seaside Court!  (2) Bedrooms, (2) Bathrooms, accommodates up to (4) guests. 1 Queen, 2 Twins. Highspeed internet, pets welcome with fee, bay front location with boat access, not far from the beach. Located in a quiet but vibrant neighborhood...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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