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Holmes Beach House Rentals

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    Travellers to Holmes Beach are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    293 Matching Rentals in Holmes BeachView all 593 rentals
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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, 3 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    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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    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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    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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    Pet friendly
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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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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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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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    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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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
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    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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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    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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    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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    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, 2 Bathrooms, Sleeps 6 Quick View
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    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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    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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    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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    ISLAND GIRL NORTH1 / 37
    (5)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
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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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    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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    SIMPLY CHIC1 / 38
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    About this property
    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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    ISLAND GIRL WEST1 / 36
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    North Beach Village 69 is the perfect Florida beach side vacation destination. Sleeping up to six guests this townhouse style Anna Maria Island vacation rental is in a great location. Not only is this home close to beaches, shopping and dining, but it offers great comfortable coastal style....
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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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    (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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    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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    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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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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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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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Private Garden
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    Smoking allowed
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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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    Gorgeous town house style Anna Maria Island vacation rental “North Beach Village 40” will be the memorable vacation spot that makes you absolutely fall in love with the island life! This stylish three bedroom two and half bathroom home accommodates up to six guests with two queen beds and two twin...
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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 6 Quick View
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    The Bollinger Duplex, Side B is a ground level one bedroom, one bath duplex located at 6909 Gulf Drive, in the preferred northern area of Holmes Beach. It only one-half block to a beautiful beach where you can stroll from one end of Anna Maria Island to the next! This ground level unit is newly...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    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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    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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    Location Information
    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 extended Florida vacation spot you have been looking for is waiting at 516 77th Street! This great canal front Anna Maria Island vacation rental home offers a laid back spot for fishing, boating and enjoying time on the beach. This Holmes Beach rental is on a canal right off Bimini Bay and...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    Anna Cabana Bungalow #4 located at 3711 4th Avenue in Holmes Beach is in a ground level five unit complex that’s fun and affordable. It adjoins three other of the Cabana Bungalow units and is next door to the Cabana Beach House. With the numerous room configurations this is a perfect complex for...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The Tequila Sunrise is an absolutely wonderful three bedroom, two bath home with a private heated pool. Located 309 B 59th Street in Holmes Beach, this lovely property is convenient to the beach and in a very convenient, Holmes Beach residential neighborhood. It features a washer and dryer,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Find the perfect Anna Maria Island vacation spot at “Sugaree”! This newly renovated duplex is comfortable, stylish and close to the beach too! When you visit “Sugaree” you’ll find everything you’ll need for up to six guests. Inside this Holmes Beach rental you’ll find a spacious main living...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Happy Heron: 1BR Perfect Getaway, Block from Beach1 / 24
    (9)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    At first glimpse, Happy Heron will make you smile! Just one short block away from the pristine water of the Gulf of Mexico and Anna Maria Island's gleaming white sand beaches, this one-bedroom, one-bath vacation rental has been updated inside and out for your vacationing pleasure. When renting...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Fun in the Sun if a fantastic pool home with outstanding features! Relax in the beautiful heated lagoon style pool or sit around the patio in your own private tropical paradise. Plenty of seating will ensure everyone can relax and enjoy the extra large pool area. This Anna Maria Island vacation...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    On Anna Maria Island, the Mediterranean design of Beach Escape promises you exactly the same enjoyment. This home is just the sort of place where relaxing will become second nature, and enjoying the company of family and friends is made so easy. (3) Bedroom, (3) Bath, accommodates up to (6): 2...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    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 room home spaciously accommodates up to six guests with one king bed, two queen beds and endless charm. Located in the central area of the...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Just 150 steps to a beautiful white sandy beach located in the preferred and more private northern end of Anna Maria Island, The Harrison Home at 6901 Gulf Drive features many new renovations and updates. This spacious four bedroom and four bath home has one of the largest private pools on the...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    While Anna Maria Island is a place that you can go barefoot about twenty two hours of the day, we still don’t like to skip on luxury.  (2) Bedrooms, (1) Bath, accommodates up to (4) people: 1 King, 2 Twins. Blue Wave Villas are cozy, comfortable, and above all, classy, making this a dream vacation...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Sirena del Mar is a three bedroom, two bath home located at 201 30th Street in Holmes Beach. This home has been totally renovated and features a small pool. Its two very short blocks to the wonderful, white sandy beaches. Sirena del Mar has a wonderful open design with all new kitchen cabinets...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    "Flip Flops Forever" welcomes you to this recently re-done and updated island home. Just steps from the Gulf of Mexico and the pure white sandy beaches of Anna Maria Island. All new furniture and custom touches throughout make your stay a pleasant and peaceful one. This five bedroom three bathroom...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Holmes Beach vacation rental “Rest Assured” is a fun tropical inspired ground level home comfortably accommodating up to 8 vacationers. Located in beautiful Holmes Beach, “Rest Assured” has 3 bedrooms, a den and 2.5 bathrooms with 2 King beds, 1 Queen bed and 2 twins in the den. Tastefully designed...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tiki Tides located at 6250 Holmes Boulevard in North Beach Village is a beautiful townhome in the heart of Holmes Beach. This property has been recently updated in a cute and beachy decor and has everything you need to enjoy Anna Maria Island. You are just a few steps away from the heated community...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    BEACHSIDE PARADISE1 / 40
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
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    Very spacious 4 bedroom/3 bath home, just a short block to the beach (just over 100 yards), and a couple houses to the free Island trolley! Beautifully tropical landscaped back yard with a Heated Pool surrounded by a large paver deck and plenty of seating options. Huge open Living/Family Room area...
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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 6 Quick View
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    Island life is simpler and slower than life anywhere else in the world. It's just hard to get too worked up about anything when you're living life with salty, gulf coast waves crashing in the distance and a seagull song overhead. Get into that mellow frame of mind, by spending your next Anna Maria...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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