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Holiday Rentals, Apartments and Homes in Holmes Beach, FL

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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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    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.;   Enjoy a magical sunset in this well maintained Gulf of Mexico direct beachfront Condo... Perfect get away condo. The large heated pool and nestled right... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Anna Maria Island's chic upscale development offers this ground level, vacation cottage at called Sunfish Cottage! Every detail has been taken care of... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Welcome to your very own private island resort: You’ll find everything you need for the perfect Anna Maria Island vacation when you stay at “Island Time”!... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; This home was completely remodeled from the ground up, so everything is new. The designer decor is sophisticated, yet fun and perfect for the island... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; You’ll enjoy an amazing Anna Maria Island vacation when you visit upscale gulf front condominium L’Plage 6420 Gulf Drive in Holmes Beach! This three bedroom... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 70
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Special Offer Sept. 1-Oct. 30 $1000.00 all-inclusive for a one week rental save $782.50. Anna Maria Island is not a place you go to the beach. When you are on Anna Maria Island you are at the beach.The Anna Maria Island 'Beach Paradise Condo' is located on Holmes Beach directly in the middle of... View all property information
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    Holmes Beach, Anna Maria Island
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 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... View all property information
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    Holmes Beach, Anna Maria Island
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    1 / 24
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Seabreeze Villa is a fabulous home for your vacation on Anna Maria Island. This beautiful Mediterranean designed home is located in central Holmes Beach, and is within walking distance of shopping, restaurants, and the white sand beach! This spacious home is equipped with a fantastic kitchen,... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 24
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.;  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... View all property information
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    Holmes Beach, Anna Maria Island
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; This vacation rental is exactly what you’ve been dreaming of – three stories of laid back luxury, with three bedrooms, two and a half bathrooms, peeks of a... View all property information
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    Holmes Beach, Anna Maria Island
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; The casual and spacious Anna Maria Island vacation rental “North Beach Village 67” is a fabulous way to make your vacation amazing! Just two blocks from the... View all property information
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    Holmes Beach, Anna Maria Island
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Located on gulf front property, “Sun Plaza West” is a beautiful beach side Holmes Beach vacation rental home perfect for 4 guests! Well equipped with... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 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... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 17
    6 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Fantastic new private vacation rental home with outstanding Gulf Views from two of the four balconies and large heated pool equipped with a swim up Tiki hut... View all property information
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    Holmes Beach, Anna Maria Island
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Anna Maria Island still maintains an old Florida feel, with peaceful beaches and glowing sunsets, while offering a diverse choice of restaurants and... View all property information
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    Holmes Beach, Anna Maria Island
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; You'll be close to all the favorite things to do on Anna Maria Island while spending a week's holiday at this well-appointed vacation home! (3) Bedroom, (2)... View all property information
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    Holmes Beach, Anna Maria Island
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    538 70th - Private home 3 Bedroom / 3 Bath with private pool , maximum occupancy of 6 people. Meticously maintained bayview home offering 3 bed/3 baths with two master suites. Large gourmet kitchen with breakfast bar overlooking the pool. Relax and enjoy your cocktail while sitting under the... View all property information
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    Holmes Beach, Anna Maria Island
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    1 / 24
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 4 Bedroom, 3 Bath (sleeps 8) - 'Jackie's Cottage' - 209 N. Harbor Drive, Holmes Beach Manatee Heaven! – Watch the manatees play from the private boat... View all property information
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    Holmes Beach, Anna Maria Island
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Beach Bound is located just a short block from the Gulf of Mexico and 7 miles of beautiful Anna Maria Beachfront. It is elegantly furnished and has been... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 9
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; The right company can be a retreat all in themselves. So when you’re looking for an escape in Anna Maria Island with someone special, consider a week spent... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 26
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; *New heated pool!* Florida is one of those few places in the world that is just as exciting, beautiful, and charming in real life as it is in your... View all property information
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    Holmes Beach, Anna Maria Island
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Fall in love with Anna Maria Island paradise when you stay at the luxury Holmes Beach vacation rental town home “North Beach Village 50”! This spacious... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 21
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.;  Welcome to Casa Varadero a new ground level vacation rental home on Anna Maria Island in the quiet upscale neighborhood of Key Royale.This canal front home... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; The quintessential Florida beach side condo, you’ll love your Anna Maria Island vacation when you stay at West Winds 6828. This fun and tropical inspired... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 10
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Adorable vacation condo with peeks of the Gulf of Mexico from your front porch!  (1) Bedroom, (1) Bathroom, accomodates up to (4) people: 1 King, Sleeper. ... View all property information
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    Holmes Beach, Anna Maria Island
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Welcome to Hideaway a new and beautifully done duplex! 1050 square feet under A/C Great looking vacation rental and sit on the porch and overlook this... View all property information
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    Holmes Beach, Anna Maria Island
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; The perfect place for a fun filled memorable vacation destination is waiting for you at the vacation rental home “Summer Breeze”! This gorgeous five bedroom... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 25
    4 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; If comfort and Luxury are what you look for in an Anna Maria Island vacation, this is the perfect place for you! Accommodating up to 9 guests this glamorous... View all property information
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    Holmes Beach, Anna Maria Island
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Welcome to Turtle Nest just a short walk to the Gulf of Mexico and the sugar sand beaches of Holmes Beach. This vacation rental duplex has everything to... View all property information
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    Holmes Beach, Anna Maria Island
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 3 Bedroom, 2 Bath (Sleeps 6) – “Gulf Place” – 6700 Gulf Drive Unit 14 in Holmes Beach. Offering everything you could want from a direct beach front... View all property information
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    Holmes Beach, Anna Maria Island
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 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... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; This two bedroom, two bath Direct gulf frontvacation condo gives room for four guest to enjoy the Gulf waves crash in the distance while a little bit closer... View all property information
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    Holmes Beach, Anna Maria Island
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    4 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; (3) Bedroom, (3) Bath (Sleeps 6) – “Beachy Blue”- 129 52nd St in Holmes Beach. “Beachy Blue” is a magnificent Anna Maria Island vacation home that will... View all property information
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    Holmes Beach, Anna Maria Island
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Enjoy spacious Florida glamour with a week at this three bedroom, three bath vacation townhome. Outfitted with lighthearted colors on the wall and... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Plum Cottage 322 is professionally decorated with a laidback island flavor, and offers everything you'll desire for a truly memorable vacation! This single... View all property information
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    Holmes Beach, Anna Maria Island
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; If you're looking to spend your holiday in luxurious and relaxing setting, La Casa Costiera is the place to be! You’ll know it’s something special from the... View all property information
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    Holmes Beach, Anna Maria Island
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 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,... View all property information
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    Holmes Beach, Anna Maria Island
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 2 Bedroom, 2 Bath (sleeps 6) - 'Pisces Playground' - 205 73rd Street The open and airy duplex at 205 73rd Street gives you the space your family needs... View all property information
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    Holmes Beach, Anna Maria Island
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 4 Bedroom, 3.5 Bath (sleeps 10) - 'Casa Morado' - 147 50th Street, Holmes Beach Welcome to Casa Morado located on beautiful Anna Maria Island. Located... View all property information
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    Holmes Beach, Anna Maria Island
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Recently updated, find the casual and relaxing Anna Maria Island paradise getaway you’ve dreamt of at North Beach Village 55. This three bedroom two and a... View all property information
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    Holmes Beach, Anna Maria Island
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; When you arrive at Anna Maria Island vacation rental home “Mermaid Crossing” you are greeted with true island style and luxury. This three bedroom three bath... View all property information
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    Holmes Beach, Anna Maria Island
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.;   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... View all property information
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    Holmes Beach, Anna Maria Island
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; This home is a restoration of an original vacation home to fully updated Florida codes and standards in all respects.  This 3 bedroom 2 bathroom ground level... View all property information
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    Holmes Beach, Anna Maria Island
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Key Lime 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... View all property information
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    Holmes Beach, Anna Maria Island
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.;   Breath-taking panoramic views of the sparkling Gulf of Mexico and sugar sand beaches.  (2) Bedrooms, (2.5) Bathroom, accommodates up to (4) people: 1... View all property information
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    Holmes Beach, Anna Maria Island
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Light and bright vacation villa with community boat ramp available for an idyllic holiday getaway.  (2) Bedroom, (2) Bath, accomodates up to (4) people: 1... View all property information
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    Holmes Beach, Anna Maria Island
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; Brand new  to our rentals - Catchin' Rays is only steps to the sugar sand beaches, making it easy to go back and forth from the beach to the heated pool and... View all property information
    Location Information
    Holmes Beach, Anna Maria Island