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Holiday Homes and Apartments 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.
    1 / 11
    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.; 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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    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
    1 / 21
    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.; Beautiful light, bright and beachy relaxing seasonal rental. (4) Bedroom, (4) Bathroom, accomodates up to (8) people: 2 Kings, 1 Queen, 2 Twins. Private... 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.; When a starfish needs to get away from something and can’t, it will sometimes need to detach an arm. After a week of staying in the Starfish Beach... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 3 Bedroom, 2.5 Bath (Sleeps 6) - “Palm Gables” 106 36th Street in Holmes Beach. Enjoy the gulf front Anna Maria Island vacation you deserve when you... 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 multi-level, single family vacation home offers casual island luxury across an open floor plan with volume ceilings, a large wooden terrace, and... 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, 2.5 Bath (Sleeps 6) - “North Beach Village” 6250 Holmes Boulevard unit 72 in Holmes Beach. Relax in casual luxury and comfort at North Beach... View all property information
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    Holmes Beach, Anna Maria Island
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    1 / 24
    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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    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 / 24
    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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    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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    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.; 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... 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
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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.; (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... 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
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 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)... 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.; 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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    1 / 12
    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.; 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... View all property information
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    Holmes Beach, Anna Maria Island
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    3 Bedrooms, 2 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.;   Elegant and chic duplex ready for your tropical escape. (3) Bedrooms, (2.5) Bath, accommodates up to (9) people: 2 King,  2 Twin Bunk Beds, 1 Trundle Bed,... 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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    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 / 55
    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 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.; 3 Bedroom, 2.5 Bath (Sleeps 8) - “North Beach Village” - 6250 Holmes Boulevard unit 27 in Holmes Beach. For a relaxing and fun Anna Maria Island... 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 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
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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
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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.; When you’re looking for a vacation home on Anna Maria Island that blends comfort, luxury, and fun, you’re looking to spend your week in Holmes Beach at Gulf... View all property information
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    Holmes Beach, Anna Maria Island
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    3.5 of 5 stars (3) Average
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Porch
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    About this property
    Just one short block away from the pristine water of the Gulf of Mexico and Anna Maria Island's gleaming white sand beaches, this two-bedroom, one-bath vacation rental has been updated inside and out for your vacationing pleasure. A well-appointed kitchen and outdoor grill may entice you to create... 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.; 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
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 4 Bedroom, 3 Bath (sleeps 8) - 'Jackie's Cottage' - 209 N. Harbor Drive, Holmes Beach Manatee Heaven! – Watch the manatees play from the private boat... View all property information
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    Holmes Beach, Anna Maria Island
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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.; Sea Breeze Sands is a fabulous three story vacation home sitting right across from the Gulf of Mexico and Anna Maria Island’s world famous, white sugar... 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 / 70
    4 of 5 stars (1) Very good
    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, 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.;   Refreshing and tropical are the perfect ways to describe this vacation rental home Mango Breeze at 141 50th Street! Spend a week here in Holmes Beach and... View all property information
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    Holmes Beach, Anna Maria Island
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    5 Bedrooms, 3 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.; Magical and stunning vacation rental with an enviable backyard that includes a wet bar and pool oasis. (5) Bedroom, (3.5) Bath, accommodates up to (12)... 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.; Key Lime Cottage East welcomes you to this recently re-done and updated island duplex. All new furniture and custom touches throughout to make your stay a... View all property information
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    Holmes Beach, Anna Maria Island
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    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; 3207 Gulf Drive at Palm Isle Village in Holmes Beach, Florida is located in one of Anna Maria Island's favorite and finest condominium resorts.  It offers... View all property information
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    Holmes Beach, Anna Maria Island
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    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 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.; 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... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 33
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Internet Access
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    • Pet-friendly
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    • x
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    • x
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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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
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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 / 21
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
    • Balcony
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    • x
    • ?
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    • x
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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 West Winds Condo. This updated 2 bedroom 2 bathroom condo comfortably accommodates up to 6 guests.  (2) Bedroom, (2) Bath, accommodates up to (6)... 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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    • x
    • x
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    • x
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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.; All newly remodeled and soooo close to the beach. This vacation rental has everything to offer with two bedrooms, new kitchen, new bathroom ,TV's in each... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 28
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Terrace
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    • x
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    • x
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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.; Luxurious custom built multi-level tropical oasis and pool paradise. (6) Bedroom, (4.5) Bath, accommodates up to (14) people: 3 Kings, 2 Queens, 1 Bunk Bed,... View all property information
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    Holmes Beach, Anna Maria Island
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    8 Bedrooms, 6 Bathrooms, Sleeps 22 | Quick View
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    • Hot Tub
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    • x
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    • x
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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 this set of elevated vacation homes with two private lagoon style perfect for large family getaways. (8) Bedroom, (7) Bath, accommodates up to (23)... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • x
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    • x
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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.; Beautifully renovated tropical paradise for your holiday getaway.Private heated pool, free wireless internet, pet friendly (up to 25lbs) with fee, less than... 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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    • x
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    • x
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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
    Location Information
    Holmes Beach, Anna Maria Island