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Holiday Rentals 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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This is the Florida view you have been dreaming of... Single family home situated at the end of a natural canal with a view over the water. Sit outside, fish off our dock, take out the kayaks, or just walk steps across the street to the beach! This is not your typical beach rental. It is our... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    5 of 5 stars (136) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | 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.... View all property information
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    Holmes Beach, Anna Maria Island 34217
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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
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Beachside Palms Anna Maria Island Resort is extremely conveniently located directly across from the famous Manatee County Public Beach on the gorgeous Gulf of Mexico. All 3 of our units were completely updated in 2016. They feature new cabinets, stainless steel appliances and granite countertops.... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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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... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    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 34217
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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.; 2 Bedroom, 2 Bath (Sleeps 4) – “Blue Lagoon 6 - Osprey” –215 6th Street Holmes Beach. Nestled into a gorgeous resort style setting, Anna Maria Island... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    1 Bedroom, 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.; Direct gulf front one bedroom and one and a half bath condo in desirable Water's Edge complex which is the best place for a holiday rental. Enjoy the... View all property information
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    Holmes Beach, Anna Maria Island 34217
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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.; Kick back and relax in this charming 2 bedroom 2 bath island oasis!. Boaters will enjoy the dock on a wide, deep water canal that leads directly out to... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Welcome to Anna Maria Island vacation rental condominium Sandy Pointe 103 “Latitude Adjustment”! Offering accommodations for up to four guests with one king and two twin beds this two bedroom two bathroom condo will feel like your home away from home with a relaxed island attitude. Located... View all property information
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    Holmes Beach, Anna Maria Island 34217
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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.; Updated Holmes Beach Island home just steps to the Gulf of Mexico beaches. Enjoy this vacation rental with a caged heated pool and a brand new paver area... View all property information
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    Holmes Beach, Anna Maria Island 34217
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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.;   Southern Comfort is a luxury three bedroom vacation home less than two blocks from the beach. (3) Bedroom, (2.5) Bathroom, accomodates up to (8) people: 1... View all property information
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    Holmes Beach, Anna Maria Island 34217
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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 34217
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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, 3 bedroom 2 bath new duplex with private heated pool.  Sleeps up to 6. Key Lime Cottage East welcomes you to this recently re-done... View all property information
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    Holmes Beach, Anna Maria Island 34217
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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.; All of the Palm Isle Villages are a good choice for family vacations.  But PIV 3206 is particularly perfect for vacations with kids thanks to a charming set... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    5 of 5 stars (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    7310 Holmes - Duplex 1 Bedroom / 1 Bath , maximum occupancy of 4 people. Fun in the Sun!~ Ground level duplex that's fun and adorable. This one bedroom, one bath unit has a private outdoor patio area. This unit has recently been renovated and is perfect for a couple with visiting guests.... View all property information
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    Holmes Beach, Anna Maria Island
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    5 of 5 stars (6) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    This elevated vacation rental will meet your high standards of vacation home living. With over 1400 square feet of living space, this home boasts three large bedrooms with a king master suite, a queen in the second bedroom, and a twin in the third. A queen sofa bed in the living area provides... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    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.; On Anna Maria Island, you hear a lot about visitors experiencing love at first sunset. By the time sun is setting on your first day, most people are hooked.... View all property information
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    Holmes Beach, Anna Maria Island 34217
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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.; Direct gulf front two bedroom and two bath condo in desirable Water's Edge complex which is the best place for a holiday rental. Enjoy the large heated... View all property information
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    Holmes Beach, Anna Maria Island 34217
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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.; Reserve Anna Maria Island vacation rental “Tropical Paradise” for your next relaxing vacation getaway!  This wonderful vacation rental home offers... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 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 Palm Isle 3201 – a two bedroom, two bathroom vacation cottage in one of the most coveted complexes on Holmes Beach. The warm tile, coastal... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    405 Bay Palms - Private home 2 Bedroom/ 2 Bath with private pool , maximum occupancy of 6 people. If privacy is calling, quit stalling and come and play at 405 bay!~ Home in a very private tropical setting with lush landscaping. Large, open and airy floorplan. Minutes from the beach and local... 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 34217
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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 34217
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | 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.; To say we live in paradise is no exaggeration and we’d like to invite you to experience it yourself with a week at Sea Palm Cottage! This vacation rental... View all property information
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    Holmes Beach, Anna Maria Island 34217
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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.; Tranquil ground level condo. (2) Bedroom, (1) Bathroom, accommodates up to (4) people: 1 Queen, 2 Twins. Shared heated pool, free wireless, no pets allowed,... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    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 34217
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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.; 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 34217
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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 34217
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    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Relax to the sound of waves crashing with views of the ocean from almost every window in this cozy cottage. This second floor cottage is only steps away from Holmes Beach and overlooks the calm waters of the Gulf of Mexico. The perfect location of this cottage also puts you less than a mile from... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    1 Bedroom, 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 the large heated pool and just steps to the Gulf of Mexico. Whether you stay a week or a month this is the perfect condo for a winter retreat, vacation... View all property information
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    Holmes Beach, Anna Maria Island 34217
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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.;   Florida Chic Bay Front Condo  -- (2) Bed: (2) Bath: Accommodates up to (4) people: 1 King & 2 Twins: No smoking: No Pets.   Desirable Westbay Point and... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    4 of 5 stars (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Cayman 104 - Condo 2 Bedroom / 2 Bath , maximum occupancy of 5 people. Nice ground level condo located across the street from the beach , pool and covered parking. The complex also offers a heated pool in the winter, grilling area and shuffleboard. There is even a designated smoking area if you'd... 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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    Anna Maria Island vacation rental home “Cozy Cottage” is the perfect place to reconnect with friends and family while making life lasting memories by the beach. This stunning four star vacation rental home offers everything to accommodate six guests comfortably with three bedrooms and three... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    2 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.; The decor inside of 5613 Gulf Drive is tasteful and with a nod to old Florida sensibilities. The gulf coast themed artwork echoes natural beauty found all... View all property information
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    Holmes Beach, Anna Maria Island 34217
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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.; One of the best vacation spots on Anna Maria Island, “La Casa Marie” is an amazing  gulf front 3 bedroom 2.5 bathroom Holmes Beach vacation rental... View all property information
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    Holmes Beach, Anna Maria Island 34217
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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 34217
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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.;   The Captains House welcomes you! Living at the beach is like living anywhere else except it's better in almost every way imaginable! Experience it for... View all property information
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    Holmes Beach, Anna Maria Island 34217
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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 34217
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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 34217
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    2 Bedrooms, 1 Bathroom, 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, 1 Bath (sleeps 4-6) - "Playa Casanas South" - 3222 Gulf Drive unit A in Holmes Beach. “Playa Casanas South” is a wonderful vacation rental... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    4.5 of 5 stars (7) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Escape to Serenity sums it up for this quaint and cozy duplex (with no shared walls). You will feel as if you have landed on your own personal island with this gem of a property. This fantastic, two-bedroom, one-bathroom vacation rental will help you find some serenity. This home boasts an all-new... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    4.5 of 5 stars (8) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Private Outdoor...
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    • Satellite TV
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    • Washer
    • DVD Player
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This four-bedroom pet-friendly vacation rental with a heated pool is just a block to the white sand beaches of Anna Maria Island and the Gulf of Mexico. Located in Holmes Beach, Beautiful Villa by the Sea offers an open floor plan with plenty of space to accommodate 10. On the main floor you will... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
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    • Smoking allowed
    • x
    About this property
    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 34217
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Balcony
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    • Hot Tub
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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 Bella Vida, a Brand New vacation home in our rental program! Some may know that "Bella Vida" means "Beautiful Life", and your time spent at this... View all property information
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    Holmes Beach, Anna Maria Island 34217
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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.; Holmes Beach vacation rental “Rest Assured” is a fun tropical inspired ground level home comfortably accommodating up to 8 vacationers. Located in beautiful... View all property information
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    Holmes Beach, Anna Maria Island 34217
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Please note these Check-in Day Requirements for this property: Jan 01 - Dec 31 : Saturday check-in required, Saturday check-out required.; “Ariel’s By the Sea” is a lovely ground level 3 bedroom 2 bathroom duplex style Holmes Beach vacation rental home suited for up to 6 vacationers. Plenty of... View all property information
    Location Information
    Holmes Beach, Anna Maria Island 34217