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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.
    1 / 16
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    3.5 of 5 stars (3) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 of 5 stars (1) Terrible
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    One bedroom one bath condo located on the poolside. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are two... View all property information
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    Holmes Beach, Anna Maria Island
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    4.5 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Horizon West 112 - Condo 2 Bedroom / 2 Bath , maximum occupancy of 4 people. Beach Bound.....This is your place!~ 2 bedroom 2 bath condo 1 very short block to beach. Beautifully decorated with comfortable furniture. Everything you need for a relaxing vacation. Pet friendly Anna Maria Island is... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 29
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5801 DePalmas - Private home 3 Bedroom / 2 Bath , maximum occupancy of 6 people. Comfy and Cozy Florida Living!~ Cute cozy ground level home 3 Bedroom/ 2Bath close to the beach on a quiet dead end street. Fully furnished with linens towels, cooking utensils, basic cable tv and telephone, just... View all property information
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    Holmes Beach, Anna Maria Island
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Come relax and enjoy your beach vacation at The Cast Away! Located conveniently across from the Manatee Public Beach and the Gulf of Mexico. This two bedroom and one bath unit sleeps six with a queen size bed, two twin beds and a sofa bed. A full size kitchen and living room are included for your... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 32
    4.5 of 5 stars (23) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    Fantastic 2 bedroom / 1.5 bath townhome just 200 steps to the beach. Relax in Paradise at #116 52nd Street in Holmes Beach on Anna Maria Island and enjoy all the comforts that this beautifully furnished townhome has to offer. Newly decorated with granite countertops, stainless steel appliances,... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 23
    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.; Plum Cottage 324 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
    1 / 20
    5 of 5 stars (89) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    PRIVATE ISLAND PARADISE - This unique custom home is hidden on a huge garden lot surrounded by palms, birds of paradise, tropical plants and a 6 ft fence. Few island homes offer this degree of privacy. SPACIOUS ELEGANCE - The home has 2,600 sq ft (240 sq m.) of ground level indoor living space with... View all property information
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    Holmes Beach, Anna Maria Island
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    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Authentic spacious beach cottage charm in a mid-century shell. Located a couple blocks from Florida's best powder sand beach and situated across from Bimini Bay with use of our dock. Explore the quiet paradise where the locals live. The Pine Ave shops and famous Beach Bistro Restaurant are less... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 31
    4.5 of 5 stars (3) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Beautiful, completely remodeled, ground level 4 bedroom/3 bath Home in a quiet neighborhood located just over a block to the beautiful white sand gulf beach. Close to shops and restaurants, and just a short block to the free trolley stop. Within an easy walk of Hurricane Hanks, A Moveable Feast,The... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Located in Holmes Beach, on Anna Maria island. This two bedroom two bath unit is a full size apartment with full size kitchen all appliances dishwasher, stove full size refrigerator, living area with fireplace, dinning area and a separate bedrooms has 1 king size bed and 2 twin size beds. Its just... 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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    What a great complex located directly on the beach. Enjoy the beautiful gulf views while swimming in the pool. Unit 206 is an updated 2BR/2BA unit with king and queen size beds. Nicely maintained unit with new furnishings, new wood laminate flooring in the living room and new carpet in the... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Note: This property requires a 28-day minimum stay. This two-bedroom, two-bath vacation rental is the perfect size for a romantic getaway, small families or close friends. Located in the Westbay Point & Moorings condominium complex in Holmes Beach, this hidden gem is tucked away from traffic,... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 40
    4 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    Relax in absolute style in this immaculate 4 bedroom, 4.5 bath home. Coastal to the core with its bright, airy, sea-side inspired design and finishes. Every detail, a perfect one, to make you feel right at home and, of course, right at the beach! The front entry spills into the spacious great room... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 27
    4 of 5 stars (1) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Make your stay in Florida fun and easy! This 2 Bedroom, 2 Bath condo is direct beachfront with wide open views up and down the coast. The condo is on the top floor (6th) of the building and is completely furnished with a dining table that seats 6 – 8, sofa and loveseat, coffee and end tables, flat... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 10
    5 of 5 stars (3) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    510 Bayview - Private canal home 3 Bedroom / 3 Bath with private pool , maximum occupancy of 6 people. Island Elegance for the whole family!~ Come to Anna Maria Island, bring family, friends and your boat to enjoy the simple pleasures of life: sun, sand, and surf. Relax in well-appointed rooms,... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 33
    5 of 5 stars (7) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Coastal living in a tropical setting! Gorgeous ground level 3 bedroom/3 bath home with designer touches at every glance. This light and airy, open-concept floor plan is generously appointed with flat screen TVs in all rooms and tile floors throughout every one of its almost 2000 square feet. You... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 17
    4 of 5 stars (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    One bedroom one bath condo located on the poolside. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are two... View all property information
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    Holmes Beach, Anna Maria Island
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    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Cayman 204 - Condo 2 Bedroom / 2 Bath , maximum occupancy of 4 people. FALL SPECIAL now through mid December 2016. Weekly rate has been dropped to $700 for the week. Now is the time to find peace and quite in paradise! Come and relax in this very comfortable two bedroom condo.Small complex in the... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 25
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Island Beach Club 2 - Condo 2 Bedroom / 1.5 Bath ground level gulf front , maximum occupancy of 4 people. Community pool. Your Ultimate Gulf Front Luxury Vacation! Look no further. You will love this ground level 2 bedroom/1.5 bath condo. This spectacular, brand new Island Beach Club luxury... View all property information
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    Holmes Beach, Anna Maria Island
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    2 Bedrooms, 1 Bathroom, 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.; Direct Gulf Front cottage in Holmes Beach! When we say that Sea la vie is right on the beach, we mean one step off the back porch!  (2) Bedroom, (1)... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 25
    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.; This two bedroom, two bath direct gulf front vacation condo gives room for six 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
    1 / 36
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Gulf View Townhouse 3 - Condo 2 Bedroom / 2 1/2 Bath , maximum occupancy of 4 people. Peaceful Anna Maria Island Living! Come relax and enjoy your beach vacation at the Gulf View Townhouses. Enjoy your vacation at this wonderful townhouse just 3 min walk from the beach! Quiet, residential area 2... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Let the "Good Times" roll at this original and fun Anna Maria Island vacation home! The location is excellent, just a few blocks to the white sand beaches of the Gulf of Mexico! This fantastic, three-bedroom, two-bath vacation rental offers everything you need for a relaxing getaway. There are two... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 45
    4 of 5 stars (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Adriel's Place in Anna Maria...located in upscale private golf club neighborhood, a stone throw from pristine beaches, restaurants and island entertainment ( less than 1 mile ). An expansive backyard dotted with majestic palms, papered terrace and pool overlooking sailboat water. Fishing and... 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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    Once you open the door to Gulf View 201, you will begin to relax. This two-bedroom, two-bath vacation rental condo will encourage you to have a fabulous vacation on Anna Maria Island. The breathtaking view of the sparkling Gulf of Mexico water through floor to ceiling windows in the open living... 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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    Fountain Head 8 - Condo 2 Bedroom / 2 Bath , maximum occupancy of 6 people. Enjoy Old Florida Quiet Island Living! Is a residential location near attractions important, particularly when this location comes at a reasonable price? Is an easy walk to the white-sand beaches, shopping or dining,... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 25
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Welcome to Big Sky Beach House, a quiet and private location for a memorable getaway with family and friends. Our freshly updated mid-century 4 bedroom, 3 bath home is all on one level with a sparkling heated pool in full view throughout the house. It is ideally situated a mere block to the... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 21
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    The number 3 island in the United States so says Trip Advisor. The best island beach sand so says Conde Nast Travelers. So who wouldn't want to stay right on the beach in an immaculate and roomy 2 bedroom, 2 bath condominium in the Tiffany Place Condominium located on the Gulf of Mexico in Holmes... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 12
    4.5 of 5 stars (6) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Beachy and bright condo on the second floor of a small 2-story-building (20 units in total), overlooking the mangroves with view to the Palma Sola Bay. Only some steps away from the ocean and the wonderful wide and powder sanded beaches. The condo is recently refurnished; masterbedroom with a... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 24
    4 of 5 stars (1) Very good
    5 Bedrooms, 4 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.; 5 Bedroom, 4 Bath (Sleeps 10) – “Banyan Breeze” – 122 White Avenue in the city of Anna Maria. Luxury Anna Maria vacation rental “Banyan Breeze” is a... 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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    Sun-Day West is the picture-perfect name for this two-bedroom, two-bath, elevated duplex. Located in Holmes Beach on Anna Maria Island, this vacation rental features a large, west-facing balcony that allows for plenty of sunshine in the afternoon and shade in the morning for that early cup of... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 14
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This is a comfortably furnished and updated home equipped with every vacation need. Washer and dryer,cable televisions, Wi-Fi, land line phone, screened rear porch for OUTDOOR SMOKING ONLY. There is an outdoor gas grill. All beach equipment such as chairs, umbrella, wagon,coolers,toys and towels... View all property information
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    Holmes Beach, Anna Maria Island
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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
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    Sandy Point 114 - Condo 3 Bedroom/ 3 Bath, maximum occupancy of 7 people. This 3 bedroom , 3 bath townhouse condo features 2 living floors and 3 verandas above an enclosed over-sized garage and located in the Cove at Sandy Pointe on beautiful Anna Maria Island! Surrounded by nature you will... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 24
    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
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    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    Located in Holmes Beach, on Anna Maria island. This one bedroom two bath unit is a full size apartment with full size kitchen all appliances dishwasher, stove full size refrigerator, living area, dinning area and a separate bedroom has king size bed. Two full size bathrooms. Its just steps to 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.; 3 Bedroom, 2 Bath (sleeps 8) - 'Almost Heaven' - 205 72nd Street, Holmes Beach Welcome to Almost Heaven! A charming single family pool home which is a... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 24
    5 of 5 stars (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    With breathtaking views of the Gulf of Mexico from almost every room and just steps to the beach, you may never want to leave the soothing and relaxing atmosphere of Starfish Villa. Located in Holmes Beach on Florida's beautiful Anna Maria Island, this two-bedroom, two-bath, elevated home equipped... 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. Blue Wave Villas are... View all property information
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    Holmes Beach, Anna Maria Island
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Old Florida charm in a completely remodeled house only 1 1/2 short blocks to an uncrowded beach. Ours is a 2 bedroom/2 bath home which sleeps 5. It is the larger 1/2 of a duplex house with exclusive use of the solar heated saltwater pool in the privately fenced backyard. A garage separating both... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 19
    4 of 5 stars (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    One bedroom one bath condo located in the courtyard. The Coconuts Beach Resort is directly on the Gulf Of Mexico Holmes Beach Anna Maria Island Florida.. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are... 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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    Fun and beachy lower duplex with pool on Anna Maria island. Only a block and a half from the beach. Wash the sand off fro the beach with the outdoor shower and foot wash. Play or relax by the pool. Outdoor furniture is perfect for eating or entertaining outside. Lounge furniture is perfect for... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 31
    4.5 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    This beautifully 2016 decorated first floor 2 bed condo is set in an idyllic, peaceful setting amongst the natural beauty of Anna Maria Island and only a short walk from the stunning white sandy beaches. This fully air conditioned condo comprises of a large lounge with a tiled floor, new leather 2... 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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    • DVD Player
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    Island Beach Club 22 - Condo 2 Bedroom / 1 Bath gulf front , maximum occupancy of 4 people. Community pool. CALL NOW FOR OUR OCTOBER SPECIAL!!! If you're looking for total serenity and magnificent gulf front views then you've found the right place. This 2 bedroom/ 1 bath beachfront condo is... 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 relaxing into that vacation frame of mind at first glimpse of this three story, key lime colored vacation home in the center of Holmes Beach. This... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 16
    4 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.; Coastal and spacious vacation paradise seasonal rental  (4) Bedroom, (2.5) Baths, accommodates up to (8) people: 1 King, 1 Queen, 2 Twin, 1T with Trundle... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 18
    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.; The peaceful and airy feeling “Sandy Point 202” is a condo style Holmes Beach vacation home located in the center of Anna Maria Island. This calming... View all property information
    Location Information
    Holmes Beach, Anna Maria Island