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Holmes Beach House Rentals

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    Travellers to Holmes Beach are booking December dates now. Secure your holiday rental today, and have the perfect trip.
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    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    4.5 of 5 stars (11) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 stars (2) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    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.; Welcome to Sunset Glow - a Brand New vacation home in our rental program! Live the life of luxury right in the heart of Anna Maria Island. This home was... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 24
    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.; Make memories that last a lifetime when you stay at gorgeous Anna Maria Island vacation rental home 7001 A. Rooming up to eight guests this spacious three... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 24
    4.5 of 5 stars (8) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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
    1 / 28
    5 of 5 stars (38) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    From the same owners of A Lime Cottage (p277325), who've been recognized as TripAdvisor "rated excellent" vacation rental, Flipkey 2012 and 2013 Top Vacation Rental, 2012 Top Rental Manager", we're delighted to now have Lemon Cottage. <BR><BR>Nestled in a quiet residential boating community across... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 39
    5 of 5 stars (1) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Beautiful, Brand New, 5 bedroom/3.5 bath Waterfront home with Heated Pool, Hot Tub, Dock, and just over a block to the beach! Covered Patio by pool area and peeks of the Gulf and Bay from the top patios. Great location in a quiet neighborhood, a few steps to the Trolley Stop, and a short walk to... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 29
    5 of 5 stars (19) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    http://www.villachezshell.com Villa Chez Shell is a newly renovated Mediterranean beach home that offers a luxurious getaway. The highlight of this newly renovated 3 bedroom and 3 bathroom property is its tropical private backyard complete with a lagoon shaped pool and a soothing stone waterfall.... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 34
    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.; Have some fun entertaining friends under the covered patio next to the refreshing pool. Brand new 5 bedroom 4 bathroom vacation home in Holmes Beach, just... View all property information
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    Holmes Beach, Anna Maria Island
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    1 / 33
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    This great 3 bedroom, 2.5 bath family pool home is just a short 1 1/2 blocks to the beach with direct beach access. Amenities include a Private heated Pool, spacious brick paver patio area, large screened lanai, outside shower and recreation room with ping pong table. Enjoy the extra comforts... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 18
    3 of 5 stars (1) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Beautiful, Brand New, 3 bedroom/2 bath home with Heated Pool and Hot Tub! Granite Countertops, vaulted ceilings, Stainless Appliances, and more. Great location in a quiet neighborhood, just a couple blocks to the beach, and a half block to the Free Island trolley. Enjoy the pool and hot tub with... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 29
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Relax and enjoy the charm of yesteryear at this elevated 3BR/3BA vintage beach cottage located just one house from the beautiful white sandy beaches of Anna Maria Island. No streets to cross to get to the beach. Large screened lanai to enjoy the Gulf breezes and the sounds of the beach. The main... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 28
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    541 67th - Private canal home 5 Bedroom / 4 Bath with private pool , maximum occupancy of 10 people. Beach Bound!~ If you are looking for s---5 bedroom 4 bath canal front home. Great rental for a large family---maximum 10 people. Light open kitchen with breakfast bar, home has a spacious open... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 10
    2.5 of 5 stars (2) Poor
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    217 84th - Private home 3 Bedroom/ 2 Bath with private pool , maximum occupancy of 6 people. Old Florida with all the comforts! of home~ 217 84th. Street 3 bedroom 2 bath home in quiet residential area of Holmes Beach. Private, screened-in, solar heated pool. 3 blocks to the beach. Spacious and... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Get your beach on at Beach n It -- the place to spend your fantastic sunny Florida vacation on Anna Maria Island!! This fabulously remodeled and updated, new pool home is located in the heart of Holmes Beach and is just a short walk to the beach! Completely decorated in beautiful shades of blue,... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 28
    4 of 5 stars (1) Very good
    8 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
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    Welcome to the ultimate in Large Family luxury vacation Homes, with beautiful views of the Gulf of Mexico and sunsets from the Roof Top Deck. This beautiful 8 bedroom/5.5 bath home resides only one short block to the beach and features a gorgeous kitchen with Granite countertops and Stainless... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 12
    3 of 5 stars (1) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Casa Del Mar is a 4 bedroom, 2.5 bath chic Key West style island home with a brand new heated swimming pool located in northern Holmes Beach. Designer decorated from top to bottom. Close to shopping, restaurants, and the trolley stop. Come and enjoy the island life at its very best! Sleeps upto 6-8... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 37
    4.5 of 5 stars (5) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Tropical, quiet, 2 bedroom/ 2 bath duplex, just over a block to the beach, and a block to the free Island trolley! Elevated, with one car garage underneath filled with beach chairs and wagon. Heated Pool surrounded by a large paver deck, lush landscape and plenty of seating. Sleeps up to 4. 1160... View all property information
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 23
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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.; Come have the full Anna Maria Island experience with a week in Coquina Sands. This beach house offers you the ultimate Anna Maria Island experience complete... View all property information
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    Holmes Beach, Anna Maria Island
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    1 / 7
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Ocean Views
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    About this property
    Only 2 houses away from the beautiful white sandy beaches of Anna Maria Island. This newly constructed Holmes Beach 2 bedrooms and 1- 1/2 bathroom house is over 2000 square foot with a heated private saltwater pool. Open floor plan, flat screen TV's, and two balconies overlooking the beach are... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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.; 3 Bedroom, 2 Bath (sleeps 8) - 'Coastal Sands' - 213 70th Street, Holmes Beach Welcome to Coastal Sands! It time to slow down and drag your feet in the... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 39
    2 of 5 stars (3) Poor
    6 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • x
    About this property
    Welcome to the ultimate in large family luxury vacation homes, with peeks of the Gulf of Mexico from the balconies! This 6 bedroom/4.5 bath beauty features a large, private, tropically landscaped backyard with heated pool and hot tub, gas grill, swim up tiki, and covered tiki bar area with flat... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 16
    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) - 202 78th Street - Holmes Beach A perfect beach is one where all you need is a bottle of sunscreen and a towel. All you... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 23
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Just two short blocks from the beautiful beach of Anna Maria Island, this adorable, elevated two-bedroom vacation rental awaits you for vacation! Jo-Joes Beach Place has been recently refurbished and is ready for you to relax and enjoy the sun and sand on Anna Maria Island. Centrally located in... 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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    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.; 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
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Come and stay in Holmes Beach at this contemporary, custom, elevated, single family home with spectacular Bimini Bay frontage. This magnificent home has all the bay-front views you would ever want from almost every room. This home was remodeled in 2013 to include a great open floor plan with 3,676... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 24
    4.5 of 5 stars (8) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    At first glimpse, Happy Heron will make you smile! Just one short block away from the pristine water of the Gulf of Mexico and Anna Maria Island's gleaming white sand beaches, this one-bedroom, one-bath vacation rental has been completely remodeled inside and out for your vacationing pleasure.... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 24
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Centrally located on Anna Maria Island in the city of Holmes Beach, this dog-friendly vacation rental is on a large corner lot just one block from the white sand beaches of the Gulf of Mexico. Upon arrival, you will be greeted by a large covered porch - the perfect location to relax and enjoy the... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 18
    4 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.; Elegant and tropical poolside paradise holiday rental. (4) Bedroom, (3.5) Bath, accommodates to (12) people: (2) Kings, (1) Queen, (4) Twin Bunks, (1) Queen... 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.; Relax and unwind in the casually luxurious Anna Maria Island vacation rental home “Sapphire Beach House”. This four star rental has everything experienced... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 15
    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.; "Forever Flip Flops" welcomes you to this recently re-done and updated island home. Just steps from the Gulf of Mexico and the pure white sandy beaches of... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 33
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    The views from this unit make you feel like your sitting right on the beach! Enjoy the beach and gulf views from this direct beach front unit (#102) at Martinique South. This spacious 1BR/1BA unit has been updated with tile floors and a new kitchen. All new furnishings and decor. Enjoy the... View all property information
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    Holmes Beach, Anna Maria Island
    1 / 20
    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
    1 / 15
    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
    1 / 27
    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 8 | Quick View
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    This beach house is "A Shore Thing" for creating fantastic vacation memories. This newly furnished ground level home is decorated in coastal living motif and has no stairs to climb. The open floor plan is ideal for one or two families to have a fantastic vacation. The living room, Florida room... 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.;   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
    1 / 24
    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
    1 / 20
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • 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.; 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
    Location Information
    Holmes Beach, Anna Maria Island
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
    • Balcony
    • Washer
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • 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.; Accommodating up to six guests for a fun laid back beach vacation, Casa Sierra 205 B offers the perfect two bedroom, two bathroom getaway for you and your... 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
    • Patio
    • Grill
    • DVD Player
    • Washer
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 13
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • 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.; 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
    1 / 28
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • 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.; Visit this marvelous private custom-built vacation rental home just a few steps from the white sandy beaches of Anna Maria Island and the Gulf of Mexico. 6... 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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    • Air Conditioning
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • 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.; Bedroom, 1.5 Bath (sleeps 5) - 'Sandy Pants' - 133 White Avenue, Anna Maria Remodel January 2015! Be the first to see all the new decor, appliances,... 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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    • Pet-friendly
    • Child-friendly
    • x
    • ?
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    • 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.;   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
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • 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.; 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
    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • 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.;   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
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 23
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Parking
    • Balcony
    • Terrace
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • 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.; 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
    Location Information
    Holmes Beach, Anna Maria Island
    1 / 33
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • 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.; 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
    Location Information
    Holmes Beach, Anna Maria Island