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Anna Maria Island Cheap Vacation Rental Deals

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    Travellers to Anna Maria Island are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    326 Matching Rentals in Anna Maria IslandView all 1,304 rentals
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    Steps to beach and bay on beautiful Anna Maria Island1 / 17
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    • Patio
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    Pet friendly
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    About this property
    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Shore Leave1 / 13
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    Reviewed July 5, 2018
    Not much to say. Nothing bad anyhow. We were very comfortable, and the location was great for us. We'd stay here again.
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    About this property
    Shore Leave is a 1 bedroom, 1 bath private ground level cottage located on the West side of Gulf Drive just across the street from the beach. Cottage is located on a quiet street in a quaint beach neighborhood. Close to shopping, restaurants and the free island trolley stops. Amenities Include:...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    About this property
    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Balcony
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    Pet friendly
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    Smoking allowed
    About this property
    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    About this property
    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Terrace
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    About this property
    4001 Gulf Drive, Holmes Beach, Anna Maria Island Beach Townhouses # 111 ... View Manatee Beach from two balconies in this spacious, freshly painted, tastefullly decorated end unit. This 2 bedroom, 2.5 bath townhouse has new windows and doors, electric fireplace, wireless internet, phones,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
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    Smoking allowed
    About this property
    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Grill
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    Smoking allowed
    About this property
    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    All you will need are your clothes and food while you enjoy your gulf coast destination! Across the street from a beach access, feels like your private beach. Full kitchen, living, & dining room. The comforts of a home away from home. Free trolley service that runs all day! Plenty of shopping,...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Smoking allowed
    About this property
    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Enjoy an endless summer at this cute and cozy 1 bedroom, 1 bath ground floor duplex unit located just a short block and half to the beach. Direct beach access at the end of the street. Kitchen has a full size refrigerator and apartment size electric range. Bedroom has 2 twin beds. Sleeper sofa in...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    About this property
    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    The Anna Maria Island Beach Retreat1 / 45
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!! The Anna Maria Island Beach Retreat is a completely remodeled two bedroom one bathroom condo, located four houses from Anna Maria Island’s exquisite white powder sand beaches. Included with your stay is one free...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    About this property
    Anna Maria island is the best place for a Florida vacation. Winter or summer - it is perfect for every age, life style, or adventure. This house is in the middle of everything. Within 100 yards off the tennis court, dog park, basketball court, boat ramp, marina, restaurants, and shops. It is a 10...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    About this property
    Location, location, location, this cozy quaint beach house is centrally located on Anna Maria Island and is less than a 2 minute walk from Holmes Beach. The 2 bedroom and 1 bathroom unit is not only a very short walking distance to the beach, but is also a short walking distance to shopping and...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    PLAYA ESMERALDA on beautiful Anna Maria Island a charming Bungalow 20 steps to the beach. This one-bedroom unit is nicely decorated with a island vibe. Unit has a well-equipped kitchen with full size refrigerator, stove with oven, microwave, toaster and all utensils. air conditioning, heat and...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Immerse yourself in the Florida island life at this beach side vacation rental just steps to Holmes Beach and within walking distance to grocery stores, restaurants, and more. Homes Beach is an active beach side community located approximately 8 miles from downtown Bradenton and offers a wide...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    About this property
    Enjoy your stay in this quaint 2 bedroom, 1 bathroom mobile home in a 55+ community. Just steps to beach or enjoy a relaxing sit on the bayside. Great for active adults looking to enjoy some time without the kids. Sandpiper 55+ Resort is on beautiful Anna Maria Island on Florida's Gulf coast. It...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    Vacation in your own tropical sanctuary on Anna Maria Island. This 2 bedroom and 2 bathroom single family home is located on a quiet cul-de-sac and only steps away from the soft sand beaches of Anna Maria Island. Enjoy amazing sunsets at the famous picturesque Bean Point Beach only a short distance...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Tropical paradise awaits at this 2BR/1BA villa located across the street from the beach at the beautiful, quiet North End of Anna Maria Island. Sleeps 4 with a double bed and two twin beds. Nicely furnished with tiled floors and updated interior. Enjoy the Gulf breezes from your screened lanai....
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    This charming 2BR/1BA cottage is located across the street from the Bay and just doors away from the Rod-n-Reel Pier. Home has a queen size bed and two double beds. The updated kitchen comes with a dishwasher and microwave. Washer/Dryer. There is a screened lanai with a view of the Bay. Bayfront...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    West Bay Cove 222 - Condo 2 Bedroom/ 2 Bath , maximum occupancy of 6 people. Distance to the Beach: 1 blocks West Bay Cove is a great location for taking advantage of everything that Anna Maria Island has to offer. Only a block from the public beach area, close to the grocery store, several...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    210 Haverkos #1-Duplex 1 Bedroom/ 1 Bath, Shared brand new Pool. Maximum occupancy of 4 people. Distance to the Beach: 3 blocks VRC18-000025 Rental fee reflects a discount for the construction disturbance while the landscaping is being done.. This is a ground level duplex that's fun and...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    About this property
    This 2 bedroom, 2 bath villa is in the heart of Anna Maria Island. It is located 500 feet to the beach in a residential neighborhood, west of Gulf Drive. Decorated with simplicity, it is fully equipped with all the amenities which include: Full kitchen, washer/dryer, microwave, dishwasher, cable...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunny Cottage is located within a 2 min. walk from the Palma Sola Bay right across from Anna Maria Island. Sit and enjoy the views in the park. 5 min. drive to the most beautiful Gulf beaches. Watch the dolphins swim and relax on the beach. Snorkeling, fishing, biking and lots more. Great...
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    Bradenton Beach, Anna Maria Island 34210
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Amazing beachfront Studio on Bradenton Beach, Anna Maria Island. Step out your door and your feet are in the sand. I doesn't get any better than this. This small studio has everything you need to enjoy your time in the Florida Sunshine. Many restaurants and shops nearby and even take the...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    This newly decorated and refurbished condo is the answer to your dreams this fall. This 2 bedroom 1.5 bath condo is 300 steps to the beautiful white sands and crystal blue waters of Anna Maria Island. The condo is completely turn-key ready--nothing to bring but your swimsuit and toothbrush. Condo...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Smoking allowed
    About this property
    Enjoy quite sunsets from your private screened balcony at this two bedroom two bathroom third floor condo with preserve views. The large kitchen with breakfast bar is well stocked wth everything you would need for preparing small meals to family dinners. The living room is furnished with a flat...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Sandy Point 109 - Condo 2 Bedroom/ 2 Bath, pet friendly, maximum occupancy of 6 people. Distance to the Beach: 4 blocks. VRC Sandy Point condo is situated in a private complex right in the heart of Holmes Beach and is conveniently located across from the island grocery store, shops and...
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    Holmes Beach, Anna Maria Island 34207
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Late Spring 2018 STILL AVAILABLE!!!!!!!!!!!!!!!!!1 / 16
    (2)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Reviewed June 2, 2018
    No unpleasant surprises .Condo was just pictured .Five miles to beachs, two minutes to Cortez Ave. Pool was kept clean, Gate is kept closes 24 hours good security.
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    Freshly renovated in an under the sea theme. Make this your yearly oasis! Master Bedroom hosts brilliant orange linens on the queen size Perfect Sleeper bed with Caribbean Blue accent wall. An oasis to drift away after a long day in the Florida sun. Full on suite bathroom and walk-in closet...
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    Bradenton Beach, Anna Maria Island 34210
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    **PARADISE RETREAT IN BRADEN RIVER LAKES**1 / 23
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Secure Parking
    • Private Outdoor Pool (Heated)
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    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 29, 2018
    We really enjoyed our stay for Memorial Day weekend. Even though the weather wasn't what we planned for, thanks to a tropical storm! Of course the first one of the season and...
    Reviewed May 5, 2017
    Such a joy to rent this beautiful home. Warm pool and all the extras. ..,, soft towels, kitchen supplies and dishes, bath soaps, a garage to use and lots of seats, space and...
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    About this property
    This tropical retreat single family home boasts 1800sq. ft.of living space on the in the Braden River Lakes subdivision. The home is nestled among lush tropical palms and Florida vegetation. The expansive plantings provide privacy and a natural preserve setting in the backyard tropical paradise....
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    Bradenton Beach, Anna Maria Island 34208
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • Hot Tub
    • Sauna
    • DVD Player
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    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
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    Kid friendly
    Smoking allowed
    About this property
    FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!! The Anna Maria Island Beach Palms 7A has just been completely remodelled with all new flooring, all new contemporary doors, all new baseboards, completely repainted from wall to wall and much more..... See our upated...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Parking
    • Terrace
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This two bedroom, one bathroom, home sleeps upto four people.  The kitchen includes an electric stove, microwave oven, coffee maker, and a toaster.  The master bedroom has a queen size bed and the second bedroom has one twin bed.  The living room has a sofa bed as well.  The home has a backyard...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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