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Holmes Beach Cheap Vacation Rental Deals

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    Travellers to Holmes Beach are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    164 Matching Rentals in Holmes BeachView all 656 rentals
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    Shore Leave1 / 13
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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, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, 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, 2 Bathrooms, Sleeps 6
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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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    1 Bedroom, 2 Bathrooms, Sleeps 4 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 - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    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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    *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 5 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, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, 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, 2 Bathrooms, 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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    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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    The Anna Maria Island Beach Retreat1 / 45
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    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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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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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    *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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    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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    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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    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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    *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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    3 Bedrooms, 2 Bathrooms, 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 - 3 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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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 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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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    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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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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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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    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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Beautiful second floor end unit fully furnished vacation condominium in Holmes Beach Florida with fabulous view of dolphins splashing in Bimini Bay and the incredible Gulf Coast sunsets from the screened lanai. Take a short walk to the white sandy beach of the Gulf of Mexico in pristine Anna Maria...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    This beautiful island condo is newly refurbished and redecorated for a perfect get-away. This quiet, 55+ community is a paradise. Situated in Anna Maria Island, Florida, the island has quiet, old-Florida charm with numerous restaurants, shops, and conveniences. A free trolly runs the length of...
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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 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...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Westbay Cove 208 located at 600 Manatee Ave West in Holmes Beach is a picturesque and luxurious one bedroom one bath bay front condo on Anna Maria Island which features gorgeous views of the Tampa Bay. From the spacious balcony, you can enjoy breathtaking sunrises over the bay and spectacular views...
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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
    Anna Cabana Bungalow #3 located at 3711 4th Avenue in Holmes Beach is in a ground level five unit complex that’s fun and affordable. It adjoins three other of the Cabana Bungalow units and is next door to the Cabana Beach House. With the numerous room configurations this is a perfect complex for...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    The Bollinger Duplex, Side B is a ground level one bedroom, one bath duplex located at 6909 Gulf Drive, in the preferred northern area of Holmes Beach. It only one-half block to a beautiful beach where you can stroll from one end of Anna Maria Island to the next! This ground level unit is...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    Coastal Hideaway: Gorgeous Family-Friendly  Condo With A View Of The Pool!1 / 24
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Reviewed June 6, 2017
    This condo is as immaculate as it is in the pictures! Very pristine and beautifully decorated. The owner has thought of just about anything you could possible need while...
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    About this property
    Come to Anna Maria Island and stay at Coastal Hideaway! This recently renovated two-bedroom, two-bath condominium, located in Holmes Beach, is a fantastic place for your vacation. A beautiful vacation rental condo with an open floor plan invites you to relax the minute you walk in the door. A new...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!! Recently remodelled with a new designer kitchen with granite counter tops, stainless steel applinaces and a new walk in shower. As added amenities enjoy one free breakfast per person at the Beach Cafe plus free daily...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Westbay Cove 208 located at 600 Manatee Ave West in Holmes Beach is a picturesque and luxurious one bedroom one bath bay front condo on Anna Maria Island which features gorgeous views of the Tampa Bay. From the spacious balcony, you can enjoy breathtaking sunrises over the bay and spectacular views...
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    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Pet friendly
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    Smoking allowed
    About this property
    Enjoy Lazy Days on Beautiful Anna Maria Island. This 2 bedroom, 1 bath single family home is located across the street from the beach in central Holmes Beach with beach access just a few properties away. This 'old Florida' home has been appointed in a sleek and modern feel and has a newly updated...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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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 Castaway 1 is located directly in the middle of Anna Maria Island. A beautiful remodelled 2 bedroom, 1 washrrom condo conveniently across from the seven acre Manatee Public Beach and the...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    • DVD Player
    • Internet Access
    • Patio
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    • Cable/satellite TV
    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
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Patio
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    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sea Pirate 1 has been recently renovated throughout and is conveniently located close to shops and restaurants; and most of all; less than 100 feet from the beach. There are eight units total in the complex with a heated pool with easy access to the beach. Amenities Include: Full kitchen, dishes,...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Smoking allowed
    About this property
    Beautiful views of Gulf. Secured entrances to building & pool areas. Tennis court on premise. FREE trolley stops at entrance. 1 enclosed garage & 2 guest parking spots. Activity room open for game nights, & cocktail parties. Walk to restaurants, post office and convince stores. Beautiful views...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Gulf Beach Place - Just a few steps from the beach1 / 21
    (45)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Ocean Views
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 days ago
    We can't thank the owners enough for such a wonderful stay. It was our first visit to the island & won't be the last! The condo exceeded our expectations; spacious, nicely...
    Reviewed 5 weeks ago
    We had a wonderful stay in this condo! It was very comfortable & spacious & had everything we needed. Working with Kay was also a pleasure. I would definitely recommend...
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    About this property
    Gulf Beach Place is in a fantastic location, just steps from the 7 mile long famous white sand beach and almost halfway from top to bottom of this quaint ‘Old Florida’ island. There are no roads to cross to get to the beach making this a great location for families. Our pretty condo offers you the...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Central Heating
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Cove at Sandy Pointe #210, at 3601 East Bay Drive is a light and very private, two bedroom and two bath condo in a secluded complex close to shopping and conveniently located to the beach. This unit was completely renovated in 2016 to a high standard. Sandy Pointe features undercover parking...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Cable/satellite TV
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come and stay at this newly renovated unit; one of two units available at this superb duplex located just 500 meter from beautiful Holmes Beach on Anna Maria Island. This spacious two bedroom two bathroom property can accommodate up to 6 persons with a queen-size bed in the master bedroom with...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Cove at Sandy Pointe #208, at 3601 East Bay Drive is a cheerful, two bedroom and two bath condo in a secluded complex close to shopping and conveniently located to the beach. Sandy Pointe features undercover parking and a large heated pool. Each unit has a large screened lanai. This well...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Grill
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    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come and stay at this beach side vacation rental on Anna Maria Island. This unit is located on the ground floor of a quaint beach cottage just steps to the sands of Holmes Beach. Shopping center and grocery store is also within walking distance. If you desire to travel the island you can enjoy the...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Washer
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come and stay at this newly renovated unit; one of two units available at this superb duplex located just 500 meter from beautiful Holmes Beach on Anna Maria Island. This spacious two bedroom two bathroom property can accommodate up to 6 persons with a queen-size bed in the master bedroom with...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beach Townhouse Condo, located at 4001 Gulf Drive in Holmes Beach is a spacious two bedroom, two and one half bath town home condo with heated pool and gulf view. There are open lanais off both the living room and the master bedroom overlooking the large pool. Beach Townhouses is conveniently...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    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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    • Balcony
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Terrace
    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,...
    View all property information
    Location Information
    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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    Amenities & Details
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sandy Pointe Condo #210, at 3607 East Bay Drive is a cheerful, two bedroom and two bath condo in a secluded complex close to shopping and conveniently located to the beach. Sandy Pointe features undercover parking and a large heated pool. This unit has a screened lanai overlooking a natural...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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