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Anna Maria Island Luxury Holiday Rentals

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    Travellers to Anna Maria Island are booking February dates now. Secure your holiday rental today, and have the perfect trip.
    201 Matching Rentals in Anna Maria IslandView all 1,343 rentals
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    8 Bedrooms, 8 Bathrooms, Sleeps 20 Quick View
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    p class='rtejustify'>Welcome to the Four Beach Lovers (Formerly Dawg Daze). Located at 2908 Avenue E in Holmes Beach, this gulf front tropical paradise features four well-appointed and comfortable one bedroom units. Each of the four units is fully equipped and tastefully furnished. All four units...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 16
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    The Absolutely Perfect Beach House, located at 3009 Avenue F in Holmes Beach is just that – absolutely perfect! This spectacular four bedroom, three and one half bath gulf front home with an extra media room. It has its own private beach and heated pool has just been built. This beautiful home is...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    About this property
    Treat yourself to the experience of a lifetime with this luxury Anna Maria Island home with a private heated pool, balcony with gorgeous views, and an unbeatable location right on the beach. Situated directly on the pristine white sands and warm waters of the Gulf of Mexico, this extravagant home...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    Dragonfly is a spacious, private retreat located right across the street from the sugary white sands of famous Bean Point Beach in Anna Maria, Florida. Glimpse sparkling turquoise waters from upper floor bedrooms, frolic in the pool with spa and sundeck, or create culinary delights in the gourmet...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    7 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Secure Parking
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    About this property
    Many homes with a high bedrooms count sprung out on the island lately, designed to maximize rents, they are built on very small lots normally 50 ft wide and packed upwards in three levels . This is a well reviewed house that I built for me and my family in 1998, it is the largest private rental...
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    Anna Maria Island, Florida 34217
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 16
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    About this property
    This fun and convenient private home is a favorite amongst guests who return year after year! Located in the heart of Anna Maria Island, 'SURFSIDE' is close to all of the beach activities, shopping, dining, and entertainment. Amenities that set it apart include a LARGE, private fenced yard with...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    8 Bedrooms, 4 Bathrooms, Sleeps 22 Quick View
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    Pet friendly
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    About this property
    The MI Happy Place  is excited to be under new ownership and management, with new amenities and improvements to make a beautiful, convenient, and relaxing location even better! When renting MI Happy Place Island Resort you will have eight bedrooms and four bathrooms sleeping twenty two making...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 8 Bedrooms, 4 Bathrooms, Sleeps 22
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    8 Bedrooms, 8 Bathrooms, Sleeps 24 Quick View
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    Seagrass Flats Condo is a four unit complex located at 101 25th Street North in Bradenton Beach that features a large heated pool and bbq area. Immediately across from the beach, you can be on the sand in less than one minute. It’s a perfect vacation retreat for large family get- togethers and...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 8 Bedrooms, 8 Bathrooms, Sleeps 24
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    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    About this property
    p class='rtejustify'>The Anna Cabana Resort, located at 3711 4th Avenue in Holmes Beach consists of four units, all located less than one block to the beach. All four units have been are decorated in a festive, tropical decor. There is also an onsite laundry room for provided for your use. A brand...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 16
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Central Heating
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    VITAMIN SEA is a brand new construction home that features 5 bedrooms and 5 bathrooms and a fantastic location-just a 10 minute stroll to the White sandy beaches of BEAN POINT on the coveted north end of Anna Maria. This lovely property offers a private heated pool with a spa, The backyard is an...
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    Anna Maria, Anna Maria Island 34216
    Condo/Apartment - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    About this property
    Welcome to the Four Beach Lovers (Formerly Dawg Daze). Located at 2908 Avenue E in Holmes Beach, this gulf front tropical paradise features four well-appointed and comfortable one bedroom units. Each of the four units is fully equipped and tastefully furnished. All four units feature a private...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 16
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    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    p class='rtejustify'>The Valhalla located at 3216 Gulf Drive in Holmes is a wonderful five bedroom, three bath Gulf front duplex on a secluded beach. While the Valhalla is tucked away in a quiet area, it is within walking distance to shopping and restaurants. The location is perfect! Each unit...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    Casa Playa - Combo1 / 52
    (3)Very good
    8 Bedrooms, 8 Bathrooms, Sleeps 20 Quick View
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    • Cable/satellite TV
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 January 2015
    We stayed at Casa Playa for the week after Christmas over New Years! The location is amazing...close to everything you need except a grocery store. The weather was perfect, the...
    Reviewed 9 April 2014
    We stayed here for the full month of March and very much really liked this unit. The owners ( Scott Deb ) were very nice, as they were wanting to make sure we had everything we...
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    About this property
    This Bradenton Beach vacation home is actually two rentals in one, in the middle of all the fun and beaches that Bradenton Beach can offer. The rental package sleeps up to 20, and everyone can enjoy the 2 private swimming pools. This is a fully equipped rental home on Anna Maria Island, with...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 20
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At 4 bedrooms and 3 full bathrooms, this is one of the most charming rentals on Anna Maria Island!! Located a few houses from the beach, it is only a two minute walk until white powdery sand is between your toes! Easy on the kids and even easier on you! Around the corner from restaurants, pubs &...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Balcony
    • Housekeeping Included
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2016 New Custom 4 Bedrooms 4.5 Bathrooms resort size pool/spa Anna Maria Island home on a residential cul-de-sac and a boat dock in your back yard. This luxury home is quality built CBS and offers a chef's kitchen for all to enjoy. This Island retreat is located walking distance to the beach and...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Villa Marisol, located at 797 North Shore Drive at the north end of Anna Maria Island and nestled on the shores of the Gulf of Mexico, offers breathtakingly beautiful views of the crystal blue waters of the gulf. This is unquestionably one of Anna Maria's loveliest homes. This spectacular home...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Internet Access
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    Pet friendly
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    About this property
    2311 Ave C is a combination of Addy's Inn and Island Retreat on beautiful Anna Maria Island is the home you will want to come back to time and time again. We are family oriented With 6 bedrooms and 4 bathrooms. The open setting has room for everyone. The living room is equipped with a 50' flat...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 16
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Beautiful luxury beach front condominium for rent for the first time. There's only 2 condo's on the entire property. This condo is 3500 square feet including gourmet kitchen, dining room, living room with fireplace and built in flat screen TV. screened in lanai overlooking the Gulf of Mexico, den...
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    Anna Maria, Anna Maria Island 34210
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    9 Bedrooms, 6 Bathrooms, Sleeps 26 Quick View
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    • Central Heating
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    About this property
    The Blue Dolphin Inn, located at 780 Jacaranda and 404 Alamanda in the tranquil City of Anna Maria features four units surrounding a tropical heated pool with tiki huts, grills, rooftop observation decks and loads of charm. Each unit has its own private patio and charcoal grill for an evening of...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 26
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    Stunning luxury newly constructed beachfront villa1 / 22
    (22)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
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    • Private Outdoor Pool (Heated)
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 July 2017
    Beautiful three level beach house on the northern end of Anna Maria Island. Relaxing and very comfortable home where our family enjoyed reconnecting during our vacation after a...
    Reviewed 1 May 2017
    If you are looking for a property to relax by the beach or a swimming pool, this is about as good as it gets. There is nothing the owner's have not thought about. Great ocean...
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    About this property
    4 Bedroom 5 bath luxury beach front house sleeping 8 with heated pool separate spa numerous decks and stunning beach views from every room. We are located on the desirable family friendly island of Anna Maria. The house is direct beach front on the quiet upmarket north end of the island. Recently...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Beautiful new 4 bedroom 3 bathroom home ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the heated pool in your own backyard oasis. This house has every luxury you could want, Flat screen TV’s, stainless steel...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    9 Bedrooms, 6 Bathrooms, Sleeps 26 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    p class='rtejustify'>The Blue Dolphin Inn, located at 780 Jacaranda and 404 Alamanda in the tranquil City of Anna Maria features four units surrounding a tropical heated pool with tiki huts, grills, rooftop observation decks and loads of charm. Each unit has its own private patio and charcoal grill...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 26
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    Jewel of the Bay: LUXURY Waterfront Home, Breathtaking Views! Pool,Spa,Elevator!1 / 24
    (6)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Grill
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    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 May 2018
    We have been renting this house in May for 3 years. It is awesome. Four king on suites so perfect for 4 couples. Beautifully appointed. Heated pool that overlooks your...
    Reviewed 5 June 2017
    Anna Maria is a wonderful place with a laid back way of life. There are some great places to eat and drink and the beaches are superb.The thing that made our holiday really...
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    About this property
    Book Now & Save 15% Off When You Stay Before Dec. 31st, 2018! + Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! This is the luxury vacation rental home of your dreams! This custom bay-front home on the north end of Anna Maria Island offers 3600 square feet of...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Terrace
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 steps from the beach with fantastic Gulf views. This home is the perfect beach getaway  with everything you could want while enjoying Anna...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    6 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
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    • Housekeeping Included
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    • Wi-Fi
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful vacation home in Bradenton Beach, has been fully renovated with brand new furnishings, and is actually two homes in one! You can enjoy a fantastic pool area for relaxing days in the sun or after a day at the beach. Right next to the heated pool, is a covered outdoor seating area...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 16
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    8 Bedrooms, 8 Bathrooms, Sleeps 24 Quick View
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    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    Seagrass Flats Condo is a four unit complex located at 101 25th Street North in Bradenton Beach that features a large heated pool and bbq area. Immediately across from the beach, you can be on the sand in less than one minute. It’s a perfect vacation retreat for large family get- togethers and...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 8 Bedrooms, 8 Bathrooms, Sleeps 24
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Air Conditioning
    • Waterfront
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Elegant, Beachfront Top Floor Condo - walk directly onto the Beautiful beaches of Anna Maria Island. Honey maple kitchen cabinets with granite tops and stainless steel sinks. Elegant baths. 50' plasma HD flat screen TV. Amenities include Dishwasher, large open balcony, two designated covered...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    510 Bayview1 / 20
    (3)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 April 2016
    Had a fantastic week here nine adults and we did not bump into one another once 4double rooms and 1 twin all with their own bathrooms pool area great pity that the water...
    Reviewed 29 December 2015
    I recently stayed at this beautiful house and it was the best decision I made for the holiday. First, the rental company was so easy to work with. There was no stress at all...
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    About this property
    510 Bayview - Private canal home 5 Bedroom / 5 Bath with private pool , maximum occupancy of 10 people. Island Elegance for the whole family!~ Distance to the Beach: 2 blocks Come to Anna Maria Island, bring family, friends and your boat to enjoy the simple pleasures of life: sun, sand, and...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for luxury, then this Anna Maria Island vacation rental home is the perfect getaway! With a private pool, ocean views, and even roof top deck, you'll have everything you need for a memorable stay. Located on the coveted west of Gulf Drive strip, you'll be just steps from the...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    The Beachcomber, located at 3306 4th Avenue in Holmes Beach is the ideal, dream vacation home. This recently built gulf front home features a heated salt water pool and spa nestled in a tropical setting. It does not get any better than this! Luxurious furnishings, an elevator, a gourmet kitchen, a...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Limefish, spectacular beachfront location!1 / 22
    (30)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Internet Access
    • Cable/satellite TV
    • Patio
    • Washer
    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 June 2015
    Just finished a 14 night stay at Limefish, and as 3 years ago it was a fantastic experience. As per the title the location is bang on, it's a 10 minute walk to the start of the...
    Reviewed 8 November 2014
    We were staying here with friends who were getting married on the beach. It is paradise. The villa was perfect for seven of us, though one couple had to have bunk beds, and we...
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    About this property
    Limefish, from Pineapplefish is one of the most stunning beachfront holiday rentals on Anna Maria Island, with direct access to a beautiful, almost private beach. With spectacular views across the Gulf, Limefish has a wonderful and spacious decked area across the whole of the property, where you...
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    Location Information
    Anna Maria Island, Florida 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Parking
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    • Cable/satellite TV
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    • Balcony
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book Now & Save 15% Off When You Stay Before Dec. 31st, 2018! + Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! Located directly across from Tampa Bay, this gorgeous new custom luxury vacation rental looks out onto the beautiful bay waters from multiple large...
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Central Heating
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Anna Cabana Resort, located at 3711 4th Avenue in Holmes Beach consists of four units, all located less than one block to the beach. All four units have been are decorated in a festive, tropical decor. There is also an onsite laundry room for provided for your use. A brand new heated pool has...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 16
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Terrace
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    • Balcony
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Coconut Breeze is a custom home on the north end of Anna Maria in the quiet residential area in the sought after City Of Anna Maria. Offering 4 bedrooms / 4 bathrooms. You will find that this home has everything you need for your perfect Anna Maria Island vacation! From the luxurious heated pool,...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Parking
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    • Private Outdoor Pool (Heated)
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    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Summer Retreat is an absolutely amazing brand new (2017) custom luxury home nestled in the quiet residential area in the heart of Bradenton Beach. Offering 4 bedrooms each with a private bathroom, a kids gaming room and 4.5 bathrooms, you will find that this home has everything you need for your...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Waterfront
    • Grill
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bask in the elegance of this three-bedroom Holmes Beach penthouse, a beachfront retreat with direct access to the sand, a wrap-around balcony with stunning Gulf views, and shared amenities that include a heated swimming pool, a patio, and a grilling area. Stunningly situated on the west coast of...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    The Valhalla located at 3216 Gulf Drive in Holmes is a wonderful five bedroom, three bath Gulf front duplex on a secluded beach. While the Valhalla is tucked away in a quiet area, it is within walking distance to shopping and restaurants. The location is perfect! Each unit features a large covered...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    5 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    • Parking
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Overview Gulf Sound is a gulf side, ground level tri-plex on the southern end of Holmes Beach. This five bedroom, three bath property is fully equipped with everything you need for your stay. Each unit has been updated and is comfortably furnished. It's quiet, yet close to shopping, restaurants and...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 16
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Ocean Views
    • Waterfront
    • Central Heating
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Direct Beach Front Home with 180 degree Gulf Views. Your backyard is a Private Beach and a beautiful view of Egmont Key & the Skyway Bridge. Walk to the Rod & Reel Pier where dolphins frolic every afternoon or walk to Pine Avenue for some local shopping. The living level has a full size kitchen,...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    6 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    • Patio
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
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    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A special time awaits you at this updated beach house on Anna Maria Island. Featuring a dog-friendly attitude, a private lagoon pool, and easy access to Bean Point Beach, this house will leave you dreaming about the tropics for weeks after your trip. Located at the tip of Anna Maria Island, a...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 16
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A fantastic vacation rental for families or small groups that includes spacious patio area to enjoy your outdoor dining. Look forward to placing your your toes in the sand about one block away, or sailing on Sarasota Bay. Enjoy both units A & B when booking Beach Breeze Combo. Both units are easily...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large 5 bedroom / 4.5 bath family home close to the best beach on AMI with a heated pool. The home is 130 steps to the beach, close to the stops for the free bus trolley which runs the island, close to the shops and restaurants of Pine Avenue. The home has a fully stocked kitchen, all the beach...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Private Outdoor Pool (Heated)
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    OVERVIEW Tranquil beachfront luxury penthouse is part of the Bradenton Beach Club that provides the very best in vacation accommodations. Amenities at the BBC include two swimming pools (one directly on the beach) and private beach access.This truly unique property with 4 bedrooms and 2.5 baths...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • DVD Player
    • Grill
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the beauty of Anna Maria Island with your large group at this pair of vacation houses. Featuring two private lagoon-style pools, island views, and beach access nearby, this rental is the perfect solution for your next getaway. Located about two blocks from the beach in the community of...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 16
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    Stunning 6 Bed 5.5 Bath Heated Pool Spa Water Slide FREE WiFi Gulf Views1 / 49
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 June 2018
    Our family of 7 adults and 4 children thoroughly enjoyed our week long stay at The Big Kahuna. The house has a great holiday feel and is divided into two separate apartments...
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    About this property
    OCEAN VIEW is a brand new construction home that features 6 bedrooms and 5.5 bathrooms and a fantastic location-just a 1 minute stroll to the White sandy beaches at the 65th st access! This lovely property offers a private heated pool with a spa, water slide and grotto. The backyard is an oasis...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Private Outdoor Pool (Heated)
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Following an extensive renovation in 2018, Dragonfly Harbour is now a handsome four-bedroom, five-bathroom private vacation home situated on a deep water canal in close proximity to Bimini Bay. This is a venue designed to allow our guests every opportunity to enjoy all facets of beautiful Anna...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Patio
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    p class='rtejustify'>Just 150 steps to a beautiful white sandy beach located in the preferred and more private northern end of Anna Maria Island, The Harrison Home at 6901 Gulf Drive features many new renovations and updates. This spacious four bedroom and four bath home has one of the largest...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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