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Pet Friendly Holiday Rentals in Anna Maria Island

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    Travellers to Anna Maria Island are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    168 Matching Rentals in Anna Maria IslandView all 1,043 rentals
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    avenue Beach house on GORGEOUS Anna Maria Island1 / 33
    (15)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Gorgeous views,spectacular home!1 / 92
    (32)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    250 Feet from the Beach1 / 25
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    White House Vacation Apartments1 / 30
    (7)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 days ago
    This was a great place to stay. Clean and I’m a great location. Neighborhood was quiet and safe. Terri was a great host Check in and out was easy. We will definitely be...
    Reviewed 5 October 2017
    My family and I and of course our family dog were welcomed with open arms. The apartment was very roomy and comfortable and had all the comforts of home with full size...
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    About this property
    Just half a block to the beach and steps to our fishing dock on Sarasota Bay, these cute and cozy apartments offer a great vacation value on Anna Maria Island. Watch the sunrise from the dock every morning and cap your busy day with sunset over the Gulf of Mexico. White House Vacation Apartments...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Sand Castle well appointed home steps from beaches1 / 50
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Grill
    • Private Outdoor Pool (Heated)
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 August 2017
    My family stayed in this home August 2016. The home is beautiful and we enjoyed our stay very much. The home was well equipped and pretty clean. I did has a couple issues at...
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    About this property
    Beautiful, recently renovated 1700 sf home that accommodates up to 8 people. Only a few steps to amazing sandy gulf beach. Enjoy all the amenities of a single level well appointed home with no stairs where you can step out to the beautifully landscaped pool area from your master bedroom or open...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    BEACHFRONT HOME, TRUE PARADISE , DOGS STAY FREE, GREAT VIEWS, WALKING BEACH1 / 22
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Wi-Fi
    • Waterfront
    • Washer
    • Cable/satellite TV
    • Grill
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 November 2017
    Awesome pet friendly beach house right on the water. It has amazing views of the Sunshine Skyway bridge and we enjoyed watching the boat traffic in the distance! So relaxing...
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    About this property
    This stunning BEACHFRONT home was designed by an award winning Architect and is true paradise. The plan is open with the Living, Dining, Kitchen and Master Bedroom on the Waterfront adjacent to the deck which runs the entire length of the home. The elevated deck is a mere 10' from the waters edge....
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cozy Cabana West - Private Pool - Close to Beach1 / 22
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Patio
    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    This rental was perfect for our family. Modern, spacious, clean, and totally stocked with everything you could possibly need. The private pool was wonderful, the beach is a 3-4...
    Reviewed 25 May 2018
    Amazing place for the family! It was our first time staying on the island and cozy cabana had everything we needed. Highly recommended this place and renting a golf cart for the...
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    About this property
    Recently renovated, 2 bed 2 bath Villa perfect for families, couples or a small group of friends. Located in a quiet neighborhood with an easy 3-minute walk to the gorgeous white sand beaches of the Gulf of Mexico. You are less than a mile from historic Pine Avenue shops, restaurants, and the Anna...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Anna Maria Island #2 Beachside Palms1 / 17
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Ocean Views
    • Housekeeping Included
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 May 2018
    The Rental was very relaxing, clean and easy to find. Location to the beach was excellent. The deadbolt lock was broken, this was unfortunate as one night someone was outside...
    Reviewed 25 February 2017
    Excellent spot. Immaculate. Close to beach (3 minute walk), Publix, Walgreens and CVS. Owner (Jerry) is super nice to deal with. You can book directly from Property...
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    About this property
    Beachside Palms Anna Maria Island Resort is extremely conveniently located directly across from the famous Manatee County Public Beach on the gorgeous Gulf of Mexico. All 3 of our units were completely updated in 2016. They feature new cabinets, stainless steel appliances and granite countertops....
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Anna Maria Island Nantucket1 / 29
    (23)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 January 2018
    My extended family stayed here this past December, and it was perfect. The place is showing it's age a bit, and there is a rather steep set of stairs to get to the main floor...
    Reviewed 10 April 2017
    We rented this home over Spring Break with my brother and his family. The layout of this house is great as well as the location of the home on the island. There were 2 master...
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    About this property
    3 Story 'Nantucket' Style - 4 bedroom/ 3 bath villa is just a short walk to the beach - Nestled in a tropical setting, only a few blocks to the Gulf beach; heated private pool great for cooling off and a large sun deck. 4 Bedrooms/3 baths, large master suite with king size bed and a roman tub,...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Beach House on Anna Maria Island-Rental Openings1 / 32
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Ocean Views
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 July 2017
    Had another great stay close to the beach and all the extras. Great weather over the July 4th. Very pet friendly.
    Reviewed 22 December 2016
    We spent only a family wedding weekend at this rental, but it was wonderful and we hated to leave. We couldn't possibly take full advantage of the Island shuttle, the beach, the...
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    About this property
    This 3 bedroom 2.5 bath villa with 2 car garage accommodates 6 guests and is 150 feet from the pristine white sandy beaches with easy access. It has a heated 16 by 34 foot pool shared with the identical rental house next door. This unit is fully furnished in tropical decor and has all the luxuries...
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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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    Beautiful Sunkst Cottage Bradenton Beach - AMI-Tropical Setting - Heated Pool1 / 14
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • DVD Player
    • Patio
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy our beautiful beach - Sunkist Cottage on Anna Maria Island. Our 3 BR/2 BA private home has a private HEATED POOL. We enjoy a quiet neighborhood setting. The large, tropical, outdoor deck area, overlooks the pool. It is ideal for grilling & outdoor dining. Sunkist Cottage is a short walk...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Casa Playa West  is a Luxury 4 bedroom home with a pool and elevator!1 / 37
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Ocean Views
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home provides you with your own private pool. It has virtually EVERYTHING you need for a perfect Island vacation. This home has a private pool and is less than a block to the beach and 1 block to Sarasota Bay for fishing. Walk to Sarasote Bay and watch the big yachts and boats pass by on the...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    On the Beach Paradise d1 / 13
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Ocean Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 January 2018
    Steps to the beach with lots of beach seating. A great outside dining area complete with grill. Our only problem was finding a comfortable bed. Some people like the foam...
    Reviewed 20 July 2017
    The most wonderful place! we rented this place for 10 days, my daughter, grandson and myself. I fall in love with the place is perfect, nice and very clean.Location is perfect...
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    About this property
    This cottage is located 'on the beach' 3007 Avenue F, beautiful Holmes beach. It is the downstairs unit (1 of 2). The cottage is very comfortable and sleeps 4 comfortably with additional space for a pull-out. This quaint cottage is hidden away on a dead end street, away from it all yet close...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Addy's Inn on beautiful Anna Maria Island is the home you will want to come back to time and time again. We are family oriented and pet-friendly. With 3 bedrooms and 2 bathrooms. The open setting has room for everyone. The living room is equipped with a 50' flat screen TV including HD TV, with...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    The Little Mermaid On Beautiful Anna Maria Island!1 / 17
    (24)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Washer
    • Parking
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 November 2016
    Can't speak too highly about the Little Mermaid and Anna Maria Island. What you see is what you get. Every possible utensil and beach toy is to hand and all spotlessly clean...
    Reviewed 5 October 2016
    Wonderful place to stay. Very clean. Hope to be a repeat guest. Pet friendly. Very close to the beach.
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    About this property
    You will enjoy this adorable newly renovated vacation cottage – THE LITTLE MERMAID -- on Anna Maria Island just across the street from the Gulf of Mexico and minutes from shopping and attractions on Bradenton Beach’s popular Bridge Street! Your three parking spaces are right at the front door!!...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Hooks Haven - 3bed beach front1 / 20
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Central Heating
    • Terrace
    • Waterfront
    • Ocean Views
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 May 2018
    We had a girls’ weekend and choose this location. Beach chairs, towels, washer-dryer, bikes.....perfect. Not a great view but only a few steps from the beach and central to...
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    About this property
    This 3 bedroom 2 bath home is on the north end of Anna Maria Island and can be combined with Pirate Cove (a separate building ) to make a 5 bedroom beach front vacation home. All bedrooms in Hooks Haven are Queen size. Two bedrooms are on the main floor and one is on the second floor. Spiral...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Tree House1 / 22
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Grill
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 March 2018
    We had a family of 6 of us stay last week, had everything we needed there. it was close to the beach! It was clean and had ample room for us all to sleep. We would definitely...
    Reviewed 5 July 2017
    Nice quiet location Has everything you need. We enjoyed our stay and would come back. Easy access. Clean!
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    About this property
    Thank you for considering my home which has been recently updated to provide the warmth and feel of a true beach cottage. Wooden ceiling planks have been added along with pine beach chic cabinets and decor. I put many hours into the design of the home to provide a feeling of tropical relaxation....
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    $200 OFF PARADISAICAL ENCLAVE 5*WaterfrontCanal/Pool/Dock/Kayak/Bikes/FamilyFun!1 / 45
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 May 2017
    My sisters and I had the best time. House in perfect area, great view. Very nice pool. Everything you need. We rented Golf Cart [AMI Golf Cart], and drove the Golf Cart...
    Reviewed 16 August 2016
    Beautiful location. Accurate description. Loved firm bedding in master bedroom. Kids complemented theirs. Nice entertainment ambiance. Confortable all around. Easy dealings with...
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    About this property
    Adriel's Place in Anna Maria... A two bedroom located in upscale private golf club neighborhood, a stone throw from pristine beaches, restaurants and island entertainment ( less than 1 mile ). An expansive backyard dotted with majestic palms, pavered terrace and pool overlooking sailboat water....
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Private Tropical Paradise in Holmes Beach!  Large home with Pool and fenced yard1 / 25
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Grill
    • Wi-Fi
    • Patio
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 April 2018
    We stayed at this house for 2 weeks. There’s a lot of room inside. House is well stocked with towels and any utensil you need. It is close to everything and the neighborhood is...
    Reviewed 22 March 2018
    Anna Maria Island is a friendly, eclectic place to visit. This is a very nice home with a fenced in yard and pool. It worked very well for our dogs and us!
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    About this property
    Tropical Paradise on Holmes Beach and ONLY 3 blocks to the beach. Anna Maria Island, noted for its old Florida ambiance, offers this Key West styled home, where you may awaken to greet the dawn sipping coffee on the balcony or swimming in your private pool. The modern interior arrangements add to...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    Anna Maria Island 'High End' Vacation Rental1 / 21
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Internet Access
    • Washer
    • Patio
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 March 2018
    The location is perfect - walking distance from both the beach and the Pine Avenue shops. This is a beautiful 2 bedroom home, outfitted with every detail. The pool and hot tub...
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    About this property
    The home is immaculately clean and whimsically decorated, professionally landscaped, and boasts one of the larger pools larger backyards and larger 2 bedroom homes on the Island. The spa is accented by iridescent glass. The 20' tall tiki hut was hand-built by Native Americans and houses the bar and...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Casa Playa East is a Luxury 4 bedroom home with a pool and elevator!1 / 33
    (2)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Washer
    • DVD Player
    • Ocean Views
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 October 2017
    We booked our stay here for our family (6 adults, 2 kids) totally unfamiliar with Anna Maria Island, coming for a wedding at a nearby venue. We couldn't have been happier...
    Reviewed 8 August 2015
    We rent a home in Anna Maria every year. Hands down, for my active group, this is the best location. Two blocks from hopping Bridge Street. Beach access 1/2 block away. Bay...
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    About this property
    This Bradenton Beach vacation home provides you and your family or small group with your very own private swimming pool, and comes fully equipped with everything you need for a wonderful vacation on this beautiful barrier island. Your accommodations are less than 1/2 block from the beach and 1...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Anna Maria Island #3 Beachside Palms1 / 12
    (1)Terrible
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Central Heating
    • Washer
    • Grill
    • Housekeeping Included
    • Patio
    • Ocean Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beachside Palms Anna Maria Island Resort is extremely conveniently located directly across from the famous Manatee County Public Beach on the gorgeous Gulf of Mexico. All 3 of our units were completely updated in 2016. They feature new cabinets, stainless steel appliances and granite countertops....
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    Holmes Beach, Anna Maria Island 34209
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A new luxury home for rent just one block from the beach on the beautiful Anna Maria Island. ISLAND RETREAT is the middle floor home of a beautiful duplex with its own private elevator and exterior entrance. You have over 1850 square feet of living space to spread out in plus a full-size back...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    AnnaMariaIsland a Paradise. MINUMIM RENTAL 2 WEEKS1 / 13
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Private Outdoor Pool (Heated)
    • Parking
    • DVD Player
    • Washer
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 June 2016
    Loved the location! Watch the sunset overnight and enjoyed the many restaurants offered nearby. Everyone was super nice and friendly. Thanks Richard for making our stay a...
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    About this property
    Just steps to a white sand beach, and blue green water. ( Bradenton Beach, across street ) Water view from Master bedroom, and Great room, 1120 square feet . 2 large bedrooms, 2 full bathrooms, living/dining combination room, kitchen, and laundry. plus screened in lanai. 3 level building with...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Cast Villa 11 / 31
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Washer
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 August 2017
    Was absolutely wonderful. Couldn't ask for better vacation. Very close to beach. Unit had everything we needed. Owner was very friendly and accomidating. Will definately be back.
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    About this property
    Anna Maria Island, This property is located directly across from the famous Manatee County Public Beach. Groomed daily, Lifeguards, restaurants, surf shop and more.. Free trolley stops there both northbound and south every 20 minutes. The location is also right in the heart of the island. Walk to...
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Housekeeping Included
    • Ocean Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beachside Palms Anna Maria Island Resort is extremely conveniently located directly across from the famous Manatee County Public Beach on the gorgeous Gulf of Mexico. All 3 of our units were completely updated in 2016. They feature new cabinets, stainless steel appliances and granite countertops....
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Inn Real Life on Anna Maria Island1 / 5
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed 19 April 2018
    This is our 2nd time staying here. The Location is perfect close to everything. Beach is on the doorstep! Terri White is amazing.
    Reviewed 12 April 2018
    Great cozy place that felt like home! The two minute walk to the beach or 30 second walk to the fishing pier was awesome! It was nice to have a place to stay that was pretty...
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    About this property
    Cute one bedroom apartment half a block to Gulf of Mexico beaches. Steps to fishing dock on Sarasota Bay. Well-mannered pets welcome. Walk or ride the free trolley to historic Bridge Street pier, shops, restaurants and night life. Bradenton Beach is being called a baby Key West. It's so much...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Cast Villa 31 / 24
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    The Cast Villa sits in the heart of Anna Maria Island directly across from the famous Manatee County public beach W/life guard which features a gift/surf shop, restaurant, Tiki bar, live music and more. Beach is groomed daily and has lifeguards. Walk to Publix grocery store, CVS drug store and...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Patio
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    About this property
    Welcome to Buddy's Beach House. A beachy chic getaway just 2 blocks to the beach. Stroll to the beach with a beverage in one hand and your beach cart in the other. After soaking up the sun all day, walk to one of the many fine restaurants, only a few blocks away. Or hop on the free trolley, which...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Stylish dog-friendly seaside cottage with a shared pool and community Tiki hut!1 / 31
    (1)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 28 April 2018
    Overall, the cottage was ok, very roomy with 2 bedrooms, 2 bathrooms, and huge showers. Disappointed about the pool waterfall not working. Broken toilet paper holder on wall...
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    About this property
    Experience casual island luxury at this Holmes Beach getaway. Boasting plenty of room for the whole crew and even the family dog (for a small nightly fee), this getaway has it all. Stay in the heart of the island and enjoy a tropical shared pool with a 10-foot waterfall, a Tiki hut, and a communal...
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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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    About this property
    Anna Maria Island is still old Florida, I am on a half acre of very Tropical Palms and landscaping. Located in the heart of the Island. Directly accross from the Famous Manatee County Public Beach. Reasturants, Free trolley all right there. Also grocery, pharmacy, shopping within walking distance....
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Beautifully renovated beach cottage in the heart of the village of Anna Maria. Walk to the beaches, shops and restaurants. Enjoy amazing sunsets at the beach or sip a glass of wine in the lush tropical gardens surrounding the cottage. 2 bedrooms with 2 full bathrooms. Quaint beach cottage in a...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    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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    About this property
    Say goodbye to stress and hello to island vibes at this spacious beach house. Featuring a private yard with tropical greenery, a dog-friendly attitude, and a great location near the beach and pier, this house will have you living in a dream! Sitting near the northern tip of Anna Maria Island, this...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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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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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Buena Vista on Anna Maria Island1 / 18
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Reviewed 14 August 2017
    After spending a week at Angie and Oliver's lovely home on Anna Maria Island, I've made a resolution to start playing the lottery, in the hopes of living waterfront full time...
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    About this property
    This is the Florida view you have been dreaming of... Single family home situated at the end of a natural canal with a view over the water. Sit outside, fish off our dock, take out the kayaks, or just walk steps across the street to the beach! This is not your typical beach rental. It is our...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Aug 12 to Aug 25, 2018 Special - $1,400/week! Write for Details!1 / 26
    (14)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    Reviewed 3 weeks ago
    This area never disappoints! The white sand beaches and clear waters are absolutely amazing. Unfortunately, during the time we were there, it seemed llike the whole island was...
    Reviewed 14 June 2018
    I really enjoyed myself at the 4-Bedrm, private, heated saltwater pool, private elevator, home hosted by Joe and Jen C. The accommodation was great not to mention they were...
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    About this property
    Google 2203AVENUEC to take a 3D Virtual Tour throughout this magnificent home! Amazing! Just like being in the home! 2-MINUTE STROLL TO WHITE SANDY GULF BEACH - Compare us to any rental on the Island for luxury and best price. Call us if you find a better deal. Breathtaking Gulf View! 5-Star...
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    Location Information
    Anna Maria Island, Florida 34217
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
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    About this property
    Bay view Home, located at 404 21st Place in Bradenton Beach is a hidden treasure! This wonderful home features 4 bedrooms and 3 bathrooms on a quiet street ending at the water. Best of all, this beautiful home is canal front with beautiful views of the bay! It features a private heated pool, BBQ...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Bask in the endless sunshine of Anna Maria Island at this three-bedroom home, a dog-friendly Florida escape with a private canalfront dock, its very own heated pool and a wondrous location only two blocks from the beach. This sleek, light-filled home is located on the quiet North End of Anna Maria...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Cast Villa #4 is the most private on this lush tropical Half acre property. Located directly across from the famous Manatee County Pubic Beach. Swim with Life guards present. Known for the pristine sugar white sand beaches. Dine early breakfast or have a beverage listening to live music daily....
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
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    About this property
    Find cool island comfort at this two-bedroom Holmes Beach escape, a bright, spacious home with a dog-friendly interior, a screened-in balcony, free WiFi, and a perfectly walkable location close to the beach and the free island trolley. You'll find this home in the northern reaches of Holmes Beach,...
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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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    Pet friendly
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    Smoking allowed
    About this property
    LUXURY RENOVATED 2 BR/2 BA ISLAND CONDO - DIRECTLY ON GULF OF MEXICO Private, Peaceful, Comfortable * Relax, Rejuvenate * Screened-in Dining Balcony/w Hi-Back Swivel Rockers, Overlooking Heated Pool, Beach and Gulf of Mexico * Spectacular Water Views, Nightly Show at Sunset, Ocean Breezes, and...
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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 4 Quick View
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    About this property
    This is the CLEANEST AND BRIGHTEST vacation rental you will find on the island! This bungalow is the SECOND FLOOR UNIT of a beachfront duplex. Welcome to paradise! ANNA MARIA ISLAND is the first of the barrier islands located along Florida's Gulf Coast. It is about 7 miles long and 1/2 a mile...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    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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    • Grill
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    About this property
    For your next Anna Maria Island adventure, enjoy a stunning, one-of-a-kind vacation destination. From an oceanfront location to a private pool and original antiques, you won’t another Florida home like this one! Built by Emma Palmer in 1912, this home is one of four Anna Maria cottages known as...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Welcome to this charming, dog-friendly Anna Maria Island house. With the private heated pool and hot tub, you will feel like you're miles away from your worries. There is a large, fenced-in backyard with lush landscaping, where you can soak up the warm island sun from a pool-side lounge chair....
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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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    Villas by the Sea #11 / 34
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Reviewed 5 May 2015
    This property was excellent. It had everything you need and was very clean.The only reason i gave it 4 stars instead of 5 is the sink in the bathroom got constantly blocked...
    Reviewed 21 August 2014
    Location is great right next to Cortez and a few steps to the beach and all the great restaurants. Nice and Clean and the bed is ok. The only negativ thing is that there is not...
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    About this property
    Sweet little 1 bedroom, 1 bath villa just a short walk from beach with a heated pool. Adorable 1 bedroom, 1 bath villa in Bradenton Beach. Recently renovated. Walking distance to shops, restaurants, and the very lovely white sand beach of the Gulf of Mexico. Very small complex of only 5 units....
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Ocean View 3 bedroom, pool, North Shore Drive1 / 123
    (36)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 November 2017
    Great place I had my birthday party here it was so fun Very close to the water every thing was to the t in cleanliness sleep 6 of us it was all around one of the best beach...
    Reviewed 30 July 2017
    We love this beach house! It has everything, is always clean, great location, and the owner is the nicest to deal with! We will definitely be back...if someone else doesn't book...
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    About this property
    Just steps to the sugar sand beaches in Anna Maria, FL. Your 3 bedroom, 2 bath, pool home with sweeping gulf views from two elevated front porches is located in the charming northern end of Anna Maria on North Shore Drive. If you are looking for a tropical vacation home to just relax, take long...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    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, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    You’re sure to fall in love with island living when you book your Anna Maria Island vacation at the dog-friendly Coastal Sands. This professionally decorated home offers everything your family needs, including a private heated pool, and a location less than two blocks from the powder fine Gulf of...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    About this property
    Two Bedroom/2bath Home in Bradenton Beach Sleeps 6. This is a two bedroom/2bath home in Bradenton beach, with washer/dryer, new kitchen (granite counters), big screen/WiFi, great fishing on your own dock, on a quiet street, five minute walk to bridge street shopping area, two minute walk to the...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Stunning 6 Bed 5.5 Bath Heated Pool Spa Water Slide FREE WiFi Gulf Views1 / 49
    (1)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
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    • Wi-Fi
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    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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