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Holiday Rentals in Anna Maria Island

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    Travellers to Anna Maria Island are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    All 1,130 Rentals in Anna Maria Island
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    Crescent Wave1 / 40
    (12)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    A Pearl of a Beach Home - with luxury private heated pool and hot tub1 / 32
    (19)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    About this property
    742 Jacaranda- Single Family home 3 bedrooms/ 2.5 baths, maximum occupancy of 6 people. This well appointed home has recently been renovated. The balconies have all been redone, new stairway and all new furniture in the living room and bedrooms The master bedroom boasts a king size bed with a...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    'Elegance' 100 Steps from the Beach!1 / 24
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Grill
    • Washer
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    From the booking process, to the welcome, to the actual house itself, the location, the island.....this place really is special. Steps from the bay or the gulf. And the beach...
    Reviewed 11 May 2017
    Everything that is said on the Web re the house is correct & the house is wonderful & will definitely be booking for next year. One min walk to beach or to the bay &amp...
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    About this property
    An elegant beach-house that redefines the idea of island comfort, built with love and an extreme attention to detail. Every room of the house has a unique ambiance combining color, textures and accent lighting. The outdoor area is one of the most spacious on the island with a large heated free form...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Gorgeous views,spectacular home!1 / 45
    (20)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Washer
    • Grill
    • Satellite TV
    • Balcony
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 2017
    This is an excellent vacation home to spend with a large family looking for a quiet getaway on AMI. Our family of eight adults, one teenager, one toddler, and one infant spent 7...
    Reviewed 27 December 2016
    We've stayed on AMI many times and this house was far and above the best one we have rented on the island! Great location....can walk everywhere and gorgeous views from all of...
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    About this property
    WELCOME TO ALL DECKED OUT! Whether getting away for a family vacation, with a group of friends, for a wedding or any other occasion, our gorgeous 5 Bedroom home offers everything you could want for a relaxing holiday on Anna Maria Island.... with incredible views of the Bay! Sit by the tropical...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Watch Sunsets, Dolphins, or Just Relax - Bermuda Bay 14531 / 21
    (8)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • DVD Player
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    • Satellite TV
    • Hot Tub
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 August 2016
    Awesome place in a great location. Superb service from the owners and Rick on an issue with the dryer. Place was awesome, clean and perfect for our vacation. Everything for the...
    Reviewed 16 July 2016
    We had a fab stay for a very relaxing week here after the madness of Disney. Everything was just perfect in the condo. The attention to detail just made it for us and all the...
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    About this property
    Anna Maria Island boasts one of the longest stretches of sugar white beaches in Florida, and clear, aqua-marine water. Enjoy the natural setting from this spectacular townhouse on Bradenton Beach. This three bedroom, two-and-a-half bath home offers direct Gulf views, a king size master suite,...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Blue Heron Waterfront House Anna Maria island1 / 23
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Ocean Views
    • Washer
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 June 2017
    We stayed for a week at the end of May 2017 after spending 10 days in Orlando. We were met at the property (even though we were a little late) and it was beautifully presented...
    Reviewed 22 May 2017
    The location is perfect. Walk 2 blocks to beach. Supermarket, drug store, bank, restaurants, salon, spa, less than 5 min. away. Many choices to dine/shop 3-10 min drive. The...
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    About this property
    Stunning ground level 3 bedroom/2 bath home with luxury finishes at every glance. Brand new to the market and recently renovated, this home is packed with designer finishes throughout from luxury linens in all three uniquely appointed bedrooms to furnishings that make this home feel like you are...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Dolphin Pointe1 / 39
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Balcony
    • Washer
    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Heated)
    • Porch
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 January 2017
    The house is just as the pictures suggests. The floor plan was very spacious. We traveled with 6 adults (4 were college students) and there was ample room to spread out. The...
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    About this property
    The lovely Dolphin Pointe resides on the highly desirable north end of Anna Maria, just a three houses away from the beach at Bean Point and a short walk to Rod and Reel Pier. The spacious open concept living area is perfect for spending quality time with the family. The home exudes an Island charm...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Sunshine Cottage - Private 30' Pool and Boat Dock, and steps away from the beach1 / 39
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Satellite TV
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Waterfront
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 October 2016
    We had a fantastic time exploring Anna Maria Island and coming home to such a fantastic place made the holiday even more special.
    Reviewed 17 February 2016
    This home is located in walking distance to restaurants and the beach with bikes available as well. It is very nicely and newly decorated. The kitchen is well stocked as well as...
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    About this property
    It doesn't get much better than being right on the water, less than one block from the bay beach, and only 7 blocks from Pine Avenue. Sunshine Cottage couldn't be a better name, because this 3 bedroom, 2 bathroom, cottage truly lets you experience the beauty of Anna Maria Island. Enjoy dangling...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Terrace
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2307 AVENUE C - Duplex 3 Bedroom / 2 Bath with pool, maximum occupancy of 6 people. Come and swim with the turtles!~ Adorable and totally renovated 3 bedroom and 2 bath duplex on the second floor, one street back from Gulf Drive on the beach. The first floor is storage for pool toys, pool and...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Shady Palms - Real Beachfront on the Gulf of Mexico1 / 15
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Washer
    • Grill
    • Satellite TV
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 September 2015
    Shady Palms brings you back to old style Florida, before condos and high rises took over the beaches. This 50's ranch house is surprisingly spacious, with multiple living areas...
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    About this property
    Perhaps Shady Palms will become "your place on the beach." Walk into a charming, Old Florida style beach cottage with a view of the beautiful Gulf of Mexico from every room in the house. Continue through the back door, and into the yard and you are one step from the wide, white, sugar-sand beach...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Tree House1 / 22
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Balcony
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Grill
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Nice quiet location Has everything you need. We enjoyed our stay and would come back. Easy access. Clean!
    Reviewed 20 June 2017
    Very nice house to stay in for vacation. Clean and up to date, with almost all the amenities that you will need on your stay. Would definitely not hesitate to say there again!
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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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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Satellite TV
    • Air Conditioning
    • Washer
    • Grill
    • Private Outdoor Pool (Heated)
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    116 Maple Breeze1 / 21
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
    • Grill
    • Internet Access
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 November 2015
    Wonderful location, The beach is at the end of Maple Ave, a quiet road only a 2 minute walk. The house is well situated, 4 bedrooms and 2 and 1/2 baths. I can only speak of...
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    About this property
    116 Maple Breeze Private home 4 Bedroom / 2 1/2 Bath , maximum occupancy of 7 people. 116 Maples is located on one of the prettiest streets in the village of Anna Maria, this gorgeous 4 bedroom, 2 and a half bath home is just steps away from the beach. This quiet, tree-lined street evokes...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Washer
    • Hot Tub
    • Balcony
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is simply the most luxurious 5-bedroom canal-front home available on the island. When you arrive at “My Sister’s Beach House,” you’ll instantly feel luxury and relaxation. This is the perfect destination for everyone to enjoy time together without feeling cramped. This is not a box of...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Bird's Nest beach vacation townhouses Gulf view1 / 23
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Washer
    • Satellite TV
    • Porch
    • Hot Tub
    • Air Conditioning
    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 April 2017
    Poor value for money Good sized accommodation, views across to beach and sea. Good parkingVery dated and noisy due to busy road right in front.
    Reviewed 21 April 2017
    We truly enjoyed our stay at Bird's nest! The location is great and the views are amazing! The master bedroom is huge and you have views of both the ocean and the bay! Condo was...
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    About this property
    Overlooking the Gulf of Mexico Beach, these 1250 square feet each two bedroom beach townhouses (complex of 4 apartments) arranged on two elevated levels offer beautiful views of Anna Maria island sound. A nice yard with a access to a barbecue area and a six persons tub make our apartments an ideal...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Happy Island Cottage with heated private Pool1 / 52
    (27)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • DVD Player
    • Patio
    • Wi-Fi
    • Washer
    • Hot Tub
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 June 2017
    Our stay was amazing. The house was exactly as described. The week went by way too quickly. Perfect weather. We booked the trip almost a year ago and have had MANY MANY...
    Reviewed 14 March 2017
    The pictures and previous great reviews are right on the money! We were very happy with this home, its features, layout, proximity to beach, restaurants, etc.Loved the outdoor...
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    About this property
    A brand NEW 2300 sq/ft, 3 bedroom modern beach house with heated and very private pool. A perfect location just steps from the beach, marina and the main plaza with great shops, a grocery store and restaurants. No need to drive anywhere. Located in a quiet neighborhood with tropical greenery, large...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    • Internet Access
    • DVD Player
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the SS Salamander located at 121 50th Street in Holmes Beach. This recently updated duplex is just a one block stroll down a side street to the beautiful white, sandy beaches. It’s located in a quiet and preferred residential neighborhood yet it's easily within walking distance to...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 11
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    Brand New Renovation Sea Waves Cottage1 / 32
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Satellite TV
    • Grill
    • Waterfront
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 May 2017
    Located on a quiet street, this cottage was exactly as advertised. It is updated and tastefully decorated. All beds (1 king, 2 queens) were very comfortable. Water pressure was...
    Reviewed 15 March 2017
    We were please to find this very clean unit on the ground floor of a two story house with private entrance, private deck, and parking. It is a 10-15 minute walk to the Anna...
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    About this property
    Sea Waves cottage is located at north end of anna maria island. Brand new renovation, 3 bedroom with 2 bath room, with private dock, sailboat direct to bimini bay, unobstructed , natural view of bimini bay. Less than three minute walk to beach, walking distance to pine ave and the city pier and...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Bradenton Beach Club 2401 / 19
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Internet Access
    • Balcony
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bradenton Beach Club 240 - Condo 3 Bedroom/ 2 Bath, maximum occupancy of 6 people. While the exterior hints of a quaint Mediterranean village, the chic interior is pure Anna Maria Island Americana. So well appointed with comfortable furniture,with fishing dock, pools, easy access to the beach,...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ohana Hale South   West Suite1 / 24
    (30)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Private Garden
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 June 2017
    We really enjoyed our stay at Ohana Hale. The suite is very comfortable and nicely updated. Though not directly on the beach, it is only a block away from a beautiful beach with...
    Reviewed 21 November 2016
    We have rented with Danny & Brenda for four years now. I originally found them on Trip Advisor and was so impressed with their reviews. Dealing directly with the owners is...
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    About this property
    Aloha and welcome to our Island Home. Ohana is Hawaiian for family and that is who you are when you stay with us. Our retreat is nestled on Anna Maria Island, Florida and is a short 5 minute walk to the white sand beaches and turquoise waters of the Gulf of Mexico. Your vacation Hale (home) has...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Bradenton Beach Club 2521 / 22
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bradenton Beach Club 252 - Condo 2 Bedroom/ 2 Bath, maximum occupancy of 6 people. So well appointed with comfortable furniture,with fishing dock, pools, easy access to the beach, and located near shopping, trolley, and restaurants, Bradenton Beach Club welcomes you to relax, relax, relax. So...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    250 Feet from the Beach1 / 25
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Balcony
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    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 April 2017
    Just came back from 4 days on AMI with my 3 sisters and daughter. What a nice little place and even though 5 of us we were very comfortable. Two blocks from the beach. We sat on...
    Reviewed 6 September 2016
    The pictures don't do it justice! Charming beach cottage that we'll book again. It was the perfect trip.
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    About this property
    *NOTE: If you cannot find availability for this unit, please contact us, there is an additional unit. 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...
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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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Coquina Beach Club 202 - Condo 2 Bedroom/ 2 Bath ocean view, maximum occupancy of 6 people. Community pool (pool closed on 9/11/2017-10/13/2017 ) Beautiful sugar sand beach, brilliant sunsets and balmy breezes await you at this two bedroom, two bath, beachfront condo. This second floor unit is...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gulf Watch 205 - Condo 2 Bedroom / 2 Bath Gulf to Bay access, maximum occupancy of 4 people. Pristine Waters Await your Arrival!~ Gulf Watch Condo---2 bedroom, 2 bath condo in 32 unit complex with heated pool. Gulf to Bay setting. washer/dryer in unit. About 1200 square ft. Convenient walk to...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    North Beach Village, unit 59  - Great Townhouse!1 / 28
    (11)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Balcony
    • Patio
    • DVD Player
    • Grill
    • Satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 June 2017
    We stayed here for a week in May and had a brilliant time. The house was clean and had everything we needed. The pool was lovely and warm and literally a stones throw away. The...
    Reviewed 18 May 2017
    This condo was perfect for our family. We stayed there with our 3 kids, brother and his wife and daughter and it could not have gone better. Condo was clean, lots of space, and...
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    About this property
    Grab your flip-flops and beach chairs! This family-friendly 3-bedroom, 2 1/2 -bath townhouse is just two quick blocks to the pristine, white sandy beaches of Anna Maria's gorgeous blue waters of the Gulf Coast. And after a relaxing day of sand and sun, come back for a refreshing dip in the heated...
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    Location Information
    Holmes Beach, Anna Maria Island 32417
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Anna Maria Island 'High End' Vacation Rental1 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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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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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
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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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    Coquina Moorings 2011 / 36
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Pet friendly
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    Smoking allowed
    About this property
    Coquina Moorings 201 - Condo 2 Bedroom/ 2 Bath with Den/3rd room , maximum occupancy of 6 people. This beautifully landscaped bay front complex has lots to offer. It features a heated pool directly on the bay and a boat dock for boating and fishing enthusiasts. Immediately across the street is the...
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    Location Information
    Bradenton 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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    Fantastic location at Runaway Bay on gorgeous Anna Maria Island. The resort has wonderful amenities including large heated pool, exercise room, tennis and bocce court, fishing pier and private access to the beach. This 2 bedroom 2 bath condo is quiet with a pretty lagoon view and has free wifi and...
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    Location Information
    Anna Maria Island, Florida 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gulf Watch 1111 / 28
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 July 2015
    104 Gulf Watch was exactly what we were looking for. Location was superb. Close to restaurants, stores and most important right across from the beautiful gulf water. Unit was...
    Reviewed 16 March 2012
    We two retired couples had a great time staying on Anna Maria Island again for 2 wks. The condo was very nice and the owner very nice to work with. The pics as shown were just...
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    About this property
    Gulf Watch 111 - Condo 2 Bedroom / 2 Bath Gulf to Bay access, maximum occupancy of 4 people. Peaceful Easy Island Living!~ Two bedrooms with en suite full baths this 2nd floor sun filled end unit condo is in the quiet Gulf Watch 32 unit complex with heated pool and sun deck. Open floor plan...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    (3) Bedroom, (3) Bath (Sleeps 8) – “Fish House” – 231 Oak Avenue in Anna Maria. For the perfect Anna Maria Island vacation, escape to the adorably rustic and comfortably elegant “Fish House”. Rooming up to 8 guests this 3 bedroom and 2 bathroom ground level vacation rental home is located at...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Gulf Watch 1041 / 14
    (1)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    About this property
    Gulf Watch 104 - Condo 2 Bedroom / 2 Bath Gulf to Bay access, maximum occupancy of 6 people. Gulf Watch Condo---2 bedroom, 2 bath condo in 32 unit complex with heated pool. Gulf to Bay setting. washer/dryer in unit. About 1200 square ft. Convenient walk to restaurants and shops.Covered parking....
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Charming 2 Bedroom/2 Bath Cottage on a Canal1 / 19
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
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    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 April 2017
    I loved that the owner went our of her way to reserve pack and plays for our two little ones. They had everything for beach trips including a wagon, beach toys, and umbrellas...
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    About this property
    Our 2 bed/2 bath cottage is the perfect home to spend your vacation. Located on a canal, you can bring your boat or rent kayaks. Fishing is great from the dock. House and yard is very private. Soak in the jacuzzi after a long day at the beach or relax in the hammock. We have 2 bikes, beach...
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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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One bedroom one bath condo located on the poolside. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are two...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Coconuts Courtyard 119 Upstairs1 / 22
    (5)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 June 2017
    The condo had moldy shower curtain. The view is deceiving , you think your getting one of the six condos in the picture, but actually it sits behind those 6. I had already...
    Reviewed 26 April 2015
    We had a wonderful few days. We were presently surprised and was upgraded to a great unit #110. We enjoyed the area very much. Looking forward to coming back next year.
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    About this property
    One bedroom one bath condo located in the courtyard. The Coconuts Beach Resort is directly on the Gulf Of Mexico Holmes Beach Anna Maria Island Florida.. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Coconuts Two Bedroom 118 Upstairs Courtyard1 / 21
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    This condo is provides rooms that are steps from the beach. Rooms are a good size and kitchen is well stocked. Staff is very friendly and the property manager, Joyce is easy to...
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    About this property
    Two bedroom two bath condo located upstairs in the courtyard. The Coconuts Beach Resort is directly on the Gulf Of Mexico Holmes Beach Anna Maria Island Florida.. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 6 to...
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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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    • Air Conditioning
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    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the sunshine state at this alluring 2-bedroom, 2-bathroom Bradenton Beach vacation rental condo that sleeps 6! Featuring a community pool, tennis courts, hot tub and prime location steps to the beach, restaurants, shops and more - your tropical vacation of a lifetime starts here! Nestled...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
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    4 Bedroom, 2 Bath (sleeps 8) - "Blue Heron Beach House" - 117 Peppertree Lane in Anna Maria.  Welcome to “Blue Heron Beach House”! This adorable Anna Maria beach cottage rental is so close to the Gulf of Mexico you can smell the salt air! Enjoy sugar sand beaches and crisp blue water only steps...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Coconuts Courtyard 116 Ground Floor1 / 15
    (5)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 November 2016
    This condo was a block from the free trolley that can take you around the island to shops and restaurants, and a quick transfer to St. Armand's Circle. It was literally only...
    Reviewed 18 April 2016
    The place was just what I expected. The rooms were large, pool was warm, it was close to the ocean. The people were friendly. If you want maid service I do not think they have...
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    About this property
    One bedroom one bath condo located in the courtyard. The Coconuts Beach Resort is directly on the Gulf Of Mexico Holmes Beach Anna Maria Island Florida.. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Bradenton Beach Club A1 / 17
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Internet Access
    • DVD Player
    • Balcony
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 June 2014
    This condo was ideally located and had excellent views. Description and views were represented accurately. Very spacious, accomadated our crew and guests well. Be advised the...
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    About this property
    Bradenton Beach Club A - Condo 3 Bedroom/ 2 Bath ocean view, maximum occupancy of 6 people. Luxury Gulf front 3 bedroom, 2 bath condo with gulf side pool and elevator. Professionally decorated with a tropical flair. Enjoy great views of the gulf from your lanai while relaxing over coffee in the...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Anthony Beach Cottages Bare Feet Retreat1 / 31
    (2)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
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    • Outdoor Dining Area
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    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 August 2016
    April was helpful and prompt. She made the whole process from booking to check out easy! The house was cozy and just what we were looking for. I would definitely book again
    Reviewed 27 July 2015
    I will be going back! From reservations to communication, from check in to location and the property itself, this place is magnificent!
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    About this property
    This newly remodeled Florida gem backs onto 17 acres of mangrove forest and is ideally located only 3 blocks from the beach. Reasonably priced, this quaint 3 bedroom, 1 bath cottage has a spacious backyard equipped with a pool, hammock, patio furniture, grill, brick fireplace, and picket fencing,...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One bedroom one bath condo located on the beach. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are two double...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Casa Playa -West1 / 37
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Ocean Views
    • DVD Player
    • Private Outdoor Pool (Heated)
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    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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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    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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    • Patio
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    Pet friendly
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    Smoking allowed
    About this property
    Newly Remodeled & Professionally Decorated Large Townhome in Desirable North Beach Village, one Block from beautiful White Sand Beaches. Brand new Upscale Furnishings in all Rooms. Big Flat Screen Smart TV's in all rooms with Premium HD Cable & WiFi powerful enough to run all your devices and...
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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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    **PARADISE RETREAT IN BRADEN RIVER LAKES**1 / 23
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Secure Parking
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 May 2017
    Such a joy to rent this beautiful home. Warm pool and all the extras. ..,, soft towels, kitchen supplies and dishes, bath soaps, a garage to use and lots of seats, space and...
    Reviewed 3 December 2016
    We were having family with children from California and Colorado visit for Thanksgiving Week and needed a home with a heated pool for their stay. This rental was perfect: roomy...
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    About this property
    This tropical retreat single family home boasts 1800sq. ft.of living space on the in the Braden River Lakes subdivision. The home is nestled among lush tropical palms and Florida vegetation. The expansive plantings provide privacy and a natural preserve setting in the backyard tropical paradise....
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    Location Information
    Bradenton Beach, Anna Maria Island 34208
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Anna Maria island beach vacation apartment1 / 16
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 June 2017
    The four of us were very happy with our stay at the condo. We stayed three nights and were very pleased. ( But I will provide a list of a few minor issues to consider before...
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    About this property
    Overlooking the Gulf of Mexico Beach, on Anna Maria island 2 bedroom unit is arranged on two elevated levels for a total of 1,250 square feet. The apartment is beautifully decorated, fully furnished and has open view of the beach and is one of the Bird's Nest vacation apartments complex. The...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beautiful Beaches and Gorgeous Sunsets. Unit 2141 / 20
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Housekeeping Included
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    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 July 2016
    Shared the condo with my wife, son, his wife and my beautiful grand daughter (16 months old) who we don't see often enough. Very comfortable accommodations. Nicely equipped...
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    About this property
    Enjoy paradise in this 2 bedroom, 2 bath suite. Newly renovated with all the amenities. The master suite features a king size bed with new dresser and night stands. The second bedroom has a queen bed with new dresser and night stands with large double closet. Each bathroom is full with either walk...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    7 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Parking
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Anna Maria Island, Florida 34217
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 16
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    Previous
    Waterfront holiday rentals on Anna Maria Island

    Whether an experienced or a first-time holiday home renter, you’ll enjoy the many choices for beachside getaways on Anna Maria Island. Luxury gulf side villas, quaint beach cottages and canal front condos offer breathing-room space and countless amenities that traditional hotel stays can’t match. Beyond the advantage of preparing some meals at home, your beach rental allows you to slide right into islander life and feel very much at home.

    “Old Florida” charm and easy island living

    Three small communities share Anna Maria Island – Bradenton Beach, Holmes Beach and Anna Maria. Each gathers along 7 miles of silky white beach overlooking the Gulf of Mexico. The island offers the village feel of Old Florida, with simple beach cottages and sandy lanes dipping under lazy Florida oaks and beachfront villas overlooking turquoise bays. There’s plenty to do on the family-friendly island, but nothing quite as important as simple relaxation. Rent a bike to roam the island or a kayak to explore the waterways. Fish, sail, comb the beaches for shells, and pack a little picnic for a sunset meal.

    One-of-a-kind dining and shopping

    Shop names reveal that island boutiques are anything but ordinary. The Painted Gate, Egret’s Landing, Paper Panache and other local establishments offer everything from resort wear to arts and crafts. The free island trolley runs North and South, as a convenient way to explore. Ginny's and Jane E's at the old IGA is a popular spot, where vintage furniture mixes with home-baked quiches and brioches in an internet café setting. One restaurant you can’t miss is Rod & Reel located at the end of a wooden pier jutting out into the bay. Kick back, fish, eat and let that tropical seascape deliver complete relaxation.

    Take a side trip south to “Shangri-la”

    Don your best resort wear and head south along Highway 789 that links Anna Maria Island to Longboat and St. Armand Keys. The gulf front drive leads you to famous St. Armand’s Circle, where elite shopping and pampered dining venues merge in an elegant European atmosphere. After a gourmet lunch, venture over to Sarasota for a visit to the cherished Ringling enclave, home to the Museum of Art and Ca d’Zan Mansion. Set in a lush 20-acre garden overlooking the water, the Venetian mansion is considered “the last of the Gilded Age mansions” built in America.

    Holiday rental homes, a superb value for families and friends

    Spacious living areas, plenty of baths and bedrooms and every imaginable amenity explain why holiday homes are today’s most popular travel choices. From the comfort of your own island getaway, you’ll enjoy every pleasure Anna Maria Island offers.

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