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Holiday Rentals in Anna Maria Island

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    ₹ 12,922 Average
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    ₹ 0₹ 64,000+
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    Travellers to Anna Maria Island are booking August dates now. Secure your holiday home today, and have the perfect trip.
    All 1,127 Rentals in Anna Maria Island
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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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    Gorgeous views,spectacular home!1 / 45
    (20)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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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    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 18 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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    Crescent Wave1 / 80
    (12)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Patio
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 January 2017
    Crescent Wave was the perfect place for us to stay. We came down to surprise our parents for their 50th Wedding Anniversary (there were three couples) and this was just the...
    Reviewed 28 November 2016
    We stayed Thanksgiving week. House was as advertised and the family loved the heated pool and hot tub. No complaints and location of the house is perfect. Would definitely...
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    About this property
    Description We are located in the heart of the beautiful city of Anna Maria FL. We are one block from the historic Pine Ave with free trolley service to the entire island. We are two blocks to the beautiful white sand beach. Three blocks in the opposite direction is the bay and the historic City...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Internet Access
    • Terrace
    • Balcony
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pelican Roost 505 - Private canal home 5 Bedroom/ 5 Bath with private pool, maximum occupancy of 10 people. This gorgeous three story home in the city of Anna Maria, is an easy walk from Pine Avenue and the City Pier, with direct water views, front and rear, from all living spaces. With 5...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Watch Sunsets, Dolphins, or Just Relax - Bermuda Bay 14531 / 42
    (8)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • DVD Player
    • Grill
    • Washer
    • Satellite TV
    • Hot Tub
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 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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    4 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    • Internet Access
    • DVD Player
    • Grill
    • Air Conditioning
    • Parking
    • Washer
    Suitability
    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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    Happy Island Cottage with heated private Pool1 / 104
    (27)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • DVD Player
    • Patio
    • Wi-Fi
    • Washer
    • Hot Tub
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 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 15 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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    Bird's Nest beach vacation townhouses Gulf view1 / 23
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Satellite TV
    • Porch
    • Hot Tub
    • Air Conditioning
    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 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 22 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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    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 3 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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    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 16 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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    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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    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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    • Washer
    • Patio
    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    The home was amazing...it made our stay even more amazing! We loved having the "at-home" feeling while being on vacation. We would definitely considered such an option...
    Reviewed 1 June 2017
    Mike and Lesley's home was spotless comfortable and welcoming. We loved the blackboard on the way in. The pool was lovely and refreshing after a day out. The trolley stops were...
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    About this property
    **DISCOUNTS FOR RENTALS OF 28 NIGHTS OR MORE ANY TIME OF YEAR** *****PLEASE ASK US ABOUT SPECIAL PRICING FOR YOUR STAY***** LARGE HEATED FREE-FORM, LUXURY POOL AND SPA WITH SPACIOUS PAVED SURROUND - ADDED AUGUST 2014 TOGETHER WITH TROPICAL LANDSCAPING, AUTOMATED GARDEN LIGHTING AND LARGE GROUND...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Internet Access
    Suitability
    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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    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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    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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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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)
    • Internet Access
    • Washer
    • Patio
    • Hot Tub
    • Satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Grill
    • Parking
    • DVD Player
    • Air Conditioning
    • Washer
    • Waterfront
    • Balcony
    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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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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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)
    • Terrace
    • DVD Player
    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 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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    On the Beach1 / 51
    (3)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Patio
    • Air Conditioning
    • Ocean Views
    • Washer
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 March 2013
    We had the most wonderful four days in this house with our baby son. The house is just two blocks from the beach and comes with basic gear (towels, umbrella, chairs, wagon...
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    About this property
    Beautiful 5 bedroom 4 bathroom vacation home in Holmes Beach, just steps from the beach with fantastic Gulf views. This home is the perfect beach getaway with everything you could want while enjoying Anna Maria Island. Just imagine waking up to the sound of the surf rolling in. Enjoy a cup of...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    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
    • DVD Player
    • Patio
    • Grill
    • Terrace
    • 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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    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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Internet Access
    • Balcony
    Suitability
    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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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 8 Quick View
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    • Terrace
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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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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 8
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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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    Anna Maria Island, Florida 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    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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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    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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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    510 Bayview1 / 10
    (3)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Reviewed 29 April 2016
    Had a fantastic week here nine adults and we did not bump into one another once 4double rooms and 1 twin all with their own bathrooms pool area great pity that the water...
    Reviewed 30 December 2015
    I recently stayed at this beautiful house and it was the best decision I made for the holiday. First, the rental company was so easy to work with. There was no stress at all...
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    About this property
    510 Bayview - Private canal home 5 Bedroom / 5 Bath with private pool , maximum occupancy of 10 people. Island Elegance for the whole family!~ Come to Anna Maria Island, bring family, friends and your boat to enjoy the simple pleasures of life: sun, sand, and surf. Relax in well-appointed...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Wi-Fi
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    About this property
    Enjoy our Luxurious Villa diPalma, a beautiful six bedroom, four bathroom luxury island home very close to the best beach in the Northshore. The Italian influence in the design is reminiscent of properties found in Venice and Tuscany. The two master suites each have their own Jacuzzi spa tub, a...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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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
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    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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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    A luxury Anna Maria Island vacation destination perfect for the entire family, you and your loved ones will enjoy a visit to “Seashell Sunsets”. This newly built four bedroom home offers lovely views of The Gulf of Mexico while providing a spacious and comfortable home where eight guests can relax...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    FAMILY/CHILD FRIEDLY CONDOMINIUM. The Beach Castle is located with-in walking distance of Anna Maria Island's best waterfront restaurants, beach shops, gift shops, shell shops, boutiques and the quaint shopping village on Bridge St. that leads right out onto the Bridge St. a pier famous for...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Coconuts Beach Front 110 Upstairs1 / 40
    (4)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
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    Reviewed 22 January 2017
    We just returned from this condo at the Coconuts Beach Resort and can only say that we wish we could have been there longer ! It is a beachfront unit and we absolutely loved it...
    Reviewed 9 November 2016
    Unit was nice, comfortable. The best was the balcony, daily we'd sit there and have a drink and watch the sunset. But the complex, washer, pool, location, all were great!.
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    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 queen...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Coconuts Poolside Unit 1041 / 24
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    Pet friendly
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    Reviewed 2 June 2016
    Awesome, already booked this for next year! Easy to fond, easy to get to beach, great people to work with.
    Reviewed 19 January 2016
    We were there in January 2016 and we were very happy with the accommodations. The decor is a little dated but all the essentials were there. We enjoyed Holmes Beach and...
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    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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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Beachy Keen 408 - Private home 3 Bedroom/ 2 Bath with private pool, maximum occupancy of 6 people. Here delightful and fun Caribbean Cool décor welcomes you to the sub tropic cozy of Anna Maria Island. A charming island home within easy walking distance to the beach, offers an ideal location...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ohana Hale Beachside  Suite D 2 Bedroom with Gulf View1 / 14
    (9)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    Reviewed 10 February 2017
    Wonderful one week stay. Rooftop deck great for watching sunset while enjoying and adult beverage, which you can't do on the beach here. Many restaurants within walking...
    Reviewed 28 August 2016
    Thank you Brenda & Danny for being a wonderful host. Our stay was short but it was well worth it. We arrived really late and Danny stopped by to make sure everything was...
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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 in Anna Maria Island, Florida. Ohana Hale Beachside is 150 feet to the white sand beaches and turquoise waters of the Gulf of Mexico. Beachside is 4 suites...
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    Location Information
    Bradenton Beach, Anna Maria Island 34221
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    AnnaMariaBeachCondo  AUGUST DATES AVAILABLE!1 / 35
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
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    About this property
    **Due to a house being built in frount of our building, we don't know how our views of the Mexican Gulf will be affected. We cannot guarantee that you will have the views depicted in our pictures.** 5 reasons why you will love our condos as much as we do: *LOCATION! Close to the...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Absolute Anna Maria1 / 72
    (20)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    Smoking allowed
    Reviewed 22 March 2016
    Had condo 101 which faced directly onto the sea, lovely condo decorated with seaside colors, hundreds of towels and everything you could need, we had a great vacation Anna Marie...
    Reviewed 30 November 2015
    Hi Terry and Sandy, We really enjoyed our stay at your Anna Marie Island condo unit #110. . We were impressed with the spacousness, tasteful furniture and decor, the wall...
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    About this property
    FAMILY/CHILD FRIEDLY CONDOMINIUM. Surrounded by water with the Gulf of Mexico to the west, the Intra-Coastal Waterway to the east, Tampa Bay to the north and Sarasota Bay to the south. We have the best location on Anna Maria Island where the island is only 150 yards wide. Our complex stretches from...
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    Anna Maria Island, Florida 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Absolutely Perfect - Cove at Sandy Pointe #2071 / 42
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
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    Pet friendly
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    Reviewed 22 June 2017
    Very nice condo in a quiet place, just 5 minutes from the beach and a pool in front of it. Carla was helpful, the instructions on how to check in and out were clear. We had a...
    Reviewed 1 June 2017
    I have to say that this was my first time booking on VRBO and I was extremely satisfied with description and pictures and location. Carla was absolutely wonderful. The unit was...
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    About this property
    Very contemporary condo (danish style), just refurnished and remodeled, and equipped with more than everything you need for a relaxing and unforgettable vacation in Paradise. The unit is inspiring and gives you a laid back feeling immediately after entering. A huge pool with lounges and sun...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    HorizonWest 1121 / 24
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Horizon West 112 - Condo 2 Bedroom / 2 Bath , maximum occupancy of 4 people. Beach Bound.....This is your place!~ 2 bedroom 2 bath condo 1 very short block to beach. Beautifully decorated with comfortable furniture. Everything you need for a relaxing vacation. Pet friendly Anna Maria Island is...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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)
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    Pet friendly
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    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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    “Vitamin Sea” offers fabulous amenities for up to eight guests with four bedrooms and 3 bathrooms all just a short walk to beaches, free trolley stops, shopping and DINING. This Anna Maria Island vacation rental is the perfect place to gather family and friends for a memorable holiday with no...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    7901 Palm B1 / 18
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed 14 April 2017
    The accommodations were very nice and clean and well equipped. We were centrally located so could walk or ride our bikes to shopping, restaurants, the fishing pier and, best of...
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    About this property
    7901 Palm Dr- Duplex-2 bedroom 1 bath-, maximum occupancy of 4 people. This is a very cute and well- appointed 2 bedroom 1 bath duplex. It has a Queen size bed in the master bedroom and a 2 twin size beds in the guest bedroom. It has a very nice comfortable sofa in the living room. The kitchen...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 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
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    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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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
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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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Periwinkles are small, sunshine loving flowers with a color so distinct they name crayons after it. On a street baring their name in Anna Maria Island, you’ll find a vacation rental home appropriate to the name - "Pretty Palms" on Periwinkle Plaza. This three bedroom, two bathroom cottage is...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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