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Beach Rentals and Cottages in Anna Maria, FL

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    All 189 Rentals in Anna Maria
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    Travelers to Anna Maria are booking December dates now. Secure your vacation rental today, and have the perfect trip.
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    $160
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    1 / 107
    5 of 5 stars (15) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    $119
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    1 / 31
    3 Bedrooms / 3 Bathrooms / Sleeps 7
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    1 / 14
    5 of 5 stars (10) Excellent
    5 Bedrooms / 4 Bathrooms / Sleeps 8
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    1 / 23
    5 of 5 stars (5) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    Amenities & Details
    • Water Views
    • Private Outdoor...
    • Air Conditioning
    • Waterfront
    • Playground
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Ahhhhhh. Welcome to Beach Nest! Ready to satisfy that oh-my-gosh-we-need-a-vacation? Kick off your shoes and throw them in the back of the closet. Promise yourselves to live in bathing suits from breakfast to bedtime! Vacationers, dreamers, honeymooners, would-be family-reunion planners and just... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed January 23, 2015
    From the blessed sunny moment we arrived until the morning we left-we smiled. Beach Nest is absolutely enchanting! We saw manatees playing off the dock in our backyard and watched...
    5 of 5 stars Reviewed July 7, 2014
    Five of us ranging in age from 7 to 80 had the pleasure of staying in this home for a week. Everyone had a fantastic time! Many hours were spent in the pool and at the beach. We...
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    1 / 38
    4.5 of 5 stars (7) Very good
    5 Bedrooms / 3 Bathrooms / Sleeps 12
    other travelers have booked this property
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    • Water Views
    • TV
    • DVD Player
    • Internet Access
    • Stereo System
    • Private Outdoor...
    • Air Conditioning
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed May 23, 2015
    Having spent hours and hours viewing many different Anna Maria houses on the internet, we eventually picked All Decked Out, as it appeared to cater for all our requirements, we...
    5 of 5 stars Reviewed February 20, 2015
    One of the deck's rails at one end was broken in several places. Needs to be fixed. Other decks were in good shape.
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    1 / 12
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Satellite TV
    • Washer
    • Dishwasher
    • Wi-Fi
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Tropical paradise awaits at this 2BR/1BA villa located across the street from the beach at the beautiful, quiet North End of Anna Maria Island. Sleeps 4 with a double bed and two twin beds. Nicely furnished with tiled floors and updated interior. Enjoy the Gulf breezes from your screened lanai.... View all property information
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    Anna Maria, Anna Maria Island 34216
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    $225
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    1 / 37
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Wi-Fi
    • Balcony
    • Terrace
    • Air Conditioning
    • Ocean Views
    • Parking
    • Grill
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Step into an ultra private, secluded, tropical paradise with a lush canal front setting in quiet cul-de-sac located on the north end of Anna Maria Island. There is a beautiful heated pool just steps outside your door. The back yard has multiple areas to relax away the day and enjoy the amazing view... View all property information
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    Anna Maria, Anna Maria Island 34217
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    1 / 8
    5 of 5 stars (14) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
    other travelers have booked this property
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    Amenities & Details
    • TV
    • Wi-Fi
    • Dryer
    • Air Conditioning
    • Washer
    • DVD Player
    • There Are Tennis...
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Charming, newly renovated, the Becker Beach Bungalow offers a comfortable stay less than 2 blocks from the beach. Accommodates 6 people comfortably; master bedroom with 1 queen bed, second bedroom with 2 twin beds, and an additional daybed with pop up in the sun room. The living room also has a... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed July 28, 2015
    This beach house was even better than we expected. Everything you need! The walk to the beach was just perfect about 2 minutes. We had perfect weather everyday. Bruce and...
    4 of 5 stars Reviewed May 13, 2015
    The accommodations were extremely reasonable for what was received. The property manager was more than accommodating, dropped off a cooler for me to use to transport flowers for...
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    $274
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    1 / 20
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • DVD Player
    • TV
    • Air Conditioning
    • Hot Tub
    • Stereo System
    • Wi-Fi
    • Private Outdoor...
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
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    $850
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    1 / 14
    2 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Make Inquiry
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Dryer
    • Deck
    • Washer
    • Patio
    • Stereo System
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This villa is quaint and adorable tucked in a quiet neighborhood just 9 houses from the Gulf of Mexico and white sandy north end Anna Maria Island beaches. Step outside your door and stroll down the street in 1 minute or less to the quaint shops and cafes along Pine Ave. Walk to everything the... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
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    $3,400
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    1 / 17
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    other travelers have booked this property
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    • Washer
    • Air Conditioning
    • Stove
    • Deck
    • Satellite TV
    • Wi-Fi
    • Refrigerator
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    As an artist this private three bedroom and two bath elevated vacation home has been a retreat that inspires many paintings of Anna Maria Island. Located on the secluded North End you will enjoy the tranquility of the Island and have an easy stroll to the Gulf of Mexico and the best white... View all property information
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    Anna Maria, Anna Maria Island 34217
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    $400
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    1 / 23
    5 of 5 stars (5) Excellent
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (5) Make Inquiry
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Washer
    • Dryer
    • Private Outdoor...
    • Air Conditioning
    • Water Views
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    We call this home 'A Time Out' cottage and you will definitely say, 'We deserve a time out at this place!' This completely remodeled private home on Anna Maria Island's north end features four bedrooms, two baths and the most wonderful tropical and lush pool and patio area! On the main level of... View all property information
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    Anna Maria, Anna Maria Island 34216
    4 of 5 stars Reviewed May 28, 2015
    Overall, this place is beautiful! Every room is well decorated and comfortable. We loved having our morning coffee on the front porch looking at the bay. We enjoyed lunch and...
    5 of 5 stars Reviewed April 7, 2015
    This special house is located perfectly away from the hustle and bustle, but at the same time everything is easily accessible. The beautiful beach is just a short stroll, and...
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    $200
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    1 / 10
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • There Are Tennis...
    • Horse Riding Nearby
    • Water Park Nearby
    • Grill
    • Linens Provided
    • Air Conditioning
    • Watersports Nearby
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Cute and Cozy Cottage just 200 steps to Beach. Walk to Shops, Free Trolley, Resturants, Pier, Museum and more. This apt is attached to another unit that shares the pool. Rent it for the whole family. All the comforts of home. Just bring you towel and suit. Beautiful Beach and Wildlife.... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
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    $980
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    1 / 20
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Water Views
    • Ocean Views
    • DVD Player
    • Wi-Fi
    • Watersports Nearby
    • Air Conditioning
    • TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This water front, two bedroom condominium (ground floor), sits on the end of Pine Avenue, across the street from the beach and has wonderful seaside views of the bay. It also has its own private fishing dock and boat slip! This unit has been completely remodeled and newly furnished to give you the... View all property information
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    Anna Maria, Anna Maria Island 34216
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    $100
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    1 / 16
    5 of 5 stars (1) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Dryer
    • Satellite TV
    • Washer
    • Wi-Fi
    • Patio
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This Charming 2BR/1BA beach cottage is just a few properties to the beach and has direct beach access. No streets to cross to get to the beach! Updated kitchen with an apartment size electric range and full size refrigerator. The bedrooms have a Queen size bed and two twin beds. There is an open... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed April 20, 2015
    This place was ideal for us. Not too big, not too small. Nice place. GREAT LOCATION!!! Very clean. Plenty of clean towels, sheets... Would definitely stay there again!
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    $325
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    1 / 19
    4 Bedrooms / 5 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • TV
    • Deck
    • Washer
    • There Are Tennis...
    • Watersports Nearby
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    4 Bedroom 3 Bath Large Family Beach House Just 200 steps to the most Beautiful Beach in the World. Crystal Clear waters with plenty of fishing, wildlife and swimming. Great for Multi-Family Gatherings, Weddings, Family reunions or just plain fun. With a 2 bedroom 1 attached apartment for... View all property information
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    Anna Maria, Anna Maria Island 34216
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    $1,700
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    1 / 24
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • TV
    • Game Room
    • Watersports Nearby
    • Private Outdoor...
    • Ping Pong Table
    • DVD Player
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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... View all property information
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    Anna Maria, Anna Maria Island 34216
    From
    $93
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    1 / 20
    4 of 5 stars (1) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Dishwasher
    • Parking
    • Satellite TV
    • Dryer
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Located in the heart of Anna Maria Village this recently updated one bedroom apartment is located just a few houses from the beautiful Gulf Beaches. Direct beach access with no streets to cross! 146 steps to the beach and less than a 2 minute walk. Bring your boats and wave runners as there is... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
    4 of 5 stars Reviewed January 6, 2015
    I was a little hesitant to rent this property because I couldn't find any reviews, but it turned out to be a good choice. It's only 4 houses away from the beach, lots of great...
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    $143
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    1 / 18
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Patio
    • DVD Player
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Bay Bungalow 607 N. Bay Blvd. Anna Maria, Fl. 34216 Brand new heated pool! Bay Bungalow is a newly updated elevated bungalow located on the North end of the island, just across from the famous Rod and Reel Pier and only 2 blocks from Bean Point beach. The custom decoration includes nautical... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed June 5, 2015
    First I have to tell you this home has been remodeling in the living room and downstairs garage area. They have removed the front deck and extended the living space. The...
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    1 / 17
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Washer
    • Parking
    • Satellite TV
    • Dryer
    • Wi-Fi
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This elevated 2BR/2BA home is located directly across from the beach at the quiet North end of the Island. Enjoy the gulf breezes from the large screened lanai. Fully equipped kitchen including a dishwasher. Laundry room with Washer/Dryer. Bed sizes are a Queen bed, two twin beds and a sleeper... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
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    $500
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    1 / 26
    5 of 5 stars (1) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • TV
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Cayman Bay 505 Magnolia Ave. Anna Maria, Fl. 34216 Cayman Bay may well be one of the most exquisite private homes available for rent on all of Anna Maria Island. This 4 bedroom/4 bathroom 5300 sq. ft. custom home has all the fine touches and professional craftsmanship one would expect in a... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed August 19, 2014
    We stayed here for two weeks this past August. This was our second trip to AMI - such a lovely place. This house was perfect for us. It is very spacious. All the bedrooms are...
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    1 / 17
    4.5 of 5 stars (35) Very good
    6 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Reviews (35) Make Inquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Berryfish is a fantastic new Caribbean style, beachfront apartment from Pineapplefish, ideal, due to its flexible accommodation, for larger groups of families and friends. Berryfish is double duplex apartment just a stroll to the beach, with 2 separate accommodations - Berryfish East and West,... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed June 10, 2015
    We stayed at Berryfish for our Wedding Weekend with some of our bridal party. It was perfect for us! The rooms were spacious and clean, the living room and kitchen were huge and...
    4 of 5 stars Reviewed September 12, 2013
    Pineapple fish we fell in love with berryfish the whole property is an amazing home from the large sun front deck to the back deck ..I want to buy it off you lol seriously it...
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    1 / 29
    4 of 5 stars (5) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (5) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Water Views
    • Washer
    • Garage
    • Refrigerator
    • Satellite TV
    • Internet Access
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Cherryfish is the latest addition to the Pineapplefish collection of houses on Anna Maria Island. It is a spectacular 4 bedroom house, in a fantastic location, just one block from Tampa Bay Beach, the amazing Waterfront Restaurant and the island's most popular tourist destination - City Pier.... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
    1 of 5 stars Reviewed July 8, 2015
    On arrival, as we walked up the stairs of the property, we were welcomed to a smell of rotten sewage and flies. Bins had not been emptied and we had to wheel the bins out on bin...
    5 of 5 stars Reviewed January 29, 2015
    Flawless! Cherryfish, a tropical hideaway I never want to leave! The landscaping is unsurpassed providing a private tropical oasis retreat. The home itself is so fresh with...
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    $171
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    1 / 24
    4.5 of 5 stars (5) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (5) Make Inquiry
    Amenities & Details
    • Private Outdoor...
    • Washer
    • Deck
    • Satellite TV
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Come and enjoy your own private Island Oasis! Located on the north end of Anna Maria Island in the city of Anna Maria, one block from the bay and a few blocks from the City Pier, this charming vacation rental will allow for some serious relaxation. This home-away-from-home offers two bedrooms and... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
    4 of 5 stars Reviewed July 23, 2015
    Nice rental,clean,well maintained,good location,but a few items that need to be taken care of. 1) The furnished outdoor grill was so rusted that it proved to be unusable,adding...
    5 of 5 stars Reviewed October 5, 2014
    This vacation rental is just perfect - the interior is so lovely, the kitchen well equiped,the surrounding amazing! We can totally recommend this home and would love to come back!
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    $104
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    1 / 18
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Satellite TV
    • Washer
    • Internet Access
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This cute 2BR/1BA beach bungalow is on the Gulf side very close to the beach and located at the quiet north end of the Island. Direct beach access just a few properties away. Enjoy the gulf breezes from the screened lanai or the open brick paver patio. This bungalow has plenty of room to relax with... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
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    $200
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    1 / 24
    5 of 5 stars (5) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (5) Make Inquiry
    Amenities & Details
    • Satellite TV
    • Private Outdoor...
    • DVD Player
    • Deck
    • Wi-Fi
    • Waterfront
    • Stereo System
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Starfish Dreams is the perfect place to start your vacation! This family-friendly vacation rental is centrally located on Pine Avenue in the city of Anna Maria on Anna Maria Island, halfway between the Gulf of Mexico and Tampa Bay. If that were not enough, it also has a heated pool and is on a... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed June 2, 2015
    loved the access to the canal and straight into the bay, had the perfect week !! House was even better than expected and AMI coastal cottages made it even better !! Loved the...
    5 of 5 stars Reviewed November 4, 2014
    My husband and I took our 15 year old son to Anna Maria for a weeks stay at Starfish Dreams. We had a really lovely relaxing holiday and the house is perfect. Excellent position...
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    $1,000
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    1 / 18
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • DVD Player
    • Dryer
    • Internet Access
    • Deck
    • Satellite TV
    • Washer
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Bay View Villa is a three bedroom, three bath private Key West style island home with bay views; tile and bamboo floors, spacious living room with large open decks, and just a short stroll to Bean Point and Bayfront Park. Very desireable area on the North end of Anna Maria Island. Sleeps up to 6... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34217
    5 of 5 stars Reviewed December 2, 2011
    everything spot on,between the 2 piers ,both walking distance,2 minutes stroll to the park opposite with the beach ,sea and picnic area,lovely. a clean peacefull area .
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    $1,950
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    4.5 of 5 stars (7) Very good
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    Amenities & Details
    • Hot Tub
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Satellite TV
    • Watersports Nearby
    • Water Views
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Upscale luxury executive four bedroom waterfront home with private pool dock and elevator. Stylishly furnished and dressed, modern build 2006 - this is our family second home - and is home from home available to you. This exclusive executive property is in the heart of lovely Anna Maria... View all property information
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    Anna Maria, Anna Maria Island FL34216
    5 of 5 stars Reviewed July 28, 2014
    This was a return visit as we loved it so much last time. We felt really relaxed here with the wonderful views from the house and the laid back attitude on the island. We were...
    5 of 5 stars Reviewed July 10, 2014
    This is the perfect vacation home!! Located on a canal with bay views, steps from the city pier and many restaurants and boutiques, this home feels like a slice of heaven. The...
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    $1,700
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    1 / 27
    4 of 5 stars (1) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    NORTH SHORE VILLA 904 North Shore Drive Anna Maria Welcome to North Shore Villa. This luxury Key West style home has it all. Expansive bay views, private heated pool, extra large master suite with a double shower and Jacuzzi tub, fresh and modern decor, two large balconies, indoor sitting area... View all property information
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    Anna Maria, Anna Maria Island 34216
    4 of 5 stars Reviewed January 5, 2015
    In August I reserved N. Shore house for 2 weeks - Our family's Christmas- 6 adults. Final deposit due early December. The Home is as described-- very beautiful, casual feel...
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    $125
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    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Internet Access
    • Parking
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    When a starfish wants to get away, it's more than happy to just detach an arm and take time to recuperate. This elevated coastal cottage might be worth giving up an arm, but we can skip that part and just focus on you relaxing. Located just east of Gulf Drive, a scenic 200-yard walk will take... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed July 18, 2014
    I found the Star Fish Cottage in Anna Maria online and was enamored by the pictures and location. The cottage is all it promised to be and then some. A short walk to the beach...
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    $110
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    1 / 14
    5 of 5 stars (7) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Seaside Views - Waterfront, Steps from Beach & Restaurants This water front, two bedroom condominium (ground floor), sits on the end of Pine Avenue, across the street from the beach and has wonderful seaside views of the bay. It also has it's own private fishing dock and boat slip! We have... View all property information
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    Anna Maria, Anna Maria Island 34217
    From
    $2,250
    / Week
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    1 / 30
    5 of 5 stars (2) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    Amenities & Details
    • DVD Player
    • Stereo System
    • Satellite TV
    • Deck
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    The Shady Mango was originally built in 1925. According to local history the heart pine used in constructing the original house came by steam boat to the City Pier and was hauled by horse-drawn lorry up Pine Avenue to the home's present site. In 2004 the home was given a major renovation... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed September 21, 2013
    My husband, 2 kids & I stayed at the Shady Mango & LOVED it! It's the perfect place for a vacation for a small family. It's in a great location with walking access to the beach...
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    $325
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    1 / 18
    4 of 5 stars (7) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 9
    Overview Reviews (7) Make Inquiry
    Amenities & Details
    • Water Views
    • Internet Access
    • Stereo System
    • Washer
    • Deck
    • Air Conditioning
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
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    • Smoking allowed
    • Elder access
    • ?
    About this property
    This 3 bedroom/2 bath beachy home has views of the gulf from all but 1 bedroom. It has a 600 sq.ft. deck. The sand is sugary white and this is a private beach, but if you want some action, you can walk to some of the nicest restaurants on the water, or drive 5 or 6 minutes into town. I have had... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed July 12, 2015
    We only were there a few days, but all we could say when we got there was "Is this for real?" It was such a wonderful place for our reunion. Very clean in all ways. We all sat...
    5 of 5 stars Reviewed June 5, 2015
    I have rented this house on the beach for the last nine years. The owner has made some much needed improvements............such as new kitchen cupboards and granite top cabinets...
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    $700
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    5 of 5 stars (16) Excellent
    4 Bedrooms / 5 Bathrooms / Sleeps 8
    Overview Reviews (16) Make Inquiry
    Amenities & Details
    • Hot Tub
    • Stereo System
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Private Outdoor...
    • Deck
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    4 Bedroom 5 bath luxury beach front house sleeping 8 with heated pool separate spa numerous decks and stunning beach views from every room. We are located on the desirable family friendly island of Anna Maria. The house is direct beach front on the quiet upmarket north end of the island. Recently... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed April 15, 2015
    After a mad week doing the theme parks in Orlando we came here for some serious relaxation - and what a great choice it was. The house is stunning and the location couldn't be...
    5 of 5 stars Reviewed March 11, 2015
    Hi Nigel and Maggie. We have enjoyed your place 3 weeks this year. Had one week in January and the other 2 in Feb/Mar. We could hardly wait to go back after our first...
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    $260
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    1 / 22
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Porch
    • Dishwasher
    • Wi-Fi
    • Washer
    • Microwave
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Nothing better than having the beach at your doorstep! Located in the heart of Anna Maria city this 2 bedroom, 2 bath Direct Gulf Front cottage has 100 feet of Gulf front beach. Enjoy the views from the enclosed sitting room or the observation deck. Amenities include washer/dryer, dishwasher,... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
    From
    $117
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    1 / 20
    4 of 5 stars (1) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Microwave
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    'The Mermaid's Purse' is a charming cottage located just one property away from the beautiful white sand beaches in the city of Anna Maria. If you are looking for a fairly priced property that is well equipped, clean and comfortable then this cottage if for you!! The cottage is nicely furnished in... View all property information
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    Anna Maria, Anna Maria Island 34216
    4 of 5 stars Reviewed November 12, 2014
    This was our second stay at Mermaid's Purse…another very positive experience. The owner provides every little convenience and more for her guests…even greeted us with a fresh...
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    $100
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    1 / 18
    5 of 5 stars (1) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Microwave
    • Dryer
    • Wi-Fi
    • Dishwasher
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This cute 2 bedroom, 1 bath unit is located at the quiet North End of Anna Maria Island just steps to beautiful white sand beaches. Only 6 properties to the beach access. Nature lovers will enjoy bird watching along the beaches at Bean Point. Rod-N-Reel Pier is not too far away for great fishing... View all property information
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    Anna Maria, Anna Maria Island 34216
    From
    $172
    / Night
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    1 / 25
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Microwave
    • Porch
    • Dishwasher
    • Dryer
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    If you’re looking for carefree living just blocks from the beach, look no further than the “Owl’s Hideout”. This 3 bedroom, 2 bathroom home is comfortably equipped with a king, queen and twin beds. There is a lovely screened-in porch that is perfect for relaxing and listening to the gentle waves of... View all property information
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    Anna Maria, Anna Maria Island 34216
    From
    $129
    / Night
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    1 / 20
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Washer
    • Dryer
    • Wi-Fi
    • Satellite TV
    • Parking
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    It doesn't get much better than this! Relaxing on the Screened lanai overlooking the blue waters of Tampa Bay and the Gulf of Mexico. This elevated 3 bedroom, 2 bath Direct Bay Front home has wonderful views from the master bedroom, living room and screened lanai. Private setting close to Anna... View all property information
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    Anna Maria, Anna Maria Island 34216
    From
    $180
    / Night
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    1 / 29
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Parking
    • Internet Access
    • Shared Outdoor Pool...
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Welcome to 721 Holly Road located on the northern end of beautiful Anna Maria Island. This lovely single family elevated three bedroom and two bath vacation rental features all that you will need to stay a week or a month! Feel the breezes through the screened lanai or lounge by the new heated pool... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
    From
    $130
    / Night
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    1 / 22
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Make Inquiry
    Amenities & Details
    • Microwave
    • Dryer
    • Wi-Fi
    • Dishwasher
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Palm Court Villas are located in the heart of Anna Maria Village with a short stroll to great local restaurants, shops and the Community Center. Beautiful white sand beaches are just one short block away. You have direct beach access to one of the best beaches on the Island. This section of beach... View all property information
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    Anna Maria, Anna Maria Island 34216
    From
    $104
    / Night
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    1 / 18
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Dryer
    • Satellite TV
    • Washer
    • Dishwasher
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Located in the heart of Anna Maria Village and walking distance to everything fun! This 2BR/1.5 Duplex apartment has been recently updated and is located a few houses from the beautiful Gulf Beaches. Direct beach access with no streets to cross. 146 steps to the beach and less than a 2 minute walk.... View all property information
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    Anna Maria, Anna Maria Island 34216
    From
    $128
    / Night
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    1 / 23
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Washer
    • Parking
    • Dishwasher
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The best of both worlds on the Island is where the Gulf meets the Bay at the 'Tip' of Island in Anna Maria. Beautiful Sunsets, Fishing Piers, a Park and Bird Watching can be found at the Northern tip of the Island. This 2BR/2BA plus a Loft is located one property from the beach access at Bean... View all property information
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    Anna Maria, Anna Maria Island 34216
    From
    $136
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    1 / 15
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Satellite TV
    • DVD Player
    • Washer
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located at the quiet North end of Anna Maria this 3BR/2BA canal front home comes with exceptional views! There are two screened lanais, a boat dock and a garage. Brand new Kitchen with granite countertops and new appliances. Updated furnishings. There are two full size beds, one twin and a queen... View all property information
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    Anna Maria, Anna Maria Island 34216
    From
    $157
    / Night
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    1 / 25
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Shared Outdoor Pool...
    • Internet Access
    • Parking
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Stay now until September 12th 2015 and save 20% off the rates!. No other discounts would apply. Welcome to the Dolphin located at 706 Rose unit B. This quaint 2 bedroom 1 bath duplex located on a quiet street on the north end of beautiful Anna Maria Island awaits the vacationer in you. Recently... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216
    From
    $104
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    1 / 28
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Dryer
    • Wi-Fi
    • Washer
    • Satellite TV
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The Canary Cottage has 2 bedrooms plus a bunkroom - and 2 full baths and will Sleep up to 8. Located in the heart of Anna Maria City- This Key West charmer is elevated and has been updated with new tile, fixtures, plus a new tub/shower! Updated furnishings, and appliances, which add to the charm... View all property information
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    Anna Maria, Anna Maria Island 34216
    From
    $3,345
    / Month
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    1 / 35
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Washer
    • Parking
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located within Anna Maria City and right next to the Gulf of Mexico, a 3 bedroom 2 1/2 bath privately gated home. Originally an 'Old Florida Home,' with added ample living space for guests to enjoy as well as provide stunning sunset views amidst the foliage and palms. This property is located just... View all property information
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    Anna Maria, Anna Maria Island
    From
    $158
    / Night
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    1 / 28
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Deck
    • Internet Access
    • Dryer
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Bring the family and come enjoy our beautiful beaches! This 4BR/4BA elevated home is only one short block to the beach with direct beach access. This spacious home has plenty of room for family with 2 king size beds, a queen bed and two twins. Large, fully equipped kitchen, laundry room with... View all property information
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    Anna Maria, Anna Maria Island 34216
    From
    $165
    / Night
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    1 / 22
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Wi-Fi
    • Dryer
    • Garage
    • Satellite TV
    • Grill
    • Shared Outdoor Pool...
    • Washer
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Updated home with Pool!! Elevated 2BR/2BA home with open floor plan and large screened lanai. One short block with direct access to the beautiful white sand beach. This home has been updated with wood flooring, new carpet and granite countertops. Enjoy the outside pool area with beautiful brick... View all property information
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    Anna Maria, Anna Maria Island 34216
    From
    $211
    / Night
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    1 / 43
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool...
    • Parking
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The special 'North End' vacation rental is immaculately clean and whimsically decorated, professionally landscaped, and boasts one of the larger pools and larger backyards on the Island. The spa is accented by iridescent glass. The 20' tall Chickee (tiki) hut was hand-built by Native Americans and... View all property information
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    Location Information
    Anna Maria, Anna Maria Island 34216