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Beach Rentals and Cottages in Anna Maria, FL

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    All 182 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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    $357
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    1 / 23
    5 of 5 stars (5) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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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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    3 Bedrooms / 3 Bathrooms / Sleeps 7
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    1 / 38
    4.5 of 5 stars (7) Very good
    5 Bedrooms / 3 Bathrooms / Sleeps 12
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    • Water Views
    • TV
    • DVD Player
    • Internet Access
    • Stereo System
    • Private Outdoor...
    • Air Conditioning
    • Watersports Nearby
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Elder access
    • x
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    About this property
    WELCOME TO ALL DECKED OUT! Whether getting away for a family vacation, with a group of friends, for a wedding or any other occasion, our gorgeous 5 Bedroom home offers everything you could want for a relaxing holiday on Anna Maria Island.... with incredible views of the Bay! Sit by the tropical... 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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    $300
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    1 / 14
    5 of 5 stars (10) Excellent
    5 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Private Outdoor...
    • Water Views
    • Internet Access
    • Air Conditioning
    • Waterfront
    • Satellite TV
    • DVD Player
    • Private Fishing...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This is our personal Vacation Home. C-view is managed by a team we have selected, not a property management company. C-view Florida is one of the few canal homes (29 foot dock) close to the Gulf of Mexico. This newly renovated, 5 bedroom, 3 1/2 bathroom home has a large and beautifully... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed April 25, 2011
    I'm torn; I want to keep this amazing house a secret, but I also want to give Ann props for building & maintaining such a gem. She thought of everything, right down to napkin...
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    1 / 15
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Internet Access
    • Parking
    • Dishwasher
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • 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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    1 / 8
    5 of 5 stars (13) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travelers have booked this property
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    • 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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    Anna Maria, Anna Maria Island 34216
    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...
    4 of 5 stars Reviewed April 29, 2015
    Stayed in this bungalow for 4 nights and very pleased . It was like home from home and had a very relaxing feel with all facilities,and an excellent location with good...
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    $850
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    1 / 14
    2 Bedrooms / 1 Bathroom / Sleeps 5
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    • 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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    Anna Maria, Anna Maria Island 34216
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    $104
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    1 / 18
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Satellite TV
    • Washer
    • Internet Access
    • Dryer
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    • 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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    $170
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    1 / 17
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
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    • Washer
    • Air Conditioning
    • Stove
    • Deck
    • Satellite TV
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    • Dryer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
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    • 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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    Location Information
    Anna Maria, Anna Maria Island 34217
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    1 / 23
    5 of 5 stars (5) Excellent
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    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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    $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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    Anna Maria, Anna Maria Island 34216
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    $110
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    1 / 14
    5 of 5 stars (7) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (7) Make Inquiry
    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
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    $250
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    1 / 17
    4.5 of 5 stars (35) Very good
    6 Bedrooms / 4 Bathrooms / Sleeps 12
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    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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    $157
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    1 / 25
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Shared Outdoor Pool...
    • Internet Access
    • Parking
    • Dishwasher
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • 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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    Anna Maria, Anna Maria Island 34216
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    $471
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    1 / 29
    4.5 of 5 stars (4) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (4) 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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    Anna Maria, Anna Maria Island 34216
    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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    1 / 21
    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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    1 / 34
    4.5 of 5 stars (7) Very good
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (7) Make Inquiry
    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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    $375
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    1 / 17
    5 of 5 stars (1) Excellent
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Dishwasher
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Breakaway 891 North Shore Dr. Anna Maria, Fl. 34216 Leaping to the top of the class- this fabulous Bay front home has just undergone a significant renovation inside and out! The makeover includes an addition of a 4th bedroom, remodelled Master bedroom with a walk in closet, new floors in the... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed June 15, 2015
    From the moment you walk in this house you are blown away by the view. Beautiful home, great location, private pool, grill, plenty of room for the 8 of us...and so much more...
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    $158
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    1 / 28
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    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
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    1 / 21
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Inquiry
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Limelight 771 Jacaranda Rd. Anna Maria, Fl. 34216 Limelight is a gorgeous newly renovated home, inside and out, located on the prestigious North End of Anna Maria Island. Only a brisk 3 minute walk away from the sandy white beaches, this home offers everything you are looking for in an Island... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed January 11, 2015
    We loved the location and the house was beautiful and well equipped. It was a perfect place for us to vacation with our three adult children. The kitchen was top notch with...
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    1 / 24
    4 of 5 stars (5) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (5) Make Inquiry
    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Private Outdoor...
    • Dryer
    • DVD Player
    • Stereo System
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    The adorable Coastal Cottage, located in the laid-back city of Anna Maria, is the perfect place to take a totally carefree vacation. The white sand beach of Anna Maria Island and the azure blue waters of the Gulf of Mexico are only a short stroll from this delightful three-bedroom, two-bath... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed October 31, 2014
    Great, private and quiet location. The house is equipped with all you and your family need. The short distance to the beach made us walk to the beach more than once a day. Any...
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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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    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 / 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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    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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    $130
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    1 / 22
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • Microwave
    • Dryer
    • Wi-Fi
    • Dishwasher
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    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
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    $93
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    1 / 20
    4 of 5 stars (1) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
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    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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    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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    $2,250
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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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    1 / 30
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    Amenities & Details
    • Water Views
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Private Outdoor...
    • Hot Tub
    • Waterfront
    • DVD Player
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    • Pet-friendly
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    About this property
    Canal Place is a restored three bedroom, three bath Old Florida island home with a pool and hot tub; neutral and relaxing decor with a spacious living room and just a short stroll to the white sand beaches if Anna Maria. Direct waterfront with beautiful canal views. Sleeps upto 8 people. Amenities... View all property information
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    Anna Maria, Anna Maria Island 34217
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    1 / 27
    4 of 5 stars (1) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Pet-friendly
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    • 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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    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 9
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    • Pet-friendly
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    • x
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    About this property
    Three Bedroom elevated recently renovated private home. This property in Anna Maria City and West of Gulf Drive! Gorgeous outdoor elevated covered deck is a perfect spot to relax and let your cares be whisked away by the Gulf Breezes. Just a few hundred steps from the Gulf of Mexico with no... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed July 15, 2014
    Where do I start! First, if you live anywhere near central Florida, this is one of those magical FL west coast places you must visit. A little, secluded, but quaint paradise just...
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    $325
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    4 of 5 stars (6) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 9
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    Amenities & Details
    • Water Views
    • Internet Access
    • Stereo System
    • Washer
    • Deck
    • Air Conditioning
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    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 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...
    5 of 5 stars Reviewed May 31, 2015
    My husband and I have been renting this home for over 24 years and can not get enough of the island. At first we only went there for one week a year and that was just too...
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    5 of 5 stars (1) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 12
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    • TV
    • DVD Player
    • Patio
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • x
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    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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    5 of 5 stars (3) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 9
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    • TV
    • DVD Player
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    • Pet-friendly
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    • x
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    • x
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    About this property
    Seaside 851 N. Shore Dr. Anna Maria, Fl. 34216 Seaside is a private, luxury home located on the very northern tip of Anna Maria Island. It looks directly at the Skyway Bridge, Egmont Key and Downtown St. Petersburg- you will not find a more breathtaking view anywhere on the island. The home... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed April 20, 2015
    I had never been to Anna Maria Island before, and the rental agent said I would fall in love with it on our first trip; she was so right. That island, with its crystal clear blue...
    5 of 5 stars Reviewed October 29, 2014
    What a wonderful vacation rental!! We had a little birthday party with family and friends and this place had it all! I got so many compliments that I had to let you know. The...
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    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Patio
    • DVD Player
    • TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • x
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    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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    5 of 5 stars (3) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Dishwasher
    • Shared Outdoor Pool...
    • Parking
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    • Pet-friendly
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    About this property
    801 Jacaranda located just two blocks from Bean Point on beautiful Anna Maria Island, FL. This recently totally remodeled home offers designer features throughout and upscale furnishings. There are 3 bedrooms and 2 bathrooms with large living room and dining area. The kitchen has an open floor plan... View all property information
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    Anna Maria, Anna Maria Island 34217
    5 of 5 stars Reviewed October 1, 2013
    We (family of 4 adults) have just returned from 2 weeks on Anna Maria Island and not only are we missing it but already making plans for a return visit to Pina Colada. The house...
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    5 of 5 stars (1) Excellent
    5 Bedrooms / 4 Bathrooms / Sleeps 12
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    • Dishwasher
    • Internet Access
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    • Pet-friendly
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    • Child-friendly
    • x
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    About this property
    Villa Marianne 111 Maple Ave. Anna Maria, Fl. 34216 Wow, you just can't say enough great things about this beautiful beach villa! This 5 bedroom, 4 bathroom home so close to the beach- no more than a 1 minute stroll and located on the prestigious North end of the island. Every room is... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed March 22, 2015
    We just returned from our week long stay at Villa Marianne and couldn't be happier. We were two families- mine and my cousin and hers. 4 adults total, and 5 kids ages 8,6, 4,3...
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    4.5 of 5 stars (4) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Boat Available
    • Stereo System
    • Washer
    • Air Conditioning
    • Deck
    • Wi-Fi
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Elder access
    • x
    About this property
    With its luscious landscaping, eclectic look and colorful Key-West style, Simpatico could be right out of Coastal Living Magazine. This bungalow is perfect for the ideal secluded island vacation! Located on the north end of Anna Maria Island, this canal home, with a boat dock and kayaks,... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed January 11, 2015
    My husband and I and another couple stayed here for one week in December. This was our first stay on the island and we would definitely go back. We have rented homes all over...
    4 of 5 stars Reviewed July 29, 2014
    The entire grounds and unit are artfully decorated with many vignettes located throughout. Very quiet neighborhood but located within easy walking or biking distance of many shops...
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    4 of 5 stars (2) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Washer
    • Dryer
    • Stereo System
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • Elder access
    • x
    About this property
    The Light House welcomes you in with its tropical landscaping, canal view and calming green exterior. This nicely furnished two-bedroom, one-bath vacation rental on Anna Maria Island has everything you need to begin a relaxing and restful vacation. Newer appliances will make quick work of... View all property information
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    Anna Maria, Anna Maria Island 34216
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    4 of 5 stars (1) Very good
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Internet Access
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    • Pet-friendly
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    • x
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    About this property
    Sunchase Villa 302 Gulf Blvd Anna Maria, Fl. 34216 Sunchase Villa is a true Old Florida, ground level beach cottage nestled on the north end of Anna Maria Island only a short walk to restaurants and shopping. There are fantastic Gulf Views from this well-appointed 4 bedroom, 4.5 bath private... View all property information
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    Anna Maria, Anna Maria Island 34216
    4 of 5 stars Reviewed December 15, 2014
    The location of this house is great---right on the beach and close to many restaurants! The house is roomy and nicely furnished, including multiple TVs for anyone who is...
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Dishwasher
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    • Pet-friendly
    • Wheelchair access
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    • x
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    About this property
    Welcome to 871 No Shore guest cottage. Enjoy the feel of 'old Florida' with this charming split level 3 bedroom 2 bathroom accommodations located behind the main house. Access to the lower level is on a sprial staricase. Great bayfront location with direct access to bay. Feel free to walk along... View all property information
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    Anna Maria, Anna Maria Island 34216
    From
    $330
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    1 / 24
    5 of 5 stars (1) Excellent
    5 Bedrooms / 3 Bathrooms / Sleeps 14
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    • Dishwasher
    • Internet Access
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    • Pet-friendly
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    • x
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    About this property
    Villa Del Sol 211 Chilson Avenue Anna Maria, FL 34217 This is an exquisite, newly remodeled 5 bedroom, 3 bath ground level home with available boat dock. Inside the home you will find quality furnishings with a Caribbean decor. The open floor plan provides the perfect space for spending... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed May 17, 2015
    Villa Del Sol is a Fabulous comfortable house in Paradise. We had 14 people stay at the house for a week. The house fit us very comfortably with awesome beds, bathroom and a...
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    5 of 5 stars (1) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 14
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • x
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    About this property
    Ocean Walk 117 Willow Avenue Anna Maria Island, Fl 34216 Ocean Walk is a brand new private home that is now ready for rental! The style of the home offers a very attractive roof line with steep pitches, lots of balconies and being located West of Gulf drive there are no busy roads to cross and... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed March 15, 2015
    Everything in this house is top notch. We've rented lots of places in Florida, but this one is beautiful. Everything is brand new, furniture is all good quality, bedding is great...
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    4.5 of 5 stars (3) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Stereo System
    • Private Outdoor...
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Deck
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
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    • Smoking allowed
    • Elder access
    • x
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    About this property
    Located in the city of Anna Maria on the north end of Anna Maria Island, this gorgeous three-bedroom dog-friendly vacation rental is the perfect place for a vacation retreat! With an estimated 2100 square feet, AMI Retreat has plenty of room to kick off your flip flops and enjoy your down time.... View all property information
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    Anna Maria, Anna Maria Island 34216
    4 of 5 stars Reviewed April 15, 2015
    Our group of 4 adults and 2 children stayed at this home over Spring Break and had a fantastic time. The house is decorated and laid out very well, and is optimized for comfort...
    5 of 5 stars Reviewed March 11, 2015
    Enjoyed our stay here. Close to nicest beach, saw dolphins at each sunset so far, very colorful and clean house, great new pool, good location in quiet neighborhood. We liked...
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    4 of 5 stars (1) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Pet-friendly
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    • Child-friendly
    • x
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    • x
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    About this property
    Anna Maria Cottage 104 Magnolia Avenue Anna Maria Island, FL 34216 This beautiful historic beach cottage is a true embodiment of 'Old Florida Charm'. This wonderful home offers 3 suites, each with their own en-suite full bathroom, a wrap around porch with stunning Gulf views and much more!... View all property information
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    Anna Maria, Anna Maria Island 34216
    4 of 5 stars Reviewed February 23, 2015
    I spent almost 3 weeks on AMI sharing this lovely cottage with my sister and some other friends and family. The location is wonderful, very close to the beautiful beach, so an...
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    4 of 5 stars (1) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Dishwasher
    • Parking
    • Shared Outdoor Pool...
    • Internet Access
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    • Pet-friendly
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    • Child-friendly
    • x
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    • x
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    About this property
    This newly remodeled two bedroom duplex is situated halfway between the Gulf of Mexico and the Tampa Bay. Not more than 3 blocks in either direction. It is located on the north end of Anna Maria Island on Magnolia Avenue. A new heated pool was just installed and only can be used by this unit.... View all property information
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    Anna Maria, Anna Maria Island 34216
    4 of 5 stars Reviewed November 25, 2014
    We usually book a house on Anna Maria a year in advance but this was a late booking, just for the two of us and we were not disappointed. The duplex was roomy, well equipped and...
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    4 of 5 stars (1) Very good
    5 Bedrooms / 3 Bathrooms / Sleeps 12
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    • TV
    • Patio
    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • x
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    About this property
    Tortuga Bay 9405 Gulf Dr. Anna Maria, FL 34216 This one is extraordinary! Tortuga Bay is a completely renovated, ground level, 5 bedroom property that has one of the most outstanding tropical pools on the island- featuring a theme-park style water-slide! Located in the prestigious city of... View all property information
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    Anna Maria, Anna Maria Island 34216
    4 of 5 stars Reviewed April 2, 2015
    The house was beautiful, spotless, and comfortable. The pool area was amazing and the walk to the beach was seriously 2 minutes tops. We like to stay beach front so if the beach...
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    5 of 5 stars (6) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    Amenities & Details
    • Patio
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Washer
    • Dryer
    • Wi-Fi
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Steps from the white sand beaches of Anna Maria, this four-bedroom, three bath, elevated house is just the place to build sand castles and memories! Located on Pine Avenue in Anna Maria, this charming beach vacation rental with a new backyard pool is beckoning you to start your vacation now. A... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed January 5, 2015
    We rented the house for a family Christmas vacation. The process was easy and the staff at AMI were very helpful and friendly. The house was large enough for our family of 8 to...
    5 of 5 stars Reviewed August 24, 2014
    We rented this house thru Coastal Cottages in August 2014. They were very friendly and professional- making the process a breeze. Both couples were thrilled with our stay. The...
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    5 of 5 stars (2) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Shared Outdoor Pool...
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    • Pet-friendly
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    • x
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    • x
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    About this property
    Southern Breeze #1 607 Fern Street #1 Anna Maria, Fl. 34216 ISLAND 6-PLEX - Newly renovated top to bottom June 2013! These are 2 bedroom, 1 bath ground level units located at the tip of Anna Maria Island just steps from the Bay. Heated pool with nicely landscaped surroundings. Each is... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed May 30, 2015
    a goon nice quit time was had by the three of us, Took a day to learn about getting around a map might help.
    5 of 5 stars Reviewed August 21, 2014
    Amei conhecer a ilha Anna Maria! tanto que estou pretendendo voltar no próximo ano para passar pelo menos um mês inteiro! Alugamos essa casa pela internet com poucos dias de...
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    4 of 5 stars (1) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Dishwasher
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    • Pet-friendly
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    • x
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    About this property
    Birds Eye View 802 Gladiolus Street Anna Maria, FL 34216 This spacious and charming 2 bedroom, 2.5 bath elevated home is just three houses from the Gulf of Mexico! It is located near popular Bean Point at the prestigious northern tip of Anna Maria Island. It has fabulous island style... View all property information
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    Anna Maria, Anna Maria Island 34216
    4 of 5 stars Reviewed September 6, 2013
    Lovely property...close to both gulf and bay beaches for sunrise/sunset. Loads of space with a huge master bedroom/bathroom. Clean and well kept but could use a few updates...
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Parking
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    • Pet-friendly
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    • x
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    About this property
    Right across from the beach! This new ground level home awaits you and your family for a wonderful vacation. Enjoy everything from the heated pool to the soft sand beaches of Anna Maria Island. Everything is new and top of the line for your all of your holiday needs. This is a well sought after... View all property information
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    Anna Maria, Anna Maria Island 34217