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Beach Rentals and Cottages in Anna Maria, FL

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    1 / 38
    4.5 of 5 stars (7) Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 12
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    5 of 5 stars (14) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6
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    5 of 5 stars (16) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8
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    About this property
    Description We are located in the heart of the beautiful city of Anna Maria FL. We are one block from the historic Pine Ave with free trolley service to the entire island. We are two blocks to the beautiful white sand beach. Three blocks in the opposite direction is the bay and the historic City... View all property information
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    Anna Maria, Anna Maria Island 34216
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    $175
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    4 Bedrooms, 3 Bathrooms, Sleeps 10
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    • Ping Pong Table
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    About this property
    In a tropical setting, complete with pool and large sun deck. Just a short walk to the beach. Our visitors love biking the island and taking walking tours to the various places of interest on the island. There are four bedrooms and three baths. The master suite has a king bed and a Roman tub. The... View all property information
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    Anna Maria, Anna Maria Island 34217
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    1 / 31
    4.5 of 5 stars (7) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8
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    About this property
    Welcome to Willow Cottage located West of Gulf Dr at 108 Willow and on beautiful Anna Maria Island.This lovely ground level Anna Maria Island beach bungalow awaits you for the vacation you deserve! This rental home is stylishly decorated with touches of both new and old Florida. Rare and highly... View all property information
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    Anna Maria, Anna Maria Island 34217
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    1 / 18
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4
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    • Microwave
    • Dryer
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    • Pet-friendly
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    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
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    1 / 20
    4 of 5 stars (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4
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    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Microwave
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
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    • ?
    • ?
    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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    1 / 25
    3 Bedrooms, 3 Bathrooms, Sleeps 7
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    About this property
    Directly on beautiful Tampa Bay and views of the Sunshine Bridge makes this the picture perfect vacation rental. 'Sangria Sunrise' Cottage is a 3 bedroom 3 bathroom ground level single family home in the City of Anna Maria. The bay front patio is perfect for soaking up the sun and you have your own... View all property information
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    Anna Maria, Anna Maria Island 34216
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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
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Satellite TV
    • DVD Player
    • Private Fishing...
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    • 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 / 18
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6
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    • DVD Player
    • Dryer
    • Internet Access
    • Deck
    • Satellite TV
    • Washer
    • Air Conditioning
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • 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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    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 / 23
    5 of 5 stars (5) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8
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    • 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 / 30
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8
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    • Water Views
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Private Outdoor...
    • Hot Tub
    • Waterfront
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    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
    From
    $119
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    3 Bedrooms, 3 Bathrooms, Sleeps 7
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    • Wi-Fi
    • Private Fishing...
    • Satellite TV
    • Watersports Nearby
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    • Waterfront
    • Air Conditioning
    • Ocean Views
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    It doesn't get much better than being right on the water, ½ block from the bay beach, and only 7 blocks from Pine Avenue. Sunshine Cottage couldn't be a better name, because this 3 bedroom, 2 bathroom, cottage truly lets you experience the beauty of Anna Maria Island. Enjoy dangling your feet off... View all property information
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    Anna Maria, Anna Maria Island 34216
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    $114
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    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Pet-friendly
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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
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    $188
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    1 / 24
    4.5 of 5 stars (9) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7
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    • Satellite TV
    • Deck
    • Washer
    • Private Outdoor...
    • DVD Player
    • Wi-Fi
    • Stereo System
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    BON AMI will be your 'good friend' after a vacation stay. Located on the north end of Anna Maria Island and a short distance to Bean Point, this heated pool stilt home will beckon you back year after year! Beautifully decorated, this three-bedroom, two-bath vacation rental is spacious, airy, and... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed June 23, 2015
    Villa was exactly what we were looking for infact better than what I imagined,location great all it's amenities good and very well kept and presented would recommend to others
    4 of 5 stars Reviewed November 1, 2014
    We're a family from Germany and booked Bon Ami via Homeaway/FeWo direkt. Our stay was all in all very nice: the location is nearly perfect, only a few steps to the beach. The...
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    1 / 23
    5 of 5 stars (9) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Wi-Fi
    • Grill
    • Refrigerator
    • Washer
    • Dryer
    • Air Conditioning
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Your time on Anna Maria Island should be perfectly charming in this classic beach-style cottage perfectly located on the west side of Gulf Drive in the city of Anna Maria. Only steps away from the azure blue waters of the Gulf of Mexico, this unique vacation rental boasts two very large bedrooms... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed September 1, 2015
    This cottage is an open and spacious layout with plenty of sleeping room for a large family or group of friends. The house is well-maintained and was impeccably clean and cool...
    5 of 5 stars Reviewed August 31, 2015
    We just stayed at this quaint house for a much deserved break and loved every minute of it. The house was perfect for entertaining a few friends and a great place to come back to...
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    1 / 12
    4 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Internet Access
    • Balcony
    • Terrace
    • Shared Outdoor Pool...
    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    At this spacious, family friendly home, grab your fishing pole, take the hand of a child and meander to the private dock, cast a line while dangling your feet and spending the day with your child or grandchild. Equipped to entertain a party of eight along with a small pet, this airy pool home... View all property information
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    Anna Maria, Anna Maria Island 34216
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    4 of 5 stars (9) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6
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    • Balcony
    • Shared Outdoor Pool...
    • Internet Access
    • Terrace
    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Nothing restores the body and soul like a stay at the beach!~ 744 Jacaranda---In City of Anna Maria---3 bedroom 3 bath raised home with private screened-in pool. 1 block to beach. Quiet residential area. Pool heat optional @ $20/day. Additional amenities include: tub or shower yes, square... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed August 31, 2015
    We loved this house for the week we spent in it. it was very clean and had all the little extras that make a holiday let in the U.S. ideal for a U.K. family - i.e. lots of beach...
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    5 of 5 stars (9) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Dishwasher
    • Shared Outdoor Pool...
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    • Internet Access
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    • Pet-friendly
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    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Stay September 2015 for ONLY $799.00 per week and no other discounts would apply. What a special place! Remember days gone by in this Key West style island getaway with sparkling pool in a tropical paradise setting. Spacious three bedroom plus den and two bath vacation rental home in desirable... View all property information
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    Anna Maria, Anna Maria Island 34217
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    1 / 14
    5 of 5 stars (7) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4
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    • Pet-friendly
    • Wheelchair access
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    • x
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    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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    $304
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    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Wi-Fi
    • Ocean Views
    • Water Views
    • Air Conditioning
    • Pool Table
    • Private Outdoor...
    • Waterfront
    • Hot Tub
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    • 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 / 34
    4.5 of 5 stars (7) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8
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    • 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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    $250
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    4.5 of 5 stars (35) Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 12
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    • 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 / 26
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Shared Outdoor Pool...
    • Internet Access
    • Parking
    • Dishwasher
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Paradise Pointe located in the quiet north end of beautiful Anna Maria awaits the vacationer in you. This picture perfect ground level three bedroom two bathroom vacation rental single family home is located on a lagoon canal and has a private heated pool & spa. Also, it is about 2 blocks to the... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed May 11, 2015
    We stayed at Paradise Pointe for a week in May and thoroughly enjoyed it. The house is located in a quiet area of AMI and is within walking distance of Bean Point and the Rod and...
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    1 / 29
    4 of 5 stars (5) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8
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    • 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
    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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    $850
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    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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    $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
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • 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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    4 of 5 stars (7) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 9
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    • 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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    $260
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    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • 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 step right out your door and have your feet buried in the sand just a... View all property information
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    Anna Maria, Anna Maria Island 34216
    From
    $1,100
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    3 Bedrooms, 2 Bathrooms, Sleeps 6
    other travelers have booked this property
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    • Washer
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    • Stove
    • Deck
    • Satellite TV
    • Wi-Fi
    • Refrigerator
    • Dryer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    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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    $100
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    1 / 16
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4
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    • Dryer
    • Satellite TV
    • Washer
    • Wi-Fi
    • Patio
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
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    • 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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    $93
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    1 / 20
    4 of 5 stars (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2
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    • Parking
    • Washer
    • Dryer
    • Satellite TV
    • Dishwasher
    • Wi-Fi
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    • 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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    $1,700
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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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    • Child-friendly
    • x
    • x
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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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    $180
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    1 / 29
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Parking
    • Internet Access
    • Shared Outdoor Pool...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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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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    Anna Maria, Anna Maria Island 34216
    From
    $700
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    1 / 13
    2.5 of 5 stars (2) Poor
    2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Amenities & Details
    • Satellite TV
    • DVD Player
    • Waterfront
    • Internet Access
    • Air Conditioning
    • Private Outdoor...
    • Water Views
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Copacabana is a 2 bedroom, 2 bath private canal front home with a pool; with tile floors throughout and a designer's stylish touch, you will feel you have found your home away from home! Copacabana will accommodate 6-8 people and offers a separate family room with a large flat screen TV that is... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 of 5 stars Reviewed June 13, 2015
    The house was not cleaned until 745 the first night. The pool was green and unusable for two days. Sewage backed up into the shower and toilets on two nights and several of us had...
    4 of 5 stars Reviewed May 15, 2015
    We fell for this precious place the moment we walked in the door, This will become an annual rental. It's exactly what we need. A real old Florida home with a great pool...
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    $165
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    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • 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
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    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
    $129
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    1 / 20
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Dishwasher
    • Washer
    • Dryer
    • Wi-Fi
    • Satellite TV
    • Parking
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
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    • 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
    $100
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    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • 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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    Anna Maria, Anna Maria Island 34216
    From
    $114
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    1 / 10
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7
    Overview Reviews (2) Make Inquiry
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    • Internet Access
    • Dishwasher
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    .This lovely elevated vacation rental home features three bedrooms, two baths and a large living/dining room area for entertainment. The large screened lanai off the living room makes a pleasant place for morning coffee, evening meals or just sitting back, relaxing and reading. The lush... View all property information
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    Anna Maria, Anna Maria Island 34216
    4 of 5 stars Reviewed January 8, 2015
    This is a very nice, roomy house with absolutely lovely grounds! We had a great week biking to a different section of beach every morning, and walking to Bean Point for the...
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    $104
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    1 / 18
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    • Wi-Fi
    • Parking
    • Dryer
    • Satellite TV
    • Washer
    • Dishwasher
    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
    $86
    / Night
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    1 / 12
    2 Bedrooms, 1 Bathroom, Sleeps 4
    Overview Make Inquiry
    Overview
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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
    From
    $104
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    1 / 18
    2 Bedrooms, 1 Bathroom, Sleeps 4
    Overview Make Inquiry
    Overview
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    • 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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    Anna Maria, Anna Maria Island 34216
    From
    $136
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    1 / 15
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Inquiry
    Overview
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    • 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
    $128
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    1 / 26
    3 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Make Inquiry
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    • Shared Outdoor Pool...
    • Parking
    • Dishwasher
    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This newly remodeled and updated island vacation rental duplex is just a stroll to the Gulf of Mexico and our beautiful sunsets. This home has been decorated to make you feel like you were in Key West. This unique unit is actually two separate living spaces that adjoin in the center.... View all property information
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    Anna Maria, Anna Maria Island 34216
    From
    $158
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    1 / 28
    4 Bedrooms, 4 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
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    • 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
    $229
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    1 / 19
    4 Bedrooms, 2 Bathrooms, Sleeps 8
    Overview Make Inquiry
    Overview
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    • Dryer
    • Dishwasher
    • Washer
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This vintage Island beachfront home has 4 sleeping rooms and 2 bathrooms. Enjoy the charm of yesterday in this great family beach house located between Palm and Magnolia Avenues. Excellent Gulf views, steps to beautiful, white sandy beaches. This home includes a washer/dryer, dishwasher, several... View all property information
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    Anna Maria, Anna Maria Island 34216
    From
    $128
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    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Inquiry
    Overview
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    • 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
    $1,400
    / Week
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    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Pet-friendly
    • Wheelchair access
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    • x
    • x
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    • Elder access
    • x
    About this property
    Casa Allegria is just perfect! Beautiful cool beachy colors throughout and only a short walk from the beach. This spacious 3 bedroom, 2 bath ground level home is located in the most sought after area on Anna Maria Island! Close to Pine Avenue, trolley stops, and the SandBar Restaurant. Come and... View all property information
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    Anna Maria, Anna Maria Island 34216
    From
    $95
    / Night
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    1 / 18
    4 of 5 stars (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6
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    • Dishwasher
    • Parking
    • Shared Outdoor Pool...
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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