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Vacation Rentals in Anna Maria, FL

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    Travellers to Anna Maria are booking February dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 40
    5 of 5 bubbles (10) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    5 of 5 bubbles (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Stunning ground level 3 bedroom/2 bath home with luxury finishes at every glance. Brand new to the market and recently renovated, this home is packed with designer finishes throughout from luxury linens in all three uniquely appointed bedrooms to furnishings that make this home feel like you are... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34217
    5 of 5 bubbles Reviewed 2 weeks ago
    Had a wonderful stay at blue heron, the house is beautifully furnished, but main thing about this property is outside. The dock with fishing and the kayaks for kayaking in the...
    5 of 5 bubbles Reviewed 28 June 2016
    Just what our family needed for a relaxing vacation. We loved the swimming pool and that you could kayak a few hundred feet and view the manatees on the canal right from the...
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    1 / 16
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Sea Waves cottage is located at north end of anna maria island. Brand new renovation, 3 bedroom with 2 bath room, with private dock, sailboat direct to bimini bay, unobstructed , natural view of bimini bay. Less than three minute walk to beach, walking distance to pine ave and the city pier and... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 2 weeks ago
    Absolutely perfect exactly as described . Owner Jenny very quick to respond . Secluded beautiful view of the bay !! Very easy to get around the island, perfect location...
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    1 / 45
    4.5 of 5 bubbles (15) Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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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 bubbles Reviewed 14 June 2016
    We had the most amazing week on Anna Maria. The property far and away exceeded all of our expectations. Our family included 5 adults and 4 children, and we found the property to...
    5 of 5 bubbles Reviewed 11 May 2016
    We were so impressed with this home. We had friends and family visit, and they were very interested in future rental. With 5 bedrooms, 3 full baths, outside hose rinse off...
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    1 / 41
    5 of 5 bubbles (4) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    It doesn't get much better than being right on the water, less than one block from the bay beach, and only 7 blocks from Pine Avenue. Sunshine Cottage couldn't be a better name, because this 3 bedroom, 2 bathroom, cottage truly lets you experience the beauty of Anna Maria Island. Enjoy dangling... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 28 October 2016
    We had a fantastic time exploring Anna Maria Island and coming home to such a fantastic place made the holiday even more special.
    5 of 5 bubbles Reviewed 17 February 2016
    This home is located in walking distance to restaurants and the beach with bikes available as well. It is very nicely and newly decorated. The kitchen is well stocked as well as...
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    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Cute and Cozy Cottage just 200 steps to Beach. Walk to Shops, Free Trolley, Resturants, Pier, Museum and more. This apt is attached to another unit that shares the pool. Rent it for the whole family. All the comforts of home. Just bring you towel and suit. Beautiful Beach and Wildlife.... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 25
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Beautiful, recently renovated 1700 sf home that accommodates up to 8 people. Only a few steps to amazing sandy gulf beach. Enjoy all the amenities of a single level well appointed home with no stairs where you can step out to the beautifully landscaped pool area from your master bedroom or open... View all property information
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    Anna Maria, Anna Maria Island 34217
    1 / 21
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    116 Maple Breeze Private home 4 Bedroom / 2 1/2 Bath , maximum occupancy of 7 people. 116 Maples is located on one of the prettiest streets in the village of Anna Maria, this gorgeous 4 bedroom, 2 and a half bath home is just steps away from the beach. This quiet, tree-lined street evokes... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 2 November 2015
    Wonderful location, The beach is at the end of Maple Ave, a quiet road only a 2 minute walk. The house is well situated, 4 bedrooms and 2 and 1/2 baths. I can only speak of the...
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    1 / 21
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    The home is immaculately clean and whimsically decorated, professionally landscaped, and boasts one of the larger pools larger backyards and larger 2 bedroom homes on the Island. The spa is accented by iridescent glass. The 20' tall tiki hut was hand-built by Native Americans and houses the bar and... View all property information
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    Anna Maria, Anna Maria Island 34216
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    5 Bedroom 3 Bath Large Family Beach House Sleeps 10. Just 200 steps to the most Beautiful Beach in the World. Crystal Clear waters with plenty of fishing, wildlife and swimming. Great for Multi-Family Gatherings, Weddings, Family reunions or just plain fun. With a 2 bedroom 1 bath attached... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 33
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    Pelican Roost 505 - Private canal home 5 Bedroom/ 5 Bath with private pool, maximum occupancy of 10 people. This gorgeous three story home in the city of Anna Maria, is an easy walk from Pine Avenue and the City Pier, with direct water views, front and rear, from all living spaces. With 5... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 15
    4.5 of 5 bubbles (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    103 Pelican - Private canal home 3 Bedroom/ 2 Bath with private pool, maximum occupancy of 6 people. At this spacious, family friendly home with private pool, 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... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    5 of 5 bubbles Reviewed 17 April 2016
    Hi! My husband and I rented this property and had the wonderful opportunity of having our adult children & their spouses come with us. There was 8 of us in total. We enjoyed...
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    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Beachy Keen 408 - Private home 3 Bedroom/ 2 Bath with private pool, maximum occupancy of 6 people. Here delightful and fun Caribbean Cool décor welcomes you to the sub tropic cozy of Anna Maria Island. A charming island home within easy walking distance to the beach, offers an ideal location... View all property information
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    Anna Maria, Anna Maria Island
    1 / 12
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    209 Spring - Private home 3 Bedroom / 2 Bath with private pool, maximum occupancy of 8 people. Spring into the waves!~ 209 Spring. 3 bedroom, 2 bath raised home in quiet, residential area of Anna Maria. Private pool. Pool heat optional @ $20/day. 1 block to the beach. Large screen high def... View all property information
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    Anna Maria, Anna Maria Island
    1 / 20
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This water front, two bedroom condominium (ground floor), sits on the end of Pine Avenue, across the street from the beach and has wonderful seaside views of the bay. It also has its own private fishing dock and boat slip! This unit has been completely remodeled and newly furnished to give you the... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 36
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 30 September 2015
    I chose Island Oasis as it ticked every box. This is a beautiful island and the beach is very easy to access, as such I wanted a property with a pool, suitable for two couples...
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    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    109 Willow Casa Nana - Cottage 2 Bedroom / 2 Bath , maximum occupancy of 6 people. Enjoy an old fashioned Florida beach vacation at this wonderful cottage just 4 houses from the beach! One Florida family has spent over four decades building happy summer memories right in this spot, and they... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 23
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    This quaint, old-Florida style rental is nestled in the north shore area of Anna Maria Island. Shabby chic style, located 2 blocks from the beach and 2 blocks from the bay! Only one block from Pine Ave., with its old-time feel with shops and salons. Steps from fine dining, the historic city pier,... View all property information
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    Anna Maria, Anna Maria Island 34216
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    1 / 21
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Sea Breeze cottage is located at north end of Anna Maria island. Brand new renovation, 2 bedrooms with 2 bath rooms, with private dock, sailboat direct to Bimini bay, unobstructed , natural view of Bimini bay. Less than three minute walk to beach, walking distance to pine ave and the city pier and... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 26
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    313 Palm Ave - Duplex 2 Bedroom /1 Bathroom , maximum occupancy of 4 people. Enjoy an old fashioned Florida beach vacation at this wonderful cottage just 5 min walk from the beach! Located right in the heart of the village of Anna Maria, not only can you walk to the beach in a matter of seconds,... View all property information
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    Anna Maria, Anna Maria Island
    1 / 25
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    **SPECIAL** 20% off bookings in September, October and November! Ask about the discount when booking! Anna Cabana B is the perfect getaway. Located on the north end of Anna Maria Island and just a short walk from the beach, this cute bungalow beckons you to relax and stay a while! This adorable... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    5 of 5 bubbles Reviewed 1 June 2016
    This modern beachy cozy home was absolutely gorgeous! Clean, and equipped w/ all the modern, brand new, full size amenities. Beachy/luxury design. Central air & on-site laundry...
    5 of 5 bubbles Reviewed 8 January 2016
    I enjoyed my vacation in this beautiful house very much. The furniture is very nice and comfortabel and the entiere house is beautiful decorated. It provided everything what I...
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    1 / 24
    4.5 of 5 bubbles (11) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Location, location, location. Welcome to the quaint and quiet north end of Anna Maria Island! This classic AMI elevated, open floor plan vacation rental boasts three bedrooms and two baths with plenty of room for a large family or group to spread out and relax! Two queen-size beds, a full-size... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 14 August 2016
    Was pleasantly surprised when arrived. Lots of space to store our gear, plenty of space and rooms inside which are more comfortable than most hotels. Comfy furniture, lovely...
    5 of 5 bubbles Reviewed 16 April 2016
    We are so very pleased with the home Mangoes on Magnolia. Clean, well equipped, and the perfect location for us. We loved the pool and the hot tub. The laundry was a godsend...
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    1 / 28
    4 of 5 bubbles (9) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Special price 20% off the rental fee between 11/22/2016 - 1/28/2017 744 Jacaranda - Private home 3 Bedroom/ 3 Bath with private pool, maximum occupancy of 6 people. Live the Florida lifestyle in this beautiful, comfortable 3 bedroom, 3 bath private home with private pool and with screened... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    5 of 5 bubbles Reviewed 16 April 2016
    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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    If you are looking for the perfect spot to vacation on Anna Maria Island, look no further! This beautiful Anna Maria vacation rental is fabulously decorated throughout! Open and airy, with a fantastic living area, Casa Palma has plenty of room for all of your family and friends. The gourmet... View all property information
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    Anna Maria, Anna Maria Island
    1 / 14
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    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
    1 / 23
    5 of 5 bubbles (7) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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! <BR>Vacationers, dreamers, honeymooners, would-be family-reunion planners and... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 22 May 2016
    The pool has sun and shade with comfortable lounging. It is an oasis. The beach is close, but it is not needed. Beach Nest is very comfortable. It is very clean. It is very...
    5 of 5 bubbles Reviewed 2 December 2015
    When I saw the photos of this house I thought it was too good to be true and that there had to be a catch. Well, it turns out that real life can be better than photos and this...
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    1 / 24
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    This lovely two bedroom family- and pet-friendly Anna Maria Island vacation rental is just a few houses from the island's white sand beach and azure blue waters of the Gulf of Mexico. Located on the quiet north end of the island in the city of Anna Maria, at 950 square feet, this classic elevated... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 17 October 2015
    We saw this rental a year or so ago when we were staying on Anna Maria Island. We looked it up on line and was happy with what we saw. The home sleeps a family of four. It was...
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    1 / 39
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Newly Remodeled 1 Bedroom/1 Bath Cottage in a serene north end location. The allure of the Gulf of Mexico Beach just 250 steps away. A back yard dock on Lake LaVista Bayou with a patio table, umbrella, and sling back chairs. Launch the provided kayaks right from the dock or choose to bring your own... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 25 August 2015
    Having visited AMI before we knew the place was fantastic and renting Summer Breeze made it even more so. The cottage has every modern facility, all of top notch specification...
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    1 / 24
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    **SPECIAL** 25% off weekly booking Now`` to December 15, 2016! Absolutely Anna is just that -- the epitome of the beach experience you want to have when you visit the beautiful north end of Anna Maria Island. Only two houses away from the footpath to Bean Point, you are on the gorgeous white... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    5 of 5 bubbles Reviewed 18 July 2016
    Very nice house and location! Plenty of room for all of us! Great inside and outside! What an incredible outdoor area for family time!! Beach is so close and convenient...
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    1 / 24
    5 of 5 bubbles (9) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Pet-friendly
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    • ?
    • Smoking allowed
    • 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
    Location Information
    Anna Maria, Anna Maria Island 34216
    4 of 5 bubbles Reviewed 25 June 2016
    Super location and gorgeous views of the canal and sunsets. Love the pool area and covered spot under the house.Great for paddle boards and kayak and fishing off the dock. We...
    5 of 5 bubbles Reviewed 15 May 2016
    Husband and I stayed here for our first anniversary after being married on the island. PERFECT location. Close to the piers and a short walk/bike ride to beach. Shops and general...
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    1 / 24
    5 of 5 bubbles (4) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Villa Marianne is the ultimate beach getaway for you and your family. Located on the north end of Anna Maria Island in the city of Anna Maria just steps from the white sand beach, this five bedroom, four bath vacation rental will make you never want to leave! Exquisitely decorated with beach... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 9 September 2016
    I think I must have viewed every property on the island in my quest to find something that ticked as many boxes as possible for our group of 2 families. Gulf side Quieter...
    5 of 5 bubbles Reviewed 5 June 2016
    Just a lovely house. Very close to the beach and to the trolley stop. Quiet street and beautiful landscaping. My family had a wonderful time at the beach, in the pool and...
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    1 / 35
    5 of 5 bubbles (2) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Toes in the Water is an amazing ground level 4 bedroom/3 bath home, just 90 Steps to the beach! This north end gem boasts a large, private, and heated pool with swim-up tiki table. Quiet setting in the beautiful north end of Anna Maria, and located west of Gulf Drive for easy beach access with no... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 27 October 2013
    My parent rented this house when they came to visit last winter. We stayed for a week in late January(?) to early Feb and my 3 year old son still asks to go back. Personally I...
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    1 / 23
    4.5 of 5 bubbles (6) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This vacation rental is located on Anna Maria Island's historic Pine Avenue, halfway between the Gulf of Mexico and the Anna Maria City Pier! This adorable, one bedroom cottage, with high beamed ceilings, wood floors and shabby chic décor throughout is ideal for a vacation getaway! This quaint... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 6 June 2016
    This was our first time to Anna Maria Island. Didn't know where to stay. We picked Island Place Cottages. It is a great place to stay! Close to everything. We were only a couple...
    5 of 5 bubbles Reviewed 11 June 2015
    We absolutely loved this place!! It was right in the middle of Pier and Beach easy walking to both actually easy walk to donut shop, pizza , ice cream or dinner. We usually come...
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    1 / 24
    4.5 of 5 bubbles (9) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 and its beautiful beaches, this elevated pool home will beckon you back year after year! Beautifully decorated, this three-bedroom, two-bath vacation rental is... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 9
    4.5 of 5 bubbles (20) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    other travellers have booked this property
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    • DVD Player
    • Air Conditioning
    • Private Garden
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The Becker Beach Bungalow offers a charming, comfortable stay less than 2 blocks from the beach. Accommodates 6 people comfortably; master bedroom with 1 queen bed and second bedroom with 2 twin beds, window air conditioning in both. The living room also has a queen size sofa bed. Relax and enjoy... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 2 weeks ago
    My husband and I stayed for 6 nights and my in-laws joined us for 3 of those nights. It was perfect for our family. As clean as a luxury hotel. Just a block and a half from the...
    4 of 5 bubbles Reviewed 11 September 2016
    We stayed here for 3 nights and thoroughly enjoyed our stay. The location is perfect for nipping down to the beach at anytime during the day as its 5 mins walk away. The shop for...
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    1 / 24
    4.5 of 5 bubbles (19) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
    • Porch
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    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Anna Maria, Anna Maria Island 34216
    4 of 5 bubbles Reviewed 3 weeks ago
    Let me start off by saying I have nothing BAD to say about this property, however there are a few suggestions I would like to make. We stayed at the Gulfshore Cottage for 4 nights...
    4 of 5 bubbles Reviewed 6 October 2016
    It was very easy to acquire this rental. Everything was better than I expected. I would recommend this site to friends and family.
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    1 / 24
    5 of 5 bubbles (9) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • DVD Player
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    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Pineapple Cottage, centrally located on historic Pine Avenue in the city of Anna Maria, is the perfect place to slow down and catch your breath! This Anna Maria Island cottage is tastefully decorated with wood floors, granite and stainless kitchen, tiled shower and comfortable furnishings. The... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 9 February 2016
    411 Pine B. Very nice cottage. Feels like home away from home. We have stayed twice. Walking distance to the City Pier, shopping & restaurants. Definitely would recommend to...
    5 of 5 bubbles Reviewed 30 June 2015
    Very nice cottage. Within walking distance to beaches and Piers. We enjoyed so much we are going back again this next Jan.
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    1 / 24
    5 of 5 bubbles (9) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Grill
    • DVD Player
    • Patio
    • Washer
    • Porch
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This two-bedroom, two-bath vacation rental is located on the quiet north end of Anna Maria Island. Whispering Pines is just three houses from one of the most beautiful beach accesses on the island. This classic 1920's beach cottage has been lovingly restored. The original wood molding, fireplace,... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 29 February 2016
    Loved this Beautiful Cottage! Steps from the White Sand and Peaceful Beach. I will be back to this Sweet Island!!
    5 of 5 bubbles Reviewed 26 October 2015
    As I was looking for a place to stay on AMI I came across Whispering Pines and this quaint cottage caught my eye, I kept coming back to it as I was searching. I was planning a...
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    1 / 24
    5 of 5 bubbles (2) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Waterfront
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This is the vacation rental home of your dreams! This custom bay-front home on the north end of Anna Maria Island offers 3600 square feet of luxury accommodations and has all the fine touches and professional craftsmanship one would expect in a high-end custom home. When walking into this amazing... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    5 of 5 bubbles Reviewed 21 March 2016
    We stayed for 7 wonderful nights in Jewel of the Bay and will for many years to come. This is a wonderful rental property with a perfect location, great amenities and privacy and...
    5 of 5 bubbles Reviewed 6 February 2016
    A beautiful home that accommodates a large family. We couldn't find a better place to celebrate our dad's 75th birthday. Extremely clean and very comfortable furnishings!! We were...
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    1 / 24
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Parking
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    • Satellite TV
    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    We have a place in paradise waiting for you! This Anna Maria Island vacation rental is located in Anna Maria and is just a short two block walk to the white sand beach of the Gulf of Mexico. A nice living area with flat screen television is great for relaxing after a day at the beach! A nice... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    5 of 5 bubbles Reviewed 3 weeks ago
    A return trip to Anna Maria Island , this time staying in this truly place in paradise . It is a very well equipped and spacious property on a quiet road, less than five minute's...
    5 of 5 bubbles Reviewed 2 November 2016
    The duplexes are in a great location, spacious, clean and one of the most affordable price in AMI. Definitely worthwhile. There were a total of 11 people in my party (2 families...
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    1 / 24
    2 Bedrooms, 1 Bathroom, Sleeps 3 | Quick View
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    • Satellite TV
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    • Outdoor Dining Area
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    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This charming, quiet, cozy, Enchanted Cottage is just steps to Tampa Bay and the Historic Anna Maria City Pier, a fun place to fish! A short five blocks to the beautiful powder-soft, white sand and turquoise Gulf water of Anna Maria Island. You may also enjoy the beautiful sunrise from the pier... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 23
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Patio
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Spend your relaxing vacation at Sea Oats, located just a block from the white sand beaches of Anna Maria Island. This lovely two-bedroom, one-bath vacation rental has just been completely remodeled and fabulously decorated! Cozy and relaxing furnishings await you and your friends and family during... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 29 June 2016
    Over the years my wife and I have visited Anna Maria 8 or 10 times and have stayed at around four different places and Sea Oats is by a long way the best property we have stayed...
    5 of 5 bubbles Reviewed 25 May 2016
    Excellent service from Coastal Cottages AMI. Bungalow was extremely well equipped/clean and was home from home. Wonderful island with the best beaches. Very friendly people and...
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    1 / 24
    4.5 of 5 bubbles (5) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    • Wi-Fi
    • Satellite TV
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    • DVD Player
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    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Located on the north end of Anna Maria Island, only 200 steps to the white sand beaches of the Gulf of Mexico, AMI Retreat is the perfect place for your vacation! With an estimated 2100 square feet, this gorgeous three-bedroom, two-bath family- and dog-friendly vacation rental has plenty of room... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    4 of 5 bubbles Reviewed 4 August 2015
    We had a great trip to AMI. The pool is lovely. We liked all of the seating around the pool, the shaded areas, and the sunbathing ledge. It was clean and well-maintained. The...
    4 of 5 bubbles Reviewed 15 April 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...
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    1 / 23
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Private Outdoor...
    • Wi-Fi
    • Parking
    • Grill
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    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Look no further for the perfect vacation rental! This three bedroom vacation rental is located on the serene north end of Anna Maria Island. Tastefully decorated with beautiful beach décor, and boasting a wonderfully open living and dining space, this vacation rental creates an exceptionally... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    5 of 5 bubbles Reviewed 2 July 2016
    This was our first visit to AMI. My booking of Bean Point Cottage was solely based on the pictures online, as it did not have any reviews. Bean Point Cottage was the perfect beach...
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    1 / 24
    4 of 5 bubbles (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Located on the north end of Anna Maria Island in the city of Anna Maria on historic Pine Avenue, this two-bedroom, one-bathroom second-floor vacation rental condo has been completely updated and is picture perfect. So much so, once you walk through the front door you'll feel as though you just... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    4 of 5 bubbles Reviewed 26 October 2015
    We love Anna Maria! This 2 bedroom condo was ideally located right on the canal, which is right off Tampa Bay. We were able to drop our paddle boards or kayaks right off the...
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    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    As an artist this private three bedroom and two bath multi-level elevated vacation home has been our family 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... View all property information
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    Anna Maria, Anna Maria Island 34217
    1 / 18
    3 of 5 bubbles (2) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Internet Access
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Completely remodeled 2 bedroom/2 bath duplex, with a beautiful tropical HEATED pool, just over a block to the beach, and the free island Trolley! There is a King and a Queen bedroom in the North Unit, and a King and Twin Bedroom in the south unit. Both units also have a queen sleeper sofa. Sleeps... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    4 of 5 bubbles Reviewed 30 December 2014
    BLN is very well located in the quieter northern part of the island. It is just a very short walk from the beach and Ginny and Jane Es. Likewise, a short walk in the opposite...
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    1 / 39
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
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    • Washer
    • DVD Player
    • Satellite TV
    • Hot Tub
    • Waterfront
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Lazy Lagoon has it all! This remodeled 2 bed/2 bath home is anchored in splendid the north end of Anna Maria on a deep water canal with dock, has its own heated pool and hot tub, and is a short walk to the beach, restaurants and free island trolley. The serene canal-front setting coupled with quiet... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 13 January 2014
    We have just come back from a 2 week stay at Lazy Lagoon. House beautiful, all on one level and flooded with light. Pool and hot tab a fantastic feature. House fully equipped and...
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