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Beach Rentals and Cottages in Anna Maria, FL

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    All 167 Rentals in Anna Maria
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    Travelers to Anna Maria are booking July dates now. Secure your vacation rental today, and have the perfect trip.
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    1 / 107
    5 of 5 stars (12) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    1 / 23
    5 of 5 stars (5) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    1 / 38
    4.5 of 5 stars (6) Very good
    5 Bedrooms / 3 Bathrooms / Sleeps 12
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    1 / 8
    5 of 5 stars (11) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    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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    5 of 5 stars Reviewed April 18, 2015
    Our new second home. Just lovely. Walking distance to beach, bar, ice cream shop..Just loved it. I really want to keep this place a secret..Lol But I wind do that. I will tell...
    5 of 5 stars Reviewed December 6, 2014
    Wonderful location and exactly as advertised. We used the wired connection for the internet and it worked just fine. Excellent turn-key property which we recommend to others.
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    1 / 14
    5 of 5 stars (10) Excellent
    5 Bedrooms / 4 Bathrooms / Sleeps 10
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    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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    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
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    Begin your relaxing vacation at Beach Walk, located just a block from the white sand beaches of Anna Maria Island. This lovely two bedroom, one bath, home has just been completely remodeled and fabulously decorated! Cozy and relaxing furnishings await you and your friends and family during your... View all property information
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    1 / 14
    2 Bedrooms / 1 Bathroom / Sleeps 5
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    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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    1 / 17
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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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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    1 / 23
    5 of 5 stars (1) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    About this property
    Welcome to Peony House! This brand NEW, custom-built, elevated vacation rental home features four bedrooms, three baths, a large living room, and a dining room area for entertainment. From the moment you walk through the front door into this light and airy house, you will be happy that you chose... View all property information
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    5 of 5 stars Reviewed August 7, 2014
    The house was awesome. The only thing that could have been better was the location on the island. It wasn't a far walk from the beach but most other things were a little out of...
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    1 / 18
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Waterfront
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    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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    $2,526
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    1 / 23
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    1 / 23
    5 of 5 stars (4) Excellent
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
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    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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    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...
    5 of 5 stars Reviewed February 20, 2014
    When we walked into this adorable cottage, we couldn't believe our eyes. This place is too cute for words! It is the kind of rental you dream about with clean bathrooms...
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    1 / 25
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Gaze out of your living room to the calming serenity of the canal as you sip on your favorite beverage at this comfortable and spacious home located in the prestigious north end of the island. This beautiful 3 bedroom 2 bath tastefully decorated home is invitingly awaiting your arrival for the... View all property information
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    5 of 5 stars Reviewed March 12, 2015
    Great accommodation in an idylic spot close to the beach and all amenities. You are in the best spot on the island.
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    $128
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    1 / 25
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    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 invite you to create some of your own treasured moments on your next visit to Anna Maria.... View all property information
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    1 / 26
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    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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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Spend your vacation just steps from our beautiful beaches and crystal-clear waters! Casa Blanca is in the heart of the village of Anna Maria, and west of Gulf Drive...there's no better place to be! Only 5 houses from the beach, you'll be steps from the sand AND just moments from shopping,... View all property information
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    $221
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    1 / 24
    4 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Located on one of the prettiest streets in the village of Anna Maria, this lovely 4 bedroom, 2 and a half bath home is just 7 houses away from the beach. The quiet, tree-lined street evokes memories of Florida Gulf Coast islands in days gone by, with a shaded path providing access to the island's... View all property information
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    1 / 21
    5 of 5 stars (16) Excellent
    4 Bedrooms / 5 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Private Outdoor...
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    • Pets allowed
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    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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    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 / 26
    5 of 5 stars (1) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 12
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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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    5 of 5 stars Reviewed August 19, 2014
    We stayed here for two weeks this past August. This was our second trip to AMI - such a lovely place. This house was perfect for us. It is very spacious. All the bedrooms are...
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    1 / 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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    1 / 18
    4 of 5 stars (1) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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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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    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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    1 / 34
    4.5 of 5 stars (7) Very good
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Gym
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    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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    5 of 5 stars Reviewed July 28, 2014
    This was a return visit as we loved it so much last time. We felt really relaxed here with the wonderful views from the house and the laid back attitude on the island. We were...
    5 of 5 stars Reviewed July 10, 2014
    This is the perfect vacation home!! Located on a canal with bay views, steps from the city pier and many restaurants and boutiques, this home feels like a slice of heaven. The...
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    1 / 22
    4 of 5 stars (1) Very good
    5 Bedrooms / 3 Bathrooms / Sleeps 12
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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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    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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    4 of 5 stars (1) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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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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    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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    4 of 5 stars (4) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Great ground level home on Maple Ave in Anna Maria CIty. West of Gulf Drive with no busy roads to cross. Three bedrooms and two baths. Extra bonus sun room off new deck perfect for a cookout. Kitchen is large enough to try your hand at island cusine, yet the Sandbar Restaurant is just up the... View all property information
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    5 of 5 stars (1) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 14
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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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    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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    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    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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    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 / 26
    5 of 5 stars (3) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 9
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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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    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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    4 of 5 stars (1) Very good
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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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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    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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    1 / 20
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    Begin 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
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    1 / 10
    5 of 5 stars (1) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    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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    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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    4.5 of 5 stars (2) Very good
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    Whispering Winds 210 Sycamore Avenue Anna Maria, Fl 34216 Key West style 4 bedroom, 2 bath home just a short walk from the Gulf of Mexico. This home offers private heated pool, three covered decks overlooking pool, BBQ grill, two car garage, cathedral ceilings, tile, carpet, open floor plan... View all property information
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    4 of 5 stars Reviewed October 4, 2014
    You can look at the photos - the house is every bit as good as the description. Everything worked, there were no problems at all with the property. We called Anna Maria Vacations...
    5 of 5 stars Reviewed May 13, 2014
    We stayed at Whisper Winds,3 houses to the wonderful White Sand... Great house with 4 bdrm ,heated pool, great location with plenty of room for Family Vacation.. This is our 2nd...
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    5 of 5 stars (1) Excellent
    5 Bedrooms / 4 Bathrooms / Sleeps 12
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    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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    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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    3 Bedrooms / 2 Bathrooms / Sleeps 10
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    Las Palmas 212 Palm Avenue Anna Maria, Fl. 34216 North-end location just a few minutes walk to Pine Ave and Gulf beaches! This lovely 3 bedroom 2 bath elevated home with private heated pool is situated in the heart of the island, centrally located to everything fun. Comfortable and charming with... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Looking for that place to kick back and relax your cares away? Check out ‘Triple Play Guest House.' There's a triple chance to play: (1) walk to the beach, (2) lounge in the pool or spa or patio or (3) launch a kayak, fish or just relax on one of our two docks on the canal. Nothing quite compares... View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    Heron House 213 Elm Ave. Anna Maria, Fl. 34216 Wow, this luxury 3/3 North-end elevated home has it all! Just newly remodeled and ready to go! Just a short walk to it all- the beautiful Gulf beach, the fun and entertainment of Pine Ave. and even walk to the fantastic Sandbar restaurant. The... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    Anna Maria Chateau 612 Fern Street Anna Maria, Fl 34216 Perfect island getaway, nestled at the North end of Anna Maria Island. Anna Maria Chateau, open and spacious, a newly and completely renovated, well equipped 3 bedroom, 2 bath home with vaulted ceilings in the living area and in all... View all property information
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    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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    1 Bedroom / 1 Bathroom / Sleeps 4
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    Hidden Oasis 777A North Shore Anna Maria, Fl. 24216 This lovely 1 bedroom, 1 bathroom gulf front hideaway has just been completely renovated from top to bottom! This second level location has a private balcony with large southern views of the beautiful blue waters of the Gulf of Mexico. Part... View all property information
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    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    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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    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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    5 Bedrooms / 4 Bathrooms / Sleeps 10
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    The Big Yellow House on Pine 104 Pine Avenue Anna Maria Fl. 34216 This home is one of a handful of very select rental properties on the island- direct Gulf front with a private heated pool! It has all the perfect ingredients for a wonderful vacation. Enjoy your front row seat to spectacular... View all property information
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    5 Bedrooms / 3 Bathrooms / Sleeps 15
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    Lighthouse Lagoon 508 Spring Avenue Anna Maria, Fl. 34216 Lighthouse Lagoon is a beautifully updated 5 bedroom, 3 bathroom Island home located on Spring Street on the North-end of Anna Maria Island. The rear of the house backs up to outstanding Pine Avenue with it's quaint shops, wonderful... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    A Sandbox by the Sea 507 Spring Avenue Anna Maria, FL 34216 A Sandbox by the Sea has a large luxurious tropical yard with a new private heated pool complete with tanning shelf and a bubbling spa tub!! Both water features have the option of digital light shows for evening fun! A press of a button... View all property information
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    Cabana Breeze 511 Spring Avenue Anna Maria Island, Fl 34217 Cabana Breeze is a newly and completely renovated 4 bedroom 2 bathroom home with multiple outdoor shaded living areas, a large lot, and a brand new custom pool and pool-side cabana. This gorgeous home is located on the prestigious... View all property information
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    4 of 5 stars (2) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    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. The living room offers an open floor plan to the kitchen to enjoy the family during your... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    Sundown North 300 N. Shore Dr. - Unit B Anna Maria, Fl. 34216 Sundown North- a unique water front property that has 4 bedrooms, 3 bathrooms and a private heated pool one block to Pine Ave. It sleeps up to 8 guests in beds and 10 total. Sundown North also has a separate living room upstairs... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    Havana Cay 109 Cedar St. Anna Maria, Fl. 34216 With this secluded and historic property, you will feel like you are vacationing at your own private 5-star resort. Havana Cay sits only 4 houses in from the beach and there are no busy streets to cross and zipping to and from the beach will be so... View all property information
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    A Snails Place 302 Spring Avenue Anna Maria, Fl. 34216 This beautifully decorated 3 bedroom, 2 bath ground level home is just a short walk to the Gulf of Mexico. With it's convenient location on Spring Avenue you are walking distance to historic Pine Avenue! This adorable cottage offers a... View all property information
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    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    Island Dream 157 Crescent Drive Anna Maria, FL 34216 An exceptional property with glorious views of the Sunshine Skyway Bridge from its entrance, this beautiful, newly built and elegantly furnished four bedroom and four bathroom home on the desirable north end of Anna Maria is situated in a... View all property information
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    5 of 5 stars (1) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
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    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
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