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Holiday Rentals with Pools in Anna Maria, FL

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    1 / 23
    4.5 of 5 stars (5) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 30
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 24
    4.5 of 5 stars (5) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    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
    1 / 24
    4.5 of 5 stars (9) Very good
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    $689
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    • Sauna
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    About this property
    Located on the north end of Anna Maria Island in the city of Anna Maria, this family-friendly vacation rental was built for rest and relaxation. Beginning with the lush landscaping that meets you at the front door, all the way through to the putting green, kayak launch and boat dock, this house has... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 25 October 2015
    This house was AMAZING. It was so open and spacious. The master suite has an entire porch overlooking a mangrove cove. My favorite was the upstairs master bath. From the outside...
    5 of 5 stars Reviewed 15 August 2014
    I searched for the perfect house for a family of 10 to celebrate our niece's vacation. All I can say is there was nothing on everyone's list that this house didn't have! We...
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    1 / 15
    3 of 5 stars (1) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Beautiful ground level 3 bedroom/2.5 bath home, with a quiet north end location only a block to the beach! There is a King in the master with a private patio, a Queen in the second, twin beds in the third, and a queen sleeper sofa in the sunroom (which has blinds for privacy), all accommodating up... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    3 of 5 stars Reviewed 2 July 2014
    We had a great time on Anna Maria with our two college-aged sons. This house is very nicely located, and the pool is wonderful. The home was spacious and comfortable for four...
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    1 / 22
    8 Bedrooms, 7 Bathrooms, Sleeps 22 | Quick View
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    About this property
    Blue Bay is a gorgeous brand new, custom luxury home that is now completed and ready for rental. This stunning high end home is comprised of two separate buildings, a main house and a guest house, with a tropical pool with tiki, spa, out door kitchen, sun deck and fire pit, in between the two.... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 22
    5 of 5 stars (19) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • x
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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
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 28 October 2015
    We couldn't have been happier with our vacation to AMI. Nigel and Maggie's home was perfect for our family! The home was pristine and stocked with anything we would need during...
    5 of 5 stars Reviewed 30 September 2015
    My family and I have enjoyed many high-end beach rental homes over the last 10 years and this home in Anna Maria is exceptional! A couple highlights that cause this property to...
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    5 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    $4,836
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Elder access
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    About this property
    Enjoy our Luxurious Villa diPalma, a beautiful six bedroom, four bathroom luxury island home very close to the best beach in the Northshore. The Italian influence in the design is reminiscent of properties found in Venice and Tuscany. The two master suites each have their own Jacuzzi spa tub, a... View all property information
    Location Information
    Anna Maria, Anna Maria Island 1234
    1 / 23
    5 of 5 stars (2) 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 stars Reviewed 2 weeks ago
    This canal home (just houses away from the bay) is lovely and well appointed. Our landlords, Mathias and Carren, met us at the home at check-in and showed us everything which was...
    5 of 5 stars Reviewed 25 August 2015
    These house is confortable,clean, cozy!! Confortable rooms!.You can see the fresh water from the window ! Walk 10 steps to a nice private deck, with beautiful birds, manatees...
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    1 / 24
    5 of 5 stars (8) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    $238
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    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • 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 stars Reviewed 1 July 2015
    Very nice cottage. Within walking distance to beaches and Piers. We enjoyed so much we are going back again this next Jan.
    4 of 5 stars Reviewed 14 November 2014
    The weather was nice several of the days and we really enjoyed less people than we encounter in July. Lots of beach walks and bike rides. My only issues were the dirty rug in...
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    1 / 43
    5 of 5 stars (10) Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
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    • Elder access
    • x
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    About this property
    WELCOME TO ALL DECKED OUT! Whether getting away for a family vacation, with a group of friends, for a wedding or any other occasion, our gorgeous 5 Bedroom home offers everything you could want for a relaxing holiday on Anna Maria Island.... with incredible views of the Bay! Sit by the tropical... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 4 November 2015
    We have just come back from this wonderful house, Love the island and really enjoyed where this property is located. We were a 2 family group and there was plenty of room. Would...
    5 of 5 stars Reviewed 26 October 2015
    The location of the home was perfect for my family and I. We enjoyed several beaches all within the same area. The home exceeded our expectations, we will be returning.
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    1 / 33
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    $263
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    • Pet-friendly
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    • x
    • x
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    • Elder access
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    About this property
    Beautifully redone 3 bedroom/2.5 bath home! Ceramic tile throughout, and brand new open kitchen area with breakfast bar. Beautiful large caged pool area with huge covered patio! Only a block to the beach, the Sandbar Restaurant, Ginny and Jane E's, Rudy's Subs, Feeling Swell and more. Just a... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 24
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $297
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    • Patio
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    • Washer
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    • Satellite TV
    • Private Outdoor...
    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Life is Good at the Beach, located on the north end of Anna Maria Island, is a fantastic place to start your vacation. This three-bedroom, two-bath, vacation rental is just a five minute walk to the beautiful north end beaches near Bean Point and two blocks to the Rod & Reel Pier. The extra-large... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 2 weeks ago
    Life is Good at the Beach vacation rental is a beautifully, well maintained home. The picutres provided on the website accurately reflect the home and the beach house more than...
    4 of 5 stars Reviewed 22 November 2015
    Great well equipt house, everything we needed and more, close location to beach 5 mins walk, and to the free trolley bus stop 10 mins walk. The only downside of this property is...
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    1 / 24
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
    From
    $952
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    • Grill
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    • Private Outdoor...
    • Waterfront
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
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    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
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    Anna Maria, Anna Maria Island
    1 / 40
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    $404
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    • Washer
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    • Patio
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Located in the heart of Anna Maria, a gorgeous and spacious Mediterranean style 4 Bedroom/3 Bath Home with a Heated Pool in a very private and peaceful setting. Only steps to Pine Avenue shopping and Trolley Stop, 2 blocks to the Beach, and walking distance to the Pier. The open floor plan features... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 35
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Parking
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    • x
    • x
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    • Smoking allowed
    • Elder access
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    About this property
    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
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 25 June 2015
    This house is nothing less than spectacular for a family. The house has been completely redone inside. The house looks very small from the front / driveway, but the inside is...
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    1 / 80
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $347
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    • Washer
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    • Air Conditioning
    • Waterfront
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • x
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    • Smoking allowed
    • Elder access
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    About this property
    The Anna Maria Island Beach Castle: Anna Maria Island is not a place where you go to the beach. When you are on Anna Maria Island you are at the beach. The Anna Maria Island Beach Palms condo is located with-in walking distance of Anna Maria Island's best waterfront restaurants including the... View all property information
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    Anna Maria, Anna Maria Island 34217
    1 / 24
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    $208
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    • Child-friendly
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    • Elder access
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    About this property
    Anna Cabana A is the perfect getaway! Located on the north end of Anna Maria Island and just a short stroll to the beach, this cute bungalow beckons you to stay and relax. This adorable vacation rental has been completely refurbished inside and out! A queen bedroom and a full bunk with twin over,... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 37
    5 of 5 stars (2) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    From
    $381
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    • Air Conditioning
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    • Patio
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
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    About this property
    Newly remodeled, 4 bedroom/3 bath home, just 90 Steps to the beach, with a large private HEATED pool! Quiet setting in the beautiful north end of Anna Maria, and located west of Gulf Drive for easy beach access with no streets to cross. Easy walking distance to many shops and restaurants, and... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 28 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...
    5 of 5 stars Reviewed 22 August 2013
    Our second year staying at "Toes" love the location, pool is great, close to everything...House was very clean, well stocked with dishes, pots, silverware etc.
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    1 / 39
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    $338
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
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    About this property
    The lovely Dolphin Pointe resides on the highly desirable north end of Anna Maria, just a short walk to the beach, bean point, and the Rod and Reel Pier. The spacious open concept living area is perfect for spending quality time with the family. The home exudes an Island charm with its over 2000... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 36
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    $423
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    • Ocean Views
    • Hot Tub
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
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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 34205
    5 of 5 stars Reviewed 1 October 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 / 107
    5 of 5 stars (25) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Wi-Fi
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Just steps to the sugar sand beaches in Anna Maria, FL. Your 3 bedroom, 2 bath, pool home with sweeping gulf views from two elevated front porches is located in the charming northern end of Anna Maria on North Shore Drive. If you are looking for a tropical vacation home to just relax, take long... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 4 days ago
    This is a great property to stay in. Very well equipped even a welcome vase of flowers with fruit! The owner is very responsive to any questions and helps whenever he can. The...
    5 of 5 stars Reviewed 4 weeks ago
    We had a lovely time in Santa Maria. Wonderful house and the location was perfect. Would highly recommend!
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    1 / 28
    4 of 5 stars (9) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    $382
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    • Balcony
    • Shared Outdoor Pool...
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    • Terrace
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • Smoking allowed
    • Elder access
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    About this property
    Live the Florida lifestyle in this beautiful, comfortable 3 bedroom, 3 bath private home with private pool and with screened lanai. The home is located on Anna Maria Island in the prestigious north end of the island. The local access to our secluded and beautiful beach is only a short walk away.... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    5 of 5 stars Reviewed 7 January 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...
    5 of 5 stars Reviewed 16 June 2011
    Nice home! Large enough for family. Decks and heated pool were great!
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    1 / 24
    4.5 of 5 stars (9) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    $261
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    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    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
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 24 June 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 1 November 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 / 34
    4.5 of 5 stars (9) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    From
    $2,710
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    • Hot Tub
    • Satellite TV
    • Waterfront
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    • DVD Player
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    • 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
    Location Information
    Anna Maria, Anna Maria Island FL34216
    4 of 5 stars Reviewed 2 weeks ago
    We spent a week in this lovely home. The weather was cool, so we didn't use the pool, but there was a beautiful pool with a dock right out the back door. The home was spacious...
    5 of 5 stars Reviewed 4 weeks ago
    We couldn't ask for a better place to have a family vacation. The atmosphere is relaxing, restful. The location is perfect.Although it is right on Pine Avenue, the backyard is a...
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    1 / 30
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    $250
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    About this property
    Completely Remodeled 3 bedroom/2 bath home with private Heated pool. Beautiful new tile, Granite countertops, all new appliances, and living room overlooking the heated pool. Bright, open kitchen, dining and living area! Sleeps up to 8. 1500 Sq. ft. 204 Archer Way, Anna Maria 3 Bedroom/2Bath... View all property information
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    Anna Maria, Anna Maria Island 34216
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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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
    1 / 29
    4 of 5 stars (5) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Cherryfish is the latest addition to the Pineapplefish collection of houses on Anna Maria Island. It is a spectacular 4 bedroom house, in a fantastic location, just one block from Tampa Bay Beach, the amazing Waterfront Restaurant and the island's most popular tourist destination - City Pier.... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 29 January 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...
    4 of 5 stars Reviewed 15 April 2014
    This home was wonderful for our two families of four. Plenty of space for everyone and the pool was perfect. The only complaint we had was the cleanliness upon arrival, there...
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    1 / 25
    5 of 5 stars (5) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • Child-friendly
    • x
    • x
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    • Elder access
    • x
    About this property
    This adorable remodeled duplex sits quietly in the highly desirable north end of the Island in the City of Anna Maria. It is a short walk of only a little more than a block to the Gulf beach where the sand is sugary white and the water is a beautiful blue-green color. There is a King in the... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 2 weeks ago
    A great 2 bedroom duplex with a waterfall pool,on the northern part of Anna Maria Island. Walking distance to the beach (2 blocks). The rental was clean and well maintained, the...
    5 of 5 stars Reviewed 3 September 2015
    Stayed here for a week. Nice apartment, clean and useful accomodation. Any small issues were sorted really quickly by agent who was very helpful and only 2 mins away in...
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    1 / 24
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    Start 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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    Anna Maria, Anna Maria Island 34216
    1 / 23
    5 of 5 stars (5) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
    • x
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    • x
    About this property
    We call this home 'A Time Out' cottage and you will definitely say, 'We deserve a time out at this place!' This completely remodeled private home on Anna Maria Island's north end features four bedrooms, two baths and the most wonderful tropical and lush pool and patio area! On the main level of... View all property information
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    Anna Maria, Anna Maria Island 34216
    4 of 5 stars Reviewed 28 May 2015
    Overall, this place is beautiful! Every room is well decorated and comfortable. We loved having our morning coffee on the front porch looking at the bay. We enjoyed lunch and...
    5 of 5 stars Reviewed 8 April 2015
    This special house is located perfectly away from the hustle and bustle, but at the same time everything is easily accessible. The beautiful beach is just a short stroll, and...
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    1 / 22
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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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
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 18 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 / 25
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • Child-friendly
    • x
    • x
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    • Elder access
    • x
    About this property
    Great Ground Level 3 Bedroom/2 Bath Home with a Heated Pool located in the quiet north end and just 3 houses to the beach!! King-Sized master bedroom with TV, Queen in the 2nd Bedroom with TV, and Twins in the Third with TV. Cable TV, DVD, and Flat Screen TV in Living Room. High speed Internet,... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 28 October 2013
    This beach house was a winner--the house was decorated tastefully and put us in the beach mood the moment we walked thought the door. Everything we needed was supplied, pool was...
    5 of 5 stars Reviewed 22 August 2013
    Anna Banana house was pristinely clean, well-decorated, cozy, had plenty of room for the 4 of us, and was the most convenient place we have ever stayed on anna Maria Island. It...
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    1 / 33
    4 of 5 stars (4) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
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    • Elder access
    • x
    About this property
    Beautiful 2B/1B cottage on the quiet North end, only 5 houses to the beach, and no streets to cross. Beautiful new Heated Pool. Twins can be converted to King in all bedrooms. NO dishwasher, no garbage disposal.Rear trash pick up! Charcoal Grill, not gas. Both units also include private... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    4 of 5 stars Reviewed 3 weeks ago
    This was our first time on the island. This house is a short 5 minute walk from a fabulous beach, and you share a pool with the other side of the duplex. The neighbourhood...
    5 of 5 stars Reviewed 9 June 2015
    The cottage was just as the picture depicts. It was close to the beach and we only had to worry about 1 other rental on the property. A lot of privacy and all the amenities...
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    1 / 40
    4.5 of 5 stars (6) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
    • x
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    • Elder access
    • x
    About this property
    Beautiful, cheerful and tropucal 4 bedroom/2 bath home with beautiful new furnishings throughout! Comfortable and roomy with split floor plan (two bedrooms on each side!). Ceramic tile throughout, beautiful open kitchen area with breakfast bar and granite countertops. The living room opens up onto... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    4 of 5 stars Reviewed 22 August 2013
    This house has it all and in excellent condition. Very clean, well distributed. But, it's a little to far from the beach to go on foot and lack of public parking next to the beach...
    5 of 5 stars Reviewed 18 August 2013
    Love the location and size of house for 4 couples. Like the open floor plan and two eating ares. Every bedroom has a TV to give each guest their privacy. Great outdoor space and...
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    1 / 22
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    • x
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    • x
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    About this property
    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 island vacation rental has been completely refurbished inside and out! A queen bedroom and a sofa bed... View all property information
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    Anna Maria, Anna Maria Island
    5 of 5 stars Reviewed 4 weeks ago
    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 / 28
    5 of 5 stars (3) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
    • x
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    • Elder access
    • x
    About this property
    Located four houses (2 min stroll) from Anna Maria's sugary beach, 'Cozy Cottage' is the ultimate retreat for relaxation and reconnecting with family or friends. Nestled on Anna Maria's cherished North End, this luxurious home features (3) bedrooms and (3) baths - two bedrooms have en-suite... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 1 September 2015
    We just returned home from a week in the Cozy Cottage on Anna Maria Island and I wish I could go right back! My parents, husband, two young sons and I loved this property. It was...
    5 of 5 stars Reviewed 22 December 2013
    Anna Maria Island is one of the nicest, most laid-back islands I have ever visited, and Cozy Cottage was a wonderful home that held our family of five very well. Everything was...
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    1 / 23
    5 of 5 stars (6) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
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    • ?
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    • 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 3 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...
    5 of 5 stars Reviewed 24 January 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...
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    1 / 39
    5 of 5 stars (3) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 11 | Quick View
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    • Pet-friendly
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    • Child-friendly
    • x
    • x
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    • Elder access
    • x
    About this property
    When you 'have anna maria' on your mind, you'll want 'hav'anna hideaway' for your vacation home. This newly constructed 4 bedroom, 4 bath home is located just one short block to the beautiful and sparkling gulf beach. The main floor of the home consists of an open concept living room, kitchen with... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 27 August 2015
    This property was everything we had hoped for and more! Centrally located in one of the best parts of Anna Maria Island, and even though it was close to one of the main streets it...
    5 of 5 stars Reviewed 8 August 2013
    The house is beautiful, very well-equipped (although we missed the grill), very comfortable, and a short walk to a wonderful beach. It was just right for the grandchildren and...
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Beachy Keen!~ 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 for those wishing to escape wild,wintry weather or sizzling city summer. Located in... View all property information
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    Anna Maria, Anna Maria Island
    1 / 30
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    $310
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    • x
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    • x
    About this property
    Newly Remodeled 3 Bedroom/3 Bath with Queen Master, Queen 2nd Bedroom, and Twin Bunk Bed with Twin Trundle. New Pool and landscape, with a quiet canalfront setting. Located on a quiet dead end street, close to the trolley, the beach, the city pier, and walking distance to Anna Maria shops and... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 30
    3 of 5 stars (1) Average
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Beautiful 2B/1B cottage on the quiet North end, only 5 houses to the beach, and no streets to cross. Beautiful new Heated Pool. Twins can be converted to King in all bedrooms. NO dishwasher, no garbage disposal.Rear trash pick up! Charcoal Grill, not gas. Both units also include private... View all property information
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    Anna Maria, Anna Maria Island 34216
    3 of 5 stars Reviewed 27 September 2015
    We stayed here in May, and the unit was tastefully decorated, and had a cozy feel to it. However, my husband and I were getting bitten at night, and we called management to have...
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    1 / 24
    4.5 of 5 stars (9) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    $238
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    • x
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    • x
    • ?
    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
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 8 September 2015
    Mangoes on Magnolia was literally a paradise! My boyfriend and I stayed towards the end of August, when school had started, so it was very peaceful. We very much enjoyed the...
    5 of 5 stars Reviewed 18 May 2015
    Fabulous location on the beautiful north end of Anna Maria Island. Lovely days starting with a walk to the Gulf. Back to Ginny and Jane E's for brunch. A swim in the pool followed...
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    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 bedrooms, 5 baths,4 balconies,3 living areas, an elevator, and a heated salt water pool, you have everything you... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 24
    4 of 5 stars (5) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Child-friendly
    • ?
    • x
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    • Elder access
    • x
    About this property
    The adorable Coastal Cottage, located in the laid-back city of Anna Maria, is the perfect place to take a totally carefree vacation. The white sand beach of Anna Maria Island and the azure blue waters of the Gulf of Mexico are only a short stroll from this delightful three-bedroom, two-bath... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 1 November 2014
    Great, private and quiet location. The house is equipped with all you and your family need. The short distance to the beach made us walk to the beach more than once a day. Any...
    5 of 5 stars Reviewed 3 April 2014
    We stayed at Coastal Cottage at the end of March 2014. Although we have stayed at other lovely places on anna Maria, we just loved the privacy and the beautiful decor of this...
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    1 / 22
    5 of 5 stars (3) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    $357
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    • Patio
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    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
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    • Elder access
    • x
    About this property
    Beautiful, Brand New, Ground Level 4 bedroom/3 bath home, just around the corner from the Rod & Reel Pier, Bayfront Park, and just a couple of blocks to Fabulous Bean Point Beaches and Sunsets. Beautiful back yard with Heated Pool surrounded by a large paver deck and beautiful outdoor lounging... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 2 weeks ago
    We recently rented this beautiful home on the north end of Anna Maria Island. We had three couples - old friends and this house was perfectly laid out for our comfort and...
    5 of 5 stars Reviewed 2 December 2013
    We arrived early on the island and were met by a friendly team that got us our keys, gave us directions to our destination and even invited us to a Friday night clam bake (sorry...
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    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    $297
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
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    • x
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    About this property
    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 <a href='http://coastalcottagesami.com/bean-point.php'>Bean Point</a>, you are on the gorgeous white sands of... View all property information
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    Anna Maria, Anna Maria Island
    1 / 20
    5 of 5 stars (3) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Wheelchair access
    • Child-friendly
    • x
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    • x
    • x
    About this property
    Description We are located in the heart of the beautiful city of Anna Maria FL. We are one block from the historic Pine Ave with free trolley service to the entire island. We are two blocks to the beautiful white sand beach. Three blocks in the opposite direction is the bay and the historic City... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 stars Reviewed 7 November 2015
    We loved this rental. Rick, the owner, was insanely responsive -- emailing back within minutes the few times we emailed. A good friend and I came here for a creative retreat...
    5 of 5 stars Reviewed 16 September 2015
    This place was great! The house had everything we needed and is in the perfect location! There was plenty of room and tons to do and I'd definitely stay again.
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    1 / 20
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $236
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    • x
    • x
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    About this property
    The Heron unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, two bath upstairs unit furnished in a tropical theme. This unit will sleep six with a queen size bed, two twin beds and a sofa bed. Many new upgrades to this unit have... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216