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Holiday Rentals with Pools in Anna Maria, FL

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    1 / 40
    5 of 5 bubbles (10) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 23
    5 of 5 bubbles (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    5 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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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
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    Anna Maria, Anna Maria Island 34216
    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
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 15 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 12 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
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    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 5 weeks ago
    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 18 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 / 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
    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
    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 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 / 33
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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
    Location Information
    Anna Maria, Anna Maria Island 34216
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    1 / 19
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    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 / 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 / 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 18 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 / 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 18 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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    1 / 23
    5 of 5 bubbles (7) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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! <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 23 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 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...
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    1 / 35
    5 of 5 bubbles (2) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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 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...
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    1 / 18
    3 of 5 bubbles (2) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    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 31 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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    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 14 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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    1 / 25
    4 of 5 bubbles (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    **SPECIAL** 20% off bookings in September, October and November! Ask about the discount when booking! 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... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    4 of 5 bubbles Reviewed 2 May 2016
    My husband and I spent a very pleasant two weeks at this cottage in April. It is bright, clean, comfortable (if you like a hard bed) and quite well equipped. The only things that...
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    1 / 23
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    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
    1 / 25
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    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
    1 / 40
    4.5 of 5 bubbles (6) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • 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
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    Anna Maria, Anna Maria Island 34216
    1 / 30
    3 of 5 bubbles (1) Average
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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 bubbles 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 / 35
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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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
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    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles 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 / 28
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Beautifully remodeled 3 bedroom/2.5 bath home with luxury amenities on the North End of Anna Maria, just 4 houses to Bean Point, one of the quietest beaches on the island, and 2 blocks to the famous Rod & Reel Pier! Private Backyard with Heated Pool, and an open floor plan with vaulted ceilings!... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 24
    4 of 5 bubbles (6) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • 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
    4 of 5 bubbles Reviewed 15 May 2016
    This is a lovely house, perfect for a family of 4 to 6 people. 300 meter to the beach. Cozy garden & pool. Everything one needs is available.
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    1 / 42
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Inspired by modern Italy, North End Zen's sleek and minimalistic touches throughout will at times have you feeling as you were vacationing on a posh Mediterranean island. The spacious open concept floor plan begins at the front door and gracefully moves its way to the back of the house which has... View all property information
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    Anna Maria, Anna Maria Island
    1 / 23
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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 / 40
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    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
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    Anna Maria, Anna Maria Island 34216
    1 / 25
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    **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 9 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 / 34
    5 of 5 bubbles (5) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • DVD Player
    • Air Conditioning
    • Patio
    • Satellite TV
    • Grill
    • Parking
    • Wi-Fi
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 bubbles Reviewed 18 January 2016
    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 bubbles 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 / 30
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
    • Washer
    • Satellite TV
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    The Shady Mango was originally built in 1925. According to local history<BR>the heart pine used in constructing the original house came by steam boat<BR>to the City Pier and was hauled by horse-drawn lorry up Pine Avenue to the<BR>home's present site.<BR><BR>In 2004 the home was given a major... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 21 September 2013
    My husband, 2 kids & I stayed at the Shady Mango & LOVED it! It's the perfect place for a vacation for a small family. It's in a great location with walking access to the beach...
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    1 / 39
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Hot Tub
    • Waterfront
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to Canal Place, an inculpable island home that is outfitted to offer occupants an unforgettable vacation experience! In your privately cultivated backyard is an assemblage of accessories providing plenty of options for fun in the sun. There is a heated pool, hot tub, kayaks, boat dock,... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 22
    5 of 5 bubbles (3) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Patio
    • DVD Player
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Washer
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 bubbles Reviewed 21 January 2016
    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...
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    1 / 39
    5 of 5 bubbles (3) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Satellite TV
    • Washer
    • Wi-Fi
    • Grill
    • Patio
    • Private Outdoor...
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 bubbles 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...
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    1 / 29
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
    • Wi-Fi
    • Washer
    • Balcony
    • Parking
    • Grill
    • Air Conditioning
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This great 2 Bed/2 Bath Home with Private Heated Pool resides in Anna Maria and is only one block to the beach and has no busy streets to cross to get there. You can quickly make your way to the Gulf Sands and to all of the great shops and restaurants that Anna Maria and Holmes Beach have to offer.... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 123
    5 of 5 bubbles (31) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
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    • Washer
    • Air Conditioning
    • Satellite TV
    • Private Outdoor...
    • DVD Player
    • Ocean Views
    • Wi-Fi
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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 bubbles Reviewed 16 May 2016
    We've been renting villa's on Anna Marie Island every year since 2002, staying on different parts of the island and found Ocean View to be by far the best villa we have ever...
    5 of 5 bubbles Reviewed 11 April 2016
    This was our first experience in renting a home for vacation. It was a terrific time. The house was beautiful as well as comfortable. Our every need was met from the heated pool...
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    1 / 30
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
    • Internet Access
    • Satellite TV
    • Patio
    • Air Conditioning
    • Washer
    • Grill
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 33
    4 of 5 bubbles (4) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Wi-Fi
    • Parking
    • Grill
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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 bubbles Reviewed 14 January 2016
    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 bubbles 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 / 24
    5 of 5 bubbles (9) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • DVD Player
    • Wi-Fi
    • Grill
    • Washer
    • Satellite TV
    • Private Outdoor...
    • Patio
    • 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 10 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 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.
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    1 / 41
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Private Outdoor...
    • Grill
    • Internet Access
    • Air Conditioning
    • Parking
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to a true Anna Maria Island treasure! Bimini Bay is an irreproachable 4 bedroom, 3 bath ground-level home tucked away on the quiet north end of Anna Maria. Previously a duplex, both units were completely gutted and combined to bring you this gorgeous 4 bedroom home with its own private... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    5 of 5 bubbles Reviewed 4 weeks ago
    Just got back from a girls trip with five friends at Bimini Bay. The house was PERFECT. Bright, clean, fresh, comfortable, and super cute. The pool and outdoor seating areas were...
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    1 / 24
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Wi-Fi
    • Air Conditioning
    • Washer
    • Satellite TV
    • Patio
    • DVD Player
    • Grill
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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 been completely remodeled and fabulously decorated! Cozy and relaxing furnishings await you and your friends and family during your... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 20 March 2016
    My partner and I stayed at Beach Walk twice and absolutely loved it. Everything here is top notch. The property is immaculate and extremely comfortable. We enjoyed the privacy of...
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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
    • Private Outdoor...
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Patio
    • Grill
    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 16 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
    • Patio
    • 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 3 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 / 26
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Wi-Fi
    • Shared Outdoor Pool...
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Anna Maria Island Oasis- Pamper yourself by staying in this brand new Island home with vaulted ceilings, custom tile and cabinetry, along with your own private heated pool. This home offers 4 Master Bedroom Suites each with it's own private Bath. Each bedroom has a King bed and each en-suite bath... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    1 / 36
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Grill
    • Parking
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 master... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 24
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Satellite TV
    • Patio
    • Grill
    • Wi-Fi
    • Private Outdoor...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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 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 / 32
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Satellite TV
    • Parking
    • Grill
    • Shared Outdoor Pool...
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Swaying palms and a beautiful paver double drive lead the way to this Tropical Retreat on Anna Maria Island, Located just one block from Tampa Bay and 3 short blocks to the beautiful white sand Gulf Beach. This three-bedroom, two-bathroom home features volume ceilings, crown moldings, and open... View all property information
    Location Information
    Anna Maria, Anna Maria Island
    1 / 24
    5 of 5 bubbles (9) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Satellite TV
    • Private Outdoor...
    • DVD Player
    • Patio
    • Wi-Fi
    • Waterfront
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • 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 16 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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