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Anna Maria Holiday Rentals

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    Travellers to Anna Maria are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 9
    4.5 of 5 bubbles (21) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    5 of 5 bubbles (4) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    It doesn't get much better than being right on the water, less than one block from the bay beach, and only 7 blocks from Pine Avenue. Sunshine Cottage couldn't be a better name, because this 3 bedroom, 2 bathroom, cottage truly lets you experience the beauty of Anna Maria Island. Enjoy dangling... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 28 October 2016
    We had a fantastic time exploring Anna Maria Island and coming home to such a fantastic place made the holiday even more special.
    5 of 5 bubbles Reviewed 17 February 2016
    This home is located in walking distance to restaurants and the beach with bikes available as well. It is very nicely and newly decorated. The kitchen is well stocked as well as...
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    1 / 20
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This water front, two bedroom condominium (ground floor), sits on the end of Pine Avenue, across the street from the beach and has wonderful seaside views of the bay. It also has its own private fishing dock and boat slip! This unit has been completely remodeled and newly furnished to give you the... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    As an artist this private three bedroom and two bath multi-level elevated vacation home has been our family retreat that inspires many paintings of Anna Maria Island. Located on the secluded North End you will enjoy the tranquility of the Island and have an easy stroll to the Gulf of Mexico and the... View all property information
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    Anna Maria, Anna Maria Island 34217
    1 / 16
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Sea Waves cottage is located at north end of anna maria island. Brand new renovation, 3 bedroom with 2 bath room, with private dock, sailboat direct to bimini bay, unobstructed , natural view of bimini bay. Less than three minute walk to beach, walking distance to pine ave and the city pier and... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 15 March 2017
    We were please to find this very clean unit on the ground floor of a two story house with private entrance, private deck, and parking. It is a 10-15 minute walk to the Anna Maria...
    5 of 5 bubbles Reviewed 20 November 2016
    Absolutely perfect exactly as described . Owner Jenny very quick to respond . Secluded beautiful view of the bay !! Very easy to get around the island, perfect location...
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    1 / 17
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Patio
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    About this property
    Anna Maria Island, This property is located directly across from the famous Manatee County Public Beach. Groomed daily, Lifeguards, restaurants, surf shop and more.. Free trolley stops there both northbound and south every 20 minutes. The location is also right in the heart of the island. Walk to... View all property information
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    Anna Maria, Anna Maria Island 34217
    1 / 40
    5 of 5 bubbles (12) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Description We are located in the heart of the beautiful city of Anna Maria FL. We are one block from the historic Pine Ave with free trolley service to the entire island. We are two blocks to the beautiful white sand beach. Three blocks in the opposite direction is the bay and the historic City... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 17 January 2017
    Crescent Wave was the perfect place for us to stay. We came down to surprise our parents for their 50th Wedding Anniversary (there were three couples) and this was just the...
    5 of 5 bubbles Reviewed 28 November 2016
    We stayed Thanksgiving week. House was as advertised and the family loved the heated pool and hot tub. No complaints and location of the house is perfect. Would definitely...
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    1 / 19
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Balcony
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    About this property
    Our 2 bed/2 bath cottage is the perfect home to spend your vacation. Located on a canal, you can bring your boat or rent kayaks. Fishing is great from the dock. House and yard is very private. Soak in the jacuzzi after a long day at the beach or relax in the hammock. We have 2 bikes, beach... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
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    1 / 23
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Anna Maria rental “Le Paradis” offers a comfortable and casual sophistication for a memorable beachside getaway. Accommodating up to six guests this home is perfectly located, and well appointed. You’ve found an Anna Maria vacation rental you’ll want to visit again! Located in a highly... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 21 January 2017
    My husband and stayed at le paradis for a week and it was incredible. The house is very well appointed and the location is hard to beat. The pool is amazing! I would highly...
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    1 / 23
    5 of 5 bubbles (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Stunning ground level 3 bedroom/2 bath home with luxury finishes at every glance. Brand new to the market and recently renovated, this home is packed with designer finishes throughout from luxury linens in all three uniquely appointed bedrooms to furnishings that make this home feel like you are... View all property information
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    Anna Maria, Anna Maria Island 34217
    5 of 5 bubbles Reviewed 22 November 2016
    Had a wonderful stay at blue heron, the house is beautifully furnished, but main thing about this property is outside. The dock with fishing and the kayaks for kayaking in the...
    5 of 5 bubbles Reviewed 28 June 2016
    Just what our family needed for a relaxing vacation. We loved the swimming pool and that you could kayak a few hundred feet and view the manatees on the canal right from the...
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    1 / 37
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Smoking allowed
    • x
    About this property
    Cast Villa #4 is the most private on this lush tropical Half acre property. Located directly across from the famous Manatee County Pubic Beach. Swim with Life guards present. Known for the pristine sugar white sand beaches. Dine early breakfast or have a beverage listening to live music daily.... View all property information
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    Anna Maria, Anna Maria Island 34217
    1 / 39
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Porch
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    About this property
    The lovely Dolphin Pointe resides on the highly desirable north end of Anna Maria, just a three houses away from the beach at Bean Point and a short walk to 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... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 30 January 2017
    The house is just as the pictures suggests. The floor plan was very spacious. We traveled with 6 adults (4 were college students) and there was ample room to spread out. The...
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    1 / 14
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Cute and Cozy Cottage just 200 steps to Beach. Walk to Shops, Free Trolley, Resturants, Pier, Museum and more. This apt is attached to another unit that shares the pool. Rent it for the whole family. All the comforts of home. Just bring you towel and suit. Beautiful Beach and Wildlife.... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 17
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    706 North Shore - Private home 3 Bedroom/ 2 Bath , maximum occupancy of 8 people. Tranquility abounds in this delightful home away from home...just a few steps to the beach, this charming 3 bedroom 2 bath home is truly a vacationer's delight! Located in the city of Anna Maria minutes from the... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 15
    4.5 of 5 bubbles (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    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 34216
    5 of 5 bubbles Reviewed 17 April 2016
    Hi! My husband and I rented this property and had the wonderful opportunity of having our adult children & their spouses come with us. There was 8 of us in total. We enjoyed...
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    1 / 45
    4.5 of 5 bubbles (19) Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | 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 2 January 2017
    This is an excellent vacation home to spend with a large family looking for a quiet getaway on AMI. Our family of eight adults, one teenager, one toddler, and one infant spent 7...
    5 of 5 bubbles Reviewed 27 December 2016
    We've stayed on AMI many times and this house was far and above the best one we have rented on the island! Great location....can walk everywhere and gorgeous views from all of...
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    1 / 23
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Sea Haze Cottage is a completely renovated and updated private beach cottage, that is just perfect for a family or for one or two couples. It has a great room that leads to a large screened porch overlooking the deck, pool, spa and canal. The cottage is located in the quiet north end of Anna Maria... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 28
    4 of 5 bubbles (9) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    ~BOOK AND STAY IN MAY OR JUNE 2017 AND GET $300 OFF~ 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 lanai. The home is... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 3 May 2013
    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 / 7
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Newly renovated beach condo just 50 steps to the sand. Over 1200 sq ft with 2 lanais and 1 spacious rooftop deck for spectacular ocean views. Granite Counter Tops Stainless Steel Appliances Washer and Dryer Heated Outdoor Pool Beach Supplies Walking distance to restaurants and Shops Close to... View all property information
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    Anna Maria, Anna Maria Island 34217
    1 / 21
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Sea Breeze cottage is located at north end of Anna Maria island. Brand new renovation, 2 bedrooms with 2 bath rooms, with private dock, sailboat direct to Bimini bay, unobstructed , natural view of Bimini bay. Less than three minute walk to beach, walking distance to pine ave and the city pier and... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 21
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    116 Maple Breeze Private home 4 Bedroom / 2 1/2 Bath , maximum occupancy of 7 people. 116 Maples is located on one of the prettiest streets in the village of Anna Maria, this gorgeous 4 bedroom, 2 and a half bath home is just steps away from the beach. This quiet, tree-lined street evokes... View all property information
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    Anna Maria, Anna Maria Island 34216
    5 of 5 bubbles Reviewed 2 November 2015
    Wonderful location, The beach is at the end of Maple Ave, a quiet road only a 2 minute walk. The house is well situated, 4 bedrooms and 2 and 1/2 baths. I can only speak of the...
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    1 / 26
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    313 Palm Ave - Duplex 2 Bedroom /1 Bathroom , maximum occupancy of 4 people. Enjoy an old fashioned Florida beach vacation at this wonderful cottage just 5 min walk from the beach! Located right in the heart of the village of Anna Maria, not only can you walk to the beach in a matter of seconds,... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 24
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    “Sugar Plum Hide Away West” is a cute ground level duplex located in the spectacular city of Anna Maria. Just a short walk to the beach, you don’t even have to cross a street, to access the white sand and blue waters of pristine gulf beaches from this adorable Anna Maria vacation home. The... View all property information
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    Anna Maria, Anna Maria Island 34216
    4 of 5 bubbles Reviewed 8 June 2016
    Very clean and great location. Plenty of towels. Important to realize a duplex - small pool and backyard ( shells not grass) shared. There was a family with small children next...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Grant's View is a private bay front home is located on the Tampa Bay where you will enjoy the amazing endless views of the open water, not to mention Dolphins swiming by! This bayfront home is furnished with beach style furniture which offers a rich and comfortable atmosphere and is fully... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 28
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    742 Jacaranda- Single Family home 3 bedrooms/ 2.5 baths, maximum occupancy of 6 people. This well appointed home has recently been renovated. The balconies have all been redone, new stairway and all new furniture in the living room and bedrooms The master bedroom boasts a king size bed with a... View all property information
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    Anna Maria, Anna Maria Island 34216
    1 / 24
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    Located at the prestigious north end of Anna Maria, Blue Waters is brand new  to the rental program!  This home is a beautiful private resort-style villa, just minutes walk from the gorgeous white sand beaches of Anna Maria Island and a few blocks away from the individual shops, restaurants and... View all property information
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    Anna Maria, Anna Maria Island 34216
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Bayou 5B - Condo ground floor 2 Bedroom / 1 Bath, maximum occupancy of 4 people. Located on historic Pine Ave., Bayou 5B has great water views and a private dock. You can walk across the street to the Anna Maria City Pier and to shops and restaurants. This comfortable unit is very well maintained.... View all property information
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    Anna Maria, Anna Maria Island 34216
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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. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki... View all property information
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    Anna Maria, Anna Maria Island 34216
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    The home is immaculately clean and whimsically decorated, professionally landscaped, and boasts one of the larger pools larger backyards and larger 2 bedroom homes on the Island. The spa is accented by iridescent glass. The 20' tall tiki hut was hand-built by Native Americans and houses the bar and... View all property information
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    Anna Maria, Anna Maria Island 34216
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    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
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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 34216
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    This stunning BEACHFRONT home was designed by an award winning Architect and is true paradise. The plan is open with the Living, Dining, Kitchen and Master Bedroom on the Waterfront adjacent to the deck which runs the entire length of the home. The elevated deck is a mere 10' from the waters edge.... View all property information
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    Anna Maria, Anna Maria Island 34216
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    3 Bedroom, 2 Bath (sleeps 8) - "Sandy's Getaway" - 122 Peppertree Lane, Anna Maria Sandy’s Getaway, tucked away at 122 Peppertree, offers spacious and peaceful place to escape to right in the heart of Anna Maria City. Up to nine guests can spend a week, month, or long weekend unwinding... View all property information
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    Anna Maria, Anna Maria Island 34216
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    Time spent on Anna Maria Island should be savored. We islanders move through our day with a slower, mellower attitude. And being able to do that comes from having a sanctuary to eat, sleep, and daydream in. This is just what you’ll find at 120 Maple. A ground level vacation cottage in Anna Maria... View all property information
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    Anna Maria, Anna Maria Island 34216
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    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    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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    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
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    For a laid back beach vacation you won’t soon forget, visit “Dolphin” in the city of Anna Maria!  “Dolphin” offers accommodations for up to four guests in a premium beach bound location. This cozy duplex is just a short two block walk from some of Anna Maria Island’s most coveted beaches on... View all property information
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    Anna Maria, Anna Maria Island 34216
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Staying at Mangrove Cottage, known to some as simply “Mangrove Cottage”, is less about vacationing and more about seeing what it means to live the island life. This two bedroom, two bath vacation cottage will feel like home from the first time you wake up in Anna Maria Island’s sunshine and salt... View all property information
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    Anna Maria, Anna Maria Island 34216
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Chic and cozy vacation rental nestled right between the Tampa Bay and the Gulf of Mexico.   (2) Bedroom, (1) Bath, accommodates up to (6) people: 1 Queen, 2 Twin, 1 Sleeper Sofa. Free wireless, sorry no pets allowed, less than three blocks to both the Bay and Gulf. The north end of Anna Maria... View all property information
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    Anna Maria, Anna Maria Island 34216
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    3 of 5 bubbles (1) Average
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Get ready to fall in love with the vacation rental of your dreams when you visit “Sea Song”! This stunning direct gulf front Anna Maria vacation rental has been upgraded from the floors to the roof providing you with a wonderful gem of a vacation experience. Everything in this home is new and... View all property information
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    Anna Maria, Anna Maria Island 34216
    3 of 5 bubbles Reviewed 7 February 2017
    My wife and I stayed here for a week beginning with the Memorial Day holiday weekend. Upon our arrival, we walked into the kitchen to find a MASSIVE cockroach in the middle of...
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    The Flamingo unit at the Blue Dolphin Inn, located at 780 Jacaranda in the Historic Village of Anna Maria is a wonderful and spacious three bedroom, two bath upstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with... View all property information
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    Anna Maria, Anna Maria Island 34216
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Welcome to your new vacation home away from home on Anna Maria Island! “Mon AMI Beach House” is a fun and relaxing Anna Maria vacation rental perfect for up to eight guests! Located on bustling Pine Avenue you’ll be in the heart of the Anna Maria city shopping, dining, and sightseeing. Not only... View all property information
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    Anna Maria, Anna Maria Island 34216
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    “Heron” is the perfect Anna Maria Island beach rental for a relaxed Florida getaway. When you arrive at this unit you’ll be greeted with a Heron on the front door letting you know you’re vacation has begun. During your visit you’ll be less than two blocks from Bean Point beaches and endless... View all property information
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    Anna Maria, Anna Maria Island 34216
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    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    The Skimmer unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, one bath downstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby... View all property information
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    Anna Maria, Anna Maria Island 34216
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    The various shades of blue throughout Sea's the Day make this a  water lover's dream vacation cottage. Sitting about 200 steps to the beach access, it's like you are a sea shell throw away from the beautiful AMI beaches, and you have a pool oasis out in your own backyard. There’s room for up... View all property information
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    Anna Maria, Anna Maria Island 34216
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Spend your holiday in Sea ‘Esta and enjoy sweet dreams, suntans, and a short walk to the beach. Sleeping arrangements make room for six guests there’s even room for four legged members of the family. Pets up to 25lbs are welcome to relax with you in this luxury vacation rental home (with fee).... View all property information
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    Anna Maria, Anna Maria Island 34216
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    3 Bedroom, 2 Bathroom (Sleeps 7) – 620 Rose Street in Anna Maria Fall in love with the perfect Anna Maria Island vacation rental! 620 Rose Street is located in the coveted north end of Anna Maria Island in the beautiful city of Anna Maria. No frills and casual, 620 Rose Street is a great... View all property information
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    Anna Maria, Anna Maria Island 34216
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    People choose Anna Maria Island for their family vacations because we have a slower, simpler way of doing things. We make the time to get to know people and when you slow down to island time, you can even get to know the people your closest with all over again. A vacation duplex is the perfect... View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216