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Anna Maria Holiday Rentals

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    Travellers to Anna Maria are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 158 Rentals in Anna Maria
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    Crescent Wave1 / 80
    (17)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Dolphin Pointe1 / 39
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Cast Villa 11 / 31
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    The Nantucket1 / 27
    (21)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2017
    We rented this home over Spring Break with my brother and his family. The layout of this house is great as well as the location of the home on the island. There were 2 master...
    Reviewed 10 February 2017
    The location couldn't be better with an easy walk to the beach and several very good restaurants and free bus service running every half hour throughout the island. The beach...
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    About this property
    3 Story 'Nantucket' Style - 4 bedroom/ 3 bath villa is just a short walk to the beach - Nestled in a tropical setting, only a few blocks to the Gulf beach; private pool great for cooling off and a large sun deck. 4 Bedrooms/3 baths, large master suite with king size bed and a roman tub, 2nd...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Sand Castle well appointed home steps from beaches1 / 25
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Grill
    • Private Outdoor Pool (Heated)
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 August 2017
    My family stayed in this home August 2016. The home is beautiful and we enjoyed our stay very much. The home was well equipped and pretty clean. I did has a couple issues at...
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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...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Gorgeous views,spectacular home!1 / 138
    (20)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Washer
    • Grill
    • Cable/satellite TV
    • Balcony
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    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...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Anna Maria Island 'High End' Vacation Rental1 / 63
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Internet Access
    • Washer
    • Patio
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Anna Maria's Coconut Breeze Estate1 / 49
    (4)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Air Conditioning
    • Grill
    • Patio
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Really beautiful home and close to everything. Huge place. 2 minute walk from Rod and Reel Pier and 5 minutes to Bean Point (though wouldn't recommend swimming there, current...
    Reviewed 9 May 2017
    This home really does have the "wow factor." The moment we walked through the door we were blown away. The best of everything is in this home...the kitchen appliances...
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    About this property
    This beautiful gem in the much coveted City of Anna Maria's north end. It is a single family home located on a quite street. Easy walk to the gorgeous white sand Bay and sugary sand Gulf of Mexico beaches with striking sunsets . With Pine Ave (our fantastic little Main St.) just a short stroll from...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    BEACHFRONT HOME, LABOR DAY SPECIAL, DOGS STAY FREE, GREAT VIEWS, WALKING BEACH1 / 22
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Parking
    • Grill
    • Terrace
    • Wi-Fi
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Awesome pet friendly beach house right on the water. It has amazing views of the Sunshine Skyway bridge and we enjoyed watching the boat traffic in the distance! So relaxing...
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    About this property
    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....
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Blue Heron Waterfront House Anna Maria island1 / 23
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Ocean Views
    • Washer
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 June 2017
    We stayed for a week at the end of May 2017 after spending 10 days in Orlando. We were met at the property (even though we were a little late) and it was beautifully presented...
    Reviewed 22 May 2017
    The location is perfect. Walk 2 blocks to beach. Supermarket, drug store, bank, restaurants, salon, spa, less than 5 min. away. Many choices to dine/shop 3-10 min drive. The...
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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...
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sunshine Cottage - Private 30' Pool and Boat Dock, and steps away from the beach1 / 38
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Waterfront
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2017
    The house was gorgeous. Pretty and comfortable furnishings. Loved all the Anna Maria touches. Fantastic kitchen appliances - I wish my washing machine was so good! We all loved...
    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.
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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...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Brand New Renovation Sea Waves Cottage1 / 16
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Waterfront
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 May 2017
    Located on a quiet street, this cottage was exactly as advertised. It is updated and tastefully decorated. All beds (1 king, 2 queens) were very comfortable. Water pressure was...
    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...
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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...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    116 Maple Breeze1 / 24
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
    • Grill
    • Internet Access
    • Balcony
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    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...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    DIRECT GULF FRONT' be right on the BEACH.Available  DECEMBER1 / 26
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Central Heating
    • Parking
    • Balcony
    • Patio
    • Terrace
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    My husband and I stayed at this beautiful condo for 1 week in October for our honeymoon. Not only was the place and view amazing but the area itself was extremely peaceful so...
    Reviewed 2 weeks ago
    We spent a week at this Awesome Condo for our honeymoon. Wonderful views...spacious, clean & relaxing.we slept with the windows opened and listened to the waves.. so...
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    About this property
    3 Miles of white sandy beaches..Beautiful beach front condo. Location is amazing for the perfect vacation bedrooms are a split design for privacy the panoramic views from the condo are breathtaking listen to the waves day and night and enjoy the beautiful SUNSETS perfect for Elderly...has...
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    Anna Maria, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Maple Cottage ~ RA433721 / 15
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Grill
    • Internet Access
    • Washer
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 June 2017
    Maple Cottage was in a great location with no major streets to cross and just a very short walk to the beach. House was overall clean and well stocked. Furniture was in good...
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    About this property
    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...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
    About this property
    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...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This quaint, old-Florida style rental is nestled in the north shore area of Anna Maria Island. Shabby chic style, located 2 blocks from the beach and 2 blocks from the bay! Only one block from Pine Ave., with its old-time feel with shops and salons. Steps from fine dining, the historic city pier,...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Central Heating
    • Terrace
    • Waterfront
    • Ocean Views
    • Balcony
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 bedroom 2 bath home is on the north end of Anna Maria Island and can be combined with Pirate Cove (a separate building ) to make a 5 bedroom beach front vacation home. All bedrooms in Hooks Haven are Queen size. Two bedrooms are on the main floor and one is on the second floor. Spiral...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Charming 2 Bedroom/2 Bath Cottage on a Canal1 / 19
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • DVD Player
    • Patio
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    • Terrace
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 April 2017
    I loved that the owner went our of her way to reserve pack and plays for our two little ones. They had everything for beach trips including a wagon, beach toys, and umbrellas...
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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...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully renovated beach cottage in the heart of the village of Anna Maria. Walk to the beaches, shops and restaurants. Enjoy amazing sunsets at the beach or sip a glass of wine in the lush tropical gardens surrounding the cottage. 2 bedrooms with 2 full bathrooms. Quaint beach cottage in a...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Grant's View ~ RA435391 / 15
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    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...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Wi-Fi
    • Washer
    • DVD Player
    • Hot Tub
    • Private Outdoor Pool (Heated)
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    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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    103 Pelican1 / 14
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Balcony
    • Terrace
    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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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...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Paradise at the Bayou1 / 20
    (3)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • DVD Player
    • Balcony
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    • Waterfront
    • Patio
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 June 2017
    The rental was extremely clean and well stocked with all the amenities needed for cooking, fishing, sitting on the beach or just reading a book while watching the fish jump. The...
    Reviewed 17 May 2017
    From the time we walked in the door you could see the care and thoughtfulness the owners put into making sure you enjoy your stay! This condo has a beachy look and feel and the...
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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...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    BEACH NEST ONLY $199 nite/Dec*Pool*Hottub*Dock*Steps to Gulfside beach*Shelling!1 / 23
    (11)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 February 2017
    Beach Nest is wonderful. Decorated with flair and beachy elegance, it feels like a home, not a rental. There is everything you need and more. You can walk to the beach with your...
    Reviewed 20 January 2017
    The Beach Nest is wonderful and relaxing!! The pool, the home, the cleanliness, the cuteness, and the canal were all such a treat for us! We will be back for sure!
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    About this property
    Ahhhh-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...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    AMICoastal Rentals ' Island Oasis'1 / 84
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
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    • Waterfront
    • DVD Player
    • Ocean Views
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 September 2015
    I chose Island Oasis as it ticked every box. This is a beautiful island and the beach is very easy to access, as such I wanted a property with a pool, suitable for two couples...
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    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...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Direct Beach Front Home with 180 degree Gulf Views. Your backyard is a Private Beach and a beautiful view of Egmont Key & the Skyway Bridge. Walk to the Rod & Reel Pier where dolphins frolic every afternoon or walk to Pine Avenue for some local shopping. The living level has a full size kitchen,...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Ocean Views
    • DVD Player
    • Central Heating
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Anna Maria Island is still old Florida, I am on a half acre of very Tropical Palms and landscaping. Located in the heart of the Island. Directly accross from the Famous Manatee County Public Beach. Reasturants, Free trolley all right there. Also grocery, pharmacy, shopping within walking distance....
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Ocean View 3 bedroom, pool, North Shore Drive1 / 113
    (36)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Ocean Views
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Great place I had my birthday party here it was so fun Very close to the water every thing was to the t in cleanliness sleep 6 of us it was all around one of the best beach...
    Reviewed 30 July 2017
    We love this beach house! It has everything, is always clean, great location, and the owner is the nicest to deal with! We will definitely be back...if someone else doesn't book...
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    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...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    744 Jacaranda Rd1 / 32
    (9)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Shared Outdoor Pool (Unheated)
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    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    About this property
    744 Jacaranda - Private home 3 Bedroom/ 3 Bath with private pool, maximum occupancy of 6 people. BOOK AND STAY NOW THROUGH THE END OF DECEMBER 2017 AND GET 15% OFF OF A WEEK LONG BOOKING. 20% OFF OF A 2 WEEK BOOKING. BOOK AND STAY 4 WEEKS AND ONLY PAY FOR 3--OFFER GOOD FOR BOOKINGS NOW THROUGH THE...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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,...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on beautiful Anna Maria Island, 'Le Paradis' (which means Paradise in French) is just a short stroll to the sugar white sand beaches of beautiful Anna Maria Island... Experience a luxurious beach vacation with over 2100 hundred square feet of tastefully living space with an expansive...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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....
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
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    Pet friendly
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    About this property
    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....
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Casa Palma1 / 23
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • DVD Player
    • Cable/satellite TV
    • Grill
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    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 June 2017
    The house was beautifully decorated but a little on the older side could have been cleaned better a lot of dust and the pool was small and not cleaned the entire time we were...
    Reviewed 14 March 2017
    We rented this wonderful house for two weeks, two years in a row. Tried to rent it this year but couldn't find it. Perhaps they switched to a new rental company?This is a...
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    About this property
    If you are looking for the perfect spot to vacation on Anna Maria Island, look no further! This beautiful Anna Maria vacation rental is fabulously decorated throughout! Open and airy, with a fantastic living area, Casa Palma has plenty of room for all of your family and friends. The gourmet...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 Bedroom, 2 Bath (sleeps 8) - 'Blue Heron Beach House' - 117 Peppertree Lane in Anna Maria.  Welcome to “Blue Heron Beach House”! This adorable Anna Maria beach cottage rental is so close to the Gulf of Mexico you can smell the salt air! Enjoy sugar sand beaches and crisp blue water only steps...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located directly across from Tampa Bay, this gorgeous new custom luxury vacation rental looks out onto the beautiful bay waters from multiple large balconies. A rooftop deck provides outstanding 180 degree views of the turquoise waters, as well as the Anna Maria City Pier and the Sunshine Skyway...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to 'Holly Hideaway' located on the northern end of beautiful Anna Maria Island. This lovely two bedroom and two bath vacation rental features all that you will need to stay a week or a month. Feel the breezes through the screened lanai or lounge by the new heated pool located in the back of...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Life is Good at the Beach: 3BR Family/Pet-Friendly1 / 21
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 January 2016
    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...
    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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    About this property
    *SPECIAL* 20% OFF A WEEKLY STAY NOW THROUGH THE END OF THE YEAR (EXCLUDES HOLIDAYS)!! 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...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Periwinkles are small, sunshine loving flowers with a color so distinct they name crayons after it. On a street baring their name in Anna Maria Island, you’ll find a vacation rental home appropriate to the name - 'Pretty Palms' on Periwinkle Plaza. This three bedroom, two bathroom cottage is...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Le Paradis 727 Jacaranda ~ RA910691 / 23
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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 desired...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sugar Plum Hideaway West ~ RA552401 / 24
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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 outdoor...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cute 2 bedroom, 1 bath cottage is located at the quiet North end of Anna Maria Island just steps to beautiful white sand beaches. Only 200 yards to the beach access. Nature lovers will enjoy bird watching along the beaches at Bean Point. The Rod-N-Reel Pier is a short walk away for great...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Salt Box Cottage is newly renovated, bright, clean, cozy and the perfect place for an Anna Maria Island vacation. This quaint vacation rental cottage is just steps to Tampa Bay and five blocks to the beautiful powder-soft, white sand beach and turquoise water of the Gulf of Mexico! Accommodations...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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