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Anna Maria Cottages

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    Travellers to Anna Maria are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    14 Matching Rentals in Anna MariaView all 239 rentals
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    Newly renovation bay side cottage: Sea Breeze1 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Whispering Pines: Beautifully Restored 1920's Cottage, Just Steps To the Beach!1 / 48
    (10)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pineapple Cottage: Lovely Pet-Friendly Cottage on Anna Maria's Historic Pine Ave1 / 21
    (15)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Island Place Cottage: Beautiful Pet-Friendly Cottage On Historic Pine Ave!1 / 23
    (9)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Parking
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Grill
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 February 2018
    We decided to go to Ana Maria Island over Christmas 2017 because this was the year we had to share our grown and married children with their in-laws. We had never vacationed...
    Reviewed 29 June 2017
    Great location with shops and restaurants within walking distance. The two piers are also just a short walk away. The cottage is basic but very clean, an ideal base for a few...
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    About this property
    This vacation rental is located on Anna Maria Island's historic Pine Avenue, halfway between the Gulf of Mexico and the Anna Maria City Pier! This adorable, one bedroom cottage, with high beamed ceilings, wood floors and shabby chic décor throughout is ideal for a vacation getaway! This quaint...
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    34216, Anna Maria, Anna Maria Island
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Brand New Renovation Sea Waves Cottage1 / 16
    (8)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Waterfront
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 April 2018
    My wife and I stayed at this nice, updated rental and really enjoyed our time. The location was great, with a deck right on a canal. We were walking distance to the beach.The...
    Reviewed 23 March 2018
    The beach house was awesome!!! Had everything we needed. It was true to the pictures on line. Jenny the owner was awesome, got back to we when I had questions right away. We...
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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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    34216, Anna Maria, Anna Maria Island
    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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    • Internet Access
    • Washer
    • Cable/satellite TV
    • Grill
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    • Air Conditioning
    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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    34216, Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Bean Point Beach Cottage:North End Private Pool Home Close To The Bay & Beach!1 / 22
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Patio
    • Internet Access
    • Cable/satellite TV
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    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 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...
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    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...
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    Location Information
    34216, Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Wave Crest: Stay ON The Beach! Gulf-Front Private Cottage With Breathtaking view1 / 25
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Air Conditioning
    • Grill
    • Waterfront
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2017
    We stayed here at the end of June 2107. We have stayed in the same area on Anna Maria a few house to the north and love this area. It is quiet even when it's busy! Wave Crest...
    Reviewed 23 May 2016
    We were excited about renting Wave Crest due to the pictures and information we had previously received. However, nothing prepared us for this beautiful cottage with the...
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    About this property
    Take just four steps from Wave Crest's back door and sink your toes into the white sand beach of Anna Maria Island or enjoy views of the Gulf of Mexico from the deck, Florida room, or the four Adirondack chairs right on the sand. This gulf-front cottage is located directly on the beach and will...
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    Location Information
    34216, Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Enchanted Cottage: Renovated Historical Anna Maria Cottage. Cute & Pet Friendly!1 / 24
    (2)Average
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Washer
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    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming, quiet, cozy, Enchanted Cottage is just steps to Tampa Bay and the Historic Anna Maria City Pier, a fun place to fish! A short five blocks to the beautiful powder-soft, white sand and turquoise Gulf water of Anna Maria Island. You may also enjoy the beautiful sunrise from the pier...
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    Location Information
    34216, Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    Gulfshore Cottage: Lovely Family-Friendly Home, Just 1 Block from Beach!1 / 24
    (24)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • Parking
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 November 2017
    I was lucky enough to secure another stay, my third at this wonderful cottage.Every facility that you would need is available within the cottage . Well stocked for your beach...
    Reviewed 6 November 2017
    This is our third stay at the cottage, and our favorite place to stay when we visit Anna Maria island. It's tough to beat the location, being just a short walk to the beach...
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    About this property
    Your time on Anna Maria Island should be perfectly charming in this classic three-bedroom beach-style cottage perfectly located on the west side of Gulf Drive in the city of Anna Maria. Only steps away from the azure blue waters of the Gulf of Mexico, this unique vacation rental boasts two very...
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    Location Information
    34216, Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Grill
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unit 1 'Still Water'... Adorable, vintage 1 bedroom cottage on Lake La Vista located at the north end of the Island . Just 250 steps to the beach and just a short stroll to historic Pine Avenue for great shopping. Exceptional, 'Old Florida' charm! Shared dock is a great spot to launch a kayak or...
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    Location Information
    34216, Anna Maria, Anna Maria Island
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • Washer
    • Parking
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    7201 Palm Drive, Holmes Beach, Anna Maria Island Palm Cottage ... Lovely 2 bedroom, 2 bath recently updated home. This ground level home offers a beachy decor, a new pool , granite countertops, and a great screened in porch. Just a short walk to the beach. Pool heat is additional....
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    Location Information
    34217, Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Parking
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lime in De Coconut - Upstairs..... Adorable, one bedroom, one bath in a 2 unit cottage. Cheery beach decor and a shared heated pool in a tropically landscaped courtyard. Flat screen TV, wireless internet access, washer & dryer, and a gas grill (propane is guest's responsibility). Located just a...
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    Location Information
    34217, Anna Maria, Anna Maria Island
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Patio
    • Parking
    • Washer
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    604 North Shore, Anna Maria Island, Fl 34216 Unit 2 'Still Water'... Adorable, vintage 1 bedroom cottage on Lake La Vista located at the north end of the Island . Just 250 steps to the beach and just a short stroll to historic Pine Avenue for great shopping. Exceptional, 'Old Florida' charm!...
    View all property information
    Location Information
    34216, Anna Maria, Anna Maria Island
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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