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Anna Maria Cottages

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    Travellers to Anna Maria are booking March 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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    Brand New Renovation Sea Waves Cottage1 / 16
    (9)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Secluded beautiful view of the bay !! Very easy to get around the island, perfect location.
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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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    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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    Wave Crest: Stay ON The Beach! Gulf-Front Private Cottage With Breathtaking view1 / 25
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    This enabled us to view our first of many sunsets during this week.
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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
    Book Now & Save 15% Off When You Stay Before Dec. 31st, 2018! + Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! 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...
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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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    Gulfshore Cottage: Lovely Family-Friendly Home, Just 1 Block from Beach!1 / 24
    (24)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Anna Maria Island remains totally unspoilt and the extremely well-appointed cottage is still the perfect base to walk to the beach, the bar and local restaurants.
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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
    Book Now & Save 15% Off When You Stay Before Dec. 31st, 2018! + Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! 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...
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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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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Internet Access
    • Washer
    • Cable/satellite TV
    • Grill
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book Now & Save 15% Off When You Stay Before Dec. 31st, 2018! + Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! 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...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Whispering Pines: Beautifully Restored 1920's Cottage, Just Steps To the Beach!1 / 24
    (10)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Loved this Beautiful Cottage!
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Patio
    • Washer
    • Parking
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 January 2018
    We stayed over Christmas a the Whispering Pines Cottage. It was well appointed and had beachy decorations which is perfect for the location. The beds were comfortable and the...
    Reviewed 29 February 2016
    Loved this Beautiful Cottage!Steps from the White Sand and Peaceful Beach.I will be back to this Sweet Island!!
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    About this property
    Book Now & Save 15% Off When You Stay Before Dec. 31st, 2018! + Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! This two-bedroom, two-bath vacation rental is located on the quiet north end of Anna Maria Island. Whispering Pines is just three houses from one of...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    We had a amazing time staying at Pineapple Cottage on Anna Maria Island.
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Parking
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 August 2018
    I loved the stay at Pineappe Cottage and I hope we will return before too long. We have stayed a couple of times on AMI and love it here. We decided to look at a property with...
    Reviewed 30 July 2017
    Pineapple Cottage is located on Pine close to shops and near the beach. I loved to stay at this very clean and well maintained cottage. It has everything what's needed and is...
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    About this property
    Book Now & Save 15% Off When You Stay Before Dec. 31st, 2018! + Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! Pineapple Cottage, centrally located on historic Pine Avenue in the city of Anna Maria, is the perfect place to slow down and catch your breath! This...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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
    Kevin, the cottage maintenance person who came by to help us also provided some great suggestions for nearby places to eat breakfast or lunch such as Rudy's, and Ginnie & James.
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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
    Book Now & Save 15% Off When You Stay Before Dec. 31st, 2018! + Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! 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...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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
    div class='rtejustify'>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,...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Grill
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>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...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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
    div class='rtejustify'>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...
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Internet Access
    • Washer
    • Parking
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>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...
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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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    • Washer
    • Parking
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book Now & Save 15% Off When You Stay Before Dec. 31st, 2018! + Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! 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...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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