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Anna Maria Island Cottages

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    Travellers to Anna Maria Island are booking February dates now. Secure your vacation rental today, and have the perfect trip.
    72 Matching Rentals in Anna Maria IslandView all 1,091 rentals
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    The Tree House1 / 22
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    AMICoastal Rentals Cracker Cottages - Fish Tales1 / 20
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    On the Beach Paradise d1 / 13
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Cable/satellite TV
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    • Washer
    • Air Conditioning
    • Ocean Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 July 2017
    The most wonderful place! we rented this place for 10 days, my daughter, grandson and myself. I fall in love with the place is perfect, nice and very clean.Location is perfect...
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    About this property
    This cottage is located 'on the beach' 3007 Avenue F, beautiful Holmes beach. It is the downstairs unit (1 of 2). The cottage is very comfortable and sleeps 4 comfortably with additional space for a pull-out. This quaint cottage is hidden away on a dead end street, away from it all yet close...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Grill
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is the last property on COQUINA BEACH, GULFSIDE, after historic Bridge Street, before the new pier. This means the pier on Coquina Beach could literally be YOUR backyard for a night, a week or even Spring Break. It doesn't get any better than this. We are booking now for our Grand Opening in...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    The Little Mermaid On Beautiful Anna Maria Island!1 / 17
    (24)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
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    • Cable/satellite TV
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    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 November 2016
    Can't speak too highly about the Little Mermaid and Anna Maria Island. What you see is what you get. Every possible utensil and beach toy is to hand and all spotlessly clean...
    Reviewed 5 October 2016
    Wonderful place to stay. Very clean. Hope to be a repeat guest. Pet friendly. Very close to the beach.
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    About this property
    You will enjoy this adorable newly renovated vacation cottage – THE LITTLE MERMAID -- on Anna Maria Island just across the street from the Gulf of Mexico and minutes from shopping and attractions on Bradenton Beach’s popular Bridge Street! Your three parking spaces are right at the front door!!...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    AMICoastal Rentals Cracker Cottages - Sea Stories1 / 20
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 June 2016
    We loved the cottage and its location. Every morning we would walk the beach and have breakfast in the Gulf Drive Cafe'. In the evening we would return to the beach for a stroll...
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    About this property
    'Cracker Cottages' Features Two Comfortable Bedrooms, One with a King-size Bed, and the Other with a Queen. Both Have Flat-panel Televisions So Everyone Can Watch What They'd Like. a Full Bath with a Combination Tub and Shower Sits at the End of the Hall Between the Two Bedrooms.Although You Can...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Anthony Beach Cottages Bare Feet Retreat1 / 31
    (2)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Grill
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Outdoor Dining Area
    • Patio
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 August 2016
    April was helpful and prompt. She made the whole process from booking to check out easy! The house was cozy and just what we were looking for. I would definitely book again
    Reviewed 27 July 2015
    I will be going back! From reservations to communication, from check in to location and the property itself, this place is magnificent!
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    About this property
    This newly remodeled Florida gem backs onto 17 acres of mangrove forest and is ideally located only 3 blocks from the beach. Reasonably priced, this quaint 3 bedroom, 1 bath cottage has a spacious backyard equipped with a pool, hammock, patio furniture, grill, brick fireplace, and picket fencing,...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Songbird Cottage1 / 23
    (21)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Patio
    • Grill
    • Parking
    • Air Conditioning
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    • Cable/satellite TV
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Songbird Cottage is an clean and very comfortable family bungalow style home with all the things you need to make your stay on the Island enjoyable. It is walking distance to...
    Reviewed 2 August 2017
    This unit was a perfect fit for us. It was a very comfortable cottage to spend our week's vacation in. The kitchen was well equipped and the furnishings were very comfortable...
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    About this property
    Songbird Cottage We live here part time and Songbird is loved. Of course, there are things that could be more high-end or updated, or there are units closer to the beach. But everything is clean and functional. And I'm pretty confident that you can't beat it at this price range. I take a...
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    Location Information
    Anna Maria Island, Florida 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Palm Cottage ~ This beautiful condo is just steps from the Beach!1 / 28
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Wi-Fi
    • Washer
    • Ocean Views
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 May 2017
    The unit was very clean and pretty. Kitchen and linens were well stocked. Located right across the street and right down the road from restaurants. Our first time to the...
    Reviewed 13 April 2016
    The unit itself was very clean and decorated nicely. However, the beach across the street was under construction and closed. The view was of construction equipment, cranes...
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    About this property
    We all know Location! Location! Location! Just yards from the beach, Palm Cottage is a beautiful cottage located in Bradenton Beach and is just steps from the Gulf. This 1 bedroom condo offers a full size, fully equipped kitchen with refrigerator, dishwasher, microwave, oven, ample cookware and...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Anna Maria The Pink Flamingo1 / 22
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Air Conditioning
    • Grill
    • DVD Player
    • Balcony
    • Washer
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 January 2017
    The photos are accurate. But, in person the home is stunning. When my husband and I walked in, the first thing I said was "they must have did a background check on...
    Reviewed 1 December 2014
    LOVED, LOVED, LOVED this property! It's perfectly located right in the heart of Anna Marie island - easy in and out parking RIGHT in front of the villa. The villa was roomy for...
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    About this property
    ANNA MARIA ISLAND #3 TOP 10 ISLAND'S IN U.S.A. Palm Isle 3203,our 2 bedroom island decorated condo is across the street from the beaches of Anna Maria Island. Steps from the heated pool and fully landscaped setting, along with all the amenities of home, your family will enjoy our beach get...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    • Grill
    • Washer
    • Wi-Fi
    • 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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    Location Information
    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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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Sea La Vie ~ RA434361 / 14
    (1)Terrible
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Direct Gulf Front cottage in Holmes Beach! When we say that Sea la vie is right on the beach, we mean one step off the back porch!  (2) Bedroom, (1) Bathroom, accommodates up to (5) people: 1 Queen, 1 Twin, 1 Sleeper Sofa. Open the windows and fall asleep to crashing waves. Sea gulls and...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    When a starfish needs to get away, it is more than prepared to detach an arm in order to do that. Don’t let yourself get that stressed! Stay for a week in Starfish Beach Cottages and feel all your cares and worries just fall away. From the moment you arrive, you’ll feel like this vacation cottage...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Grill
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Willow Cottage is a lovely ground level bungalow in Anna Maria just waiting to give you that tropical vacation you dream of and deserve! This private rental home is stylishly decorated with touches of both new and old Florida. From the whimsical coastal print comforters to cool tile floors under...
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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, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautiful brand new pool and tropical outdoor area await you in the newest of our vacation rentals, A Mermaid''s Lair! Located on the quiet north end of Anna Maria right across the street from Tampa Bay, this tastefully designed island décor house is waiting for you to settle in, relax, and...
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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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    Steps to the Beach/Renovated/Heated, Private Pool1 / 19
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Washer
    • Grill
    • Patio
    • Internet Access
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Blue Turtle Cottage is a private house 1 property from the beach in Holmes Beach on Anna Maria Island. You will love the location, newness and private pool. Holmes Beach is the central of 3 small cities on Anna Maria Island and convenient to all the Island's amenities. INSIDE The cottage is newly...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    4 Bedroom, 2.5 Bath (sleeps 8) - 'Shoreline Terrace' - 901 North Shore Drive, Anna Maria Anna Maria Island is' Old Florida' – we take things a little slower and our beaches are more famous for having flour soft sands than reliable cell phone reception. But that’s why people spend time with us in...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
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    Smoking allowed
    About this property
    To say we live in paradise is no exaggeration and we’d like to invite you to experience it yourself with a week at Sea Palm Cottage! This vacation rental home offers room for seven guests, making it ideal for families with children. (3) Bedroom, (2) Bathroom, accommodates up to (7) people: 2...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2-Unit Beach to Bay Cottage...NOT Grandma's place!...100 feet to beach!1 / 49
    (8)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Outdoor Dining Area
    • Air Conditioning
    • Porch
    • Washer
    • DVD Player
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 April 2017
    Clean, well appointed, great area. A block from the beach or the bay. Beach was beautiful. Would recommend without hesitation.
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    About this property
    This is a beautifully renovated 2 UNIT 'Old Florida' style cottage......Great Views of the Beach & BAY..... JUST 100 FEET to the most stunning, sugar-sand beaches on the Gulf. 1 BR Beachside Unit sleeps 2-4.......2BR Bayside Unit sleeps 2-6. The rates shown are for the 1 BR unit. 2 BR unit is...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Balcony
    • Terrace
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Plum Cottage 324 is professionally decorated with a laidback island flavor, and offers everything you'll desire for a truly memorable vacation! This single story, candy colored rental is directly in the heart of Anna Maria Island. Get on beat with plenty of island flavor as you’ll be close to some...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    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
    • DVD Player
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    • Washer
    • Grill
    Suitability
    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 6 Quick View
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    • Terrace
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    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Absolutely adorable vintage Bradenton Beach vacation rental cottage “A Pirates Cove” will have you wishing you could stay here forever! This two bedroom one bathroom cottage accommodates up to six guests with one king bed, one double bed, a twin bunk bed. Just one block from pristine Gulf of...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    The panoramic views from this dreamy vacation home are something that you will need to tell absolutely everyone back home about – you’ll be sitting literally footsteps from the Gulf of Mexico and our world famous sugar sand beaches! Close enough to spot gulls and crashing waves from your dining...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • DVD Player
    • Washer
    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tucked Away is a brand new listing and is destined to be one of the most popular homes on Anna Maria! It is a newly renovated custom home with everything you could possibly need for the vacation of a life time. The incredibly private setting includes a 38’ X 15’ heated and cooled pool with spa and...
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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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    PURPLE PARROT- HEATED POOL   SHORT WALK TO BEACH1 / 69
    (17)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Internet Access
    • Patio
    • Private Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Too Cute!! Cottage with that Olde Florida Charm. NEW on market with NEW HEATED PRIVATE POOL. Bring your boat the neighborhood boat ramp just across street. Not a busy ramp, only for this street and trailers go back to the house. We also have a fenced in area for your trailer. 2 Bedrooms w/ 2 Full...
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    Location Information
    Anna Maria Island, Florida 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Smoking allowed
    About this property
    The right company can be a retreat all in themselves. When you’re looking for an escape in Anna Maria Island with someone special, consider a week spent at PIV3215 in Holmes Beach.  (1) Bedroom, (1.5) Bathroom, accommodates up to (4) people: 1 King, 1 Sleeper sofa. You’ll have plenty of privacy,...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Pineapple Cottage: 2BR Quaint Pet-Friendly Cottage1 / 21
    (14)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 18 May 2017
    We stayed at the Pineapple Cottage from May 11 to May 18.Just my husband and I. We loved the location. You can walk to the beach either on the gulf or the bay. Walked to Beach...
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    About this property
    Pineapple Cottage, centrally located on historic Pine Avenue in the city of Anna Maria, is the perfect place to slow down and catch your breath! This Anna Maria Island cottage is tastefully decorated with wood floors, granite and stainless kitchen, tiled shower,professional linen service and...
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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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    About this property
    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 to...
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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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    Enchanted Cottage: 2BR Pet-Friendly Cottage1 / 24
    (2)Average
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    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
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    When a starfish needs to get away from something and can’t, it will sometimes need to detach an arm. After a week of staying in the Starfish Beach Cottages, you’ll find yourself facing a similar problem – how are you ever going to leave? The answer is, of course, by rebooking it for your next...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    All of the Palm Isle Villages are a good choice for family vacations.  But PIV 3206 is particularly perfect for vacations with kids thanks to a charming set of bunk beds in the guest bedroom.  (2) Bedroom, (1) Bathroom, accommodates up to (4) people: 1 Queen, Set of short bunk beds, 1 Sleeper Sofa....
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Island Place Cottage: 1BR Pet-Friendly Cottage1 / 23
    (8)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 2 January 2017
    My husband and I stayed for a week at the Island Place Cottage. Ourvacation, both in terms of weather and accommodations, was perfect. Thecity of Anna Maria reflects old...
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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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    'SUGAR SHACK' private POOL & Walk to BEACH1 / 67
    (68)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Private Outdoor Pool (Heated)
    • Waterfront
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 May 2017
    My wife and I had a great time on this trip to the island. We have vacationed here a great deal over the years. The Sugar Shack was a wonderful place to stay during our vacation...
    Reviewed 3 May 2016
    Imagine our surprise when us winter weary northerners pulled up in front of the cutest Florida bungalow we had ever seen! Three bedrooms, two full and beautifully appointed...
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    About this property
    Charming Chic- In our unique, brightly decorated 'Old Florida' cottage. Just a very short stroll to the sugary Beach and a very private heated Pool nestled around a lush tropical oasis. A large screened lanai overlooks the pool with lots of seating, table and chairs, comfy sofa and love seat....
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cozy enough for honeymooners but room for a family of eight, you’re not going to feel any guilt about indulging in a vacation at this holiday cottage rental. Three bedrooms and two bathrooms, all decorated in cheerful colors and outfitted with premium linens, spread out across 1,250 square feet....
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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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    Gulfshore Cottage: 3BR Family-Friendly, Block from Beach1 / 25
    (24)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    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 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 large bedrooms...
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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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Blue Lagoon!  This complex has one of the best community pools on the island!  Large, tropical pool with a 10' waterfall right outside your back door! Dogs under 50lbs are welcome with a pet fee. The lovely upgraded kitchen offers granite countertops, stainless steel appliances and...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Cabin 1 Spinnakers Cottages: Perfect for a Couple1 / 23
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 June 2017
    I spent a great deal of time on the Internet pouring over property after property, hoping to find the perfect setup for an 20th Anniversary AMI trip. My wife and I work hard...
    Reviewed 26 April 2017
    We loved spinnakers! It was such a nice cottage! It was clean and decorated with a beachy theme.The pool was amazing!We already booked it for next yr.
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    About this property
    Part of the Spinnakers Vacation Cottages Cabin 1 is a one bedroom, one bath cottage nestled in a lush tropical landscape. Great for an anniversary celebration, honeymoon or just a getaway! Want to bring the kids? No problem, they will love it here as well! Cabin 1 sits beside the pool area, so...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Bean Point Beach Cottage1 / 22
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    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
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Palm Isle 3210, a one bedroom and one bathroom villa in the heart of quiet, friendly Holmes Beach on Anna Maria Island. Honeymoons, couples escapes, and smaller family vacations are just waiting to happen.  (1) Bedroom, (1) Bathroom, accommodates up to (4) people: 1 King, 1 Sleeper sofa....
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This STAND ALONE, VERY CHARMING, cottage is in a very peaceful setting with huge brick courtyard. This is not like most other vacation rentals that require you to climb 1-2 stories. This is a stand alone ground level home! We have just invested in a new kitchen, bathroom, lanai, living area and...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Steps to the beach - adorable 'Old Florida' beach cottage located in the heart of the city of Anna Maria. The two bedroom and two bath beach cottage rental so close to the beach you can smell the salt air. (2) Bedrooms, (2) Bath, accommodates up to (6) people: 1 King, 2 Twins, 1 Sleeper Sofa....
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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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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Smoking allowed
    About this property
    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...
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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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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    About this property
    3207 Gulf Drive at Palm Isle Village in Holmes Beach, Florida is located in one of Anna Maria Island's favorite and finest condominium resorts.  It offers a fabulous holiday villa which has been designer decorated in charming Old Florida style. The one bedroom-one bath ground level villa has an...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Create lasting memories at this island oasis just steps from eight continuous miles of uncrowded sugar-sand beach. Relax, unwind, and immerse yourself in the tropical ambience of your own private sun-dappled courtyards, but know that world-famous Anna Maria Island, and all it has to offer, is right...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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