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Anna Maria Island Cottages

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    Travellers to Anna Maria Island are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    32 Matching Rentals in Anna Maria IslandView all 1,007 rentals
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    Songbird Cottage1 / 23
    (22)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    AMICoastal Beach Dreams 'Dream Away'.1 / 31
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    About this property
    Sea Breeze cottage is located at north end of Anna Maria island. Brand new renovation, 2 bedrooms with 2 bath rooms, with private dock, sailboat direct to Bimini bay, unobstructed , natural view of Bimini bay. Less than three minute walk to beach, walking distance to pine ave and the city pier and...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 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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    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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Whispering Pines: 2BR Classic Cottage Near Beach1 / 48
    (10)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    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 the most beautiful beach accesses on the island. This classic 1920's beach cottage has been lovingly restored. The original wood molding, fireplace,...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Island Place Cottage: 1BR Pet-Friendly Cottage1 / 23
    (9)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Wave Crest: 3BR Gulf-Front Beachfront Cottage1 / 25
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    Gulfshore Cottage: 3BR Family-Friendly, Block from Beach1 / 24
    (24)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
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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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    Pet friendly
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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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    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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    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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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
    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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Brand New Renovation Sea Waves Cottage1 / 16
    (7)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Anna Maria The Pink Flamingo1 / 22
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Smoking allowed
    About this property
    Walk onto the white sands and into the clear waters of the Gulf of Mexico from your beach retreat, the Sunny Daze cottage, one half of a duplex nestled in Holmes Beach on picturesque Anna Maria Island, Florida. Once you arrive at this bright two bedroom/one bath cottage, you can leave your car...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Cabin 2 Spinnakers Cottages: Perfect for a Couple1 / 24
    (5)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Part of the Spinnakers Vacation Cottages Cabin 2 is a one bedroom, one bath cottage nestled in a lush tropical landscape. Surrounded by palms, plumeria, jasmine and more palms you will find our little paradise the perfect spot for a getaway! Cabin 2 offers a comfortable queen size bed as well as a...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Cabin 1 Spinnakers Cottages: Perfect for a Couple1 / 46
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Smoking allowed
    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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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Crows Nest Spinnakers Cottages: 1BR Unique Rental1 / 23
    (4)Very good
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Part of the Spinnakers Vacation Cottages, Crows Nest is what some have called an adult version of a tree house, so you know kids will love it! A one bedroom, one bath vacation rental that sleeps six, Crows Nest features an awesome private deck where you'll have a great space to enjoy coffee, tea...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
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    • Ocean Views
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Bedroom 1 Bath Cottage On The Beach This cottage is located 'on the beach' 3007 Avenue F on beautiful Holmes beach. It is the upstairs unit (2 of 2). The cottage is very comfortable and sleeps 4 comfortably with additional space. This quaint cottage is hidden away on a dead end street, away from...
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    Holmes 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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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    On the Beach Paradise d1 / 26
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    AMICoastal Rentals Cracker Cottages - Sea Story1 / 36
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    CRACKER COTTAGES CONSISTS OF 2 SEPARATE COTTAGES IN ONE BUILDING...SEA STORY (733597) AND FISH TALES (739543). IF THE DATES YOU ARE LOOKING FOR ARE BOOKED ON SEA STORY, CHECK OUT THE OTHER SIDE 'FISH TALES' #739543. If you are looking to book a property that has at least 4 bedrooms, you would...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    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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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Lovely 2 bedroom, 1.5 bath Bay front home with boat/fishing dock. Beautiful views of the Bay. Located on a quiet street just one block to the beach. Located on Ana Maria Island.
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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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
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    2-Unit Beach to Bay Cottage...NOT Grandma's place!...100 feet to beach!1 / 98
    (10)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Outdoor Dining Area
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    • Porch
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    The Tree House1 / 22
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
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    About this property
    Thank you for considering my home which has been recently updated to provide the warmth and feel of a true beach cottage. Wooden ceiling planks have been added along with pine beach chic cabinets and decor. I put many hours into the design of the home to provide a feeling of tropical relaxation....
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    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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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    HISTORIC WATERFRONT COTTAGES..DOCK...BEACH...Couples, Families, Reunions!1 / 42
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    • Waterfront
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    Pet friendly
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    About this property
    We have some openings available April 8-15! Our family has lovingly restored this HISTORIC 1939 FISHING CAMP located on beautiful Sarasota Bay. You'll be surrounded by water living on the narrowest point of Anna Maria Island. Sugar sand BEACH only a 1 minute stroll away! Located at 115 South...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 15
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    AMICoastal Rentals Cracker Cottages - Fish Tales1 / 33
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Ocean Views
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    Pet friendly
    Kid friendly
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    About this property
    The CRACKER COTTAGES are two individual cottages. Rent one or both: SEA STORY (733597) AND FISH TALES (739543). IF THE DATES YOU ARE LOOKING FOR ARE BOOKED ON SEA STORY, CHECK OUT THE OTHER SIDE 'FISH TALES', #739543. Each side sleeps four guests. If you need to rent a larger home please look at...
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    Bradenton Beach, Anna Maria Island 34217
    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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    Pet friendly
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    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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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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