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Anna Maria Island Vacation Rentals

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    Travellers to Anna Maria Island are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    1 Review
    2 Bedrooms, Sleeps 6Quick View
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    3 Bedrooms, Sleeps 8Quick View
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    5 Bedrooms, Sleeps 10Quick View
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    About this property
    Saddle up for a visit to Seahorse Cove and the vacation of your dreams! This Anna Maria Island vacation rental was built for rest and relaxation. Beginning with the lush landscaping that meets you at the front door, all the way through to the boat dock, this house has high standards. A view of the...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, Sleeps 4Quick View
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    Pet friendly
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    About this property
    Welcome to "Holly Hideaway" located on the northern end of beautiful Anna Maria Island. This lovely two bedroom and two bath vacation rental features all that you will need to stay a week or a month. Feel the breezes through the screened lanai or lounge by the new heated pool located in the back...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, Sleeps 4Quick View
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    One bedroom one bath condo located on the beach. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are two queen...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Review
    2 Bedrooms, Sleeps 4Quick View
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    Located on the north end of Anna Maria Island in the city of Anna Maria on historic Pine Avenue, this two-bedroom, one-bathroom second-floor vacation rental condo has been completely updated and is picture perfect. So much so, once you walk through the front door you'll feel as though you just...
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    Anna Maria, Anna Maria Island 34216
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    About this property
    Beautiful 2B/1B cottage on the quiet North end, only 5 houses to the beach, and no streets to cross. Beautiful new Heated Pool. Twins can be converted to King in all bedrooms. NO dishwasher, no garbage disposal.Rear trash pick up! Charcoal Grill, not gas. Both units also include private...
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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, Sleeps 4Quick View
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    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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    3 Bedrooms, Sleeps 8Quick View
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    • Patio
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The lovely Dolphin Pointe resides on the highly desirable north end of Anna Maria, just a short walk to the beach, bean point, and the Rod and Reel Pier. The spacious open concept living area is perfect for spending quality time with the family. The home exudes an Island charm with its over 2000...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 6Quick View
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    About this property
    Aloha and welcome to our Island Home. Ohana is Hawaiian for family and that is who you are when you stay with us. Our retreat is nestled on Anna Maria Island, Florida and is a short 5 minute walk to the white sand beaches and turquoise waters of the Gulf of Mexico. We offer three locations on Anna...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, Sleeps 4Quick View
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    Pet friendly
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    One bedroom one bath condo located on the beach. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are two double...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    This condo has just been totally renovated and redecorated in a contemporary yet comfortable style. The apartment is a ground floor unit with easy access to the pool, Gulf of Mexico and Bay of Sarasota. Runaway Bay resort features 13 acres of lush landscaping and is full of amenities including the...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 4Quick View
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    • Shared Outdoor Pool (Unheated)
    • Balcony
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    Pet friendly
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    Smoking allowed
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    Sun Plaza West 115 - Condo 2 Bedroom/ 2 Bath , maximum occupancy of 4 people. Sun Plaza West is a condominium complex located in the preferred and quieter northern end of Holmes Beach. Come experience amazing views from this gorgeous 2 bedroom 2 bath Gulf Front corner unit condo. You have...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, Sleeps 11Quick View
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    This rental home on Anna Maria Island sleeps up to 10 and comes fully equipped. This Bradenton Beach vacation home provides you and your family or small group with your very own private swimming pool, and comes fully equipped with everything you need for a wonderful vacation on this beautiful...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    1 Review
    6 Bedrooms, Sleeps 12Quick View
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    • Internet Access
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    • Private Outdoor Pool (Unheated)
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    • Ocean Views
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    OCEAN VIEW is a brand new construction home that features 6 bedrooms and 5.5 bathrooms and a fantastic location-just a 1 minute stroll to the White sandy beaches at the 65th st access! This lovely property offers a private heated pool with a spa, water slide and grotto. The backyard is an oasis...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Reviews
    1 Bedroom, Sleeps 4Quick View
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    Pet friendly
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    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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    1 Review
    6 Bedrooms, Sleeps 12Quick View
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    • Grill
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    About this property
    Fantastic new private vacation rental home with outstanding Gulf Views from two of the four balconies and large heated pool equipped with a swim up Tiki hut in tropical paradise setting. Ample seating will ensure everyone can relax and enjoy the extra large pool area. Your outdoor paradise is...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    5 Reviews
    2 Bedrooms, Sleeps 4Quick View
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    • Satellite TV
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    Pet friendly
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    Smoking allowed
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    Grab your flip flops and get ready to head to the beach when staying in this Gulf Sands condo! With a private balcony overlooking the turquoise waters of the Gulf of Mexico, this vacation rental is a fantastic place to stay during your Anna Maria Island vacation. There is plenty of space for...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Reviews
    3 Bedrooms, Sleeps 6Quick View
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    Smoking allowed
    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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    2 Bedrooms, Sleeps 6Quick View
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    • Patio
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    Pet friendly
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    Smoking allowed
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    Casa Sierra Resort is a private Mediterranean style four unit complex in the heart of Anna Maria Island with just a two minute walk to the beautiful white sand beach! Each unit offers an outdoor patio with the spacious common area providing a large heated pool, gazebo, lush tropical landscaping,...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, Sleeps 6Quick View
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    About this property
    This two bedroom, two bath direct gulf front vacation condo gives room for six guest to enjoy the Gulf waves crash in the distance while a little bit closer you can spot the shimmering, heated community pool. (2) Bedrooms, (2) Bath, accommodates up to (6) people: 1 Queen, 2 Twins, 1 Sleeper Sofa....
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, Sleeps 8Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
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    Inspired by modern Italy, North End Zen's sleek and minimalistic touches throughout will at times have you feeling as you were vacationing on a posh Mediterranean island. The spacious open concept floor plan begins at the front door and gracefully moves its way to the back of the house which has...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 6Quick View
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    Pet friendly
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    About this property
    Great 2 Bedroom/2 Bath Home with a private Heated Pool, located on a quiet street west of Gulf Drive, just 3 houses to the beach!! King sized master bedroom with TV/DVD, Twins in guest room with TV/DVD, and sleeper sofa in living room! Cable TV/DVD and Wii Console in living Room, High speed...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, Sleeps 4Quick View
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    • Grill
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    One bedroom one bath condo located on the beach. The Coconuts Beach Resort is a beach front property in Holmes Beach on Anna Maria Island. Each unit is individually owned. The unit is a full size apartment with a separate bedroom living room and kitchen sleeps up to 4. There are two double...
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    Holmes Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    4 Bedrooms, Sleeps 8Quick View
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    4 Bedroom, 3 Bath (Sleeps 14) - “Tina's Piece of Paradise” - 407 80th Street in Holmes Beach. When looking to accommodate a large group during you paradise Anna Maria Island vacation look no further than “Tina’s Piece of Paradise”. This fun four bedroom, three bathroom Holmes Beach vacation...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Reviews
    4 Bedrooms, Sleeps 8Quick View
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    • Grill
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    About this property
    Beautiful, Brand New, Ground Level 4 bedroom/3 bath home, just a short block to the beach. Beautiful back yard with Heated Pool surrounded by a large paver deck and beautiful outdoor dining and gas grill area by pool. Open Living/Family/Dining Room area for everyone to gather, and attention to...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    About this property
    Bird's Nest vacation rentals is a complex of 4 town houses in Anna Maria island, Bradenton Beach, overlooking the Gulf of Mexico Bird's Nest vacation rental apartments, 2 bedroom/2 bath, are arranged on two elevated levels for a total of 1,250 sq.f. each unit. Each apartment is beautifully...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Reviews
    4 Bedrooms, Sleeps 8Quick View
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    Welcome to Endless Summer - a delightful ground level 4 bedroom, 3 bath home situated on a quiet residential street on Anna Maria Island! Family-friendly amenities abound at this superior vacation getaway, with its very own heated pool in a private setting. Away from busy streets and a mere...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Reviews
    2 Bedrooms, Sleeps 4Quick View
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    Immerse yourself in the Florida island life at this beach side vacation rental just steps to Holmes Beach and within walking distance to grocery stores, restaurants, and more. Homes Beach is an active beach side community located approximately 8 miles from downtown Bradenton and offers a wide...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, Sleeps 4Quick View
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    Runaway Bay 115 - Condo 1 Bedroom/ 1 Bath , maximum occupancy of 4 people. Runaway Bay ----Large complex ---right across the street from the beach. Easy beach access. Tastefully decorated 1 bedroom, 1 bath unit with a nice pond view. Relax in the inviting pool, or play a game of tennis,...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, Sleeps 6Quick View
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    FAMILY/CHILD FRIEDLY CONDOMINIUM. Surrounded by water with the Gulf of Mexico to the west, the Intra-Coastal Waterway to the east, Tampa Bay to the north and Sarasota Bay to the south. We have the best location on Anna Maria Island where the island is only 150 yards wide. Our complex stretches from...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 6Quick View
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    Spacious, cute, perfectly located and stylishly decorated “Little Miss Magic” is the perfect Holmes Beach vacation rental for your next island style getaway! Accommodating up to six guests this gorgeous three bedroom two bathroom home offers two queen sized beds and two twin beds with all the...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, Sleeps 6Quick View
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    About this property
    You’ll be relaxing into that vacation frame of mind at first glimpse of this three story, key lime colored vacation home in the center of Holmes Beach. This luxury rental offers refreshing island luxury, an open floor plan with volume ceilings, a sprawling terrace, and private tropical yard with...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Elegant and comfortable, Anna Maria Island vacation rental home “Neolinda” is the luxurious vacation destination you’ve been dreaming of! This stylishly decorated 3 bedroom, 2 bathroom vacation rental home accommodates up to 6 guests with 1 king bed, 1 queen bed and a twin bunk bed. This newly...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    9 Reviews
    2 Bedrooms, Sleeps 6Quick 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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    38 Reviews
    2 Bedrooms, Sleeps 6Quick View
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    • Grill
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    From the same owners of A Lime Cottage (p277325), who've been recognized as TripAdvisor "rated excellent" vacation rental, Flipkey 2012 and 2013 Top Vacation Rental, 2012 Top Rental Manager", we're delighted to now have Lemon Cottage. <BR><BR>Nestled in a quiet residential boating community across...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    Anna Maria rental “Le Paradis” offers a comfortable and casual sophistication for a memorable beachside getaway. Accommodating up to six guests this home is perfectly located, and well appointed. You’ve found an Anna Maria vacation rental you’ll want to visit again! Located in a highly...
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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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    Pet friendly
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    Situated on an enormous lot within the quiet north end of Anna Maria, you will find this treasure of a vacation home. Fins Up is a uniquely perfect 3 bedroom, 2.5 bath home with its own private pool, hot tub, 2 docks, and fully enclosed spacious outdoor shower. Privacy fenced is the huge backyard...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    A luxury Anna Maria Island vacation destination perfect for the entire family, you and your loved ones will enjoy a visit to “Seashell Sunsets”. This newly built four bedroom home offers lovely views of The Gulf of Mexico while providing a spacious and comfortable home where eight guests can...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, Sleeps 6Quick View
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    About this property
    The beach is steps away, dead end street with no cross through streets. Walk around the corner to anything you need. Location, location! This Holmes Beach/Anna Maria Island 2 bedroom unit has been completely remodeled & exquisitely decorated!! It is just 500 feet from the beach with no streets to...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    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...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pet friendly
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    About this property
    COMPLETELY REMODELED 2 bedroom/ 2 bath duplex unit. Tastefully furnished and decorated, you will feel right at home. A plush King bed in one bedroom and queen bed in the other. It's just over a block to the beach, and a block to the free Island trolley! Elevated, with one car garage underneath...
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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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    Smoking allowed
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    FAMILY/CHILD FRIEDLY CONDOMINIUM. Surrounded by water with the Gulf of Mexico to the west, the Intra-Coastal Waterway to the east, Tampa Bay to the north and Sarasota Bay to the south. We have the best location on Anna Maria Island where the island is only 150 yards wide. Our complex stretches from...
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    Bradenton Beach, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    6 Bedrooms, Sleeps 16Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Chianti is a luxurious Anna Maria Island vacation home in Holmes Beach that boasts one of the largest beach entry pools on the island. The world-famous Old Florida charm of Anna Maria meets modern living in Villa Chianti. With every modern convenience and a high level of attention to detail...
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    Location Information
    Holmes Beach, Anna Maria Island 34216
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 16
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    Pet friendly
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    Smoking allowed
    About this property
    Sun-Day West is the picture-perfect name for this two-bedroom, two-bath, elevated duplex. Located in Holmes Beach on Anna Maria Island, this vacation rental features a large, west-facing balcony that allows for plenty of sunshine in the afternoon and shade in the morning for that early cup of...
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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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    2 Bedrooms, Sleeps 6Quick View
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    Smoking allowed
    About this property
    Shady Pines is a tastefully updated 2 BR, 1-1/2 bath beach house right on the beautiful Gulf of Mexico. Walk out the door to a wide, white, powdery beach and the Gulf. This 2 bedroom beach house is located in the most perfect spot you willl ever find! Great views and privacy. This quiet beach...
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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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    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...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, Sleeps 10Quick View
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    About this property
    Welcome to Sunset Glow - a Brand New vacation home in our rental program! Live the life of luxury right in the heart of Anna Maria Island. This home was designed from the ground up to inspire the ultimate family vacation. Sunset Glow's light and coastal themed architecture makes for a truly...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, Sleeps 8Quick View
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    • Grill
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    • Ocean Views
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Limefish, from Pineapplefish is one of the most stunning beachfront holiday rentals on Anna Maria Island, with direct access to a beautiful, almost private beach. With spectacular views across the Gulf, Limefish has a wonderful and spacious decked area across the whole of the property, where you...
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    Location Information
    Anna Maria Island, Florida 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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