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Anna Maria Island House Rentals

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    Travellers to Anna Maria Island are booking August dates now. Secure your holiday home today, and have the perfect trip.
    514 Matching Rentals in Anna Maria IslandView all 1,131 rentals
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    617 Dundee Lane1 / 24
    (1)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    If you’re looking for a relaxed beach vacation on Anna Maria Island visit Windshore! Not only does this Holmes Beach rental have a great location, but it also offers all the amenities of a well-appointed and gold rated home. “Windshore” sleeps up to six guests with three bedrooms and two bathrooms....
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    529 Key Royale Drive1 / 10
    (2)Very good
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    529 Key Royale - Private canal home 6 Bedroom / 5 Bath with private pool , maximum occupancy of 12 people. Outstanding large home perfect for a family! This beautiful Florida pool home is on a canal offering 6 bedrooms- 5 bathrooms . Luxury at its best! Sip your coffee in the morning on the...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    On Anna Maria Island, you hear a lot about visitors experiencing love at first sunset. By the time sun is setting on your first day, most people are hooked. But when you pull up the east side of this elevated vacation home at 131 White Ave, it might be good old fashioned love at first sight....
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Luxurious custom built multi-level tropical oasis and pool paradise. (6) Bedroom, (4.5) Bath, accommodates up to (14) people: 3 Kings, 2 Queens, 1 Bunk Bed, 1 Sleeper Sofa. Private heated pool, free wireless, less than a block to the beach. Fantastic private custom-built vacation rental home on...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    217 84th - Private home 3 Bedroom/ 2 Bath with private pool , maximum occupancy of 6 people. Old Florida with all the comforts! of home~ 217 84th. Street 3 bedroom 2 bath home in quiet residential area of Holmes Beach. Private, screened-in, solar heated pool. 3 blocks to the beach. Spacious and...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    “Hideaway” is a fantastic Anna Maria Island vacation rental in Holmes Beach offering space for up to six guests just a few blocks from the beach. During your stay you’ll find everything you need for a laid back island getaway. Inside this Holmes Beach rental you’ll enjoy updated decor with a...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    FAMILY/CHILD FRIEDLY HOUSE. Anna Maria Island is not a place where you go to the beach. When you are on Anna Maria Island you are at the beach. Welcome to paradise. Featured here is a new gorgeous 4 bedroom 3 bathroom home providing you with uncompromising luxury beyond imagination. What you will...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    7001 B Holmes Boulevard is where Anna Maria Island vacations become lifetime memories! This beautiful Holmes Beach vacation rental home provides accommodations for up to 8 guests including 3 Bedrooms, 2 Bathroom with 1 King bed, 1 Queen bed, 2 Twin beds, and a Queen Sleeper sofa. Located a short...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Terrace
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    Have some fun entertaining friends under the covered patio next to the refreshing pool. Brand new 5 bedroom 4 bathroom vacation home in Holmes Beach, just steps from the beach with fantastic Gulf views. This home is the perfect beach getaway  with everything you could want while enjoying Anna...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
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    Tropical Paradise on Holmes Beach and ONLY 3 blocks to the beach. Anna Maria Island, noted for its old Florida ambiance, offers this Key West styled home, where you may awaken to greet the dawn sipping coffee on the balcony or swimming in your private pool. The modern interior arrangements add to...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Make memories that last a lifetime when you stay at gorgeous Anna Maria Island vacation rental home 7001 A. Rooming up to eight guests this spacious three bedroom two bathroom duplex style home offers one king bed, one queen bed, two twin beds and a queen sleeper sofa. Just a couple short blocks to...
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    Holmes Beach, Anna Maria Island 34217
    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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    • Hot Tub
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    520 67th - Private canal home 2 Bedroom / 2 Bath with private pool , maximum occupancy of 4 people. Fabulous canal-front two bedroom and two bathroom home with all the comforts of home. Filled with lots of sitting areas to read a book or totally relax looking at the water view. Located on a quiet...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
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    About this property
    “Time for the Sea” is an excellent choice for your next Anna Maria Island vacation! This centrally located home offers everything for the perfect getaway for up to eight guests in paradise. Anna Maria Island boasts seven miles of pristine Gulf of Mexico beaches making it one of Florida’s best beach...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    As an artist this private three bedroom and two bath multi-level elevated vacation home has been our family retreat that inspires many paintings of Anna Maria Island. Located on the secluded North End you will enjoy the tranquility of the Island and have an easy stroll to the Gulf of Mexico and the...
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick 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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Welcome to Heavenly Holly located on the northern end of beautiful Anna Maria Island! This lovely single family elevated three bedroom and two bath vacation rental features all that you will need to stay a week or a month!  (3) Bedroom, (2) Bath, accommodates (6) people: 1 King, 1 Queen, 2...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Casa Sierra 205 A 36th ST ~ RA754991 / 24
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Casa Sierra 205 A has everything you’ll need for a fun Anna Maria Island paradise vacation. This two bedroom two bathroom Mediterranean style Holmes Beach vacation rental condo offers accommodations for up to six guest with one king bed,two twin beds and a queen sleeper sofa. When you arrive...
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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 6 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    About this property
    The Skimmer unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, one bath downstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    8 Bedrooms, 8 Bathrooms, Sleeps 20 Quick View
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    This rental home on Anna Maria Island sleeps up to 20 and comes fully equipped. This Bradenton Beach vacation home is actually two rentals in one, in the middle of all the fun and beaches that Bradenton Beach can offer. The rental package sleeps up to 20, and everyone can enjoy the private...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 20
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    8 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Balcony
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    Enjoy these new elevated vacation rental homes with two private lagoon style pools and lush tropical plants about two blocks to the beach in Holmes Beach. Fashionably yet comfortably decorated living rooms offers big comfy furniture centered around a new 50" flat screen TV with DVD/BluRay player...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 16
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Beautifully renovated beach cottage in the heart of the village of Anna Maria. Walk to the beaches, shops and restaurants. Enjoy amazing sunsets at the beach or sip a glass of wine in the lush tropical gardens surrounding the cottage. 2 bedrooms with 2 full bathrooms. Quaint beach cottage in a...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    744 Jacaranda Rd1 / 32
    (9)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    744 Jacaranda - Private home 3 Bedroom/ 3 Bath with private pool, maximum occupancy of 6 people. BOOK AND STAY NOW THROUGH THE END OF DECEMBER 2017 AND GET 10% OFF. EXCLUDES HOLIDAYS. Live the Florida lifestyle in this beautiful, comfortable 3 bedroom, 3 bath private home with private pool and...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    The Dolphin Dance, located at 803 and 805 Gulf Drive South is an impressive duplex with unobstructed, panoramic views of the Gulf of Mexico. Each side has two bedrooms and one and one half baths. Each sleeps six with a queen size bed, two double beds and a sofa bed. There is a shared washer and...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Garden
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    Located on beautiful Anna Maria Island, "Le Paradis" (which means Paradise in French) is just a short stroll to the sugar white sand beaches of beautiful Anna Maria Island... Experience a luxurious beach vacation with over 2100 hundred square feet of tastefully living space with an expansive...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    4 Bedroom, 3 Bath - “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”. After spending a week at this fabulous Holmes Beach vacation rental home...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Villa Chianti1 / 54
    (3)Very good
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
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    • Ocean Views
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    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 34217
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedroom, 2 Bath (sleeps 6) - "Almost Heaven" - 205 72nd Street, Holmes Beach Welcome to Almost Heaven! A charming single family pool home which is a very short stroll to the beautiful gulf beaches. This tropical 3 bedroom and 2 bath beach vacation rental cottage is completely renovated with...
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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, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Sea Haze Cottage is a completely renovated and updated private beach cottage, that is just perfect for a family or for one or two couples. It has a great room that leads to a large screened porch overlooking the deck, pool, spa and canal. The cottage is located in the quiet north end of Anna Maria...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Just 150 steps to a beautiful white sandy beach located in the preferred and more private northern end of Anna Maria Island, The Harrison Home at 6901 Gulf Drive features many new renovations and updates. This spacious four bedroom and four bath home has one of the largest private pools on the...
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    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    4 Bedroom, 4 Bath (Sleeps 8) - “Bimini Bay” 4807 2nd Avenue in Holmes Beach. The perfect holiday getaway for family and friends, “Bimini Bay” is a gorgeous four bedroom, four bathroom Holmes Beach vacation rental home, west of Gulf Drive, just a short walk from pristine Gulf of Mexico beaches....
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    “103 South Beach Village” is the perfect Anna Maria Island vacation rental home to make memories that last a lifetime! This 3 bedroom 2.5 bathroom town house style vacation rental rooms up to six guests with one king bed, one queen bed and two twin beds in a casual paradise getaway. Located just...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Flamingo Cay, private boat dock, Palma Sola Bay1 / 16
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
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    • Waterfront
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    About this property
    If you're seeking relaxation of recreation, this the rental home for you! Large solar heated pool in a screened-in lanai, dock facility featuring a floating dock, with a boat launch within 500 yards at Palma Sola Bay Beach. It is a short walk to the Bay Beach, and only 2.5 miles to the main beach...
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    Location Information
    Anna Maria Island, Florida 34209
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    532 70th Street1 / 14
    (2)Very good
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
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    532 70th - Private canal home 5 Bedroom / 5 Bath with private pool , maximum occupancy of 10 people. Our Sandsational family home!~ Would you care to escape to Florida with style and sophistication? Indulge friends and family while pampering yourself vacationing at this elegant residence...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Fall in love with Anna Maria Island paradise when you stay at the luxury Holmes Beach vacation rental town home “North Beach Village 50”! This spacious vacation rental for up to 6 guests has 3 bedrooms and 2.5 bathrooms offering 1 king bed, 1 queen bed and 2 twin beds. Located in a quiet Holmes...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    This spacious 2 bedroom oceanfront vacation condo in Bradenton Beach on Anna Maria Island has breathtaking views from your large beach side balcony. You'll be very comfortable in this lovely top floor condo that sits directly on the Gulf of Mexico with a full view of the ocean. You'll especially...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    2 Bedroom, 1 Bath (sleeps 4-6) - "Playa Casanas South" - 3222 Gulf Drive unit A in Holmes Beach. “Playa Casanas South” is a wonderful vacation rental home directly on the sparkling white quartz sands of the Gulf of Mexico. Sleeping up to six guests comfortably in two bedrooms and one bathroom...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    “Ariel’s By the Sea” is a lovely ground level 3 bedroom 2 bathroom duplex style Holmes Beach vacation rental home suited for up to 6 vacationers. Plenty of space for everyone, this rental home has 1 king bed, 1 queen bed, and 2 twin beds. Spacious, but not too big, “Ariel’s By the Sea” is...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Welcome to Tropical Oasis, NEW to our vacation rental program! Located in the heart of Anna Maria Island, you will endure the ultimate relaxation within this spacious and bright single family home. With (3) bedrooms and (2) bathrooms, Tropical Oasis promises sweet dreams each night of your...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    A Wright Place, located at 6803 Holmes Blvd., is a comfortable two bedroom, two bath duplex with poolside den which can easily serve as a third bedroom. It's exactly what you are looking for in a peaceful Anna Maria Island retreat. Located in a quiet, lakeside residential neighborhood, this unit...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Key Lime Cottages 202 & 204  welcomes you to this recently re-done and updated island duplex. Just steps from the Gulf of Mexico and the pure white sandy beaches of Anna Maria. (6) Bedroom, (4) Bath, accommodates (12) people: 4 Queens, 4 Times.  Two heated pools, free wireless internet, pets are...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    “Salt Shack” is an adorable 3 bedroom 2 bathroom Anna Maria Island vacation rental home spacious enough for up to 7 guests. This ground level duplex in Holmes Beach has everything you need for a luxurious island vacation in a great location. Offering 1 king bed, 1 queen bed, 2 twin beds & full...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedroom, 2 Bath (sleeps 8) - "Heron-Dolphin" -706 Rose Street in Anna Maria. Anna Maria Island vacation rental home “Heron-Dolphin” is a fabulous ground level duplex perfect for any family getaway. Each unit has 2 bedrooms and 1 bathroom with a combined total of 2 queen beds, 2 twin beds and 2...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Fantastic private "Coastal Cottage" vacation home just a few houses to the white sandy beaches of Anna Maria Island and the Gulf of Mexico. Enjoy the large heated pool with large tiki umbrella in pool bar area all in a tropical paradise setting! Enjoy the feel of this cottage for your next holiday...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5801 DePalmas - Private home 3 Bedroom / 2 Bath , maximum occupancy of 6 people. Comfy and Cozy Florida Living!~ Cute cozy ground level home 3 Bedroom/ 2Bath close to the beach on a quiet dead end street. Fully furnished with linens towels, cooking utensils, basic cable tv and telephone, just...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Enjoy a beautifully remodeled Anna Maria Island home with a taste of history. This 3 bedroom/3.5 bath home was once the center for AMI's phone services. Make this landmark home part of your ultimate family vacation retreat. Enjoy an ocean view from the ground floor as well as from a large upper...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    “Beachy Villa Vista” is a fantastically comfortable luxury Anna Maria Island vacation rental home accommodating up to 10 guests in tropical paradise. This stylish 5 bedroom 4.5 bathroom home offers 1 King bed, 2 Queen beds, 2 Twin beds, 1 Twin bunk bed and 1 Queen sleeper sofa. “Beachy Villa Vista”...
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    This home provides you with your own private pool. It has virtually everything you need for a perfect Island vacation. This home has a private pool and is less than a block to the beach and 1 block to Sarasota Bay for fishing. Walk to Sarasote Bay and watch the big yachts and boats pass by on the...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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