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Holiday Rentals with Pools in Anna Maria

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    ₹ 23,144 Average
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    Travellers to Anna Maria are booking March dates now. Secure your holiday home today, and have the perfect trip.
    114 Matching Rentals in Anna MariaView all 192 rentals
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    Ocean View 3 bedroom, pool, North Shore Drive1 / 123
    (38)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Stay & Spoil yourself! Pool, Hot tub,Fish, Dock, Kayak* Steps to Gulfside beach!1 / 50
    (13)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Waterfront and dog-friendly home with private pool, dock, views, and lanai!1 / 29
    (1)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Charming house with private heated pool, patio, and grill - steps from beach1 / 37
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 November 2018
    Very spacious and open layout- Great for my parents as the use walkers. Master bath was perfect with the walk in shower! It was nice having space enough to be able to be...
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    About this property
    Pretty Palms Align yourself to island time with this cozy and colorful Anna Maria cottage! With a heated pool, shallow tanning area, and a lush tropical oasis right out back, any post-flight crankiness will melt right away. A stunning Anna Maria sunset completes your backyard paradise scene....
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Blue Heron Waterfront House Anna Maria island1 / 23
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Ocean Views
    • Washer
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 June 2017
    We stayed for a week at the end of May 2017 after spending 10 days in Orlando. We were met at the property (even though we were a little late) and it was beautifully presented...
    Reviewed 22 May 2017
    The location is perfect. Walk 2 blocks to beach. Supermarket, drug store, bank, restaurants, salon, spa, less than 5 min. away. Many choices to dine/shop 3-10 min drive. The...
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    About this property
    Stunning ground level 3 bedroom/2 bath home with luxury finishes at every glance. Brand new to the market and recently renovated, this home is packed with designer finishes throughout from luxury linens in all three uniquely appointed bedrooms to furnishings that make this home feel like you are...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Crescent Wave1 / 40
    (31)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Patio
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 August 2019
    I never left a review, but our trip was so great i figured it was better late than never! We stayed at this house in Dec 2016 for our friends’ wedding on the island. (Month...
    Reviewed 8 August 2019
    The owner Richard was fantastic to work with. He answered all my questions and was very accommodating and got back to me in a timely manner. The house was clean and the beds...
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    About this property
    Description We are located in the heart of the beautiful city of Anna Maria FL. We are one block from the historic Pine Ave with free trolley service to the entire island. We are two blocks to the beautiful white sand beach. Three blocks in the opposite direction is the bay and the historic City...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    5 Star - Private Pool & Dock, and Steps Away from the Beach - Fall Availability1 / 38
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Waterfront
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2017
    The house was gorgeous. Pretty and comfortable furnishings. Loved all the Anna Maria touches. Fantastic kitchen appliances - I wish my washing machine was so good! We all loved...
    Reviewed 28 October 2016
    We had a fantastic time exploring Anna Maria Island and coming home to such a fantastic place made the holiday even more special.
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    About this property
    It doesn't get much better than being right on the water, less than one block from the bay beach, and only 7 blocks from Pine Avenue. Sunshine Cottage couldn't be a better name, because this 3 bedroom, 2 bathroom, cottage truly lets you experience the beauty of Anna Maria Island. Enjoy dangling...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Patio
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    • Washer
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pineapple Cottage You're sure to fall in love with this charming, dog-friendly Anna Maria cottage! Enjoy a fantastic location, beautiful beaches, and perks like a private heated pool. You, your loved ones, and dogs under 25 pounds (for a small nightly fee) will adore this home on Spring Avenue....
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
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    • Waterfront
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    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Heavenly Holly Bask in the endless sunshine of Anna Maria Island at this three-bedroom home, a Florida escape with a private canalfront dock, its very own heated pool and a wondrous location only two blocks from the beach. This sleek, light-filled home is located on the quiet North End of Anna...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Ocean Views
    • Waterfront
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    • Private Outdoor Pool (Heated)
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Emma's Cottage For your next Anna Maria Island adventure, enjoy a stunning, one-of-a-kind vacation destination. From an oceanfront location to a private pool and original antiques, you won’t another Florida home like this one! Built by Emma Palmer in 1912, this home is one of four Anna Maria...
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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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    Sand Castle well appointed home steps from beaches1 / 25
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Grill
    • Private Outdoor Pool (Heated)
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 July 2019
    This is our second stay at this home. Could not be more pleased. Very clean and equipped with everything you could need.
    Reviewed 24 May 2019
    Sandcastles was perfect for the four of us. Anna Marie Island is a great place to stay, very relaxed with plenty of places to eat out, many golf courses near by and wonderful...
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    About this property
    Beautiful, recently renovated 1700 sf home that accommodates up to 8 people. Only a few steps to amazing sandy gulf beach. Enjoy all the amenities of a single level well appointed home with no stairs where you can step out to the beautifully landscaped pool area from your master bedroom or open...
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Washer
    • Patio
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Blue Bayou You'll fall in love with the island life in no time when you stay at this canal front Anna Maria vacation rental! Platinum-rated and featuring a private pool, private spa, and three parking spots, this home features all the amenities you need for a relaxing Florida beach vacation....
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Grill
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    • Washer
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    • Patio
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sundance Cottage Pack your flip flops and sunscreen and come stay in this beautiful three-bedroom house in Anna Maria ideally located within walking distance to the beach, dining, and more. With a private pool and a classic Florida atmosphere, your days will be a little brighter here. You'll be...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
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    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sea Shack This newly-remodeled, dog-friendly home comes equipped with a private pool, heated spa, and spacious backyard for barbecues. It's also only moments from shopping, dining, and Anna Maria Island's famous beaches. What's nearby: A sandy path to the beach lies at the end of the street,...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Washer
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    • Private Outdoor Pool (Heated)
    • DVD Player
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Paradise Pointe Retreat to your very own garden oasis at this three-bedroom Anna Maria home, a waterfront escape with a private dock on the canal, an outdoor pool, and an enviable location mere blocks from Bean Point Beach. You'll find this home on the serene North End of Anna Maria Island,...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Heated)
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Mangrove Cottage Come live the island life when you stay in this charming 'Old Florida' style cottage with a private saltwater pool and close proximity to the beach. You'll also have room for three cars in the roomy carport and access to Anna Maria's free trolley. With only one house between...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Patio
    • DVD Player
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    • Cable/satellite TV
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Shell House Chase sunsets and island vibes at this lovely beach house on Anna Maria Island. Offering a private heated pool, dog-friendly attitude, and access to a beach nearby, this house will ease you into vacation mode in no time! Located just over half a mile from the beach at City Park and a...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Dog-friendly duplex with two separate spaces, private pool, blocks to the beach!1 / 40
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Long Board and Short Board Book this elevated Anna Maria vacation duplex and you'll understand the feeling of love at first sunset. Consisting of both Long Board and Short Board rentals, this vacation option offers a private heated pool and a spacious Key West-style deck, plus, you can even bring...
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Private Outdoor Pool (Heated)
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    • Wi-Fi
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Bonita Surround yourself with elegance and luxury at this four-bedroom Anna Maria home, where you'll enjoy a private heated pool, a canal-front dock, and a wonderfully convenient location mere blocks from sugar sand beaches. You'll find this upscale home on a quiet street in Anna Maria,...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
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    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dream Maker This home's backyard is your ticket to island life, whether you're lounging in the saltwater pool, soaking in the private spa, relaxing under the palm trees, or firing up the gas grill. Access the bedrooms and living room via the windowed walkway that surrounds the house. Dream Maker...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sugar Plum Hideaway This delightful Anna Maria Island duplex is the perfect destination for your next group Florida vacation. Comprising both Sugar Plum Hideaway West and Sugar Plum Hideaway East, this spacious rental offers room for up to 12 guests - and their dogs! Plus, you'll enjoy a big fenced...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Short Board This property has a 7-night stay requirement. However, select properties have the flexibility for shorter stays. This elevated Anna Maria Island vacation rental will have you discovering love at first sunset. Short Board includes a heated pool (shared with Long Board - located...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Private Outdoor Pool (Heated)
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Le Paradis Enjoy a memorable beachside getaway with your loved ones on Anna Maria Island! Nothing is cookie-cutter about this dog-friendly home, which is perfectly located, well appointed with all the comforts you need, and features perks like a private pool. Located in a desirable area of Anna...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Au Soleil Sunshine and beach vibes are a given at this luxurious island rental, where you'll be within walking distance of the beach while enjoying a private pool in your backyard! Feel free to bring Fido along for the fun, because this house is dog-friendly (please note a small nightly pet fee...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sugar Plum Hideaway East Reserve this adorable ground-level vacation rental for a Florida getaway you'll never forget! Located on the highly sought-after north end of Anna Maria Island, this dog-friendly duplex lies less than a block from the sugar white beaches of the Gulf of Mexico and boasts a...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Balcony
    • Air Conditioning
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    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    La Casa Karen Sitting in a privileged location just steps to the beach, this high-end condo in Holmes Beach is just the place for your next vacation! Boasting amenities including a private jetted bathtub and a large deck space, plus access to a shared pool, you'll have everything you need for an...
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    LaRaya Retreat A special time awaits you at this updated beach house on Anna Maria Island. Featuring a dog-friendly attitude, a private lagoon pool, and easy access to Bean Point Beach, this house will leave you dreaming about the tropics for weeks after your trip. Located at the tip of Anna...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Long Board Discover love at first sunset with a stay at this elevated Anna Maria Island vacation rental. Long Board boasts a heated pool (shared with <b><a href='https://www.**********/unit.php?UnitID=13533' target='_blank'>Short Board</a></b>- right next door), a dog-friendly attitude, and a...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sea's The Day Adorned with shades of blue reminiscent of the waters surrounding Anna Maria Island, this charming cottage is a dream vacation home. Perched less than 200 steps from the beach, you're just a sea shell's throw away from Anna Maria's beautiful shore, and you have a heated pool oasis in...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sugar Plum Hideaway West Steal away to this ground-level duplex in the spectacular city of Anna Maria! The white sand and blue waters of the island's pristine gulf beach are just a quick walk away, and you'll also have access to a shared heated pool. You can even bring your dogs along! This...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Cable/satellite TV
    • Terrace
    • Private Outdoor Pool (Heated)
    • Wi-Fi
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spring Haven This lovely island home, newly built, is a perfect place to spend your family vacation. Its spacious layout is complemented with island decor and modern amenities, from brand new appliances in the kitchen to large, flatscreen tv's. When not enjoying the comfortable interior take a...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Patio
    • Washer
    • Wi-Fi
    • Grill
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Harmony House Come to historic Anna Maria Island and remember days gone by when you stay in this three-bedroom Key West-style cottage. With a sparkling cocktail-style pool, close proximity to the beach, dining, and Bayfront Park, you'll soon see why this beautiful rental is such a special place!...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Waterfront
    • Air Conditioning
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    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Coconut Tree Adorned with charming Old Florida sensibility, this house has you feeling right at home from the moment you set your suitcase down. The whole family is welcome, and that includes the boat! This Anna Maria Island beauty is situated canal-front with dock access. No citronella candles...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Grill
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    • DVD Player
    • Patio
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Blue Heron Beach House Sugar sand beaches and the smell of salt air await at this delightful four-bedroom beach house with a private pool and close proximity to the beach. You'll be tucked away in a quiet neighborhood in charming Anna Maria, only six houses away from the sand and water. Just a...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Wi-Fi
    • Private Outdoor Pool (Heated)
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    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sweet Retreat Cottage This Anna Maria Island rental was given the name Sweet Retreat Cottage for a reason. Offering a private heated pool, views of the Gulf, and beach access nearby, it won't take long to discover for yourself why this house is so spectacular! Located a block from the beach on...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
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    • Terrace
    • Air Conditioning
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Twin Palms This Holmes Beach rental is located in a peaceful, quite neighborhood where you can truly enjoy island time. Clean, neat, and elevated the home offers a wonderful view of the island canals, and a spacious backyard for relaxing. This home even comes with a heated pool where you can relax...
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Ocean Views
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dancing Dolphin This wonderful home is an ideal getaway for your next family beach vacation. The spacious bedrooms all offer TVs, and the full kitchen is perfect for preparing meals. The home comes equipped various, stunning amenities. Relax in the private oasis of the backyard while enjoying the...
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    Location Information
    Anna Maria, Anna Maria Island 32416
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Waterfront
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Island Oasis at Lakeview Place The Anna Maria home is a great place to spend your island vacation. Ultra private, with a canal front setting, this home is quite, secluded and peaceful. It's placement offers a splendid view of the Anna Maria water ways, views that can be enjoyed from the properties...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Washer
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    La Casa Poulos This property has a 7-night stay requirement. However, select properties have the flexibility for shorter stays. Experience luxury living at this three-bedroom seaside home with a fireplace, tropical accents, casually sophisticated decor, and updated amenities. Spend lazy days...
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Washer
    • Grill
    • Wi-Fi
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Blue By You You're sure to have a one-of-a-kind Anna Maria vacation with this spacious beachside home! With soft sands at Bean Point Beach nearby and million-dollar views at home, enjoy a beach getaway like never before! The closest attraction is easily Bean Point Beach, which lies only a few...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beach to Bay Getaway This Anna Maria home is a great place to spend your island time. Spread out in the living room includes that features a 48' flat screen TV and BlueRay player which include Netflix and Hulu Plus access (need your own login). The house is nicely equipped with everything from...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Washer
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bay Bungalow Located on the north end of Anna Maria Island, Bay Bungalow is less than two blocks from popular and secluded Bean Point beaches. This family-friendly destination offers a heated pool, a game console, Ping-Pong, foosball, and bikes for cruising around on island time. What’s...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Grill
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beach Hideaway This lovely beach home is freshly decorated with coastal decor. This dog-friendly home comes equipped with a private heated pool, a grand poolside lounge, and a spacious outside dining area for barbecues . and picnic. It's also only moments from shopping, dining, and Anna Maria...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 8
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Waterfront
    • Ocean Views
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Washer
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    La Casa O'Bar This property has a 7-night stay requirement. However, select properties have the flexibility for shorter stays. Plan your next seaside getaway to this gorgeous Gulf-front Anna Maria Island vacation condo and unwind in style. Boasting amenities like two shared pools, 2,000...
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Washer
    • Private Garden
    • Patio
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Shady Mango This charming, vintage cottage is placed right at the heart of historic Pine Ave, and comes with stunning amenities. Newly updated, it boasts a modern look while retaining it's original, cozy charm. This home's beautiful, large pool can be enjoyed in a spacious backyard surrounded by...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    • Private Outdoor Pool (Heated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A Cozy Cottage A Cozy Cottage is the ultimate retreat for relaxation and reconnecting with family or friends. Each bedroom is appointed with a built-in closet system, and offers direct access to the pool area. The kitchen is abundantly stocked, offering the ability to prepare any meal you decide...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
    • Wi-Fi
    • Washer
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rest a Shore Whether you're lounging in privacy on your sunny patio, soaking up the ocean view from the private pool, or exploring the island, your life back home will feel like a distant dream at this bayfront home in paradise! You'll find this house pleasantly tucked away behind a cascade of...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    2 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    South Bay Inn 1 This romantic getaway is a great place to spend some time on Anna Maria Island. Located right across the street from the bay, this rental is just a short stroll from the beach! It comes with a shared pool and comfortable outdoor furniture for relaxing in the island breeze. What's...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 2
    2 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    South Bay Inn 3 This condo's location makes it a great place for a romantic getaway on Anna Maria Island. Situated right across the street from the bay, this property puts the beach just a short walk away! It comes equipped with great amenities including a shared pool, an updated, full kitchen,...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 2
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
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    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    South Bay Inn 2 This spacious condo with spectacular views of Tampa Bay offers wonderful access to some of the best attractions in Anna Maria! Located right across the street from the beach and the bayshore, this property comes equipped with a shared swimming pool, a full kitchen, a game table for...
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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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