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Anna Maria House Rentals

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    Travellers to Anna Maria are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    168 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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    19 Palms. Quaint Old-Florida Charm1 / 23
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Beachfront Paradise w/ Private Beach, Dogs Free, Military disc. Stunning Views1 / 22
    (8)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Blue Heron Waterfront House Anna Maria island1 / 23
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Ocean Views
    • Washer
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 10, 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 May 22, 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
    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
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    • DVD Player
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 3, 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
    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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    • Washer
    • DVD Player
    • Hot Tub
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    • Wi-Fi
    • Waterfront
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 7, 2018
    My family and I had a wonderful stay at Beach Nest. Liza was more than accommodating. We had to cancel due to unforeseen reasons and she allowed us to pick from a number of...
    Reviewed February 24, 2017
    Beach Nest is wonderful. Decorated with flair and beachy elegance, it feels like a home, not a rental. There is everything you need and more. You can walk to the beach with your...
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    About this property
    Water lovers too! Ahhhh-Welcome to Beach Nest! Ready to satisfy that oh-my-gosh-we-need-a-vacation? Kick off your shoes and throw them in the back of the closet. Promise yourselves to live in bathing suits from breakfast to bedtime! Vacationers, dreamers, honeymooners, would-be family-reunion...
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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 August 19, 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 October 28, 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
    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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    • Patio
    • DVD Player
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    • Waterfront
    • Washer
    • Private Indoor Pool
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Anna Maria's Finest Spacious and sophisticated, this waterfront and dog-friendly Anna Maria Island home puts the best of everything at your fingertips. Featuring a private dock, pool, and amazing water views, you’ll experience the luxurious side of Anna Maria Island paradise during your stay....
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Crescent Wave1 / 40
    (31)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
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    • Patio
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 8, 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 August 7, 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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Charming cottage w/ island views, entertainment & nearby beach access!1 / 33
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Wi-Fi
    • DVD Player
    • Washer
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 25, 2019
    We enjoyed the cottage very much for location and quiet. Very close to beach and other local establishments. The cottage was very well maintained and appointed.Our two...
    Reviewed July 29, 2018
    If your looking for a laid back beach cottage in a laid back beach community this is it. Little delay getting in the door because the key pad didn’t work, but once I stepped...
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    About this property
    Starfish Cottage A dose of sunshine and relaxation awaits you at this comfortable cottage on Anna Maria Island, featuring island views, entertainment, and easy access to the beach. Located immediately east of Gulf Drive, a quick 200-yard walk will bring you right to the white-sand beach and...
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Terrace
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    742 Jacaranda- Single Family home 3 bedrooms/ 2.5 baths, maximum occupancy of 6 people. Distance to the Beach: 50 yards Pet friendly. There is a required pet fee please ask. This well appointed home has recently been renovated. The balconies have all been redone, new stairway and all new...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    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 July 26, 2019
    This is our second stay at this home. Could not be more pleased. Very clean and equipped with everything you could need.
    Reviewed May 23, 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
    Anna Maria Island 'High End' Vacation Rental1 / 21
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Internet Access
    • Washer
    • Patio
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 15, 2019
    Amazing home. My wife and I stayed there for a week with our three teenagers. Quick access (12 minute walk) to the best beach in the area in my opinion, Bean Point. The kids...
    Reviewed February 23, 2019
    Perfect location for access to beaches, restaurants and shopping. Great House with an incredible pool & hot tub that got a lot of use. Three weeks of solitude & fun...
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    About this property
    The home is immaculately clean and whimsically decorated, professionally landscaped, and boasts one of the larger pools larger backyards and larger 2 bedroom homes on the Island. The spa is accented by iridescent glass. The 20' tall tiki hut was hand-built by Native Americans and houses the bar and...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Sunny, dog-friendly cottage w/ a spacious patio and grill, steps from the beach!1 / 40
    (1)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • DVD Player
    • Washer
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    • Wi-Fi
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Seashell Cottage This two bedroom, two bathroom beach cottage is so close to the beach you can smell the salt air! That's especially true on the spacious patio, where you can relax, dine al fresco, and grill out. The family dog is also welcome here for a small nightly fee. The beach's sugary...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Gorgeous views,spectacular home!1 / 49
    (36)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Washer
    • Grill
    • Cable/satellite TV
    • Balcony
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 29, 2019
    Our family had a wonderful time on AMI! This house was wonderful. We had a few questions about things in the house and when I emailed them the management company was quick to...
    Reviewed February 10, 2019
    We spent two weeks at this house January 19-Feb 2.Upon arrival we found the house sparkling clean and ready for our very important family vacation. My husband and I plus 3...
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    About this property
    WELCOME TO ALL DECKED OUT! JUST REMODELED OCTOBER 2019! Whether getting away for a family vacation, with a group of friends, for a wedding or any other occasion, our gorgeous 5 Bedroom home offers everything you could want for a relaxing holiday on Anna Maria Island.... with incredible views of...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
    116 Maple Breeze1 / 24
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
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    • Balcony
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 2, 2015
    Wonderful location, The beach is at the end of Maple Ave, a quiet road only a 2 minute walk. The house is well situated, 4 bedrooms and 2 and 1/2 baths. I can only speak of...
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    About this property
    116 Maple Breeze Private home 4 Bedroom / 2 1/2 Bath , maximum occupancy of 7 people. Distance to the Beach: 200 Yards 116 Maples is located on one of the prettiest streets in the village of Anna Maria, this gorgeous 4 bedroom, 2 and a half bath home is just steps away from the beach. This...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Internet Access
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Flamingo unit at the Blue Dolphin Inn, located at 780 Jacaranda in the Historic Village of Anna Maria is a wonderful and spacious three bedroom, two bath upstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Dolphin Pointe1 / 39
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Balcony
    • Washer
    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Heated)
    • Porch
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 10, 2017
    My sister and 2 friends came here for 6 days. The house was perfect, the weather was cool and windy the 1st couple of days, but with the pool being secluded, we got to hang out...
    Reviewed January 30, 2017
    The house is just as the pictures suggests. The floor plan was very spacious. We traveled with 6 adults (4 were college students) and there was ample room to spread out. The...
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    About this property
    The lovely Dolphin Pointe resides on the highly desirable north end of Anna Maria, just a three houses away from the beach at Bean Point and a short walk to 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...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Washer
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • 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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
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    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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    Anna Maria, Anna Maria Island 34216
    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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    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 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Maple Cottage Savor your time on Anna Maria Island with a stay at this whimsical one-level cottage! With room for everyone to enjoy a slower and mellower pace, you’ll be living like a local in no time. 

 Take a ride on the island’s free trolley to explore the sugar sand beaches (Palmetto Avenue...
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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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    • DVD Player
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    • 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, 3 Bathrooms, Sleeps 6 Quick View
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Once Upon a Time... This bright oceanfront house has the comforts of home but with the luxury of beach living. While there is a TV, who needs it when you have incredible ocean views from the large windows? There is a private deck on the back of the house with space for outdoor dining and a path...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Private Garden
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sea 'Esta Say goodbye to stress and hello to island vibes at this spacious beach house. Featuring a private yard with tropical greenery, a dog-friendly attitude, and a great location near the beach and pier, this house will have you living in a dream! Sitting near the northern tip of Anna Maria...
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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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    • Waterfront
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Azure Seas is a glorious three bedroom, two bath Gulf front home located at 779 North Shore Drive in the much desired and tranquil northern end of Anna Maria Island. Tropical paradise found!! This is the perfect place to forget your troubles and soak in the unbelievable views of the Gulf of...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    The Ibis unit at the Blue Dolphin Inn, located at 780 Jacaranda 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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Anna Maria Escape located at 725 North Shore Drive in Anna Maria city is just that - a peaceful, relaxed place to get away from it all. You can stroll on the beach for miles in either direction! It’s a perfect Anna Maria Island vacation home! This spacious and charming two bedroom, two bath...
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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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    • Private Outdoor Pool (Heated)
    • Grill
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • 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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    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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Dog-friendly duplex with two separate spaces, private pool, blocks to the beach!1 / 40
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    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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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    9 Bedrooms, 6 Bathrooms, Sleeps 26 Quick View
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    Pet friendly
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    About this property
    The Blue Dolphin Inn, located at 780 Jacaranda and 404 Alamanda in the tranquil City of Anna Maria features four units surrounding a tropical heated pool with tiki huts, grills, rooftop observation decks and loads of charm. Each unit has its own private patio and charcoal grill for an evening of...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 9 Bedrooms, 6 Bathrooms, Sleeps 26
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    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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    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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    Pet friendly
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    Smoking allowed
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    Sandy's Getaway Sandy’s Getaway offers two distinct spaces to accommodate the whole family or multiple couples - a ground-level bedroom and a larger upstairs suite, connected by outdoor stairs. Everyone is welcome here, and that does include the family dog! Canine members of the family, up to 30...
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    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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    • Patio
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    • Waterfront
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    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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    The Heron unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, two bath upstairs 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, 2 Bathrooms, Sleeps 6
    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, 4 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
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    • 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
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    • Air Conditioning
    Suitability
    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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Air Conditioning
    • 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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    Suitability
    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, 3 Bathrooms, Sleeps 6 Quick View
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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
    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, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Grill
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    • 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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    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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    • Waterfront
    • Balcony
    • Air Conditioning
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    • Shared Outdoor Pool (Unheated)
    • Grill
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    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
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
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    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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    • Grill
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    • 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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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