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Anna Maria
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Anna Maria Luxury Holiday Homes

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    Travellers to Anna Maria are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    28 Matching Rentals in Anna MariaView all 192 rentals
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    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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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • DVD Player
    • Patio
    • Air Conditioning
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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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    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 29 July 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 11 February 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
    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 11 November 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 30 January 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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    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
    • Grill
    • Air Conditioning
    • DVD Player
    • Washer
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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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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Washer
    • Cable/satellite TV
    • Patio
    • Grill
    • 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
    9 Bedrooms, 6 Bathrooms, Sleeps 26 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 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
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Cable/satellite TV
    • DVD Player
    • Grill
    • Private Outdoor Pool (Heated)
    • Patio
    • Wi-Fi
    • Air Conditioning
    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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    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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    Anna Maria, Anna Maria Island 32416
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    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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    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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    • 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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Stunning luxury newly constructed beachfront villa1 / 22
    (22)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 July 2017
    Beautiful three level beach house on the northern end of Anna Maria Island. Relaxing and very comfortable home where our family enjoyed reconnecting during our vacation after a...
    Reviewed 2 May 2017
    If you are looking for a property to relax by the beach or a swimming pool, this is about as good as it gets. There is nothing the owner's have not thought about. Great ocean...
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    About this property
    4 Bedroom 5 bath luxury beach front house sleeping 8 with heated pool separate spa numerous decks and stunning beach views from every room. We are located on the desirable family friendly island of Anna Maria. The house is direct beach front on the quiet upmarket north end of the island. Recently...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    Anna Maria Island Best Location Best Prices1 / 79
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 February 2019
    We were here in January and the weather was perfect. Sunny and bright days and not much rain. The home had everything we needed. Beds were comfortable and the house was very...
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    About this property
    Best location on the island Best value on the BEACH!. Mango Beach House is paradise found. White sugar sand, warm waters of the Gulf of Mexico and the definition of relaxation can be found at the Mango Beach house. Your escape to paradise and serenity awaits you on Northern tip of Anna Maria. You...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    C-viewFlorida, Canal/Dock/Heated Pool/Near Gulf - A Hidden Gem1 / 14
    (10)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Private Outdoor Pool (Heated)
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 April 2011
    I'm torn; I want to keep this amazing house a secret, but I also want to give Ann props for building & maintaining such a gem. She thought of everything, right down to...
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    About this property
    This is our personal Vacation Home and is managed by a team we have carefully selected. Please see our reviews. C-view Florida is one of the few canal homes (29-foot dock) AND close to the Gulf of Mexico(240 yards). It is a single story home spread out over 2,220 square feet offering privacy for...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Grill
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    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful luxury beach front condominium for rent for the first time. There's only 2 condo's on the entire property. This condo is 3500 square feet including gourmet kitchen, dining room, living room with fireplace and built in flat screen TV. screened in lanai overlooking the Gulf of Mexico, den...
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    Anna Maria, Anna Maria Island 34210
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    Old Island Charm - Newly Renovated1 / 26
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Secure Parking
    • Private Garden
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 February 2019
    This home is beautifully decorated with all new furniture and comfy beds that made it feel like home! The kitchen supplied everything needed to cook a full Christmas dinner but...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Private Outdoor Pool (Heated)
    • Patio
    • Grill
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bayou Escape's stunning location on the waterfront provides a panoramic view down the bayou. Relax in the heated pool and glimpse native manatee, fish, birds, and tropical vegetation. With your own private dock, enjoy watercraft and fishing at its best. Bask on secluded beaches with sunset views...
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    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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    About this property
    3 bedrooms and 2.5 baths directly on the beach in Anna Maria, Florida Enjoy spectacular views of the turquoise waters that are directly out the wall of glass and huge sliding doors. This high end Mediterranean style home has 3 bedrooms and 2.5 baths and best of all it is directly on the beach....
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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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful waterfront home located on the north end of Anna Maria Island. Located on North Shore Drive, approx 9 houses east of the Rod n Reel Pier and half a mile from the Historical City Pier. Anna Maria Island is a piece of old Florida. Perfect for family vacations, swimming, and watching the...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Lazy Hammock! This amazing north-end canal front home has everything you need to make this your best Anna Maria Island vacation ever. Park your car in the circular drive, enter through a jasmine pergola to this stunning ground level beach house and never leave! The vacation home is...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Waves Edge' located at 101 Cedar Avenue, Anna Maria...Let the warm gulf breezes welcome you as you enter. Fabulously upscale and beach chic. Completely renovated from the inside out using top of the line building materials to the most thought out details to make living on the gulf care free. This...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    Smoking allowed
    About this property
    215 Spring Avenue, Anna Maria, Anna Maria Island Exceptional 6 bedroom, 4 bath home located at the north end of Anna Maria Island. Recently renovated home offers top of the line amenities, a gourmet kitchen and spacious floor plan. Heated pool and private, tropical courtyard for enjoying true...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Washer
    • Balcony
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    • Grill
    • Terrace
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Pier to Pier Paradise! This beautiful brand new luxury home is one of a kind! Three stories high and ideally situated on Anna Maria's North end, the property is tucked into a quiet little neighborhood across the street from the beach and a short walk from the Rod and Reel pier, the city...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Parking
    • Balcony
    • Grill
    • Washer
    • Terrace
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Coconut Breeze is a custom home on the north end of Anna Maria in the quiet residential area in the sought after City Of Anna Maria. Offering 4 bedrooms / 4 bathrooms. You will find that this home has everything you need for your perfect Anna Maria Island vacation! From the luxurious heated pool,...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Washer
    • Parking
    • Wi-Fi
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    West O' Gulf is a mere 212 steps to the beach and the crystalline Gulf of Mexico! As you take your short walk to the Gulf beaches, you will take in the sights of the dense banyans, spectacular homes of Park Avenue, and the tropical sea grapes. West O' Gulf is perfectly located - West of Gulf...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Cherryfish, a spectacular spacious 4-bed home!1 / 29
    (10)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Washer
    • Balcony
    • Porch
    • Cable/satellite TV
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 March 2019
    This is house is big and beautiful, but...on arrival we relalized many high points in the advertised video were not working. Ice maker, wine refrigerator, staircase to viewing...
    Reviewed 1 November 2017
    Cherryfish is the ultimate vacation home. We have vacationed in Anna Maria numerous times and have stayed at Cherryfish twice it is our favorite home and we will stay there...
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    About this property
    Cherryfish is the latest addition to the Pineapplefish collection of houses on Anna Maria Island. It is a spectacular 4 bedroom house, in a fantastic location, just one block from Tampa Bay Beach, the amazing Waterfront Restaurant and the island's most popular tourist destination - City Pier....
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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