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Anna Maria Luxury Vacation Rentals

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    Travellers to Anna Maria are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    16 Matching Rentals in Anna MariaView all 110 rentals
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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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    Gorgeous views,spectacular home!1 / 49
    (36)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    Location Information
    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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    Amenities & Details
    • Grill
    • DVD Player
    • Patio
    • Air Conditioning
    • Wi-Fi
    • 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
    Dolphin Pointe1 / 78
    (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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    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
    • Wi-Fi
    • 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
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Amenities & Details
    • 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
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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
    Stunning luxury newly constructed beachfront villa1 / 22
    (22)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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 July 22, 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 May 1, 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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
    Mango Beach House - Unforgettable vacations and sunsets1 / 79
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 8, 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
    Mango Beach House is in the Best location on the island and Best value on the BEACH. DIRECTLY ON BEAN POINT 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. Your escape to paradise and serenity awaits you...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Grill
    • Washer
    • 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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    Location Information
    Anna Maria, Anna Maria Island 34210
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    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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    Amenities & Details
    • DVD Player
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Private Outdoor Pool (Heated)
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 25, 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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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