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Holiday Rentals in Anna Maria

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    Travellers to Anna Maria are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 114 Rentals in Anna Maria
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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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    Stay & Spoil yourself! Pool, Hot tub,Fish, Dock, Kayak* Steps to Gulfside beach!1 / 50
    (12)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Anna Maria Island 'High End' Vacation Rental1 / 21
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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 4 weeks ago
    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 23 February 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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    • 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 23 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
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    BEACHFRONT HOME, PRIVATE BEACH, DOGS STAY FREE, GREAT VIEWS, WALKING BEACH1 / 22
    (6)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Wi-Fi
    • Waterfront
    • Cable/satellite TV
    • Ocean Views
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    location of this house is awesome. it is within an easy walk to ice cream parlor, shops and great restaurant. There is wonderful view of the bay from every room across back of...
    Reviewed 1 October 2018
    Six of us ladies had a great time and loved the house! Laura was very helpful. Hope we can do it again.
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    About this property
    This stunning BEACHFRONT home was designed by an award winning Architect and is true paradise. The plan is open with the Living, Dining, Kitchen and Master Bedroom on the Waterfront adjacent to the deck which runs the entire length of the home. The elevated deck is a mere 10' from the waters edge....
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    • 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
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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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    • Patio
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • 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
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    Crescent Wave1 / 40
    (29)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 April 2019
    Spent the week enjoying Crescent Wave. The house is a little tired but it was clean and had most everything we needed. It is only about 3 blocks from the beach and has a wagon...
    Reviewed 23 February 2019
    The location of this clean, nice floor plan house is in a quiet residential area. It is within blocks to the ocean, bayside and shops/restaurants on Pine Street. Whether you...
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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
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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 4 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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    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
    (3)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 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...
    Reviewed 24 August 2017
    My family stayed in this home August 2016. The home is beautiful and we enjoyed our stay very much. The home was well equipped and pretty clean. I did has a couple issues at...
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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
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • 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
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    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 26 January 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 29 July 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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Anna Maria Island Nantucket1 / 48
    (23)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 January 2018
    My extended family stayed here this past December, and it was perfect. The place is showing it's age a bit, and there is a rather steep set of stairs to get to the main floor...
    Reviewed 10 April 2017
    We rented this home over Spring Break with my brother and his family. The layout of this house is great as well as the location of the home on the island. There were 2 master...
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    About this property
    3 Story 'Nantucket' Style - 4 bedroom/ 3 bath villa is just a short walk to the beach - Nestled in a tropical setting, only a few blocks to the Gulf beach; heated private pool great for cooling off and a large sun deck. 4 Bedrooms/3 baths, large master suite with king size bed and a roman tub,...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    'Island Oasis'  A single family North end canal home with pool1 / 68
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Washer
    • Air Conditioning
    • Waterfront
    • DVD Player
    • Ocean Views
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 June 2018
    The location is amazing for boats/jet skis. The house is perfect for up to two families with two master suites and an additional half bath. The kitchen is well-equipped with...
    Reviewed 1 October 2015
    I chose Island Oasis as it ticked every box. This is a beautiful island and the beach is very easy to access, as such I wanted a property with a pool, suitable for two couples...
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    About this property
    Step into an ultra private, secluded, tropical paradise with a lush canal front setting in quiet cul-de-sac located on the north end of Anna Maria Island. There is a beautiful heated pool just steps outside your door. The back yard has multiple areas to relax away the day and enjoy the amazing view...
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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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    • Cable/satellite TV
    • DVD Player
    • Patio
    • Waterfront
    • Wi-Fi
    • 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
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    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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Washer
    • Patio
    • Private Outdoor Pool (Heated)
    • 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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    744 Jacaranda Rd1 / 31
    (9)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 May 2013
    We loved this house for the week we spent in it. it was very clean and had all the little extras that make a holiday let in the U.S. ideal for a U.K. family - i.e. lots of beach...
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    About this property
    744 Jacaranda - Private home 3 Bedroom/ 3 Bath with private pool, maximum occupancy of 6 people. Distance to the Beach: 1 1/2 block Live the Florida lifestyle in this beautiful, comfortable 3 bedroom, 3 bath private home with private pool and with screened lanai. The home is located on Anna...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Washer
    • DVD Player
    • Grill
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    • Wi-Fi
    Suitability
    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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Grill
    • Private Garden
    • Wi-Fi
    • DVD Player
    • Washer
    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
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    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
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Patio
    • DVD Player
    • Air Conditioning
    • 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
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Washer
    • Wi-Fi
    • Air Conditioning
    • 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
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • DVD Player
    • 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
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • DVD Player
    • Washer
    • Air Conditioning
    • 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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    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 8 Quick View
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    • Central Heating
    • Internet Access
    • Grill
    Suitability
    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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 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
    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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Wi-Fi
    • Balcony
    • Ocean Views
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    • Waterfront
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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
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Terrace
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Heated)
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    • 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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
    • Grill
    • Central Heating
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    Pet friendly
    Kid friendly
    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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Central Heating
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    Pet friendly
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    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
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Patio
    Suitability
    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. Let us do the searching for you! Please call *******-8791 and one of our knowledgable reservation specialists will be happy to assist you in finding a property for the dates...
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Hot Tub
    • Internet Access
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Marisol, located at 797 North Shore Drive at the north end of Anna Maria Island and nestled on the shores of the Gulf of Mexico, offers breathtakingly beautiful views of the crystal blue waters of the gulf. This is unquestionably one of Anna Maria's loveliest homes. This spectacular home...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
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    • Air Conditioning
    • DVD Player
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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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    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
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Private Outdoor Pool (Heated)
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    • 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
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
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    Smoking allowed
    About this property
    The Skimmer unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, one bath downstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Gorgeous views,spectacular home!1 / 46
    (35)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 10 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...
    Reviewed 24 January 2019
    The location is amazing. We were steps away from the Bay and a short walk to the fabulous Waterfront restaurant and dozens of other delightful shops.The home was very nicely...
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    About this property
    WELCOME TO ALL DECKED OUT! 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 the Bay! Sit by the tropical...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Cable/satellite TV
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    • Balcony
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Grill
    Suitability
    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
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    9 Bedrooms, 6 Bathrooms, Sleeps 26 Quick View
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    • Central Heating
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    Pet friendly
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    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
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    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
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Grill
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • DVD Player
    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
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Grill
    • Internet Access
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    Pet friendly
    Kid friendly
    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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Waterfront
    • DVD Player
    • Private Outdoor Pool (Heated)
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    • Air Conditioning
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront Retreat The perfect spot for a large family getaway, this canalfront Anna Maria Island vacation rental home has room for everyone! Offering a dog-friendly atmosphere (dogs up to 50 lbs. are welcome with a small pet fee), parking for five vehicles, a private pool, and tons of space for...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Long Board This property has a 7-night stay requirement. However, select properties have the flexibility for shorter stays. Let us do the searching for you! Please call *******-8791 and one of our knowledgable reservation specialists will be happy to assist you in finding a property for the dates...
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Air Conditioning
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    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
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