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Anna Maria House Rentals

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    Travellers to Anna Maria are booking August dates now. Secure your holiday rental today, and have the perfect trip.
    134 Matching Rentals in Anna MariaView all 158 rentals
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    Gorgeous views,spectacular home!1 / 46
    (32)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 / 39
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Charming 2 Bedroom/2 Bath Cottage on a Canal1 / 22
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Sand Castle well appointed home steps from beaches1 / 25
    (2)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 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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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Crescent Wave1 / 40
    (24)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 May 2018
    This house had everything we needed! Very clean and the pool was a big hit with the kids. Richard was very friendly and easy to work with. From booking to checkout it was as...
    Reviewed 27 May 2018
    Our family had a fun and relaxing stay with plenty of space and convenient walks to the beach, shops and restaurants. There was a wi fi issue the first day, but Richard had it...
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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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    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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Terrace
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    Pet friendly
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    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 This well appointed home has recently been renovated. The balconies have all been redone, new stairway and all new furniture in the living room and bedrooms The master bedroom...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Anna Maria Island 'High End' Vacation Rental1 / 21
    (2)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 21 March 2018
    The location is perfect - walking distance from both the beach and the Pine Avenue shops. This is a beautiful 2 bedroom home, outfitted with every detail. The pool and hot tub...
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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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    BEACHFRONT HOME, TRUE PARADISE , DOGS STAY FREE, GREAT VIEWS, WALKING BEACH1 / 22
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Wi-Fi
    • Waterfront
    • Washer
    • Cable/satellite TV
    • Grill
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 November 2017
    Awesome pet friendly beach house right on the water. It has amazing views of the Sunshine Skyway bridge and we enjoyed watching the boat traffic in the distance! So relaxing...
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Terrace
    • DVD Player
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    209 Spring - Private home 3 Bedroom / 2 Bath with private pool, maximum occupancy of 8 people. Distance to the Beach: 1 Block Spring into the waves!~ 209 Spring. 3 bedroom, 2 bath raised home in quiet, residential area of Anna Maria. Private pool. Pool heat optional * $20/day. 1 block to...
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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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    Hooks Haven - 3bed beach front1 / 20
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Central Heating
    • Terrace
    • Waterfront
    • Ocean Views
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 May 2018
    We had a girls’ weekend and choose this location. Beach chairs, towels, washer-dryer, bikes.....perfect. Not a great view but only a few steps from the beach and central to...
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    About this property
    This 3 bedroom 2 bath home is on the north end of Anna Maria Island and can be combined with Pirate Cove (a separate building ) to make a 5 bedroom beach front vacation home. All bedrooms in Hooks Haven are Queen size. Two bedrooms are on the main floor and one is on the second floor. Spiral...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    116 Maple Breeze1 / 24
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
    • Grill
    • Internet Access
    • Balcony
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 November 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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    Dolphin Pointe1 / 39
    (2)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
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    Anna Maria Island Nantucket1 / 29
    (23)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 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 10
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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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    • Secure Parking
    • Wi-Fi
    • Private Garden
    • Washer
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 March 2018
    My husband and I come to Anna Maria Island annually and always stay here. It’s spotless, beautifully decorated, ultra comfortable beds and new shower heads. The location...
    Reviewed 5 March 2018
    The location of the house is close to the beach and you can also walk to all the shops and dinning or bike ride. Parking is right at the doorstep and it is on a quiet street...
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    About this property
    This quaint, old-Florida style rental is nestled in the north shore area of Anna Maria Island. Shabby chic style, located 2 blocks from the beach and 2 blocks from the bay! Only one block from Pine Ave., with its old-time feel with shops and salons. Steps from fine dining, the historic city pier,...
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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, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • DVD Player
    • Grill
    • Balcony
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sea Haze Cottage is a completely renovated and updated private beach cottage, that is just perfect for a family or for one or two couples. It has a great room that leads to a large screened porch overlooking the deck, pool, spa and canal. The cottage is located in the quiet north end of Anna Maria...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Jacaranda Artist Retreat1 / 17
    (2)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Parking
    • Washer
    • Wi-Fi
    • Outdoor Dining Area
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 December 2017
    The house came complete with everything to make our stay comfortable. We loved the cozy charm of the home, with the owner's original artwork, and comfortable furniture. The...
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    About this property
    As an artist this private three bedroom and two bath multi-level elevated vacation home has been our family retreat that inspires many paintings of Anna Maria Island. Located on the secluded North End you will enjoy the tranquility of the Island and have an easy stroll to the Gulf of Mexico and the...
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    Anna Maria, Anna Maria Island 34217
    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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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is the CLEANEST AND BRIGHTEST vacation rental you will find on the island! This bungalow is the SECOND FLOOR UNIT of a beachfront duplex. Welcome to paradise! ANNA MARIA ISLAND is the first of the barrier islands located along Florida's Gulf Coast. It is about 7 miles long and 1/2 a mile...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    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
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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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    • Central Heating
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    Pet friendly
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    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
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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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Balcony
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pelican Roost 505 - Private canal home 5 Bedroom/ 5 Bath with private pool, maximum occupancy of 10 people. Distance to the Beach: 5 long blocks This gorgeous three story home in the city of Anna Maria, is an easy walk from Pine Avenue and the City Pier, with direct water views, front and rear,...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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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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    • 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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, 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 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
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Central Heating
    • Internet Access
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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
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    744 Jacaranda Rd1 / 32
    (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 Rates just reduced!! Book your holiday getaway today. $200 off any booking for the first two weeks in December 2018. Exclued the Holidays.(December 22, 2018 -January...
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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, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Patio
    • Grill
    • DVD Player
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    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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. This great Anna...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Ocean View 3 bedroom, pool, North Shore Drive1 / 123
    (36)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Ocean Views
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 November 2017
    Great place I had my birthday party here it was so fun Very close to the water every thing was to the t in cleanliness sleep 6 of us it was all around one of the best beach...
    Reviewed 30 July 2017
    We love this beach house! It has everything, is always clean, great location, and the owner is the nicest to deal with! We will definitely be back...if someone else doesn't book...
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    About this property
    Just steps to the sugar sand beaches in Anna Maria, FL. Your 3 bedroom, 2 bath, pool home with sweeping gulf views from two elevated front porches is located in the charming northern end of Anna Maria on North Shore Drive. If you are looking for a tropical vacation home to just relax, take long...
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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 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bask in the endless sunshine of Anna Maria Island at this three-bedroom home, a dog-friendly 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 Maria...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    AMI Coastal Retreats- 'Island Oasis'1 / 42
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
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    • 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 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 crystal-clear waves. Go...
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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 5 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    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 Island, this...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Stay & Spoil yourself! Pool, Hot tub,Fish, Dock, Kayak* Steps to Gulfside beach!1 / 23
    (13)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Waterfront
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 May 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 24 February 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
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Beachy Keen 408 - Private home 3 Bedroom/ 2 Bath with private pool, maximum occupancy of 6 people. Distance to the Beach: 1 1/2 block Here delightful and fun Caribbean Cool décor welcomes you to the sub tropic cozy of Anna Maria Island. A charming island home within easy walking distance to the...
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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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    6 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    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 Maria Island, a...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 16
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Beautifully renovated beach cottage in the heart of the village of Anna Maria. Walk to the beaches, shops and restaurants. Enjoy amazing sunsets at the beach or sip a glass of wine in the lush tropical gardens surrounding the cottage. 2 bedrooms with 2 full bathrooms. Quaint beach cottage in a...
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    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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    Pet friendly
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    About this property
    Book and Stay Now thru Dec. 31st with a 20% discount! Excludes most holidays but call our office for details! Spacious and beautifully appointed 2 bedroom, 2 bathroom canal front cottage with a large living/dining room, kitchen, family room, and idyllic patio. There is a beautiful backyard with a...
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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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    Pet friendly
    Kid friendly
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    About this property
    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 cottages known as...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tequila Sunset: 2BR Pet-Friendly with Heated Pool1 / 24
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 October 2015
    We saw this rental a year or so ago when we were staying on Anna Maria Island. We looked it up on line and was happy with what we saw. The home sleeps a family of four. It was...
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    About this property
    Begin your Tequila Sunset vacation in this lovely vacation rental that is just a few houses from the white sand beaches of Anna Maria Island! Once inside, an island cottage feel will surround you with an open floor plan, lively colors, and wood floors. This two-bedroom, two-bath home features a...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is truly a unique home that is becoming a vacation rental for the first time ever. Built in 1974 and designed by Frank Lloyd Wright's protege, Albert Robson, this sprawling mid Century design boasts over 3400 square feet of living space, with 3 bedrooms and 3.5 baths. The king sized master...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    103 Pelican1 / 14
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Balcony
    • Terrace
    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 April 2016
    Hi! My husband and I rented this property and had the wonderful opportunity of having our adult children & their spouses come with us. There was 8 of us in total. We...
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    About this property
    103 Pelican - Private canal home 3 Bedroom/ 2 Bath with private pool, maximum occupancy of 6 people. At this spacious, family friendly home with private pool, grab your fishing pole, take the hand of a child and meander to the private dock, cast a line while dangling your feet and spending the...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sea Oats: 2BR Elderly-Friendly Pool Home on Canal1 / 23
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 March 2018
    Having had a disasterous week at another property the week before moving to Sea Oats, it was such a relief to walk into a very clean and welcoming property. A great location...
    Reviewed 6 May 2017
    How could you not love this location- a few hundred feet from the beach with the added bonus of a pool & canal in the backyard.We loved the flow of the house,the openness...
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    About this property
    Spend your relaxing vacation at Sea Oats, located just a block from the white sand beaches of Anna Maria Island. This lovely two-bedroom, one-bath vacation rental has just been completely remodeled and fabulously decorated! Cozy and relaxing furnishings await you and your friends and family during...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Balcony
    • Housekeeping Included
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    • Central Heating
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2016 New Custom 4 Bedrooms 4.5 Bathrooms resort size pool/spa Anna Maria Island home on a residential cul-de-sac and a boat dock in your back yard. This luxury home is quality built CBS and offers a chef's kitchen for all to enjoy. This Island retreat is located walking distance to the beach and...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    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 lbs, are welcome...
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    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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    About this property
    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 backyard, a shared...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Managed by an agency no direct bookings here. Located on beautiful Anna Maria Island, 'Le Paradis' (which means Paradise in French) is just a short stroll to the sugar white sand beaches of beautiful Anna Maria Island... Experience a luxurious beach vacation with over 2100 hundred square feet of...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Cable/satellite TV
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Blue Bay is a gorgeous brand new, custom luxury home that is a the perfect rental home for your next vacation. This stunning high end home is comprised of two separate buildings, a main house and a guest house, with a tropical pool with tiki, spa, grill, sun deck and fire pit, in between the two....
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 16
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Tastefully decorated with an island flair! The White Egret has furnished and decorated this adorable two bedroom/one bath half duplex on the north end of Anna Maria Island! The master bedroom has a king sized bed, with sliding doors out onto a deck area, and the second bedroom has a queen sized...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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