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Anna Maria House Rentals

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    Travellers to Anna Maria are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    145 Matching Rentals in Anna MariaView all 173 rentals
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    Crescent Wave1 / 40
    (24)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    BEACHFRONT HOME, TRUE PARADISE , DOGS STAY FREE, GREAT VIEWS, WALKING BEACH1 / 44
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    5 Star - Private Pool & Dock - May Availability - Special Pricing1 / 39
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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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 May 3, 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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    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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Terrace
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    742 Jacaranda- Single Family home 3 bedrooms/ 2.5 baths, maximum occupancy of 6 people. Distance to the Beach: 50 yards 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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    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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    • Balcony
    • DVD Player
    • Patio
    • Grill
    • Terrace
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 25, 2017
    I loved that the owner went our of her way to reserve pack and plays for our two little ones. They had everything for beach trips including a wagon, beach toys, and umbrellas...
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    About this property
    Our 2 bed/2 bath cottage is the perfect home to spend your vacation. Located on a canal, you can bring your boat or rent kayaks. Fishing is great from the dock. House and yard is very private. Soak in the jacuzzi after a long day at the beach or relax in the hammock. We have 2 bikes, beach...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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 January 5, 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 April 10, 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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    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
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 2, 2015
    Wonderful location, The beach is at the end of Maple Ave, a quiet road only a 2 minute walk. The house is well situated, 4 bedrooms and 2 and 1/2 baths. I can only speak of...
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    About this property
    116 Maple Breeze Private home 4 Bedroom / 2 1/2 Bath , maximum occupancy of 7 people. Distance to the Beach: 200 Yards 116 Maples is located on one of the prettiest streets in the village of Anna Maria, this gorgeous 4 bedroom, 2 and a half bath home is just steps away from the beach. This...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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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 June 10, 2017
    We stayed for a week at the end of May 2017 after spending 10 days in Orlando. We were met at the property (even though we were a little late) and it was beautifully presented...
    Reviewed May 22, 2017
    The location is perfect. Walk 2 blocks to beach. Supermarket, drug store, bank, restaurants, salon, spa, less than 5 min. away. Many choices to dine/shop 3-10 min drive. The...
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    About this property
    Stunning ground level 3 bedroom/2 bath home with luxury finishes at every glance. Brand new to the market and recently renovated, this home is packed with designer finishes throughout from luxury linens in all three uniquely appointed bedrooms to furnishings that make this home feel like you are...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gorgeous views,spectacular home!1 / 46
    (30)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 2 weeks ago
    unfortunately for our 2 weeks on AMI we had lousy weather..... which meant we spent more time in the house than we had originally planned. The rooms are spacious and nicely...
    Reviewed May 17, 2018
    This was our second visit to "All Decked out", and we were not disappointed. The house is really lovely, great location, extremely spacious and great views from the...
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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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    Hooks Haven - 3bed beach front1 / 20
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Central Heating
    • Terrace
    • Waterfront
    • Ocean Views
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 7, 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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    Sand Castle well appointed home steps from beaches1 / 50
    (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 August 24, 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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    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 November 10, 2017
    My sister and 2 friends came here for 6 days. The house was perfect, the weather was cool and windy the 1st couple of days, but with the pool being secluded, we got to hang out...
    Reviewed January 30, 2017
    The house is just as the pictures suggests. The floor plan was very spacious. We traveled with 6 adults (4 were college students) and there was ample room to spread out. The...
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    About this property
    The lovely Dolphin Pointe resides on the highly desirable north end of Anna Maria, just a three houses away from the beach at Bean Point and a short walk to Rod and Reel Pier. The spacious open concept living area is perfect for spending quality time with the family. The home exudes an Island charm...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Garden
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    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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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Balcony
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Grill
    Suitability
    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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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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 December 5, 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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    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 March 20, 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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    Anna Maria's Coconut Breeze Estate - no cleaning fee1 / 49
    (5)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Air Conditioning
    • Grill
    • Patio
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 13, 2017
    Really beautiful home and close to everything. Huge place. 2 minute walk from Rod and Reel Pier and 5 minutes to Bean Point (though wouldn't recommend swimming there, current...
    Reviewed May 9, 2017
    This home really does have the "wow factor." The moment we walked through the door we were blown away. The best of everything is in this home...the kitchen appliances...
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    About this property
    This beautiful gem in the much coveted City of Anna Maria's north end. It is a single family home located on a quite street. Easy walk to the gorgeous white sand Bay and sugary sand Gulf of Mexico beaches with striking sunsets . With Pine Ave (our fantastic little Main St.) just a short stroll from...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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)
    • Washer
    • Air Conditioning
    • Waterfront
    • DVD Player
    • Ocean Views
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    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 September 30, 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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Discount July 4th week! Pool, Hottub,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
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 7, 2018
    My family and I had a wonderful stay at Beach Nest. Liza was more than accommodating. We had to cancel due to unforeseen reasons and she allowed us to pick from a number of...
    Reviewed February 24, 2017
    Beach Nest is wonderful. Decorated with flair and beachy elegance, it feels like a home, not a rental. There is everything you need and more. You can walk to the beach with your...
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    About this property
    Water lovers too! Ahhhh-Welcome to Beach Nest! Ready to satisfy that oh-my-gosh-we-need-a-vacation? Kick off your shoes and throw them in the back of the closet. Promise yourselves to live in bathing suits from breakfast to bedtime! Vacationers, dreamers, honeymooners, would-be family-reunion...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • DVD Player
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Sauna
    • Washer
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 17, 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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    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 6 Quick View
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    • Patio
    • Parking
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Terrace
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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 March 4, 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 March 4, 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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, 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 November 5, 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 July 30, 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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    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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    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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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    About this property
    Direct Beach Front Home with 180 degree Gulf Views. Your backyard is a Private Beach and a beautiful view of Egmont Key & the Skyway Bridge. Walk to the Rod & Reel Pier where dolphins frolic every afternoon or walk to Pine Avenue for some local shopping. The living level has a full size kitchen,...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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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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    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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Special May Pricing - The Best Time To Be On AMI! Welcome to Yellowbird; your home away from home at the north end of beautiful Anna Maria Island. Here you will enjoy unforgettable views and sunsets over the white sands of the Gulf from the home's multiple decks. This 4 bedroom custom home is the...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    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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    Starfish Dreams: 2BR Canal Home w/Dock & Pool1 / 24
    (12)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed January 24, 2018
    Our friends rented this beautiful home, and invited us to stay for a few days - lucky us! Love the little touches the new owners have made - really cute silverware, more pots...
    Reviewed October 8, 2017
    Wow what an amazing place! Located on the canal so my husband can fish and I can sit and read my book on the screened porch is perfect,The whole outlook of this house is...
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    About this property
    Starfish Dreams is the perfect place to start your vacation! This family-friendly vacation rental is centrally located on Pine Avenue in the city of Anna Maria on Anna Maria Island, halfway between the Gulf of Mexico and Tampa Bay. If that were not enough, it also has a heated pool and is on 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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    4 bed luxury upscale executive waterfront home1 / 50
    (10)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Hot Tub
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 27, 2017
    Bayview Dream did not disappoint! It truly was a dream holiday for us. The house itself is beautifully decorated and very well equipped - plenty of towels (indoor and pool...
    Reviewed January 17, 2016
    We spent a week in this lovely home. The weather was cool, so we didn't use the pool, but there was a beautiful pool with a dock right out the back door. The home was spacious...
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    About this property
    Location, Location, Location. Upscale luxury executive four bedroom waterfront home with private pool dock and elevator. Stylishly furnished and dressed, modern build 2006 - this is our family second home - and is home from home available to you. This exclusive executive property is in the...
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    Location Information
    Anna Maria, Anna Maria Island FL34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Pet friendly
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    Smoking allowed
    About this property
    Located directly across from Tampa Bay, this gorgeous new custom luxury vacation rental looks out onto the beautiful bay waters from multiple large balconies. A rooftop deck provides outstanding 180 degree views of the turquoise waters, as well as the Anna Maria City Pier and the Sunshine Skyway...
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Absolutely Anna1 / 25
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed July 18, 2016
    Very nice house and location! Plenty of room for all of us! Great inside and outside! What an incredible outdoor area for family time!! Beach is so close and convenient...
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    About this property
    LAST MINUTE SPECIAL - BOOK AND STAY NOW THRU 5/25/18 FOR 20% OFF!!! Absolutely Anna is just that -- the epitome of the beach experience you want to have when you visit the beautiful north end of Anna Maria Island. Only two houses away from the footpath to Bean Point, you are on the gorgeous white...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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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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    BON AMI: 3BR Family-Friendly Pool Home1 / 24
    (10)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 8, 2017
    Had the pleasure of staying at Bon Ami for three weeks from mid February to mid March 2017. The house is very clean and comfortable with lots of sheets and towels, fully...
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    BON AMI will be your 'good friend' after a vacation stay. Located on the north end of Anna Maria Island and a short distance to Bean Point and its beautiful beaches, this elevated pool home will beckon you back year after year! Beautifully decorated, this three-bedroom, two-bath vacation rental is...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    On Island Time is exactly how you will feel when you stay in our newest vacation rental at Coastal Cottages AMI! This is the quintessential island cottage located on the north end of Anna Maria. It has 2 bedrooms, plus a den with sleeper sofa, two walk in shower bathrooms and has been totally...
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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 6 Quick View
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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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    8 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
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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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 16
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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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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    • Housekeeping Included
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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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    Jewel of the Bay: 4BR INCREDIBLE Waterfront Home1 / 24
    (5)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We have been renting this house in May for 3 years. It is awesome. Four king on suites so perfect for 4 couples. Beautifully appointed. Heated pool that overlooks your...
    Reviewed June 5, 2017
    Anna Maria is a wonderful place with a laid back way of life. There are some great places to eat and drink and the beaches are superb.The thing that made our holiday really...
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    About this property
    This is the vacation rental home of your dreams! This custom bay-front home on the north end of Anna Maria Island offers 3600 square feet of luxury accommodations and has all the fine touches and professional craftsmanship one would expect in a high-end custom home. When walking into this amazing...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 your dogs along. The...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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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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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 17, 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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Life is Good at the Beach: 3BR Family/Pet-Friendly1 / 20
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 17, 2016
    Life is Good at the Beach vacation rental is a beautifully, well maintained home. The picutres provided on the website accurately reflect the home and the beach house more than...
    Reviewed November 22, 2015
    Great well equipt house, everything we needed and more, close location to beach 5 mins walk, and to the free trolley bus stop 10 mins walk. The only downside of this property is...
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    About this property
    Life is Good at the Beach, located on the north end of Anna Maria Island, is a fantastic place to start your vacation. This three-bedroom, two-bath, vacation rental is just a five minute walk to the beautiful north end beaches near Bean Point and two blocks to the Rod & Reel Pier. The extra-large...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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