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Anna Maria Island House Rentals

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    Travellers to Anna Maria Island are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    671 Matching Rentals in Anna Maria IslandView all 1,246 rentals
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    Ohana Hale North  2  Bedroom on Anna Maria1 / 17
    (23)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Happy Island Cottage with heated private Pool1 / 52
    (30)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    A Pearl of a Beach Home - with luxury private heated pool and hot tub1 / 32
    (28)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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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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    Gorgeous views,spectacular home!1 / 46
    (33)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 August 6, 2018
    I can't believe I never wrote a review for our stay at this FABULOUS HOME! We booked it for our family for our wedding celebration and we love it from top to bottom! IT was...
    Reviewed July 9, 2018
    It pains me to give this beautiful home anything other than a stellar review. The owner, Chris, has been prompt and thorough with communication. The house itself is lovely and...
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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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    'Elegance' 100 Steps from the Beach!1 / 24
    (11)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Grill
    • Washer
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 16, 2018
    We all really enjoyed our stay at Elegance villa, pool was amazing, location was excellent and Shawna was very helpful. We hope to visit again soon.
    Reviewed November 2, 2017
    Just returned from 6 nights stay at this beautiful house. The house was just lovely- clean, well equipped and very comfortable. The provision of plenty clean towels including...
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    About this property
    An elegant beach-house that redefines the idea of island comfort, built with love and an extreme attention to detail. Every room of the house has a unique ambiance combining color, textures and accent lighting. The outdoor area is one of the most spacious on the island with a large heated free form...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Ohana Hale South   West Suite1 / 24
    (33)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Private Garden
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 14, 2018
    Ohana Hale South - West SuiteWe found that the accommodation accurately matched the posted description and photos. Excellent communications from renter - very fast responses...
    Reviewed November 28, 2017
    My family came to visit me every year and I always booked Ohana beach condo. Everything is perfect here: the beach is across the street, the unit is very clean and beautiful...
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    About this property
    Aloha and welcome to our Island Home. Ohana is Hawaiian for family and that is who you are when you stay with us. Our retreat is nestled on Anna Maria Island, Florida and is a short 5 minute walk to the white sand beaches and turquoise waters of the Gulf of Mexico. Your vacation Hale (home) has...
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    Bradenton Beach, Anna Maria Island 34217
    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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    • 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
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Grill
    • Washer
    • DVD Player
    • Central Heating
    • Hot Tub
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 2, 2018
    We thoroughly enjoyed our stay at this lovely cottage located on the northern tip of Anna Maria Island. The home is charming and well-cared for. The shaded yard was on the...
    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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    Luxury 3BR/3BA, Private Heated Pool, Beach1 / 34
    (36)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Air Conditioning
    • Grill
    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    We have traveled to Anna Maria numerous times, and this is the best house by far! The pool is the best part of the house! Very private, outside T.V., game room, 3 bedrooms with...
    Reviewed July 5, 2018
    We really enjoyed our stay for the week. The owners contacted us in advance to ensure we would have everything needed. We were impressed by how clean and updated it was. The...
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    About this property
    http://www.villachezshell.com Villa Chez Shell is a newly renovated Mediterranean beach home that offers a luxurious getaway. The highlight of this newly renovated 3 bedroom and 3 bathroom property is its tropical private backyard complete with a lagoon shaped pool and a soothing stone waterfall....
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    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Anna Maria Great Townhouse, Great Value!1 / 28
    (14)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Balcony
    • Patio
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 23, 2018
    We've stayed at a number of places on Anna Maria Isl. and this beautiful house is one the best. You can see the new heated pool from the kids bedroom. Holmes Beach is only a 5-6...
    Reviewed August 7, 2017
    Tranquil and friendly people good beaches. Very family friendly,good neighbor Doddy, Very close to markets and restaurants.
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    About this property
    Grab your flip-flops and beach chairs! This family-friendly 3-bedroom, 2 1/2 -bath townhouse is just two quick blocks to the pristine, white sandy beaches of Anna Maria's gorgeous blue waters of the Gulf Coast. And after a relaxing day of sand and sun, come back for a refreshing dip in the heated...
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    Holmes Beach, Anna Maria Island 32417
    Holiday Rental House - 3 Bedrooms, 3 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 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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    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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    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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    • Housekeeping Included
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Waterfront
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 19, 2017
    The house was gorgeous. Pretty and comfortable furnishings. Loved all the Anna Maria touches. Fantastic kitchen appliances - I wish my washing machine was so good! We all loved...
    Reviewed October 28, 2016
    We had a fantastic time exploring Anna Maria Island and coming home to such a fantastic place made the holiday even more special.
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    About this property
    It doesn't get much better than being right on the water, less than one block from the bay beach, and only 7 blocks from Pine Avenue. Sunshine Cottage couldn't be a better name, because this 3 bedroom, 2 bathroom, cottage truly lets you experience the beauty of Anna Maria Island. Enjoy dangling...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    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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    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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    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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
    About this property
    5801 DePalmas - Private home 3 Bedroom / 2 Bath , maximum occupancy of 6 people. Comfy and Cozy Florida Living!~ Distance to the Beach: 1/2 block Cute cozy ground level home 3 Bedroom/ 2Bath close to the beach on a quiet dead end street. Fully furnished with linens towels, cooking utensils,...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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 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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    Casa Playa West  is a Luxury 4 bedroom home with a pool and elevator!1 / 37
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Ocean Views
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home provides you with your own private pool. It has virtually EVERYTHING you need for a perfect Island vacation. This home has a private pool and is less than a block to the beach and 1 block to Sarasota Bay for fishing. Walk to Sarasote Bay and watch the big yachts and boats pass by on the...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    New! 'The Pelican' 50 seconds walk to beach! Beach cart, umbrella, chairs incl!1 / 28
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Parking
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 5, 2018
    This condo was beautiful and everything we needed for our long weekend away!It was very clean and fresh and decorated beautifully.The kitchen was great and all the little...
    Reviewed September 17, 2017
    Staying at The Pelican was a fantastic experience from start to finish. The rental seemed freshly renovated and felt like our home away from home. We had access to everything we...
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    About this property
    Location, location, location! Less than a min stroll to beach! We have just invested in a total makeover to our single story elevated vacation rental. Upgrades incl; granite counters. New Italian tile & oak (Pergo) floors throughout. Solid cherry wood cabinets & new premium stainless appliances....
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Casa Playa East is a Luxury 4 bedroom home with a pool and elevator!1 / 33
    (2)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Washer
    • DVD Player
    • Ocean Views
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 15, 2017
    We booked our stay here for our family (6 adults, 2 kids) totally unfamiliar with Anna Maria Island, coming for a wedding at a nearby venue. We couldn't have been happier...
    Reviewed August 8, 2015
    We rent a home in Anna Maria every year. Hands down, for my active group, this is the best location. Two blocks from hopping Bridge Street. Beach access 1/2 block away. Bay...
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    About this property
    This Bradenton Beach vacation home provides you and your family or small group with your very own private swimming pool, and comes fully equipped with everything you need for a wonderful vacation on this beautiful barrier island. Your accommodations are less than 1/2 block from the beach and 1...
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    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Wi-Fi
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bay view Home, located at 404 21st Place in Bradenton Beach is a hidden treasure! This wonderful home features 4 bedrooms and 3 bathrooms on a quiet street ending at the water. Best of all, this beautiful home is canal front with beautiful views of the bay! It features a private heated pool, BBQ...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Stunning 5 bedroom Pool Home just steps from the beach!1 / 49
    (4)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Ocean Views
    • Washer
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 3, 2017
    This wonderful house is located about in the middle of the island, close to Walgreens (if you forgot something) and a couple of minutes from Publix (for your culinary needs...
    Reviewed March 3, 2013
    We had the most wonderful four days in this house with our baby son. The house is just two blocks from the beach and comes with basic gear (towels, umbrella, chairs, wagon...
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    About this property
    Beautiful 5 bedroom 4 bathroom vacation home in Holmes Beach, just steps from the beach with fantastic Gulf views. This home is the perfect beach getaway with everything you could want while enjoying Anna Maria Island. Just imagine waking up to the sound of the surf rolling in. Enjoy a cup of...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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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 May 28, 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 May 27, 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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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)
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    • Washer
    • Patio
    • Hot Tub
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    • 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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beach Front House - Shady Pines - Anna Maria Island,, FL.1 / 25
    (28)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 9, 2017
    My friends and I go to Shady Pines every year, it is a highlight for us. The house is perfect, steps to the beach to enjoy swimming in the Gulf, or walking the beach and...
    Reviewed October 8, 2017
    My wife and I stay at Shady Pines each year and it's the highlight of our year. It is an outstanding beach front property. We love it and look forward to it each year. There...
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    About this property
    Shady Pines is a tastefully decorated, 2 BR, 1-1/2 bath, beach house right on the beautiful Gulf of Mexico. Walk out the door to a wide, white, powdery beach and the Gulf. This 2 bedroom beach house is located in the most perfect spot you will ever find! Great views and privacy. This quiet beach...
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    Location Information
    Anna Maria Island, Florida 34217
    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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    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property is unavailable but for limited time we're matching the rates at our newly remodeled 'Seaclusion' Tripadvisor listing 6528563. Check out our Low intro rates! Your search for most awesome vacation rental is over. Sleeps 4-5 persons in 2 bedrm en-suites We are in the most sought after...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Anna Maria Island Nantucket1 / 29
    (23)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • DVD Player
    • Private Outdoor Pool (Unheated)
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    • 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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    Location Information
    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Waterfront and dog-friendly home with private pool, dock, views, and lanai!1 / 29
    (1)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious and sophisticated, this waterfront and dog-friendly Anna Maria Island home puts the best of everything at your fingertips. Featuring a private dock, pool, and amazing water views, you’ll experience the luxurious side of Anna Maria Island paradise during your stay. This canalfront home...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    North Shore Villa Anna Maria1 / 27
    (3)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Reviewed September 14, 2016
    My family and I stayed with our friends and their children in late June 2016. We have teens and they have small children. This house is amazing! Its close to the water, you...
    Reviewed February 28, 2016
    This North Shore Villa is spacious, comfortable, and very clean. As close to the beach as you can be without being on the beach. The beach on the northern point of the island...
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    About this property
    NORTH SHORE VILLA 904 North Shore Drive Anna Maria Welcome to North Shore Villa. This luxury Key West style home has it all. Expansive bay views, private heated pool, extra large master suite with a double shower and Jacuzzi tub, fresh and modern decor, two large balconies, indoor sitting area...
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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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    Private Tropical Paradise in Holmes Beach!  Large home with Pool and fenced yard1 / 25
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
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    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 11, 2018
    We stayed at this house for 2 weeks. There’s a lot of room inside. House is well stocked with towels and any utensil you need. It is close to everything and the neighborhood is...
    Reviewed March 21, 2018
    Anna Maria Island is a friendly, eclectic place to visit. This is a very nice home with a fenced in yard and pool. It worked very well for our dogs and us!
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    About this property
    Tropical Paradise on Holmes Beach and ONLY 3 blocks to the beach. Anna Maria Island, noted for its old Florida ambiance, offers this Key West styled home, where you may awaken to greet the dawn sipping coffee on the balcony or swimming in your private pool. The modern interior arrangements add to...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    Spacious and bright home w/ heated private pool, one block to white sand beach!1 / 44
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
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    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Planning a fun family getaway or a trip with friends? Beach Retreat is the relaxing Anna Maria Island vacation rental just for you! The backyard's heated private pool is like a tropical oasis and this home's other top-notch amenities include a Ping-Pong table in the garage, free WiFi, and an...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    BAY FRONT HOUSE WITH PRIVATE DOCK1 / 19
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Private Garden
    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    House was in a good location right on the bay. Nice sitting area outside to watch the boats go by! The large Poinciana tree out back provided a ton of shade during the warm...
    Reviewed August 8, 2018
    House was perfect for the 2 of us plus 17 yoa son and dog. Walking distance to a couple of great restaurants and beach was about 2-3 min walk. Fished off the dock nearly every...
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    About this property
    Two Bedroom/2bath Home in Bradenton Beach Sleeps 6. This is a two bedroom/2bath home in Bradenton beach, with washer/dryer, new kitchen (granite counters), big screen/WiFi, great fishing on your own dock, on a quiet street, five minute walk to bridge street shopping area, two minute walk to the...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    7 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Secure Parking
    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Many homes with a high bedrooms count sprung out on the island lately, designed to maximize rents, they are built on very small lots normally 50 ft wide and packed upwards in three levels . This is a well reviewed house that I built for me and my family in 1998, it is the largest private rental...
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    Location Information
    Anna Maria Island, Florida 34217
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 16
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    Sandy Beach Access1 / 10
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sandy Beach Access Duplex, 2 bedrooms, 2 baths, 6 Places Newly renovated, fully furnished, 2 BR 2 Bath duplex. 202B 76th Street, Holmes Beach, FL 34217 New landscaping. 1 1/2 blocks (300 yards) to a beautiful sandy beach. Cable TV's, Wireless Internet, DVD Player. Laundry room. Anna Maria Island...
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    Location Information
    Holmes Beach, Anna Maria Island 34217
    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
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    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 2, 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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2206 Ave B1 / 23
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
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    Reviewed August 1, 2017
    My kids rented this place for me since I asked for a last minute date. I wished for something right on the beach but I'll take a block and a half from the back driveway. Having...
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    About this property
    2206 Ave. B - Private Bungalow 2 Bedroom / 1 Bath, maximum occupancy of 4 people and one small dog. Distance to the Beach: 2 blocks Quaint Island bungalow with an enclosed garage. In a friendly neighborhood in Bradenton Beach where the water is sparkling blue and the beaches are beautiful. Enjoy...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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 Crow's Nest, located directly on the beach at 2416 Gulf Drive in Bradenton Beach is a unique three bedroom, two bath home that was designed by a man with a passion for boats and a love of the sea. From its lofty view, enjoy a perspective of Bradenton Beach from the spacious screened lanai that...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    The Anna Cabana Beach House is an adorable two bedroom, two bath home located at 3709 Gulf Drive in Holmes Beach. This quaint home has a large open deck with a great view of the beach. Watch the sunsets or enjoy the tropical landscaping on the large deck facing the Gulf. Numerous fruit trees and...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 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
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    • Balcony
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    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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    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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    The Anna Maria Island Beach Palace1 / 68
    (1)Terrible
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    FAMILY/CHILD FRIENDLY CONDOMINIUM - ALL BABIES AND CHILDREN ARE WELCOME!!!! Anna Maria Island is not a place where you go to the beach. When you are on Anna Maria Island you are at the beach. Welcome to paradise. Featured here is a new gorgeous 4 bedroom 3 bathroom home providing you with...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 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
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    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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    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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    • Grill
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    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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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    About this property
    Escape to the Breakers, one of the finest luxury gulf front vacation homes on Anna Maria Island, located at 102 31st Street in Holmes Beach. Enjoy the tropical breezes and aqua-blue surf from the deck overlooking the white sand beach and sparkling Gulf of Mexico. Watch the dolphins cavort in the...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Casa Playa - Combo1 / 52
    (3)Very good
    8 Bedrooms, 8 Bathrooms, Sleeps 20 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
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    • Ocean Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 27, 2015
    We stayed at Casa Playa for the week after Christmas over New Years! The location is amazing...close to everything you need except a grocery store. The weather was perfect, the...
    Reviewed April 9, 2014
    We stayed here for the full month of March and very much really liked this unit. The owners ( Scott Deb ) were very nice, as they were wanting to make sure we had everything we...
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    About this property
    This Bradenton Beach vacation home is actually two rentals in one, in the middle of all the fun and beaches that Bradenton Beach can offer. The rental package sleeps up to 20, and everyone can enjoy the 2 private swimming pools. This is a fully equipped rental home on Anna Maria Island, with...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 20
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    Charming cottage w/ island views, entertainment & nearby beach access!1 / 33
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 29, 2018
    If your looking for a laid back beach cottage in a laid back beach community this is it. Little delay getting in the door because the key pad didn’t work, but once I stepped...
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    About this property
    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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    **PARADISE RETREAT IN BRADEN RIVER LAKES**1 / 23
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Secure Parking
    • Private Outdoor Pool (Heated)
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 29, 2018
    We really enjoyed our stay for Memorial Day weekend. Even though the weather wasn't what we planned for, thanks to a tropical storm! Of course the first one of the season and...
    Reviewed May 5, 2017
    Such a joy to rent this beautiful home. Warm pool and all the extras. ..,, soft towels, kitchen supplies and dishes, bath soaps, a garage to use and lots of seats, space and...
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    About this property
    This tropical retreat single family home boasts 1800sq. ft.of living space on the in the Braden River Lakes subdivision. The home is nestled among lush tropical palms and Florida vegetation. The expansive plantings provide privacy and a natural preserve setting in the backyard tropical paradise....
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    Location Information
    Bradenton Beach, Anna Maria Island 34208
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    The Dolphin Dance North side, located at 803 Gulf Drive South is an impressive, two bedroom one and one half bath duplex with panoramic views of the Gulf of Mexico. This spacious, town home unit will sleep six with a queen size bed, a full size bed and a sofa bed. Extras include washer, dryer, VCR,...
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    Location Information
    Bradenton Beach, Anna Maria Island 34217
    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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    About this property
    Cast Away #1, located at 4101 Gulf Drive in Holmes Beach is a delightful condo situated conveniently across from the Manatee Public Beach and the shimmering Gulf of Mexico. This two bedroom and one bath unit sleeps six with a queen size bed, two twin beds and a sofa bed. A full size kitchen and...
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    Location Information
    Holmes Beach, Anna Maria Island 34218
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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