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Holiday Homes near Anna Maria City Pier

100 S Bay Blvd, Anna Maria, Anna Maria Island, Florida 34216
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    Travellers to Anna Maria are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    All 100 Rentals in Anna Maria
    19 Palms. Quaint Old-Florida Charm1 / 23
    (4)Excellent
    0.4 kilometres from Anna Maria City Pier
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    BEACHFRONT HOME, PRIVATE BEACH, DOGS STAY FREE, GREAT VIEWS, WALKING BEACH1 / 22
    (4)Excellent
    0.4 kilometres from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    5 Star - Private Pool & Dock, and Steps Away from the Beach - Fall Availability1 / 39
    (5)Excellent
    0.7 kilometres from Anna Maria City Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Crescent Wave1 / 80
    (26)Very good
    0.6 kilometres from Anna Maria City Pier
    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 2 weeks ago
    We had a wonderful time on BEAUTIFUL Anna Marie Island, we will definitely be back! Richard was awesome to work with from start to finish! The home fit our family perfectly. Our...
    Reviewed 30 October 2018
    Anna Maria island is absolutely beautiful! We went to a wedding at the sandbar. We can’t wait to go back. Our place was the perfect location. Good restaurants shops and beach...
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    About this property
    Description We are located in the heart of the beautiful city of Anna Maria FL. We are one block from the historic Pine Ave with free trolley service to the entire island. We are two blocks to the beautiful white sand beach. Three blocks in the opposite direction is the bay and the historic City...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Gorgeous views,spectacular home!1 / 92
    (33)Very good
    0.4 kilometres from Anna Maria City Pier
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Washer
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    • Private Outdoor Pool (Heated)
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 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 9 July 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
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    744 Jacaranda Rd1 / 32
    (9)Very good
    0.9 kilometres from Anna Maria City Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 May 2013
    We loved this house for the week we spent in it. it was very clean and had all the little extras that make a holiday let in the U.S. ideal for a U.K. family - i.e. lots of beach...
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    744 Jacaranda - Private home 3 Bedroom/ 3 Bath with private pool, maximum occupancy of 6 people. Distance to the Beach: 1 1/2 block Live the Florida lifestyle in this beautiful, comfortable 3 bedroom, 3 bath private home with private pool and with screened lanai. The home is located on Anna...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.9 kilometres from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Terrace
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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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Stay & Spoil yourself! Pool, Hot tub,Fish, Dock, Kayak* Steps to Gulfside beach!1 / 46
    (12)Excellent
    0.8 kilometres from Anna Maria City Pier
    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 8 May 2018
    My family and I had a wonderful stay at Beach Nest. Liza was more than accommodating. We had to cancel due to unforeseen reasons and she allowed us to pick from a number of...
    Reviewed 25 February 2017
    Beach Nest is wonderful. Decorated with flair and beachy elegance, it feels like a home, not a rental. There is everything you need and more. You can walk to the beach with your...
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    About this property
    Water lovers too! Ahhhh-Welcome to Beach Nest! Ready to satisfy that oh-my-gosh-we-need-a-vacation? Kick off your shoes and throw them in the back of the closet. Promise yourselves to live in bathing suits from breakfast to bedtime! Vacationers, dreamers, honeymooners, would-be family-reunion...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    1.0 kilometres from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Central Heating
    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Anna Maria Escape located at 725 North Shore Drive in Anna Maria city is just that - a peaceful, relaxed place to get away from it all. You can stroll on the beach for miles in either direction! It’s a perfect Anna Maria Island vacation home! This spacious and charming two bedroom, two bath...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Paradise at the Bayou1 / 20
    (4)Excellent
    0.1 kilometres from Anna Maria City Pier
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • DVD Player
    • Balcony
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    • Waterfront
    • Patio
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 April 2018
    We loved staying at Greg and Lori's condo. Just as shown on site, hosts provide everything needed to enjoy vacation in their place including kayaks, beach chairs, towels etc as...
    Reviewed 8 June 2017
    The rental was extremely clean and well stocked with all the amenities needed for cooking, fishing, sitting on the beach or just reading a book while watching the fish jump. The...
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    About this property
    This water front, two bedroom condominium (ground floor), sits on the end of Pine Avenue, across the street from the beach and has wonderful seaside views of the bay. It also has its own private fishing dock and boat slip! This unit has been completely remodeled and newly furnished to give you the...
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    Anna Maria, Anna Maria Island
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Brand New Renovation Sea Waves Cottage1 / 16
    (9)Very good
    0.7 kilometres from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
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    • Waterfront
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 April 2018
    My wife and I stayed at this nice, updated rental and really enjoyed our time. The location was great, with a deck right on a canal. We were walking distance to the beach.The...
    Reviewed 23 March 2018
    The beach house was awesome!!! Had everything we needed. It was true to the pictures on line. Jenny the owner was awesome, got back to we when I had questions right away. We...
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    About this property
    Sea Waves cottage is located at north end of anna maria island. Brand new renovation, 3 bedroom with 2 bath room, with private dock, sailboat direct to bimini bay, unobstructed , natural view of bimini bay. Less than three minute walk to beach, walking distance to pine ave and the city pier and...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Anna Maria Island 'High End' Vacation Rental1 / 21
    (2)Excellent
    0.7 kilometres from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Internet Access
    • Washer
    • Patio
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 March 2018
    The location is perfect - walking distance from both the beach and the Pine Avenue shops. This is a beautiful 2 bedroom home, outfitted with every detail. The pool and hot tub...
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    About this property
    The home is immaculately clean and whimsically decorated, professionally landscaped, and boasts one of the larger pools larger backyards and larger 2 bedroom homes on the Island. The spa is accented by iridescent glass. The 20' tall tiki hut was hand-built by Native Americans and houses the bar and...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Hooks Haven - 3bed beach front1 / 20
    (1)Excellent
    1.0 kilometres from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Central Heating
    • Terrace
    • Waterfront
    • Ocean Views
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 May 2018
    We had a girls’ weekend and choose this location. Beach chairs, towels, washer-dryer, bikes.....perfect. Not a great view but only a few steps from the beach and central to...
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    About this property
    This 3 bedroom 2 bath home is on the north end of Anna Maria Island and can be combined with Pirate Cove (a separate building ) to make a 5 bedroom beach front vacation home. All bedrooms in Hooks Haven are Queen size. Two bedrooms are on the main floor and one is on the second floor. Spiral...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.4 kilometres from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Parking
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    • 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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    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    AMI Coastal Retreats- 'Island Oasis'1 / 42
    (2)Excellent
    0.3 kilometres from Anna Maria City Pier
    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 15 June 2018
    The location is amazing for boats/jet skis. The house is perfect for up to two families with two master suites and an additional half bath. The kitchen is well-equipped with...
    Reviewed 1 October 2015
    I chose Island Oasis as it ticked every box. This is a beautiful island and the beach is very easy to access, as such I wanted a property with a pool, suitable for two couples...
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    About this property
    Step into an ultra private, secluded, tropical paradise with a lush canal front setting in quiet cul-de-sac located on the north end of Anna Maria Island. There is a beautiful heated pool just steps outside your door. The back yard has multiple areas to relax away the day and enjoy the amazing view...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.6 kilometres from Anna Maria City Pier
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Balcony
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    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pelican Roost 505 - Private canal home 5 Bedroom/ 5 Bath with private pool, maximum occupancy of 10 people. Distance to the Beach: 5 long blocks This gorgeous three story home in the city of Anna Maria, is an easy walk from Pine Avenue and the City Pier, with direct water views, front and rear,...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    1.0 kilometres from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
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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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    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.7 kilometres from Anna Maria City Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sea Haze Cottage is a completely renovated and updated private beach cottage, that is just perfect for a family or for one or two couples. It has a great room that leads to a large screened porch overlooking the deck, pool, spa and canal. The cottage is located in the quiet north end of Anna Maria...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Newly renovation bay side cottage: Sea Breeze1 / 21
    (1)Excellent
    0.7 kilometres from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Cable/satellite TV
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    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sea Breeze cottage is located at north end of Anna Maria island. Brand new renovation, 2 bedrooms with 2 bath rooms, with private dock, sailboat direct to Bimini bay, unobstructed , natural view of Bimini bay. Less than three minute walk to beach, walking distance to pine ave and the city pier and...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Charming 2 Bedroom/2 Bath Cottage on a Canal1 / 22
    (2)Excellent
    0.4 kilometres from Anna Maria City Pier
    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 3 August 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 26 April 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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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    North Shore Villa Anna Maria1 / 27
    (3)Very good
    0.7 kilometres from Anna Maria City Pier
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Reviewed 15 September 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 29 February 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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    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Copacabana1 / 21
    (1)Excellent
    0.7 kilometres from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Garden
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 November 2017
    We have had a wonderful two week stay at Copacabana, it is a very well presented and comfortable holiday home, which has recently been modernised to a high standard throughout...
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    About this property
    Copacabana is newly remodeled 3 bedroom, 2 bath private home that sits right on the canal in Anna Maria in a very quiet neighborhood. There is now a brand new kitchen for entertaining and new tile floors flow throughout and with a designer’s stylish touch, you will feel you have found your home...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.7 kilometres from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    209 Spring - Private home 3 Bedroom / 2 Bath with private pool, maximum occupancy of 8 people. Distance to the Beach: 1 Block Spring into the waves!~ 209 Spring. 3 bedroom, 2 bath raised home in quiet, residential area of Anna Maria. Private pool. Pool heat optional * $20/day. 1 block to...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.8 kilometres from Anna Maria City Pier
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Washer
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! 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....
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Mangoes on Magnolia1 / 46
    (12)Excellent
    0.6 kilometres from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Parking
    • Patio
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 December 2017
    I can't recommend this property enough. We parked our car on Friday night, and didn't have to get back in it until we drove home on Sunday. Everything is close by and the...
    Reviewed 15 August 2016
    Was pleasantly surprised when arrived. Lots of space to store our gear, plenty of space and rooms inside which are more comfortable than most hotels. Comfy furniture, lovely...
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    About this property
    Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! Location, location, location. Welcome to the quaint and quiet north end of Anna Maria Island! This classic AMI elevated, open floor plan vacation rental boasts three bedrooms and two baths with plenty of room for a...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.5 kilometres from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Grill
    • Washer
    • Internet Access
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    • Air Conditioning
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! If you are looking for the picture-perfect spot to vacation on Anna Maria Island, look no further! This beautiful Anna Maria vacation rental is spectacularly decorated throughout! Open and airy, with a fantastic...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.8 kilometres from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the Pier House! What a location and north of Pine Avenue! An old style florida three bedroom/two bathroom cottage on the north end of the Island! Pier House is right around the corner from the Rod and Reel Pier where you can enjoy the famous grouper sandwich. The Cottage is a short walk...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beach Walk1 / 23
    (3)Excellent
    0.7 kilometres from Anna Maria City Pier
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 June 2017
    What on earth can I say about beach walk ,well I arrived with my husband and 2 daughters ,one 27 yrs old and one 34,yrs old and as soon as we walked into this home my eldest...
    Reviewed 20 March 2016
    My partner and I stayed at Beach Walk twice and absolutely loved it. Everything here is top notch. The property is immaculate and extremely comfortable. We enjoyed the privacy...
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    About this property
    Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! Start your relaxing vacation at Beach Walk, located just a block from the white sand beaches of Anna Maria Island. This lovely two bedroom, one bath, home has been completely remodeled and fabulously decorated! Cozy...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.5 kilometres from Anna Maria City Pier
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Grill
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    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful luxury beach front condominium for rent for the first time. There's only 2 condo's on the entire property. This condo is 3500 square feet including gourmet kitchen, dining room, living room with fireplace and built in flat screen TV. screened in lanai overlooking the Gulf of Mexico, den...
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    Location Information
    Anna Maria, Anna Maria Island
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Sea Oats1 / 23
    (4)Excellent
    0.7 kilometres from Anna Maria City Pier
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Patio
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    • Air Conditioning
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 March 2018
    Having had a disasterous week at another property the week before moving to Sea Oats, it was such a relief to walk into a very clean and welcoming property. A great location...
    Reviewed 6 May 2017
    How could you not love this location- a few hundred feet from the beach with the added bonus of a pool & canal in the backyard.We loved the flow of the house,the openness...
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    About this property
    Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! Spend your relaxing vacation at Sea Oats, located just a block from the white sand beaches of Anna Maria Island. This lovely two-bedroom, one-bath vacation rental has just been completely remodeled and fabulously...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1.0 kilometres from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Ocean Views
    • Waterfront
    • Central Heating
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    0.5 kilometres from Anna Maria City Pier
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    313 Palm Ave - Duplex 2 Bedroom /1 Bathroom , maximum occupancy of 4 people. Distance to the Beach: 5 min walk Enjoy an old fashioned Florida beach vacation at this wonderful cottage just 5 min walk from the beach! Located right in the heart of the village of Anna Maria, not only can you walk to...
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    Location Information
    Anna Maria, Anna Maria Island
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.7 kilometres from Anna Maria City Pier
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Washer
    • DVD Player
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Latitude Adjustment! Here it is: that stress-free attitude you've been wishing for in the 'Old Florida' at Latitude Adjustment. This super-walkable villa is within steps of beach, bay, restaurants, bars, shops, piers, and more. A charming 2 bedroom, 1 bath home, Latitude has been recently...
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    Location Information
    Anna Maria, Anna Maria Island
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Casa Palma1 / 23
    (2)Very good
    0.4 kilometres from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Washer
    • Air Conditioning
    • Balcony
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 June 2017
    The house was beautifully decorated but a little on the older side could have been cleaned better a lot of dust and the pool was small and not cleaned the entire time we were...
    Reviewed 14 March 2017
    We rented this wonderful house for two weeks, two years in a row. Tried to rent it this year but couldn't find it. Perhaps they switched to a new rental company?This is a...
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    About this property
    Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! If you are looking for the perfect spot to vacation on Anna Maria Island, look no further! This beautiful Anna Maria vacation rental is fabulously decorated throughout! Open and airy, with a fantastic living area,...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.6 kilometres from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! 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 private deep water dock,...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.5 kilometres from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Beach to Bay Getaway! Anna Maria Island was a quaint historic fishing village and has become one of the top travel destinations by travelers from around the world. Known for world class beaches, top rated restaurants, fishing/boating and laid back stmosphere. This...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    A Place in Paradise A1 / 23
    (6)Excellent
    0.7 kilometres from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 October 2018
    This is so perfect! Excellent accomodations and exceptionally clean which is a must! They literally have everything you need here for a lovely stay at the beach and beyond. Very...
    Reviewed 1 June 2018
    We have been coming to Anna Maria for a while, and for obvious reasons, the island is becoming very popular. Inevitably, this has made rentals at a reasonable price tough to...
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    About this property
    Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! We have a place in paradise waiting for you! This Anna Maria Island vacation rental is located in Anna Maria and is just a short two block walk to the white sand beach of the Gulf of Mexico. A nice living area with...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Little Slice of Paradise1 / 24
    (2)Very good
    0.1 kilometres from Anna Maria City Pier
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Internet Access
    • Parking
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 July 2017
    This Apartment was perfect for us. Very clean and a great location on Pine Avenue. We were early but the apartment was ready. Great having a balcony as well. So peaceful sitting...
    Reviewed 27 October 2015
    We love Anna Maria! This 2 bedroom condo was ideally located right on the canal, which is right off Tampa Bay. We were able to drop our paddle boards or kayaks right off the...
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    About this property
    Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! Located on the north end of Anna Maria Island in the city of Anna Maria on historic Pine Avenue, this two-bedroom, one-bathroom second-floor vacation rental condo has been completely updated and is picture perfect. So...
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    Location Information
    Anna Maria, Anna Maria Island
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.5 kilometres from Anna Maria City Pier
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the crystal clear pool at Oleander House! An appealing blend of comfort and Florida casual in this pretty four bedroom vacation rental home which is spacious and airy and extremely family friendly. Located directly across from the bay with views of the Sunshine Skyway Bridge and children's...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    0.5 kilometres from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Internet Access
    • Grill
    • Terrace
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Gladiolus House and what a location, north of Pine Avenue! An old style florida two bedroom/two bathroom cottage on the north end of the Island! Not enough room for all the family, Gladiolus House is right behind Hibiscus House so why not rent both properties to accommodated...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.4 kilometres from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
    • Internet Access
    • Grill
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The desirable North end of Anna Maria and a peaceful canal front setting make this beautiful home a perfect vacation getaway! Gladiolus on the Water was recently updated with new furnishings and fresh paint, all tied together with a festive and tropical theme! With a comfortable couch and...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Starfish Dreams1 / 22
    (12)Excellent
    0.3 kilometres from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Washer
    • Grill
    • Air Conditioning
    • Waterfront
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 January 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 8 October 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
    Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! 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...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.6 kilometres from Anna Maria City Pier
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Balcony
    • Housekeeping Included
    • Patio
    • Washer
    • Grill
    • Central Heating
    • Waterfront
    Suitability
    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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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    0.8 kilometres from Anna Maria City Pier
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Washer
    • Grill
    • Balcony
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! Welcome to 5 O'Clock Somewhere! Discover outdoor living at it's finest! 5 O'Clock somewhere has a downstairs cabana room that you may never leave. It offers indoor and outdoor dining, complete with a flat screen...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Life is Good at the Beach1 / 20
    (2)Very good
    0.9 kilometres from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Washer
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 January 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 23 November 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
    Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! 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...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.8 kilometres from Anna Maria City Pier
    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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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.1 kilometres from Anna Maria City Pier
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Washer
    • Cable/satellite TV
    • Grill
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! Salt Box Cottage is newly renovated, bright, clean, cozy and the perfect place for an Anna Maria Island vacation. This quaint vacation rental cottage is just steps to Tampa Bay and five blocks to the beautiful...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Bradley's Beach House1 / 21
    (13)Very good
    0.8 kilometres from Anna Maria City Pier
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Internet Access
    • Cable/satellite TV
    • Washer
    • Patio
    • Grill
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 February 2018
    We rented Bradley Beach House for Super Bowl week and couldn’t ask for a better place to stay with friends and family for the week! Clean, well kept property close to everything...
    Reviewed 30 June 2017
    Great location! Steps to the beach and walking distance to nice shop and restaurants. But wish we would have known construction was going on at two different properties right...
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    About this property
    Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! Steps from the white sand beaches of Anna Maria, this four-bedroom, three bath, elevated house is just the place to build sand castles and memories! Located on Pine Avenue in Anna Maria, this charming beach vacation...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    0.3 kilometres from Anna Maria City Pier
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Washer
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Balcony
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! 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...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    1.0 kilometres from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come discover 'Paradise Cottage' with all it's old Florida charm as well as newly updated appliances and decor.  This lovely and colorful two bedroom, two bath home feels brand new.  You'll enjoy tile floors throughout, a large eat-in kichen, comfortable and attractive furnishings with an updated...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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