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Holiday Rentals 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 December dates now. Secure your holiday rental today, and have the perfect trip.
    All 100 Rentals in Anna Maria
    Gorgeous views,spectacular home!1 / 138
    (33)Very good
    0.4 kilometres from Anna Maria City Pier
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Crescent Wave1 / 120
    (24)Very good
    0.6 kilometres from Anna Maria City Pier
    4 Bedrooms, 3 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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    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
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Patio
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 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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    BEACHFRONT HOME, TRUE PARADISE , DOGS STAY FREE, GREAT VIEWS, WALKING BEACH1 / 44
    (4)Excellent
    0.4 kilometres from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Wi-Fi
    • Waterfront
    • Washer
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    • Grill
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Six of us ladies had a great time and loved the house! Laura was very helpful. Hope we can do it again.
    Reviewed 2 weeks ago
    Very nice location, perfect if seeking a private and quiet location. All amenities necessary for us were included. Will return.
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    About this property
    This stunning BEACHFRONT home was designed by an award winning Architect and is true paradise. The plan is open with the Living, Dining, Kitchen and Master Bedroom on the Waterfront adjacent to the deck which runs the entire length of the home. The elevated deck is a mere 10' from the waters edge....
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    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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    • Secure Parking
    • Wi-Fi
    • Private Garden
    • Washer
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 March 2018
    My husband and I come to Anna Maria Island annually and always stay here. It’s spotless, beautifully decorated, ultra comfortable beds and new shower heads. The location...
    Reviewed 5 March 2018
    The location of the house is close to the beach and you can also walk to all the shops and dinning or bike ride. Parking is right at the doorstep and it is on a quiet street...
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    About this property
    This quaint, old-Florida style rental is nestled in the north shore area of Anna Maria Island. Shabby chic style, located 2 blocks from the beach and 2 blocks from the bay! Only one block from Pine Ave., with its old-time feel with shops and salons. Steps from fine dining, the historic city pier,...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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
    • 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
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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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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    • Balcony
    • Grill
    • Washer
    • 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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    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 20 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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    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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    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
    • 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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Waterfront and dog-friendly home with private pool, dock, views, and lanai!1 / 29
    (1)Very good
    0.7 kilometres from Anna Maria City Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Washer
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Brand New Renovation Sea Waves Cottage1 / 16
    (8)Excellent
    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
    • Grill
    • 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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    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 2 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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    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
    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
    Watch the Dolphin's play from your deck, covered patio or right on your beach! You will enjoy this direct Bay Front home that has direct Bay Views from almost every room and the outside deck. The owners have done a wonderful job decorating this charming 2BR/2BA home in the true Island spirit! This...
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    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
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
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    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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    Anna Maria, Anna Maria Island
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Sea Oats:Family & Elderly Friendly Pool Home On Canal, One Block From The Beach!1 / 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
    • Parking
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • 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
    Spend your relaxing vacation at Sea Oats, located just a block from the white sand beaches of Anna Maria Island. This lovely two-bedroom, one-bath vacation rental has just been completely remodeled and fabulously decorated! Cozy and relaxing furnishings await you and your friends and family during...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    North Shore Villa Anna Maria1 / 54
    (3)Very good
    0.7 kilometres from Anna Maria City Pier
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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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 28 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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    Key West Condo - 1201 Gulf Drive North1 / 29
    (1)Excellent
    0.2 kilometres from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Terrace
    • Grill
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Island living at it's best! Vacation and Relax in this luxury condo located directly across the street from the beach. Key West North condo is a cozy 4 unit elevated complex with private pool, elevator and covered parking. This completely remodeled 2 Bedroom, 2 Bath unit features laminate flooring,...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Palm Court Villas- 210 B Magnolia Ave, Anna Maria1 / 26
    (1)Excellent
    0.7 kilometres from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 June 2017
    We brought two of our grandchildren to FL for a few days. We stayed in this little gem which is a block from the beach. So nice that we had the cart and beach items right...
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    About this property
    Palm Court Villas are located in the heart of Anna Maria Village with a short stroll to great local restaurants, shops and the Community Center. Beautiful white sand beaches are just one short block away. You have direct beach access to one of the best beaches on the Island. This section of 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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    Beach Walk: 2BR Family-Friendly Pool Home on Canal1 / 24
    (3)Excellent
    0.7 kilometres from Anna Maria City Pier
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Internet Access
    • Patio
    • Cable/satellite TV
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    • Parking
    • DVD Player
    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
    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 and relaxing furnishings await you and your friends and family during your...
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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, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It doesn't get much better than this! Relaxing on the Screened lanai overlooking the blue waters of Tampa Bay and the Gulf of Mexico. This elevated 3 bedroom, 2 bath Direct Bay Front home has wonderful views from the master bedroom, living room and screened lanai. Private setting close to Anna...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Island Oasis - 94 North Shore Drive, Anna Maria1 / 26
    (1)Excellent
    0.6 kilometres from Anna Maria City Pier
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 January 2017
    This home was immaculate. This was our first time to AMI and this by far was the best vacation ever. The locals are so nice and very helpful. So laid back and peaceful. There...
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    About this property
    Anna Maria Island Oasis- Pamper yourself by staying in this brand new Island home with vaulted ceilings, custom tile and cabinetry, along with your own Private heated pool. This home offers 4 Master Bedroom Suites each with it's own private Bath. Each bedroom has a King bed and each en-suite bath...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    0.7 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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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Tarpon Point - 302 Tarpon Street, Anna Maria1 / 70
    (2)Excellent
    0.2 kilometres from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Washer
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 2018
    Location is amazing, a wonderful property and great family home, with every amenity you could wish for in a rental. Hopefully one day in the near future we will be back.
    Reviewed 9 August 2018
    We had an excellent holiday here, this is our 4th rental villa on the island and I have to say it's gorgeous. So private with a huge pool, a small portion sheltered (which was...
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    About this property
    Swaying palms and a beautiful paver double drive lead the way to this Tropical Retreat on Anna Maria Island, Located just one block from Tampa Bay and 3 short blocks to the beautiful white sand Gulf Beach. This three-bedroom, two-bathroom home features volume ceilings, crown moldings, and open...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Island Place Cottage: Beautiful Pet-Friendly Cottage On Historic Pine Ave!1 / 46
    (9)Very good
    0.4 kilometres from Anna Maria City Pier
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 February 2018
    We decided to go to Ana Maria Island over Christmas 2017 because this was the year we had to share our grown and married children with their in-laws. We had never vacationed...
    Reviewed 29 June 2017
    Great location with shops and restaurants within walking distance. The two piers are also just a short walk away. The cottage is basic but very clean, an ideal base for a few...
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    About this property
    This vacation rental is located on Anna Maria Island's historic Pine Avenue, halfway between the Gulf of Mexico and the Anna Maria City Pier! This adorable, one bedroom cottage, with high beamed ceilings, wood floors and shabby chic décor throughout is ideal for a vacation getaway! This quaint...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located directly across from Tampa Bay, this gorgeous new custom luxury vacation rental looks out onto the beautiful bay waters from multiple large balconies. A rooftop deck provides outstanding 180 degree views of the turquoise waters, as well as the Anna Maria City Pier and the Sunshine Skyway...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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
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    • Terrace
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully renovated beach cottage in the heart of the village of Anna Maria. Walk to the beaches, shops and restaurants. Enjoy amazing sunsets at the beach or sip a glass of wine in the lush tropical gardens surrounding the cottage. 2 bedrooms with 2 full bathrooms. Quaint beach cottage in a...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Little Slice of Paradise: Very Nice Canal-Front Condo on Historic Pine Ave!1 / 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
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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 26 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
    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 much so, once you walk through the front door you'll feel as though you just...
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    Location Information
    Anna Maria, Anna Maria Island
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Gladiolus Hideaway - 712 Gladiolus St, Anna Maria Villa B1 / 26
    (1)Excellent
    0.2 kilometres from Anna Maria City Pier
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Central Heating
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 August 2018
    Perfect location & amenities for our family of 4. The owner has stocked the home with everything needed for a wonderful beach vacation. We loved it & hope to return one...
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    About this property
    712 Gladiolus, Anna Maria 'Villa B' - This cute 2 bedroom, 1 bath Villa is located at the quiet North End of Anna Maria Island just steps to beautiful white sand beaches. Just recently remodeled with all new kitchen, appliances and furnishings. Only 6 properties to the beach access. Nature lovers...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.3 kilometres from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On Island Time is exactly how you will feel when you stay in our newest vacation rental at Coastal Cottages AMI! This is the quintessential island cottage located on the north end of Anna Maria. It has 2 bedrooms, plus a den with sleeper sofa, two walk in shower bathrooms and has been totally...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.6 kilometres from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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, where you will have access straight out to Tampa Bay and the Gulf of Mexico! Located...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Canary Cottage- 317 Magnolia Ave, Anna Maria1 / 27
    (4)Very good
    0.5 kilometres from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 August 2018
    The house was very comfortable, clean, convenient and well supplied with all we wanted or needed for a wonderful week on AMI.
    Reviewed 11 August 2018
    The cottage was beautiful. Nice, updated decor and furnishings. Two very nice, large, bathrooms. The only thing i didn’t love about the house was the bonus room with the bunk...
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    About this property
    The Canary Cottage has 2 bedrooms plus a bunkroom - and 2 full baths and will Sleep up to 6. Located in the heart of Anna Maria City- This Key West charmer is elevated and has been updated with a new kitchen, new tile, fixtures, plus a new tub/shower! Updated furnishings, and appliances, which add...
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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 6 Quick View
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    • Terrace
    • Grill
    • Washer
    • Internet Access
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 living area, Villa Palma has plenty of room for all of your family and friends. A...
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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 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Washer
    • Air Conditioning
    • Private Garden
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cute beachy Canal front 3 bedroom, 2 bathroom Home has a Private Pool and a boat dock and is just 2 short blocks to the beach. Kitchen includes a dishwasher and microwave. Enjoy the Gulf breezes down the canal from the screened lanai or the back yard area. Bring your boat and go fishing or...
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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 Dreams: Beautiful Pine Avenue Canal Home With A Private Dock & Pool!1 / 24
    (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
    15% off bookings made arriving now to Dec. 15th, 2018 Starfish Dreams is the perfect place to start your vacation! This family-friendly vacation rental is centrally located on Pine Avenue in the city of Anna Maria on Anna Maria Island, halfway between the Gulf of Mexico and Tampa Bay. If that...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.3 kilometres from Anna Maria City Pier
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Waterfront
    • Air Conditioning
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A truly luxurious vacation experience is waiting for you at this canal-front Anna Maria vacation rental. This home is well-appointed with a private pool, dock access, five parking pots, and free trolley stops within walking distance. You'll have everything your family and friends need for an...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Pineapple Cottage: Lovely Pet-Friendly Cottage on Anna Maria's Historic Pine Ave1 / 21
    (15)Excellent
    0.4 kilometres from Anna Maria City Pier
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Parking
    • Patio
    • Cable/satellite TV
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    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2018
    I loved the stay at Pineappe Cottage and I hope we will return before too long. We have stayed a couple of times on AMI and love it here. We decided to look at a property with...
    Reviewed 31 July 2017
    Pineapple Cottage is located on Pine close to shops and near the beach. I loved to stay at this very clean and well maintained cottage. It has everything what's needed and is...
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    About this property
    Pineapple Cottage, centrally located on historic Pine Avenue in the city of Anna Maria, is the perfect place to slow down and catch your breath! This Anna Maria Island cottage is tastefully decorated with wood floors, granite and stainless kitchen, tiled shower,professional linen service and...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.2 kilometres from Anna Maria City Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a spacious home that is just steps to the beach? This nicely appointed 3BR/2.5BA lsland home is just steps from the beautiful white sand beach in the quaint city of Anna Maria. The home is decorated in true Island style and is cute, cute cute!!. Nice large bedrooms. The Master Bedroom...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 bed luxury upscale executive waterfront home1 / 50
    (10)Very good
    0.3 kilometres from Anna Maria City Pier
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    • Waterfront
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 February 2017
    Bayview Dream did not disappoint! It truly was a dream holiday for us. The house itself is beautifully decorated and very well equipped - plenty of towels (indoor and pool...
    Reviewed 17 January 2016
    We spent a week in this lovely home. The weather was cool, so we didn't use the pool, but there was a beautiful pool with a dock right out the back door. The home was spacious...
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    About this property
    Location, Location, Location. Upscale luxury executive four bedroom waterfront home with private pool dock and elevator. Stylishly furnished and dressed, modern build 2006 - this is our family second home - and is home from home available to you. This exclusive executive property is in the...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Mangoes on Magnolia: 3BR Classic Beach Home w/Pool1 / 24
    (12)Excellent
    0.6 kilometres from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Patio
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 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
    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 large family or group to spread out and relax! Two queen-size beds, a full-size...
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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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    • Grill
    • Washer
    • Waterfront
    • Cable/satellite TV
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located at the quiet North end of Anna Maria this 3BR/2BA canal front home comes with exceptional views! There are two screened lanais, a boat dock and a garage. Brand new Kitchen with granite countertops and new appliances. Updated furnishings. There are two full size beds, one twin and a queen...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 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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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Casa Palma: Absolutely  Gorgeous Family-Friendly Pool Home In Anna Maria!1 / 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
    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, Casa Palma has plenty of room for all of your family and friends. The gourmet...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.1 kilometres from Anna Maria City Pier
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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 powder-soft, white sand beach and turquoise water of the Gulf of Mexico! Accommodations...
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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
    • Washer
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    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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    Palm Court Villas- 210 A Magnolia Ave, Anna Maria1 / 22
    (1)Very good
    0.6 kilometres from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Grill
    • Wi-Fi
    • Cable/satellite TV
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 2018
    Everything was great except the circuit breaker in the rental stop working towards the last day, affected the refrigerator and was an inconvinience. The beach was superb and a...
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    About this property
    Palm Court Villas are located in the heart of Anna Maria Village with a short stroll to great local restaurants, shops and the Community Center. Beautiful white sand beaches are just one short block away. You have direct beach access to one of the best beaches on the Island. This section of 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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    0.6 kilometres from Anna Maria City Pier
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Grill
    • Waterfront
    • Patio
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *Please note, all guests occupying this property who are under the age of 25 must be accompanied by a parent or legal guardian. Thank you!* *Check in time is 4:30 PM ET - If Early check-in becomes available you will receive an email stating it is available. If you do not receive an email,...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    0.5 kilometres from Anna Maria City Pier
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Cable/satellite TV
    • Internet Access
    • DVD Player
    • Parking
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cute one bedroom/one bath with open floor plan and adorable furnishings and now featuring our professional linen service! Colorful decor and beadboard accents adorn the unit. There is a queen sized bedroom with flat screen TV and sliders going out to an outdoor deck and sitting area. This...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.2 kilometres from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious and comfortable three bedroom, two bath home located only one house to the beach! Enjoy the 'beachy' atmosphere in this great beach house with it's cute decor and updated furnishings. Enjoy the gulf breezes on the screened lanais or enjoy the Florida sunshine in the enclosed Florida room....
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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