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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 March dates now. Secure your holiday rental today, and have the perfect trip.
    All 84 Rentals in Anna Maria
    Gorgeous views,spectacular home!1 / 46
    (33)Very good
    0.4 kilometres from Anna Maria City Pier
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    BEACHFRONT HOME, TRUE PARADISE , 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 / 40
    (25)Very good
    0.6 kilometres from Anna Maria City Pier
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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 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...
    Reviewed 28 May 2018
    This house had everything we needed! Very clean and the pool was a big hit with the kids. Richard was very friendly and easy to work with. From booking to checkout it was as...
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    About this property
    Description We are located in the heart of the beautiful city of Anna Maria FL. We are one block from the historic Pine Ave with free trolley service to the entire island. We are two blocks to the beautiful white sand beach. Three blocks in the opposite direction is the bay and the historic City...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 3 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
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    • 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 4 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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    Cute cottage with patio and amazing location near Pine St. and the beach1 / 28
    (1)Excellent
    0.7 kilometres from Anna Maria City Pier
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    This cottage was a perfect size for 2 to 3 people. It had all the amenities we needed to live in immediately. It also was within short walking distance to the beach and several...
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    About this property
    Fall in love with this adorable, renovated island bungalow! Your location near the beach is hard to beat, and the outdoor sitting area ensures you're never far from the ocean breeze. Stay a while with the family or a group of friends and experience life on Anna Maria Island! You're about a block...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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
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    • Waterfront
    • Air Conditioning
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    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious and sophisticated, this waterfront and dog-friendly Anna Maria Island home puts the best of everything at your fingertips. Featuring a private dock, pool, and amazing water views, you’ll experience the luxurious side of Anna Maria Island paradise during your stay. This canalfront home...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    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
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    • Balcony
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    • 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 7 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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    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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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 5 Bedrooms, 5 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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    • 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 14 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 30 September 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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    0.7 kilometres from Anna Maria City Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • DVD Player
    • Grill
    • Balcony
    • Terrace
    Suitability
    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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    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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    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
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    • 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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    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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    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
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    • 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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    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 14 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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    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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    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 14 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
    Book Now & Save 15% Off When You Stay Before Dec. 31st, 2018! + 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...
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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
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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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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    0.5 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
    Book Now & Save 15% Off When You Stay Before Dec. 31st, 2018! + 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...
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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 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
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    • Patio
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    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 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 19 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
    Book Now & Save 15% Off When You Stay Before Dec. 31st, 2018! + 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,...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 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
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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 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
    Book Now & Save 15% Off When You Stay Before Dec. 31st, 2018! + 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...
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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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    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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    Anna Maria, Anna Maria Island
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    0.4 kilometres from Anna Maria City Pier
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You're sure to fall in love with this charming, dog-friendly Anna Maria cottage! Enjoy a fantastic location, beautiful beaches, and perks like a private heated pool. You, your loved ones, and dogs under 25 pounds (for a small nightly fee) will adore this home on Spring Avenue. The street stretches...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    0.7 kilometres from Anna Maria City Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You'll fall in love with the island life in no time when you stay at this canal front Anna Maria vacation rental! Platinum-rated and featuring a private pool, private spa, and three parking spots, this home features all the amenities you need for a relaxing Florida beach vacation. This great Anna...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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
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    • 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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    Book Now & Save 15% Off When You Stay Before Dec. 31st, 2018! + 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...
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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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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book Now & Save 15% Off When You Stay Before Dec. 31st, 2018! + 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....
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    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
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    • 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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    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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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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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 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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    Book Now & Save 15% Off When You Stay Before Dec. 31st, 2018! + 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...
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    Location Information
    Anna Maria, Anna Maria Island
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Starfish Dreams: Beautiful Pine Avenue Canal Home With A Private Dock & Pool!1 / 23
    (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
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    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 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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    Book Now & Save 15% Off When You Stay Before Dec. 31st, 2018! + 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...
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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
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Grill
    • Shared Outdoor Pool (Unheated)
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    • 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
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
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    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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    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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)
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    • 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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    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
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    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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    Anna Maria, Anna Maria Island
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, 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
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    • Waterfront
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    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located at the prestigious north end of Anna Maria, Blue Waters is a beautiful resort-style villa, just minutes walk from the gorgeous white sand beaches of Anna Maria Island and a few blocks away from the individual shops and restaurants of Pine Avenue. Situated on a peaceful residential street,...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    0.1 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
    Book Now & Save 15% Off When You Stay Before Dec. 31st, 2018! + 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...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.7 kilometres from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Chase sunsets and island vibes at this lovely beach house on Anna Maria Island. Offering a private heated pool, dog-friendly attitude, and access to a beach nearby, this house will ease you into vacation mode in no time! Located just over half a mile from the beach at City Park and a free trolley...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    0.3 kilometres from Anna Maria City Pier
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Parking
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    • Cable/satellite TV
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book Now & Save 15% Off When You Stay Before Dec. 31st, 2018! + 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...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    0.7 kilometres from Anna Maria City Pier
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Smoking allowed
    About this property
    604 North Shore Drive, Anna Maria FL 34216 Unit 4 Still Water'. Adorable, vintage 2 bedroom cottage on Lake La Vista located at the north end of the Island . Just 250 steps to the beach and just a short stroll to historic Pine Avenue for great shopping. Exceptional, 'Old Florida' charm! Shared...
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    Location Information
    Anna Maria, Anna Maria Island
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 5
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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
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    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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    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
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 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 30 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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    Book Now & Save 15% Off When You Stay Before Dec. 31st, 2018! + Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! 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...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.3 kilometres from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Kid friendly
    Smoking allowed
    About this property
    Book Now & Save 15% Off When You Stay Before Dec. 31st, 2018! + Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! 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...
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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, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Grill
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    • Internet Access
    • Waterfront
    • Cable/satellite TV
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Living The Dream' is a spacious 2,650 sq. ft. full-size private vacation rental home that has been recently remodeled with ALL NEW FURNISHINGS walk-in. (4) Bedroom, (3) Bath, accommodates (8) people: 2 Kings, 2 XL Twins, 2 Twins. NEW Stearns & Foster and new Sealy Posturpedic mattresses. The...
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    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
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Cable/satellite TV
    • Internet Access
    • DVD Player
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    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Book Now & Save 15% Off When You Stay Before Dec. 31st, 2018! + Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! Cute one bedroom/one bath with open floor plan and adorable furnishings and now featuring our professional linen service! Colorful decor and beadboard...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Island Place Cottage: Beautiful Pet-Friendly Cottage On Historic Pine Ave!1 / 23
    (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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    • Washer
    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
    Book Now & Save 15% Off When You Stay Before Dec. 31st, 2018! + Save 10% OFF When You Book Now & Stay Between January 5th & February 28th, 2019! 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...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    0.6 kilometres from Anna Maria City Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Grill
    • Internet Access
    • Terrace
    • Patio
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Haupia House is a newly remodeled two bedroom, two bathroom elevated canal front home with a pool, spa and a new boat dock in the city of Anna Maria. This fabulous house is only 2 short blocks to the white sand beaches of Anna Maria Island and a short walk to the restaurants and shops on Pine...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.4 kilometres from Anna Maria City Pier
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Private Outdoor Pool (Heated)
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Following an extensive renovation in 2018, Dragonfly Harbour is now a handsome four-bedroom, five-bathroom private vacation home situated on a deep water canal in close proximity to Bimini Bay. This is a venue designed to allow our guests every opportunity to enjoy all facets of beautiful Anna...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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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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    • 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 27 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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    0.7 kilometres from Anna Maria City Pier
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Terrace
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    div class='rtejustify'>Surrounded by water this 3 bedroom home sits on the beach with bay and intercoastal views! Relax and enjoy a cocktail while watching the dolphins on your spacious outdoor deck over looking the beach and views out to the Skyway Bridge. This ground level three...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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