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Holiday Rentals near Happy Paddler Kayak Tours & EcoVentures

Anna Maria Island, Florida 34421
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    Travellers to Anna Maria Island are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    All 100 Rentals in Anna Maria Island
    BEACHFRONT HOME, TRUE PARADISE , DOGS STAY FREE, GREAT VIEWS, WALKING BEACH1 / 22
    (2)Excellent
    0.7 kilometres from Happy Paddler Kayak Tours & EcoVentures
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Crescent Wave1 / 80
    (22)Very good
    0.7 kilometres from Happy Paddler Kayak Tours & EcoVentures
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Gorgeous views,spectacular home!1 / 46
    (26)Very good
    0.8 kilometres from Happy Paddler Kayak Tours & EcoVentures
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Anna Maria's Coconut Breeze Estate - no cleaning fee1 / 49
    (4)Excellent
    0.6 kilometres from Happy Paddler Kayak Tours & EcoVentures
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Air Conditioning
    • Grill
    • Patio
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 November 2017
    Really beautiful home and close to everything. Huge place. 2 minute walk from Rod and Reel Pier and 5 minutes to Bean Point (though wouldn't recommend swimming there, current...
    Reviewed 9 May 2017
    This home really does have the "wow factor." The moment we walked through the door we were blown away. The best of everything is in this home...the kitchen appliances...
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    About this property
    This beautiful gem in the much coveted City of Anna Maria's north end. It is a single family home located on a quite street. Easy walk to the gorgeous white sand Bay and sugary sand Gulf of Mexico beaches with striking sunsets . With Pine Ave (our fantastic little Main St.) just a short stroll from...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Dolphin Pointe1 / 39
    (2)Excellent
    0.7 kilometres from Happy Paddler Kayak Tours & EcoVentures
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Balcony
    • Washer
    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Heated)
    • Porch
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 November 2017
    My sister and 2 friends came here for 6 days. The house was perfect, the weather was cool and windy the 1st couple of days, but with the pool being secluded, we got to hang out...
    Reviewed 30 January 2017
    The house is just as the pictures suggests. The floor plan was very spacious. We traveled with 6 adults (4 were college students) and there was ample room to spread out. The...
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    About this property
    The lovely Dolphin Pointe resides on the highly desirable north end of Anna Maria, just a three houses away from the beach at Bean Point and a short walk to Rod and Reel Pier. The spacious open concept living area is perfect for spending quality time with the family. The home exudes an Island charm...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    0.6 kilometres from Happy Paddler Kayak Tours & EcoVentures
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Central Heating
    • Terrace
    • Waterfront
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    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 bedroom 2 bath home is on the north end of Anna Maria Island and can be combined with Pirate Cove (a separate building ) to make a 5 bedroom beach front vacation home. All bedrooms in Hooks Haven are Queen size. Two bedrooms are on the main floor and one is on the second floor. Spiral...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.6 kilometres from Happy Paddler Kayak Tours & EcoVentures
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
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    Smoking allowed
    About this property
    742 Jacaranda- Single Family home 3 bedrooms/ 2.5 baths, maximum occupancy of 6 people. Distance to the Beach: 50 yards This well appointed home has recently been renovated. The balconies have all been redone, new stairway and all new furniture in the living room and bedrooms The master bedroom...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.8 kilometres from Happy Paddler Kayak Tours & EcoVentures
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Balcony
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    • 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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    Charming 2 Bedroom/2 Bath Cottage on a Canal1 / 22
    (1)Excellent
    0.7 kilometres from Happy Paddler Kayak Tours & EcoVentures
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • DVD Player
    • Patio
    • Grill
    • Terrace
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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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    Anna Maria Island 'High End' Vacation Rental1 / 21
    (2)Excellent
    0.4 kilometres from Happy Paddler Kayak Tours & EcoVentures
    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 4 weeks ago
    The location is perfect - walking distance from both the beach and the Pine Avenue shops. This is a beautiful 2 bedroom home, outfitted with every detail. The pool and hot tub...
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    About this property
    The home is immaculately clean and whimsically decorated, professionally landscaped, and boasts one of the larger pools larger backyards and larger 2 bedroom homes on the Island. The spa is accented by iridescent glass. The 20' tall tiki hut was hand-built by Native Americans and houses the bar and...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Paradise at the Bayou1 / 20
    (4)Excellent
    0.2 kilometres from Happy Paddler Kayak Tours & EcoVentures
    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 2 weeks ago
    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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    BEACH NEST  * Pool * Hot tub * Fishing Dock * Kayaking * Steps to Gulfside beach1 / 23
    (12)Very good
    0.5 kilometres from Happy Paddler Kayak Tours & EcoVentures
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 February 2017
    Beach Nest is wonderful. Decorated with flair and beachy elegance, it feels like a home, not a rental. There is everything you need and more. You can walk to the beach with your...
    Reviewed 21 January 2017
    The Beach Nest is wonderful and relaxing!! The pool, the home, the cleanliness, the cuteness, and the canal were all such a treat for us! We will be back for sure!
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    About this property
    Calling all sun worshipers and water lovers! Ahhhh-Welcome to Beach Nest! Ready to satisfy that oh-my-gosh-we-need-a-vacation? Kick off your shoes and throw them in the back of the closet. Promise yourselves to live in bathing suits from breakfast to bedtime! Vacationers, dreamers, honeymooners,...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    0.3 kilometres from Happy Paddler Kayak Tours & EcoVentures
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    • Terrace
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pelican Roost 505 - Private canal home 5 Bedroom/ 5 Bath with private pool, maximum occupancy of 10 people. Distance to the Beach: 5 long blocks This gorgeous three story home in the city of Anna Maria, is an easy walk from Pine Avenue and the City Pier, with direct water views, front and rear,...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    0.7 kilometres from Happy Paddler Kayak Tours & EcoVentures
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Little Slice of Paradise: 2BR Canal-Front Condo1 / 24
    (2)Very good
    0.2 kilometres from Happy Paddler Kayak Tours & EcoVentures
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    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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    Anna Maria, Anna Maria Island
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Ocean View 3 bedroom, pool, North Shore Drive1 / 123
    (36)Excellent
    0.8 kilometres from Happy Paddler Kayak Tours & EcoVentures
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Ocean Views
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 November 2017
    Great place I had my birthday party here it was so fun Very close to the water every thing was to the t in cleanliness sleep 6 of us it was all around one of the best beach...
    Reviewed 30 July 2017
    We love this beach house! It has everything, is always clean, great location, and the owner is the nicest to deal with! We will definitely be back...if someone else doesn't book...
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    About this property
    Just steps to the sugar sand beaches in Anna Maria, FL. Your 3 bedroom, 2 bath, pool home with sweeping gulf views from two elevated front porches is located in the charming northern end of Anna Maria on North Shore Drive. If you are looking for a tropical vacation home to just relax, take long...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 bed luxury upscale executive waterfront home1 / 50
    (10)Very good
    0.4 kilometres from Happy Paddler Kayak Tours & EcoVentures
    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 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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    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Whispering Pines: 2BR Classic Cottage Near Beach1 / 24
    (10)Excellent
    0.6 kilometres from Happy Paddler Kayak Tours & EcoVentures
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Patio
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 January 2018
    We stayed over Christmas a the Whispering Pines Cottage. It was well appointed and had beachy decorations which is perfect for the location. The beds were comfortable and the...
    Reviewed 1 March 2016
    Loved this Beautiful Cottage!Steps from the White Sand and Peaceful Beach.I will be back to this Sweet Island!!
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    About this property
    This two-bedroom, two-bath vacation rental is located on the quiet north end of Anna Maria Island. Whispering Pines is just three houses from one of the most beautiful beach accesses on the island. This classic 1920's beach cottage has been lovingly restored. The original wood molding, fireplace,...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pineapple Cottage: 2BR Quaint Pet-Friendly Cottage1 / 21
    (14)Excellent
    0.4 kilometres from Happy Paddler Kayak Tours & EcoVentures
    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 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...
    Reviewed 19 May 2017
    We stayed at the Pineapple Cottage from May 11 to May 18.Just my husband and I. We loved the location. You can walk to the beach either on the gulf or the bay. Walked to Beach...
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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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    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Wave Crest: 3BR Gulf-Front Beachfront Cottage1 / 25
    (6)Excellent
    0.8 kilometres from Happy Paddler Kayak Tours & EcoVentures
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Waterfront
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2017
    We stayed here at the end of June 2107. We have stayed in the same area on Anna Maria a few house to the north and love this area. It is quiet even when it's busy! Wave Crest...
    Reviewed 23 May 2016
    We were excited about renting Wave Crest due to the pictures and information we had previously received. However, nothing prepared us for this beautiful cottage with the...
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    About this property
    Take just four steps from Wave Crest's back door and sink your toes into the white sand beach of Anna Maria Island or enjoy views of the Gulf of Mexico from the deck, Florida room, or the four Adirondack chairs right on the sand. This gulf-front cottage is located directly on the beach and will...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.7 kilometres from Happy Paddler Kayak Tours & EcoVentures
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Beachy Keen 408 - Private home 3 Bedroom/ 2 Bath with private pool, maximum occupancy of 6 people. Distance to the Beach: 1 1/2 block Here delightful and fun Caribbean Cool décor welcomes you to the sub tropic cozy of Anna Maria Island. A charming island home within easy walking distance to the...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Mangoes on Magnolia: 3BR Classic Beach Home w/Pool1 / 24
    (12)Excellent
    0.7 kilometres from Happy Paddler Kayak Tours & EcoVentures
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    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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    0.3 kilometres from Happy Paddler Kayak Tours & EcoVentures
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    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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    Sea Oats: 2BR Elderly-Friendly Pool Home on Canal1 / 23
    (4)Excellent
    0.6 kilometres from Happy Paddler Kayak Tours & EcoVentures
    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
    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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    Jacaranda Artist Retreat1 / 17
    (2)Average
    0.7 kilometres from Happy Paddler Kayak Tours & EcoVentures
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Outdoor Dining Area
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 December 2017
    The house came complete with everything to make our stay comfortable. We loved the cozy charm of the home, with the owner's original artwork, and comfortable furniture. The...
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    About this property
    As an artist this private three bedroom and two bath multi-level elevated vacation home has been our family retreat that inspires many paintings of Anna Maria Island. Located on the secluded North End you will enjoy the tranquility of the Island and have an easy stroll to the Gulf of Mexico and the...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Absolutely Anna1 / 24
    (1)Excellent
    0.8 kilometres from Happy Paddler Kayak Tours & EcoVentures
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
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    • Internet Access
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 July 2016
    Very nice house and location! Plenty of room for all of us! Great inside and outside! What an incredible outdoor area for family time!! Beach is so close and convenient...
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    LAST MINUTE SPECIAL - BOOK AND STAY NOW THRU 5/25/18 FOR 20% OFF!!! Absolutely Anna is just that -- the epitome of the beach experience you want to have when you visit the beautiful north end of Anna Maria Island. Only two houses away from the footpath to Bean Point, you are on the gorgeous white...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    AMICoastal Rentals ' Island Oasis'1 / 42
    (1)Excellent
    0.3 kilometres from Happy Paddler Kayak Tours & EcoVentures
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Washer
    • Air Conditioning
    • Waterfront
    • DVD Player
    • Ocean Views
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 October 2015
    I chose Island Oasis as it ticked every box. This is a beautiful island and the beach is very easy to access, as such I wanted a property with a pool, suitable for two couples...
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    About this property
    Step into an ultra private, secluded, tropical paradise with a lush canal front setting in quiet cul-de-sac located on the north end of Anna Maria Island. There is a beautiful heated pool just steps outside your door. The back yard has multiple areas to relax away the day and enjoy the amazing view...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Bradley's Beach House: 4BR Pool Home Steps From Beach1 / 23
    (13)Very good
    0.8 kilometres from Happy Paddler Kayak Tours & EcoVentures
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Internet Access
    • Cable/satellite TV
    • Washer
    • Patio
    • Grill
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 February 2018
    We rented Bradley Beach House for Super Bowl week and couldn’t ask for a better place to stay with friends and family for the week! Clean, well kept property close to everything...
    Reviewed 30 June 2017
    Great location! Steps to the beach and walking distance to nice shop and restaurants. But wish we would have known construction was going on at two different properties right...
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    About this property
    Steps from the white sand beaches of Anna Maria, this four-bedroom, three bath, elevated house is just the place to build sand castles and memories! Located on Pine Avenue in Anna Maria, this charming beach vacation rental with a newer backyard pool is beckoning you to start your vacation now. A...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Starfish Dreams: 2BR Canal Home w/Dock & Pool1 / 24
    (12)Excellent
    0.3 kilometres from Happy Paddler Kayak Tours & EcoVentures
    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
    Starfish Dreams is the perfect place to start your vacation! This family-friendly vacation rental is centrally located on Pine Avenue in the city of Anna Maria on Anna Maria Island, halfway between the Gulf of Mexico and Tampa Bay. If that were not enough, it also has a heated pool and is on a...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    BON AMI: 3BR Family-Friendly Pool Home1 / 72
    (10)Very good
    0.8 kilometres from Happy Paddler Kayak Tours & EcoVentures
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Grill
    • Balcony
    • DVD Player
    • Washer
    • Air Conditioning
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 March 2017
    Had the pleasure of staying at Bon Ami for three weeks from mid February to mid March 2017. The house is very clean and comfortable with lots of sheets and towels, fully...
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    About this property
    BON AMI will be your 'good friend' after a vacation stay. Located on the north end of Anna Maria Island and a short distance to Bean Point and its beautiful beaches, this elevated pool home will beckon you back year after year! Beautifully decorated, this three-bedroom, two-bath vacation rental is...
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    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    19 Palms. Quaint Old-Florida Charm1 / 23
    (4)Excellent
    0.5 kilometres from Happy Paddler Kayak Tours & EcoVentures
    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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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Life is Good at the Beach: 3BR Family/Pet-Friendly1 / 40
    (2)Very good
    0.6 kilometres from Happy Paddler Kayak Tours & EcoVentures
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Washer
    • Patio
    • Air Conditioning
    • Cable/satellite TV
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    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 January 2016
    Life is Good at the Beach vacation rental is a beautifully, well maintained home. The picutres provided on the website accurately reflect the home and the beach house more than...
    Reviewed 22 November 2015
    Great well equipt house, everything we needed and more, close location to beach 5 mins walk, and to the free trolley bus stop 10 mins walk. The only downside of this property is...
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    About this property
    Life is Good at the Beach, located on the north end of Anna Maria Island, is a fantastic place to start your vacation. This three-bedroom, two-bath, vacation rental is just a five minute walk to the beautiful north end beaches near Bean Point and two blocks to the Rod & Reel Pier. The extra-large...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.7 kilometres from Happy Paddler Kayak Tours & EcoVentures
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    313 Palm Ave - Duplex 2 Bedroom /1 Bathroom , maximum occupancy of 4 people. Distance to the Beach: 5 min walk Enjoy an old fashioned Florida beach vacation at this wonderful cottage just 5 min walk from the beach! Located right in the heart of the village of Anna Maria, not only can you walk to...
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    Location Information
    Anna Maria, Anna Maria Island
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    744 Jacaranda Rd1 / 32
    (9)Very good
    0.6 kilometres from Happy Paddler Kayak Tours & EcoVentures
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 May 2013
    We loved this house for the week we spent in it. it was very clean and had all the little extras that make a holiday let in the U.S. ideal for a U.K. family - i.e. lots of beach...
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    About this property
    744 Jacaranda - Private home 3 Bedroom/ 3 Bath with private pool, maximum occupancy of 6 people. Distance to the Beach: 1 1/2 block Rates just reduced!! Book your holiday getaway today. $200 off any booking for the first two weeks in December 2018. Exclued the Holidays.(December 22, 2018 -January...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    AMI Retreat: 3BR Pool Home 200 Steps from Beach1 / 24
    (6)Very good
    0.6 kilometres from Happy Paddler Kayak Tours & EcoVentures
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Internet Access
    • Washer
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 December 2017
    This lovely house was close to the beach with a gorgeous heated pool. It has two spacious master-like bedrooms and a kids bedroom. One master bedroom was on the main floor and...
    Reviewed 4 August 2015
    We had a great trip to AMI. The pool is lovely. We liked all of the seating around the pool, the shaded areas, and the sunbathing ledge. It was clean and well-maintained. The...
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    About this property
    Located on the north end of Anna Maria Island, only 200 steps to the white sand beaches of the Gulf of Mexico, AMI Retreat is the perfect place for your vacation! With an estimated 2100 square feet, this gorgeous three-bedroom, two-bath family- and dog-friendly vacation rental has plenty of 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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    Beach Walk: 2BR Family-Friendly Pool Home on Canal1 / 72
    (3)Excellent
    0.6 kilometres from Happy Paddler Kayak Tours & EcoVentures
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Internet Access
    • Patio
    • Cable/satellite TV
    • Grill
    • Washer
    • 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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    Enchanted Cottage: 2BR Pet-Friendly Cottage1 / 24
    (2)Average
    0.3 kilometres from Happy Paddler Kayak Tours & EcoVentures
    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming, quiet, cozy, Enchanted Cottage is just steps to Tampa Bay and the Historic Anna Maria City Pier, a fun place to fish! A short five blocks to the beautiful powder-soft, white sand and turquoise Gulf water of Anna Maria Island. You may also enjoy the beautiful sunrise from the pier...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    0.2 kilometres from Happy Paddler Kayak Tours & EcoVentures
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bayou 5B - Condo ground floor 2 Bedroom / 1 Bath, maximum occupancy of 4 people. Distance to the Beach: 3 blocks Located on historic Pine Ave., Bayou 5B has great water views and a private dock. You can walk across the street to the Anna Maria City Pier and to shops and restaurants. This...
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    Location Information
    Anna Maria, Anna Maria Island
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Casa Palma1 / 23
    (2)Very good
    0.5 kilometres from Happy Paddler Kayak Tours & EcoVentures
    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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    Stunning luxury newly constructed beachfront villa1 / 22
    (22)Excellent
    0.7 kilometres from Happy Paddler Kayak Tours & EcoVentures
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 July 2017
    Beautiful three level beach house on the northern end of Anna Maria Island. Relaxing and very comfortable home where our family enjoyed reconnecting during our vacation after a...
    Reviewed 2 May 2017
    If you are looking for a property to relax by the beach or a swimming pool, this is about as good as it gets. There is nothing the owner's have not thought about. Great ocean...
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    About this property
    4 Bedroom 5 bath luxury beach front house sleeping 8 with heated pool separate spa numerous decks and stunning beach views from every room. We are located on the desirable family friendly island of Anna Maria. The house is direct beach front on the quiet upmarket north end of the island. Recently...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    0.4 kilometres from Happy Paddler Kayak Tours & EcoVentures
    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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    0.7 kilometres from Happy Paddler Kayak Tours & EcoVentures
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • DVD Player
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    • Wi-Fi
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cute 2 bedroom, 1 bath cottage is located at the quiet North end of Anna Maria Island just steps to beautiful white sand beaches. Only 200 yards to the beach access. Nature lovers will enjoy bird watching along the beaches at Bean Point. The Rod-N-Reel Pier is a short walk away for great...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.6 kilometres from Happy Paddler Kayak Tours & EcoVentures
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Ocean Views
    • Waterfront
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Direct Beach Front Home with 180 degree Gulf Views. Your backyard is a Private Beach and a beautiful view of Egmont Key & the Skyway Bridge. Walk to the Rod & Reel Pier where dolphins frolic every afternoon or walk to Pine Avenue for some local shopping. The living level has a full size kitchen,...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    0.7 kilometres from Happy Paddler Kayak Tours & EcoVentures
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tastefully decorated with an island flair! The White Egret has furnished and decorated this adorable two bedroom/one bath half duplex on the north end of Anna Maria Island! The master bedroom has a king sized bed, with sliding doors out onto a deck area, and the second bedroom has a queen sized...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    103 Pelican1 / 14
    (3)Very good
    0.2 kilometres from Happy Paddler Kayak Tours & EcoVentures
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Balcony
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 April 2016
    Hi! My husband and I rented this property and had the wonderful opportunity of having our adult children & their spouses come with us. There was 8 of us in total. We...
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    About this property
    103 Pelican - Private canal home 3 Bedroom/ 2 Bath with private pool, maximum occupancy of 6 people. At this spacious, family friendly home with private pool, grab your fishing pole, take the hand of a child and meander to the private dock, cast a line while dangling your feet and spending the...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Bean Point Beach Cottage1 / 22
    (1)Excellent
    0.7 kilometres from Happy Paddler Kayak Tours & EcoVentures
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Patio
    • Internet Access
    • Cable/satellite TV
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    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 July 2016
    This was our first visit to AMI. My booking of Bean Point Cottage was solely based on the pictures online, as it did not have any reviews. Bean Point Cottage was the perfect...
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    About this property
    Look no further for the perfect vacation rental! This three bedroom vacation rental is located on the serene north end of Anna Maria Island. Tastefully decorated with beautiful beach décor, and boasting a wonderfully open living and dining space, this vacation rental creates an exceptionally...
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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 Place Cottage: 1BR Pet-Friendly Cottage1 / 46
    (9)Very good
    0.4 kilometres from Happy Paddler Kayak Tours & EcoVentures
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Parking
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Grill
    • Air Conditioning
    • 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
    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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    0.6 kilometres from Happy Paddler Kayak Tours & EcoVentures
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Balcony
    • Patio
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Special May Pricing - The Best Time To Be On AMI! Welcome to Yellowbird; your home away from home at the north end of beautiful Anna Maria Island. Here you will enjoy unforgettable views and sunsets over the white sands of the Gulf from the home's multiple decks. This 4 bedroom custom home is the...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Lemonfish, stunning and spacious 4-bed rental!1 / 12
    (31)Very good
    0.7 kilometres from Happy Paddler Kayak Tours & EcoVentures
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Waterfront
    • Grill
    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 October 2015
    We were excited to book Lemonfish for our third visit to AMI. Having previously stayed in the centre of the island we were keen to check out the north end of the island. The...
    Reviewed 29 January 2015
    Perfection!Liza and the Sato Real Estate team went above and beyond in making my two week retreat flawless. I have never dealt with such a responsive rental team. Lemonfish...
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    About this property
    Lemonfish is a large, southern style rental property from unique designers Pineapplefish. Perched on a canal leading to Bimini Bay and minutes from the gorgeous beaches of Anna Maria Island, Lemonfish is a 3 storey sumptuous home that will accommodate up to 8 guests. The spacious open plan living...
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    Location Information
    Anna Maria Island, Florida
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    0.5 kilometres from Happy Paddler Kayak Tours & EcoVentures
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Balcony
    • DVD Player
    • Washer
    • Waterfront
    • Air Conditioning
    • Patio
    • Grill
    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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