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Holiday Rentals in Anna Maria

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    Travellers to Anna Maria are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 221 Rentals in Anna Maria
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    Sunshine Cottage - Private 30' Pool and Boat Dock, and steps away from the beach1 / 39
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Anna Maria Island Tropical getaway,Castvilla #1 Ground floor Retreat1 / 28
    (2)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Gorgeous views,spectacular home!1 / 44
    (20)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Blue Heron Waterfront House Anna Maria island1 / 23
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Ocean Views
    • Washer
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 June 2017
    We stayed for a week at the end of May 2017 after spending 10 days in Orlando. We were met at the property (even though we were a little late) and it was beautifully presented...
    Reviewed 23 May 2017
    The location is perfect. Walk 2 blocks to beach. Supermarket, drug store, bank, restaurants, salon, spa, less than 5 min. away. Many choices to dine/shop 3-10 min drive. The...
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    About this property
    Stunning ground level 3 bedroom/2 bath home with luxury finishes at every glance. Brand new to the market and recently renovated, this home is packed with designer finishes throughout from luxury linens in all three uniquely appointed bedrooms to furnishings that make this home feel like you are...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    116 Maple Breeze1 / 21
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
    • Grill
    • Internet Access
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 November 2015
    Wonderful location, The beach is at the end of Maple Ave, a quiet road only a 2 minute walk. The house is well situated, 4 bedrooms and 2 and 1/2 baths. I can only speak of...
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    About this property
    116 Maple Breeze Private home 4 Bedroom / 2 1/2 Bath , maximum occupancy of 7 people. 116 Maples is located on one of the prettiest streets in the village of Anna Maria, this gorgeous 4 bedroom, 2 and a half bath home is just steps away from the beach. This quiet, tree-lined street evokes...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    Anna Maria Island 'High End' Vacation Rental1 / 21
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Internet Access
    • Washer
    • Patio
    • Hot Tub
    • Satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Dolphin Pointe1 / 39
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Balcony
    • Washer
    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Heated)
    • Porch
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    The Nantucket1 / 27
    (21)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2017
    We rented this home over Spring Break with my brother and his family. The layout of this house is great as well as the location of the home on the island. There were 2 master...
    Reviewed 10 February 2017
    The location couldn't be better with an easy walk to the beach and several very good restaurants and free bus service running every half hour throughout the island. The beach...
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    About this property
    3 Story 'Nantucket' Style - 4 bedroom/ 3 bath villa is just a short walk to the beach - Nestled in a tropical setting, only a few blocks to the Gulf beach; private pool great for cooling off and a large sun deck. 4 Bedrooms/3 baths, large master suite with king size bed and a roman tub, 2nd...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Sand Castle well appointed home steps from beaches1 / 25
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Satellite TV
    • Air Conditioning
    • Washer
    • Grill
    • Private Outdoor Pool (Heated)
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    My family stayed in this home August 2016. The home is beautiful and we enjoyed our stay very much. The home was well equipped and pretty clean. I did has a couple issues at...
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    About this property
    Beautiful, recently renovated 1700 sf home that accommodates up to 8 people. Only a few steps to amazing sandy gulf beach. Enjoy all the amenities of a single level well appointed home with no stairs where you can step out to the beautifully landscaped pool area from your master bedroom or open...
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    Anna Maria, Anna Maria Island 34217
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    742 Jacaranda- Single Family home 3 bedrooms/ 2.5 baths, maximum occupancy of 6 people. 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 boasts a king size bed with a...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Crescent Wave1 / 40
    (13)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Patio
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 July 2017
    This house was close to everything(Beach, Souvenir Stores, Ice Cream Shops)!! The whole family enjoyed the awesome pool and hot tub and was a very close walk to the beach which...
    Reviewed 17 January 2017
    Crescent Wave was the perfect place for us to stay. We came down to surprise our parents for their 50th Wedding Anniversary (there were three couples) and this was just the...
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    About this property
    Description We are located in the heart of the beautiful city of Anna Maria FL. We are one block from the historic Pine Ave with free trolley service to the entire island. We are two blocks to the beautiful white sand beach. Three blocks in the opposite direction is the bay and the historic City...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Parking
    • Grill
    • Terrace
    • Wi-Fi
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning BEACHFRONT home was designed by an award winning Architect and is true paradise. The plan is open with the Living, Dining, Kitchen and Master Bedroom on the Waterfront adjacent to the deck which runs the entire length of the home. The elevated deck is a mere 10' from the waters edge....
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Anna Maria's Coconut Breeze Estate1 / 56
    (3)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Air Conditioning
    • Grill
    • Patio
    • Washer
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 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...
    Reviewed 8 May 2017
    What a great trip place!! Beautiful views - accessible to everything and great outdoor living space!! Loved the morning sunrise and evening sunsets from the rooftop. Thank you...
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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 34216
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Internet Access
    • Terrace
    • Balcony
    • Shared Outdoor Pool (Unheated)
    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. 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, from all living spaces. With 5...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Charming 2 Bedroom/2 Bath Cottage on a Canal1 / 19
    (1)Excellent
    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 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    BEACH NEST **Pool*Hottub*Dock*Steps to Gulfside beach* Shelling*SPOIL YOURSELF!1 / 23
    (11)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Hot Tub
    • 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
    DISCOUNT!! October and November only $199 per night! Thanksgiving discount $3500. YAH! Family Reunion at the beach! 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...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    103 Pelican1 / 14
    (3)Very good
    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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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Brand New Renovation Sea Waves Cottage1 / 16
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Satellite TV
    • Grill
    • Waterfront
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 May 2017
    Located on a quiet street, this cottage was exactly as advertised. It is updated and tastefully decorated. All beds (1 king, 2 queens) were very comfortable. Water pressure was...
    Reviewed 16 March 2017
    We were please to find this very clean unit on the ground floor of a two story house with private entrance, private deck, and parking. It is a 10-15 minute walk to the Anna...
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    About this property
    Sea Waves cottage is located at north end of anna maria island. Brand new renovation, 3 bedroom with 2 bath room, with private dock, sailboat direct to bimini bay, unobstructed , natural view of bimini bay. Less than three minute walk to beach, walking distance to pine ave and the city pier and...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    744 Jacaranda Rd1 / 32
    (9)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Terrace
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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. BOOK AND STAY NOW THROUGH THE END OF DECEMBER 2017 AND GET 10% OFF. EXCLUDES HOLIDAYS. Live the Florida lifestyle in this beautiful, comfortable 3 bedroom, 3 bath private home with private pool and...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Internet Access
    • Balcony
    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. 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 the beach. Large screen high def...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Satellite TV
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    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sea Breeze cottage is located at north end of Anna Maria island. Brand new renovation, 2 bedrooms with 2 bath rooms, with private dock, sailboat direct to Bimini bay, unobstructed , natural view of Bimini bay. Less than three minute walk to beach, walking distance to pine ave and the city pier and...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Grant's View ~ RA435391 / 15
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Grant's View is a private bay front home is located on the Tampa Bay where you will enjoy the amazing endless views of the open water, not to mention Dolphins swiming by! This bayfront home is furnished with beach style furniture which offers a rich and comfortable atmosphere and is fully...
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    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Starfish Dreams: 2BR Canal Home w/Dock & Pool1 / 24
    (10)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • DVD Player
    • Washer
    • Grill
    • Air Conditioning
    • Waterfront
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 January 2017
    Starfish Dreams is a great vacation rental: comfortable, cheery, bright, great screened in porch overlooking the canal. Very pet friendly. And the rental agency, Costal...
    Reviewed 25 June 2016
    Super location and gorgeous views of the canal and sunsets. Love the pool area and covered spot under the house.Great for paddle boards and kayak and fishing off the dock. We...
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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 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Fun In The Sun- 304 Gulf Blvd, Anna Maria1 / 20
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 April 2017
    This vacation home was perfect for our family - felt like home away from home! Everything we could possibly need came with! Home was clean! Location could not have been better...
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    About this property
    This vintage Island beachfront home has 4 sleeping rooms and 2 bathrooms. Enjoy the charm of yesterday in this great family beach house located between Palm and Magnolia Avenues. Excellent Gulf views, steps to beautiful, white sandy beaches. Centrally located in the City of Anna Maria walking...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Ocean View 3 bedroom, pool, North Shore Drive1 / 123
    (35)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Ocean Views
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 3 February 2017
    We arrived to an obvious effort to provide for above and beyond the norm in regards to service and accommodations. A bottle of wine and fresh flowers made for a welcome...
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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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    AMICoastal Rentals " Island Oasis"1 / 42
    (1)Excellent
    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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Balcony
    • 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. 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 the beach in a matter of seconds,...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Maple Cottage ~ RA433721 / 15
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Terrace
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 June 2017
    Maple Cottage was in a great location with no major streets to cross and just a very short walk to the beach. House was overall clean and well stocked. Furniture was in good...
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    About this property
    Time spent on Anna Maria Island should be savored. We islanders move through our day with a slower, mellower attitude. And being able to do that comes from having a sanctuary to eat, sleep, and daydream in. This is just what you’ll find at 120 Maple. A ground level vacation cottage in Anna Maria...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beachy Keen 408 - Private home 3 Bedroom/ 2 Bath with private pool, maximum occupancy of 6 people. 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 beach, offers an ideal location...
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    Location Information
    Anna Maria, Anna Maria Island
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Wi-Fi
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    • DVD Player
    • Hot Tub
    • Private Outdoor Pool (Heated)
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    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy our Luxurious Villa diPalma, a beautiful six bedroom, four bathroom luxury island home very close to the best beach in the Northshore. The Italian influence in the design is reminiscent of properties found in Venice and Tuscany. The two master suites each have their own Jacuzzi spa tub, a...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Garden
    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on beautiful Anna Maria Island, "Le Paradis" (which means Paradise in French) is just a short stroll to the sugar white sand beaches of beautiful Anna Maria Island... Experience a luxurious beach vacation with over 2100 hundred square feet of tastefully living space with an expansive...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Paradise at the Bayou1 / 20
    (3)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
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    • Waterfront
    • Patio
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 17 May 2017
    From the time we walked in the door you could see the care and thoughtfulness the owners put into making sure you enjoy your stay! This condo has a beachy look and feel and 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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Life is Good at the Beach: 3BR Family/Pet-Friendly1 / 20
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    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
    *SPECIAL* 20% OFF A WEEKLY STAY NOW THROUGH THE END OF THE YEAR (EXCLUDES HOLIDAYS)!! 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...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sugar Plum Hideaway West ~ RA552401 / 24
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 June 2016
    Very clean and great location. Plenty of towels. Important to realize a duplex - small pool and backyard ( shells not grass) shared. There was a family with small children next...
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    About this property
    “Sugar Plum Hide Away West” is a cute ground level duplex located in the spectacular city of Anna Maria. Just a short walk to the beach, you don’t even have to cross a street, to access the white sand and blue waters of pristine gulf beaches from this adorable Anna Maria vacation home. The outdoor...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    AMI Retreat: 3BR Pool Home 200 Steps from Beach1 / 24
    (5)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 16 April 2015
    Our group of 4 adults and 2 children stayed at this home over Spring Break and had a fantastic time. The house is decorated and laid out very well, and is optimized for comfort...
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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 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Pineapple Cottage: 2BR Quaint Pet-Friendly Cottage1 / 21
    (14)Excellent
    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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Le Paradis 727 Jacaranda ~ RA910691 / 23
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 January 2017
    My husband and stayed at le paradis for a week and it was incredible. The house is very well appointed and the location is hard to beat. The pool is amazing! I would highly...
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    About this property
    Anna Maria rental “Le Paradis” offers a comfortable and casual sophistication for a memorable beachside getaway. Accommodating up to six guests this home is perfectly located, and well appointed. You’ve found an Anna Maria vacation rental you’ll want to visit again! Located in a highly desired...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Sundrenched and colorful, Dolphin Watch is as beautiful inside as the landscape surrounding it. Which is something really special when you're directly on the flour soft, Gulf of Mexico beaches. Take in the vista of slowly rolling sand dunes and deep turquoise waters from all throughout the...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tropical paradise awaits at this 2BR/1BA villa located across the street from the beach at the beautiful, quiet North End of Anna Maria Island. Sleeps 4 with a double bed and two twin beds. Nicely furnished with tiled floors and updated interior. Enjoy the Gulf breezes from your screened lanai....
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Bean Point Beach Cottage1 / 22
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Internet Access
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    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 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Central Heating
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nothing better than having the beach at your doorstep! Located in the heart of Anna Maria city this 2 bedroom, 2 bath Direct Gulf Front cottage has 100 feet of Gulf front beach. Enjoy the views from the enclosed sitting room or step right out your door and have your feet buried in the sand just a...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This quaint, old-Florida style rental is nestled in the north shore area of Anna Maria Island. Shabby chic style, located 2 blocks from the beach and 2 blocks from the bay! Only one block from Pine Ave., with its old-time feel with shops and salons. Steps from fine dining, the historic city pier,...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cute 2BR/1BA beach bungalow is on the Gulf side very close to the beach and located at the quiet north end of the Island. Direct beach access just a few properties away. Enjoy the gulf breezes from the screened lanai or the open brick paver patio. This bungalow has plenty of room to relax with...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Anna Cabana B1 / 24
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 June 2016
    This modern beachy cozy home was absolutely gorgeous! Clean, and equipped w/ all the modern, brand new, full size amenities. Beachy/luxury design. Central air & on-site...
    Reviewed 9 January 2016
    I enjoyed my vacation in this beautiful house very much. The furniture is very nice and comfortabel and the entiere house is beautiful decorated. It provided everything what I...
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    About this property
    Anna Cabana B is the perfect getaway. Located on the north end of Anna Maria Island and just a short walk from the beach, this cute bungalow beckons you to relax and stay a while! This adorable island vacation rental has been completely refurbished inside and out! A queen bedroom and a sofa bed...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Periwinkles are small, sunshine loving flowers with a color so distinct they name crayons after it. On a street baring their name in Anna Maria Island, you’ll find a vacation rental home appropriate to the name - 'Pretty Palms' on Periwinkle Plaza. This three bedroom, two bathroom cottage is...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Terrace
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    Pet friendly
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    Smoking allowed
    About this property
    706 North Shore - Private home 3 Bedroom/ 2 Bath , maximum occupancy of 8 people. Tranquility abounds in this delightful home away from home...just a few steps to the beach, this charming 3 bedroom 2 bath home is truly a vacationer's delight! Located in the city of Anna Maria minutes from the...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Smoking allowed
    About this property
    4 Bedroom, 2.5 Bath (sleeps 8) - 'Shoreline Terrace' - 901 North Shore Drive, Anna Maria Anna Maria Island is' Old Florida' – we take things a little slower and our beaches are more famous for having flour soft sands than reliable cell phone reception. But that’s why people spend time with us in...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Bradley's Beach House: 4BR Pool Home Steps From Beach1 / 23
    (11)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Internet Access
    • Satellite TV
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    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 17 January 2017
    We thoroughly enjoyed our stay at Bradley beach house. We were a large family group wanting a relaxing week after our daughters wedding. This house was perfect for us, the newly...
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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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Canary Cottage- 317 Magnolia Ave, Anna Maria1 / 28
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 July 2017
    Our first experience renting a cottage. Usually we rent a condo. We were really happy with the cottage. It was clean and had everything we needed. Centrally located we could...
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    About this property
    The Canary Cottage has 2 bedrooms plus a bunkroom - and 2 full baths and will Sleep up to 6. Located in the heart of Anna Maria City- This Key West charmer is elevated and has been updated with new tile, fixtures, plus a new tub/shower! Updated furnishings, and appliances, which add to the charm...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Balcony
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    • Terrace
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Skimmer unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, one bath downstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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