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Holiday Rentals in Anna Maria, FL

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    All 167 Rentals in Anna Maria
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    Travellers to Anna Maria are booking July dates now. Secure your holiday rental today, and have the perfect trip.
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    €268
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    1 / 14
    5 of 5 stars (10) Excellent
    5 Bedrooms / 4 Bathrooms / Sleeps 10
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    €259
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    1 / 38
    4.5 of 5 stars (6) Very good
    5 Bedrooms / 3 Bathrooms / Sleeps 12
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    €112
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    1 / 8
    5 of 5 stars (11) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    €319
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    1 / 23
    5 of 5 stars (5) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (5) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
    • ?
    About this property
    Ahhhhhh. Welcome to Beach Nest! Ready to satisfy that oh-my-gosh-we-need-a-vacation? Kick off your shoes and throw them in the back of the closet. Promise yourselves to live in bathing suits from breakfast to bedtime! Vacationers, dreamers, honeymooners, would-be family-reunion planners and just... View all property information
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    5 of 5 stars Reviewed 24 January 2015
    From the blessed sunny moment we arrived until the morning we left-we smiled. Beach Nest is absolutely enchanting! We saw manatees playing off the dock in our backyard and watched...
    5 of 5 stars Reviewed 7 July 2014
    Five of us ranging in age from 7 to 80 had the pleasure of staying in this home for a week. Everyone had a fantastic time! Many hours were spent in the pool and at the beach. We...
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    €357
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    1 / 23
    5 of 5 stars (4) Excellent
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (4) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    We call this home 'A Time Out' cottage and you will definitely say, 'We deserve a time out at this place!' This completely remodeled private home on Anna Maria Island's north end features four bedrooms, two baths and the most wonderful tropical and lush pool and patio area! On the main level of... View all property information
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    5 of 5 stars Reviewed 8 April 2015
    This special house is located perfectly away from the hustle and bustle, but at the same time everything is easily accessible. The beautiful beach is just a short stroll, and...
    5 of 5 stars Reviewed 20 February 2014
    When we walked into this adorable cottage, we couldn't believe our eyes. This place is too cute for words! It is the kind of rental you dream about with clean bathrooms...
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    €5,271
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    1 / 22
    4.5 of 5 stars (5) Very good
    4 Bedrooms / 4 Bathrooms / Sleeps 14
    Overview Reviews (5) Make Enquiry
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    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Wheelchair access
    • Elder access
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    About this property
    The Golden Dolphin, located at 801 North Shore Drive in Anna Maria, is the ultimate in beach front luxury. This executive level gulf front home has a tropical heated pool with waterfalls, four bedrooms, a library, three and one half baths a gourmet kitchen and much more. It was custom built with... View all property information
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    4 of 5 stars Reviewed 13 July 2014
    Great location, great size for multiple families. impressive kitchen and great for preparing large breakfasts/dinners; Master Suite very impressive and the showers where awesome...
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    €179
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    1 / 107
    5 of 5 stars (12) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
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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... View all property information
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    5 of 5 stars Reviewed 13 August 2014
    We booked this home based upon other Trip Advisor reviews and were more than pleased! We have talked about booking it again for a stay next year! We had two different family...
    5 of 5 stars Reviewed 29 July 2013
    We stayed in the house at the end of June 2013. We had done a lot of research to find an affordable rental for our 6 person group and ended up with this house. Green Realty was...
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    €1,608
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    1 / 25
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
    • x
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    About this property
    Gaze out of your living room to the calming serenity of the canal as you sip on your favorite beverage at this comfortable and spacious home located in the prestigious north end of the island. This beautiful 3 bedroom 2 bath tastefully decorated home is invitingly awaiting your arrival for the... View all property information
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    5 of 5 stars Reviewed 12 March 2015
    Great accommodation in an idylic spot close to the beach and all amenities. You are in the best spot on the island.
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    €1,188
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    1 / 21
    4 of 5 stars (18) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Reviews (18) Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
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    • Wheelchair access
    • Elder access
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    About this property
    The Anna Maria Escape located at 725 North Shore Drive in Anna Maria city is just that - a peaceful, relaxed place to get away from it all. You can stroll on the beach for miles in either direction! It’s a perfect Anna Maria Island vacation home!This spacious and charming two bedroom, two bath Gulf... View all property information
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    3 of 5 stars Reviewed 25 March 2015
    We were quite pleased when we saw the exterior of the house - very attractive. When we walked in, the house was clean and presented well. There were two of us - college...
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    €114
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    1 / 25
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
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    About this property
    Enjoy an old fashioned Florida beach vacation at this wonderful cottage just 4 houses from the beach! One Florida family has spent over four decades building happy summer memories right in this spot, and they invite you to create some of your own treasured moments on your next visit to Anna Maria.... View all property information
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    €339
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    1 / 18
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    It doesn't get much better than being right on the water, ½ block from the bay beach, and only 7 blocks from Pine Avenue. Sunshine Cottage couldn't be a better name, because this 3 bedroom, 2 bathroom, cottage truly lets you experience the beauty of Anna Maria Island. Enjoy dangling your feet off... View all property information
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    €759
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    1 / 14
    2 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Safe
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    This villa is quaint and adorable tucked in a quiet neighborhood just 9 houses from the Gulf of Mexico and white sandy north end Anna Maria Island beaches. Step outside your door and stroll down the street in 1 minute or less to the quaint shops and cafes along Pine Ave. Walk to everything the... View all property information
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    €2,257
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    1 / 23
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
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    €152
    / Night
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    1 / 17
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    About this property
    As an artist this private three bedroom and two bath elevated vacation home has been a 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 best white... View all property information
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    €223
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    1 / 14
    3 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Make Enquiry
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    • Dishwasher
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
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    About this property
    Las Palmas 212 Palm Avenue Anna Maria, Fl. 34216 North-end location just a few minutes walk to Pine Ave and Gulf beaches! This lovely 3 bedroom 2 bath elevated home with private heated pool is situated in the heart of the island, centrally located to everything fun. Comfortable and charming with... View all property information
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    €3,350
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    1 / 25
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
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    About this property
    Spend your vacation just steps from our beautiful beaches and crystal-clear waters! Casa Blanca is in the heart of the village of Anna Maria, and west of Gulf Drive...there's no better place to be! Only 5 houses from the beach, you'll be steps from the sand AND just moments from shopping,... View all property information
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    €197
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    1 / 24
    4 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
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    About this property
    Located on one of the prettiest streets in the village of Anna Maria, this lovely 4 bedroom, 2 and a half bath home is just 7 houses away from the beach. The quiet, tree-lined street evokes memories of Florida Gulf Coast islands in days gone by, with a shaded path providing access to the island's... View all property information
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    €421
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    1 / 29
    4.5 of 5 stars (4) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
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    About this property
    Cherryfish is the latest addition to the Pineapplefish collection of houses on Anna Maria Island. It is a spectacular 4 bedroom house, in a fantastic location, just one block from Tampa Bay Beach, the amazing Waterfront Restaurant and the island's most popular tourist destination - City Pier.... View all property information
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    5 of 5 stars Reviewed 29 January 2015
    Flawless! Cherryfish, a tropical hideaway I never want to leave! The landscaping is unsurpassed providing a private tropical oasis retreat. The home itself is so fresh with...
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    €223
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    1 / 30
    5 of 5 stars (2) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
    • x
    About this property
    The Shady Mango was originally built in 1925. According to local history the heart pine used in constructing the original house came by steam boat to the City Pier and was hauled by horse-drawn lorry up Pine Avenue to the home's present site. In 2004 the home was given a major renovation... View all property information
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    5 of 5 stars Reviewed 21 September 2013
    My husband, 2 kids & I stayed at the Shady Mango & LOVED it! It's the perfect place for a vacation for a small family. It's in a great location with walking access to the beach...
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    €199
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    1 / 29
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Grill
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
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    About this property
    This great 2 Bed/2 Bath Home with Private Heated Pool resides in Anna Maria and is only one block to the beach and has no busy streets to cross to get there. You can quickly make your way to the Gulf Sands and to all of the great shops and restaurants that Anna Maria and Holmes Beach have to offer.... View all property information
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    €134
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    1 / 18
    4 of 5 stars (1) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
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    About this property
    Completely remodeled 2 bedroom/2 bath duplex, with a beautiful tropical HEATED pool, just over a block to the beach, and the free island Trolley! There is a King and a Queen bedroom in the North Unit, and a King and Twin Bedroom in the south unit. Both units also have a queen sleeper sofa.. 708... View all property information
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    4 of 5 stars Reviewed 31 December 2014
    BLN is very well located in the quieter northern part of the island. It is just a very short walk from the beach and Ginny and Jane Es. Likewise, a short walk in the opposite...
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    €223
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    1 / 18
    4 of 5 stars (1) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Wheelchair access
    • Elder access
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    About this property
    Anna Maria Cottage 104 Magnolia Avenue Anna Maria Island, FL 34216 This beautiful historic beach cottage is a true embodiment of 'Old Florida Charm'. This wonderful home offers 3 suites, each with their own en-suite full bathroom, a wrap around porch with stunning Gulf views and much more!... View all property information
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    4 of 5 stars Reviewed 24 February 2015
    I spent almost 3 weeks on AMI sharing this lovely cottage with my sister and some other friends and family. The location is wonderful, very close to the beautiful beach, so an...
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    €179
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    1 / 24
    5 of 5 stars (4) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
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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... View all property information
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    5 of 5 stars Reviewed 4 November 2014
    My husband and I took our 15 year old son to Anna Maria for a weeks stay at Starfish Dreams. We had a really lovely relaxing holiday and the house is perfect. Excellent position...
    5 of 5 stars Reviewed 16 August 2014
    Having stayed on AMI before, we knew that we would love the island, but the location of this home made our trip even more successful. The property is on Pine Avenue, so walking...
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    €119
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    1 / 39
    5 of 5 stars (1) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Reviews (1) Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Newly Remodeled 1 Bedroom/1 Bath Cottage in a serene north end location. The allure of the Gulf of Mexico Beach just 250 steps away. A back yard dock on Lake LaVista Bayou with a patio table, umbrella, and sling back chairs. Launch the provided kayaks right from the dock or choose to bring your own... View all property information
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    €156
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    1 / 22
    4 of 5 stars (6) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
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    • Wheelchair access
    • Elder access
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    About this property
    The Heron unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, two bath upstairs 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... View all property information
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    €625
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    1 / 21
    5 of 5 stars (16) Excellent
    4 Bedrooms / 5 Bathrooms / Sleeps 8
    Overview Reviews (16) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
    • ?
    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... View all property information
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    5 of 5 stars Reviewed 15 April 2015
    After a mad week doing the theme parks in Orlando we came here for some serious relaxation - and what a great choice it was. The house is stunning and the location couldn't be...
    5 of 5 stars Reviewed 11 March 2015
    Hi Nigel and Maggie. We have enjoyed your place 3 weeks this year. Had one week in January and the other 2 in Feb/Mar. We could hardly wait to go back after our first...
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    1 / 13
    4 of 5 stars (1) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Dishwasher
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
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    About this property
    Birds Eye View 802 Gladiolus Street Anna Maria, FL 34216 This spacious and charming 2 bedroom, 2.5 bath elevated home is just three houses from the Gulf of Mexico! It is located near popular Bean Point at the prestigious northern tip of Anna Maria Island. It has fabulous island style... View all property information
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    4 of 5 stars Reviewed 7 September 2013
    Lovely property...close to both gulf and bay beaches for sunrise/sunset. Loads of space with a huge master bedroom/bathroom. Clean and well kept but could use a few updates...
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    €167
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    1 / 22
    4.5 of 5 stars (12) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    About this property
    The Flamingo unit at the Blue Dolphin Inn, located at 780 Jacaranda in the Historic Village of Anna Maria is a wonderful and spacious three bedroom, two bath upstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains... View all property information
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    2 of 5 stars Reviewed 13 January 2015
    clean and nice location. the appliances are out dated as the decor and linens. both queen mattresses where so uncomfortable my spouse and i slept in separate beds.the kitchen is...
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    €542
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    1 / 22
    5 of 5 stars (5) Excellent
    9 Bedrooms / 6 Bathrooms / Sleeps 26
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    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
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    • Wheelchair access
    • Elder access
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    About this property
    The Blue Dolphin Inn, located at 780 Jacaranda and 404 Alamanda in the tranquil City of Anna Maria features four units surrounding a tropical heated pool with tiki huts, grills, rooftop observation decks and loads of charm. Each unit has its own private patio and gas grill for an evening of... View all property information
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    €139
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    1 / 22
    3.5 of 5 stars (9) Average
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (9) Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    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... View all property information
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    2 of 5 stars Reviewed 10 March 2013
    I have mixed feelings about this rental property, and that is because I feel it is very overpriced certainly not value for money. The photos on the web are accurate, however it is...
    3 of 5 stars Reviewed 25 February 2011
    I would have given the Skimmer one star on the first couple of days of our stay basically for 2 reasons: paint fumes and noisy pool equipment. The management had decided to...
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    4.5 of 5 stars (7) Very good
    5 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Sauna
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    Located on the north end of Anna Maria Island in the city of Anna Maria, this family-friendly vacation rental was built for rest and relaxation. Beginning with the lush landscaping that meets you at the front door, all the way through to the putting green, kayak launch and boat dock, this house has... View all property information
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    5 of 5 stars Reviewed 15 August 2014
    I searched for the perfect house for a family of 10 to celebrate our niece's vacation. All I can say is there was nothing on everyone's list that this house didn't have! We...
    5 of 5 stars Reviewed 2 August 2014
    This house was exactly as pictured and described. The attention to detail in how it was build was amazing. This place had everything you could imagine or want. Pool was...
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    4.5 of 5 stars (15) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (15) Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
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    About this property
    The Azure Seas is a glorious three bedroom, two bath Gulf front home located at 779 North Shore Drive in the much desired and tranquil northern end of Anna Maria Island. Tropical paradise found!! This is the perfect place to forget your troubles and soak in the unbelievable views of the Gulf of... View all property information
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    5 of 5 stars Reviewed 11 March 2015
    What an amazing spot on the beach. House comfortable &,nautical. Therapy sweeping the pine needles and cones off deck. Bean Point great shelling spot, get there early. South of...
    3 of 5 stars Reviewed 23 August 2014
    The views and the location of this house were simply amazing. The beach is clean, the sand is soft and white and the beach is very wide. There were a lot of sea turtle nests...
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    €98
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    5 of 5 stars (7) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Seaside Views - Waterfront, Steps from Beach & Restaurants 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 it's own private fishing dock and boat slip! We have... View all property information
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    €223
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    4.5 of 5 stars (34) Very good
    6 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Reviews (34) Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Berryfish is a fantastic new Caribbean style, beachfront apartment from Pineapplefish, ideal, due to its flexible accommodation, for larger groups of families and friends. Berryfish is double duplex apartment just a stroll to the beach, with 2 separate accommodations - Berryfish East and West,... View all property information
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    4 of 5 stars Reviewed 13 September 2013
    Pineapple fish we fell in love with berryfish the whole property is an amazing home from the large sun front deck to the back deck ..I want to buy it off you lol seriously it...
    5 of 5 stars Reviewed 21 May 2013
    Visited Anna Maria for the first time and we will visit again! Loved the location, the house and its wonderful furnishings and the nearness of the lovely white sands and blue...
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    €191
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
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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... View all property information
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    €1,519
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    1 / 27
    4 of 5 stars (1) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    NORTH SHORE VILLA 904 North Shore Drive Anna Maria Welcome to North Shore Villa. This luxury Key West style home has it all. Expansive bay views, private heated pool, extra large master suite with a double shower and Jacuzzi tub, fresh and modern decor, two large balconies, indoor sitting area... View all property information
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    4 of 5 stars Reviewed 5 January 2015
    In August I reserved N. Shore house for 2 weeks - Our family's Christmas- 6 adults. Final deposit due early December. The Home is as described-- very beautiful, casual feel...
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    €893
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    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
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    About this property
    Bay View Villa is a three bedroom, three bath private Key West style island home with bay views; tile and bamboo floors, spacious living room with large open decks, and just a short stroll to Bean Point and Bayfront Park. Very desireable area on the North end of Anna Maria Island. Sleeps upto 8... View all property information
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    5 of 5 stars Reviewed 2 December 2011
    everything spot on,between the 2 piers ,both walking distance,2 minutes stroll to the park opposite with the beach ,sea and picnic area,lovely. a clean peacefull area .
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    €245
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    4.5 of 5 stars (6) Very good
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Beautiful, cheerful and tropucal 4 bedroom/2 bath home with beautiful new furnishings throughout! Comfortable and roomy with split floor plan (two bedrooms on each side!). Ceramic tile throughout, beautiful open kitchen area with breakfast bar and granite countertops. The living room opens up onto... View all property information
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    From
    €253
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    1 / 28
    5 of 5 stars (2) Excellent
    3 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
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    • Pets allowed
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    About this property
    Beautifully remodeled 3 bedroom/2.5 bath home with luxury amenities on the North End of Anna Maria, just 4 houses to Bean Point, one of the quietest beaches on the island, and 2 blocks to the famous Rod & Reel Pier! Private Backyard with Heated Pool, and an open floor plan with vaulted ceilings!... View all property information
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    From
    €335
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    1 / 17
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Breakaway 891 North Shore Dr. Anna Maria, Fl. 34216 Leaping to the top of the class- this fabulous Bay front home has just undergone a significant renovation inside and out! The makeover includes an addition of a 4th bedroom, remodelled Master bedroom with a walk in closet, new floors in the... View all property information
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    €199
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    1 / 26
    5 of 5 stars (4) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Newly remodeled 2 bedroom/2 bath home. Brand new pool, hot tub, and landscape with a serene canalfront setting. Located on a quiet dead-end street, close to the trolley, the beach, and walking distance to Anna Maria shops and restaurants. Bring your boat and take part in some of the best fishing on... View all property information
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    5 of 5 stars Reviewed 13 January 2014
    We have just come back from a 2 week stay at Lazy Lagoon. House beautiful, all on one level and flooded with light. Pool and hot tab a fantastic feature. House fully equipped and...
    5 of 5 stars Reviewed 10 January 2014
    Lazy Lagoon was more than we hoped for. The pictures don't do the house justice. Sun shines through the whole house. The high ceilinged lounge was perfect to relax after a day...
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    €447
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    1 / 26
    5 of 5 stars (1) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Reviews (1) Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Cayman Bay 505 Magnolia Ave. Anna Maria, Fl. 34216 Cayman Bay may well be one of the most exquisite private homes available for rent on all of Anna Maria Island. This 4 bedroom/4 bathroom 5300 sq. ft. custom home has all the fine touches and professional craftsmanship one would expect in a... View all property information
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    5 of 5 stars Reviewed 19 August 2014
    We stayed here for two weeks this past August. This was our second trip to AMI - such a lovely place. This house was perfect for us. It is very spacious. All the bedrooms are...
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    €223
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    4 of 5 stars (1) Very good
    5 Bedrooms / 3 Bathrooms / Sleeps 12
    Overview Reviews (1) Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Tortuga Bay 9405 Gulf Dr. Anna Maria, FL 34216 This one is extraordinary! Tortuga Bay is a completely renovated, ground level, 5 bedroom property that has one of the most outstanding tropical pools on the island- featuring a theme-park style water-slide! Located in the prestigious city of... View all property information
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    4 of 5 stars Reviewed 3 April 2015
    The house was beautiful, spotless, and comfortable. The pool area was amazing and the walk to the beach was seriously 2 minutes tops. We like to stay beach front so if the beach...
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    €214
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    1 / 25
    5 of 5 stars (2) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Great Ground Level 3 Bedroom/2 Bath Home with a Heated Pool located in the quiet north end and just 3 houses to the beach!! King-Sized master bedroom with TV, Queen in the 2nd Bedroom with TV, and Twins in the Third with TV. Cable TV, DVD, and Flat Screen TV in Living Room. High speed Internet,... View all property information
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    From
    €179
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    1 / 12
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Internet Access
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    A Snails Place 302 Spring Avenue Anna Maria, Fl. 34216 This beautifully decorated 3 bedroom, 2 bath ground level home is just a short walk to the Gulf of Mexico. With it's convenient location on Spring Avenue you are walking distance to historic Pine Avenue! This adorable cottage offers a... View all property information
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    From
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    1 / 21
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Limelight 771 Jacaranda Rd. Anna Maria, Fl. 34216 Limelight is a gorgeous newly renovated home, inside and out, located on the prestigious North End of Anna Maria Island. Only a brisk 3 minute walk away from the sandy white beaches, this home offers everything you are looking for in an Island... View all property information
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    5 of 5 stars Reviewed 11 January 2015
    We loved the location and the house was beautiful and well equipped. It was a perfect place for us to vacation with our three adult children. The kitchen was top notch with...
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    €283
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    5 of 5 stars (2) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 9
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • x
    About this property
    Newly remodeled, 4 bedroom/3 bath home, just 90 Steps to the beach, with a large private HEATED pool! Quiet setting in the beautiful north end of Anna Maria, and located west of Gulf Drive for easy beach access with no streets to cross. Easy walking distance to many shops and restaurants, and... View all property information
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    5 of 5 stars Reviewed 28 October 2013
    My parent rented this house when they came to visit last winter. We stayed for a week in late January(?) to early Feb and my 3 year old son still asks to go back. Personally I...
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    4.5 of 5 stars (3) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • x
    About this property
    This adorable remodeled duplex sits quietly in the highly desirable north end of the Island in the City of Anna Maria. It is a short walk of only a little more than a block to the Gulf beach where the sand is sugary white and the water is a beautiful blue-green color. There is a King in the... View all property information
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    5 of 5 stars Reviewed 21 January 2015
    we loved staying at Tutrtle Trax. The house is so nicely decorated, was very clean & had everything we needed. We rented bikes & enjoyed the pool greatly. We will stay there...
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    5 of 5 stars (1) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 14
    Overview Reviews (1) Make Enquiry
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Ocean Walk 117 Willow Avenue Anna Maria Island, Fl 34216 Ocean Walk is a brand new private home that is now ready for rental! The style of the home offers a very attractive roof line with steep pitches, lots of balconies and being located West of Gulf drive there are no busy roads to cross and... View all property information
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    5 of 5 stars Reviewed 15 March 2015
    Everything in this house is top notch. We've rented lots of places in Florida, but this one is beautiful. Everything is brand new, furniture is all good quality, bedding is great...
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    €223
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    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    Heron House 213 Elm Ave. Anna Maria, Fl. 34216 Wow, this luxury 3/3 North-end elevated home has it all! Just newly remodeled and ready to go! Just a short walk to it all- the beautiful Gulf beach, the fun and entertainment of Pine Ave. and even walk to the fantastic Sandbar restaurant. The... View all property information
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