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Anna Maria Rentals with Pools

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    Travelers to Anna Maria are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    106 Matching Rentals in Anna MariaView all 262 rentals
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    Crescent Wave1 / 40
    (12)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 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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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Gorgeous views,spectacular home!1 / 90
    (20)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Washer
    • Grill
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    Reviewed January 2, 2017
    This is an excellent vacation home to spend with a large family looking for a quiet getaway on AMI. Our family of eight adults, one teenager, one toddler, and one infant spent 7...
    Reviewed December 27, 2016
    We've stayed on AMI many times and this house was far and above the best one we have rented on the island! Great location....can walk everywhere and gorgeous views from all of...
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    About this property
    WELCOME TO ALL DECKED OUT! Whether getting away for a family vacation, with a group of friends, for a wedding or any other occasion, our gorgeous 5 Bedroom home offers everything you could want for a relaxing holiday on Anna Maria Island.... with incredible views of the Bay! Sit by the tropical...
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    Anna Maria, Anna Maria Island 34216
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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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
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    • Patio
    • Private Outdoor Pool (Heated)
    • Porch
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 30, 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
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Satellite TV
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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
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    • Hot Tub
    • Satellite TV
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    • DVD Player
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    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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Wi-Fi
    • Washer
    • DVD Player
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    • Private Outdoor Pool (Heated)
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    • Satellite TV
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    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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    Anna Maria, Anna Maria Island 34216
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 16
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    Sunshine Cottage - Private 30' Pool and Boat Dock, and steps away from the beach1 / 39
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Housekeeping Included
    • Satellite TV
    • DVD Player
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    • Air Conditioning
    • Ocean Views
    • Waterfront
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 28, 2016
    We had a fantastic time exploring Anna Maria Island and coming home to such a fantastic place made the holiday even more special.
    Reviewed February 17, 2016
    This home is located in walking distance to restaurants and the beach with bikes available as well. It is very nicely and newly decorated. The kitchen is well stocked as well as...
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    About this property
    It doesn't get much better than being right on the water, less than one 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...
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    Anna Maria, Anna Maria Island 34216
    Rental Home - 3 Bedrooms, 3 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
    Rental Home - 3 Bedrooms, 2 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)
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    Pet friendly
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    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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
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    • Wi-Fi
    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Anna Maria Island, This property is located directly across from the famous Manatee County Public Beach. Groomed daily, Lifeguards, restaurants, surf shop and more.. Free trolley stops there both northbound and south every 20 minutes. The location is also right in the heart of the island. Walk to...
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    Anna Maria, Anna Maria Island 34217
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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 April 17, 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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Yard
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    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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    Anna Maria, Anna Maria Island 34216
    Rental Home - 3 Bedrooms, 3 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 May 3, 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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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cast Villa #4 is the most private on this lush tropical Half acre property. Located directly across from the famous Manatee County Pubic Beach. Swim with Life guards present. Known for the pristine sugar white sand beaches. Dine early breakfast or have a beverage listening to live music daily....
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    Anna Maria, Anna Maria Island 34217
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Anna Maria's Coconut Breeze Estate1 / 47
    (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 May 9, 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 May 7, 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
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    DISCOUNT 40% *AUGUST 19-26 **Pool*Hot Tub*Dock*Steps to Gulfside beach*BOOK NOW!1 / 23
    (9)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 February 24, 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 January 20, 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
    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...
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    Anna Maria, Anna Maria Island 34216
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    The Nantucket1 / 27
    (19)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 April 10, 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 February 10, 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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    Location Information
    Anna Maria, Anna Maria Island 34217
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated beach condo just 50 steps to the sand. Over 1200 sq ft with 2 lanais and 1 spacious rooftop deck for spectacular ocean views. Granite Counter Tops Stainless Steel Appliances Washer and Dryer Heated Outdoor Pool Beach Supplies Walking distance to restaurants and Shops Close to...
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    Anna Maria, Anna Maria Island 34217
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 bed luxury upscale executive waterfront home1 / 50
    (10)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Waterfront
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 27, 2017
    Bayview Dream did not disappoint! It truly was a dream holiday for us. The house itself is beautifully decorated and very well equipped - plenty of towels (indoor and pool...
    Reviewed January 17, 2016
    We spent a week in this lovely home. The weather was cool, so we didn't use the pool, but there was a beautiful pool with a dock right out the back door. The home was spacious...
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    About this property
    Upscale luxury executive four bedroom waterfront home with private pool dock and elevator. Stylishly furnished and dressed, modern build 2006 - this is our family second home - and is home from home available to you. This exclusive executive property is in the heart of lovely Anna Maria...
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    Location Information
    Anna Maria, Anna Maria Island FL34216
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Satellite TV
    • Grill
    • Washer
    • Internet Access
    • Parking
    • Air Conditioning
    • Patio
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Anna Maria, Anna Maria Island 34216
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Ocean View 3 bedroom, pool, North Shore Drive1 / 123
    (34)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 February 2, 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...
    Reviewed January 2, 2017
    Vacation Island House is a charming, beautifully maintained pool home. My husband and I have been renting beach houses for over twenty years, and this is the best appointed one...
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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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Hot Tub
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Situated on an enormous lot within the quiet north end of Anna Maria, you will find this treasure of a vacation home. Fins Up is a uniquely perfect 3 bedroom, 2.5 bath home with its own private pool, hot tub, 2 docks, and fully enclosed spacious outdoor shower. Privacy fenced is the huge backyard...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    OURPLACEBYTHESEA1 / 40
    (1)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Parking
    • Satellite TV
    • Wi-Fi
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 1, 2014
    We had a great time on Anna Maria with our two college-aged sons. This house is very nicely located, and the pool is wonderful. The home was spacious and comfortable for four...
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    About this property
    eBeautiful ground level 3 bedroom/2.5 bath home, with a quiet north end location only a block to the beach! There is a King in the master with a private patio, a Queen in the second, twin beds in the third, and a queen sleeper sofa in the sunroom (which has blinds for privacy), all accommodating...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Wi-Fi
    • Washer
    • Balcony
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    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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....
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Hot Tub
    • Waterfront
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Canal Place, an inculpable island home that is outfitted to offer occupants an unforgettable vacation experience! In your privately cultivated backyard is an assemblage of accessories providing plenty of options for fun in the sun. There is a heated pool, hot tub, kayaks, boat dock,...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the exceptional beach house that is Blue Turtle! This 4 bed/3 bath gem is perfectly positioned on the north end of Anna Maria and will positively provide a picturesque vacation experience. The gorgeous backyard is your private, tropical paradise complete with heated pool and dock to take...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Washer
    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The lovely Dolphin Pointe resides on the highly desirable north end of Anna Maria, just a short walk to the beach, bean point, and the 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 with its over 2000...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    BIMINI BAY1 / 41
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Grill
    • Internet Access
    • Air Conditioning
    • Parking
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 29, 2016
    Just got back from a girls trip with five friends at Bimini Bay. The house was PERFECT. Bright, clean, fresh, comfortable, and super cute. The pool and outdoor seating areas...
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    About this property
    Welcome to a true Anna Maria Island treasure! Bimini Bay is an irreproachable 4 bedroom, 3 bath ground-level home tucked away on the quiet north end of Anna Maria. Previously a duplex, both units were completely gutted and combined to bring you this gorgeous 4 bedroom home with its own private...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Private Yard
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, location, location. If you are looking to be close to the GULF beach, this is the one. Beach Cay is perfectly situated at the very desirable North End of Anna Maria Island, just steps to the Gulf of Mexico's white sugar sand beaches (the Gulf side of the island, not the bay side!). Beach...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cherryfish, a spectacular spacious 4-bed home!1 / 29
    (8)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Washer
    • Balcony
    • Porch
    • Satellite TV
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    We've just come back from an amazing holiday staying at Cherryfish. I couldn't recommend it enough for a large family or two sharing.Cherryfish is a beautifully maintained...
    Reviewed May 24, 2016
    We are a family with young children and thoroughly enjoyed staying at this property. There was plenty of space and bathrooms for all and the pool was a great hit with everyone...
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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....
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    TRIPLEPLAY1 / 70
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Private Outdoor Pool (Heated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 24, 2015
    This house is nothing less than spectacular for a family. The house has been completely redone inside. The house looks very small from the front / driveway, but the inside is...
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    About this property
    Looking for that place to kick back and relax your cares away? Check out ‘Triple Play Guest House.' There's a triple chance to play: (1) walk to the beach, (2) lounge in the pool or spa or patio or (3) launch a kayak, fish or just relax on one of our two docks on the canal. Nothing quite compares...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    YELLOWBIRD COTTAGE B1 / 33
    (4)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Grill
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 13, 2016
    This was our first time on the island. This house is a short 5 minute walk from a fabulous beach, and you share a pool with the other side of the duplex. The neighbourhood...
    Reviewed June 8, 2015
    The cottage was just as the picture depicts. It was close to the beach and we only had to worry about 1 other rental on the property. A lot of privacy and all the amenities...
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    About this property
    Beautiful 2B/1B cottage on the quiet North end, only 5 houses to the beach, and no streets to cross. Beautiful new Heated Pool. Twins can be converted to King in all bedrooms. NO dishwasher, no garbage disposal.Rear trash pick up! Charcoal Grill, not gas. Both units also include private...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Grill
    • Satellite TV
    • Waterfront
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    .Inspired by modern Italy, North End Zen's sleek and minimalistic touches throughout will at times have you feeling as you were vacationing on a posh Mediterranean island. The spacious open concept floor plan begins at the front door and gracefully moves its way to the back of the house which has...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    HAWAIIAN PUNCH1 / 40
    (6)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Patio
    • Air Conditioning
    • Satellite TV
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful, cheerful and tropucal 4 bedroom/2 bath home with beautiful new furnishings throughout! Quiet surrounds yet just a few steps from Pine Avenue shops and restaurants. One block away from free trolley. Comfortable and roomy with split floor plan (two bedrooms on each side!). The living room...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    HURRICANE HOUSE1 / 33
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Washer
    • Internet Access
    • Patio
    • Grill
    • DVD Player
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 3, 2016
    Beautiful home. 1 block to the Gulf, restaurant and music on the beach. Free breakfast, on Sunday, at Harry's Restaurant on Gulf Blvd. Music, shopping, and the sunsets! Wow...
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    About this property
    Beautifully redone 3 bedroom/2.5 bath home! Ceramic tile throughout, and brand new open kitchen area with breakfast bar. Beautiful large caged pool area with huge covered patio! Only a block to the beach, the Sandbar Restaurant, Ginny and Jane E's, Rudy's Subs, Feeling Swell and more. Just a...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    LA HACIENDA1 / 40
    (1)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the heart of Anna Maria, a gorgeous and spacious Mediterranean style 4 Bedroom/3 Bath Home with a Heated Pool in a very private and peaceful setting. Only steps to Pine Avenue shopping and Trolley Stop, 2 blocks to the Beach, and walking distance to the Pier. The open floor plan features...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    HAV'ANNA HIDEAWAY1 / 39
    (3)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Washer
    • Wi-Fi
    • Grill
    • Patio
    • Private Outdoor Pool (Heated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 27, 2015
    This property was everything we had hoped for and more! Centrally located in one of the best parts of Anna Maria Island, and even though it was close to one of the main streets...
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    About this property
    When you 'have anna maria' on your mind, you'll want 'hav'anna hideaway' for your vacation home. This 4 bedroom, 4 bath home is located just one short block to the beautiful and sparkling gulf beach. The main floor of the home consists of an open concept living room, kitchen with breakfast bar...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Internet Access
    • Washer
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Patio
    • Satellite TV
    • Air Conditioning
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful gem of a home is located in the much coveted north end of Anna Maria Island in the City of Anna Maria. It is a single family home located on a quite street. Just a 2 minute walk to the gorgeous white sand beaches on the bay side of the island and about a 10 minute walk to the sugary...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    TOES IN THE WATER1 / 35
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Grill
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Satellite TV
    • Patio
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 27, 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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    About this property
    Toes in the Water is an amazing ground level 4 bedroom/3 bath home, just 90 Steps to the beach! This north end gem boasts a large, private, and heated pool with swim-up tiki table. Quiet setting in the beautiful north end of Anna Maria, and located west of Gulf Drive for easy beach access with no...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Washer
    • Satellite TV
    • Air Conditioning
    • Patio
    • DVD Player
    • Internet Access
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Remodeled 2 bedroom/2 bath duplex with connecting door, a beautiful tropical HEATED pool, just over a block to the beach and the free island Trolley! Amazing location on north end of Anna Maria, a 2 minute walk to Ginny's and Jane E's Cafe, and a 4 minute walk to the beach. The heated pool is...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Stunning luxury newly constructed beachfront villa1 / 22
    (21)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Hot Tub
    • Washer
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 days ago
    Beautiful three level beach house on the northern end of Anna Maria Island. Relaxing and very comfortable home where our family enjoyed reconnecting during our vacation after a...
    Reviewed May 1, 2017
    If you are looking for a property to relax by the beach or a swimming pool, this is about as good as it gets. There is nothing the owner's have not thought about. Great ocean...
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    About this property
    4 Bedroom 5 bath luxury beach front house sleeping 8 with heated pool separate spa numerous decks and stunning beach views from every room. We are located on the desirable family friendly island of Anna Maria. The house is direct beach front on the quiet upmarket north end of the island. Recently...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Parking
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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 master...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Grill
    • Washer
    • DVD Player
    • Satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 2B/1B cottage on the quiet North end, only 5 houses to the beach, and no streets to cross. Beautiful new Heated Pool. Twins can be converted to King in all bedrooms. NO dishwasher, no garbage disposal.Rear trash pick up! Charcoal Grill, not gas. Both units also include private...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Grill
    • Patio
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Washer
    • DVD Player
    • Grill
    • Patio
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    Anna Maria, Anna Maria Island 34217
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    LAZY LAGOON1 / 40
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Washer
    • DVD Player
    • Satellite TV
    • Hot Tub
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 13, 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...
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    About this property
    Lazy Lagoon has it all! This remodeled 2 bed/2 bath home is anchored in splendid the north end of Anna Maria on a deep water canal with dock, has its own heated pool and hot tub, and is a short walk to the beach, restaurants and free island trolley. The serene canal-front setting coupled with quiet...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    BEACHCOMBERS1 / 40
    (7)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Satellite TV
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Patio
    • Washer
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 19, 2017
    The beautiful backyard with pool, refreshing cross breeze in the house, front deck, well equipped kitchen and quiet yet close location were all wonderful. We loved that there...
    Reviewed September 6, 2016
    We had a fabulous holiday during our 7 night stay at Beachcombers in June 2016. The villa was beautifully decorated with its bright fresh colours and beach house theme. The...
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    About this property
    Beachcombers is a spacious 3 bedroom/2 bath home with all of the "Old Florida Charm" you could ask for. Situated on Spring Avenue, just a couple of blocks to the Gulf of Mexico on Anna Maria's beautiful north end! Easy walking distance to many shops, restaurants, the Anna Maria City Pier and a...
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    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Washer
    • Satellite TV
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Anna Maria, Anna Maria Island 34216
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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