Pineapple Cottage | 2 Bedroom, 1 Bath, Sleeps 6

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First time staying in Anna Maria Island. We had passed through on a trip a few years back and vowed to come back and stay for a week of relaxation. Pineapple Cottage was a great dose of just that. Our boys & our nieces enjoyed the pools and puzzles. My husband and I love it here. The beach is beautiful with powdery white sand which I refer to as warm snow! I am thankful for the days we have had here but sad that we must leave soon. One day, I will probably check-in and plan to never check-out!
Submitted via Glad to Have You by Marta Herrera from Miami, Florida, for her stay in 8/2014

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Great home, the owners have thought of every mortal thing . . . would def stay again and have also recommended already to friends of mine.
Submitted via FlipKey/TripAdvisor by Sarah from Palmetto Bay, Florida, for her stay in 8/2014

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It’s very clear the owners and agents care very much for their property. Beautifully maintained and very comfortable for a family of 4. The location is ideal as it’s halfway down Pine Avenue and whilst you need a car to get there you don’t have to drive it much once you have arrived. 10 mins one direction is the fantastic Sandbar restaurant and bar and the beach along with other great places like Ginny’s and Jane’s shop and diner. 10 minutes the other way and you’ve walked to the City Pier restaurant and the great 2 Scoops ice cream shop. The cottage itself has everything you need including a beautiful pool area with loungers, multi-coloured pool seats and a lovely shell covered surrounding. The water in the open air private pool was so much cleaner than the ones in Orlando that have the lanai covering and it was joy to sit out there soaking up the sun. I wish I was still there.
Submitted via FlipKey/TripAdvisor by Andrew Torrance from Edinburgh, United Kingdom, for his stay in 7/2014

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Enjoyed our stay on the island, as always! The cottage was great! We enjoyed the parade that came right by the cottage on the 4th of July! Lots of fun and happy people. I guess the only thing that would make the cottage better would be that the yard around the pool wasn’t crushed shells. Other than that it was an awesome, relaxing week and we are heading back to the cottage in October!
Submitted via FlipKey/TripAdvisor by Sally Locey from Elmira, New York, for her stay in 7/2014

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This is the third different property we’ve rented from Sue Carlson’s rental company, Coastal Cottages AMI, and everyone has been great. Nice secluded pool area which is a real sun trap. Sue’s team are really helpful and nothing is too much trouble. Accommodation is great, with nice individual touches all around. Wouldn’t hesitate to rent this one again!
Submitted via FlipKey/TripAdvisor by Bill M. from Edinburgh, United Kingdom, for his stay in 6/2014

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I can’t say enough good things about our stay at the Pineapple Cottage and Anna Maria Island! The location was great. It was only a short walk to the beach or to the pier. Anna Maria Island is a great way to enjoy Florida and not feel like you are surrounded by high-rise condos. Lots of great little shops right near the house. We found a great restaurant called The Sandbar and it was a short walk away. The free trolley was a great way to get around the island and avoid driving and parking. We found the house to be really comfortable and cozy. We traveled with our pets and they loved the fenced in backyard. The weather was not the greatest, so we could not take full advantage of the pool, but it was still great. On one side was a storage unit building (we never saw anyone there) and a neighbor next door (hardly ever saw anyone there either). Despite it being on a somewhat busy street, you could hardly hear anything. The kitchen was great with updated appliances. The grill was nice to use for dinner and the covered patio area was great to sit out and enjoy dinner. The washer and dryer were great so that we did not have to pack so much for the trip. Plenty of closet space for everything. This was a great place to rent and we cannot wait to come back to AMI and stay at the pineapple cottage next year!
Submitted via FlipKey by Paul from Kayuta Lake, New York, for their stay in 1/2014

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I had the best time ever! Florida is for sure the number one best vacation place! I saw a manatee and stayed in the best house EVER! The pool was also a favorite! We swam in it almost every day! Thank you so much for the best vacation ever! We all enjoyed this very much!
Guest Book entry by Emerson & Gabriel for their stay in 07/2013

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I love AMI, I am a visitor since 2003 from Miami. I love, love this place and Pineapple Cottage was the best place for us to stay. I felt right at home with all the commodities anyone can desire. We thank you for sharing this house with us.
Submitted via FlipKey by Marissa G. of Miami, Florida, for her stay in 06/2013

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This was our first visit to Anna Maria and it won’t our last, Pineapple Cottage is lovely it has everything you would need to make a fantastic holiday. The pool was great for cooling off in the late afternoons before we went out for evening meals, It was lovely to just cross the road to get the free trolley bus that takes you all over the Island. I could go on and on but I will just say it was “perfect”
Submitted via VRBO by Kenny and Doreen of Liverpool, England, for their stay in 5/2013

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Our two weeks on AMI has been fantastic. Pineapple Cottage was great, with everything you could wish for, and the pool was an added bonus for us. The beaches on the island are the best we’ve ever been to. Also, the trolley bus was very useful for getting around. It was pure paradise!
Guest Book entry by Kenny and Doreen of Liverpool, England, for their stay in 5/2013

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It was our first visit to Anna Maria Island. Perfect vacation! The cottage was great for our family of four. The beaches were amazing . . . picturesque. My husband took the two boys to fish off the Rod and Reel Pier. Not one rainy day. Thank you, Florida! We already booked a place for next year as we enjoyed this area so much. We will book this cottage again. Thank you for the memories.
Guest Book entry by Jason, Lori, TJ and Carter of Goffstown, New Hampshire, for their stay in 4/2013

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Great time and location. Enjoyed the pool immensely. Loved Anna Maria Island. Hope to return someday.
Guest Book entry by Karen and Gaston Bernier of Holyoke, Massachusetts, for their stay in 10/2012

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We enjoyed our stay. We had many activities planned with family over the week we were here, and the location of Pineapple Cottage served as a great home base. We loved the private backyard and pool, and cooking our meals on the front patio. We will miss the sun and sand as we’ll head back to Ontario, Canada!
Guest Book entry by Dylan, Kim and Erin Mader of Warsaw, Ontario, Canada, for their stay in 9/2012

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We had a most enjoyable stay. The cottage is very comfortable and convenient. Now I know what island time is.
Guest Book entry by Dick and Carolyn Miller of Mount Juliet, Tennessee, for their stay in 9/2012

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We had a great time! Love the cottage! Hope to be back next year!
Guest Book entry by Dawn, Jaine and Dolly of Ormond Beach, Florida, for their stay in 9/2012

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We had a great time during our first trip to Anna Maria! The cottage was perfect in every way—cute, clean and the best location. We will definitely be back and bring our daughter next time. AMI is ideal for families. Have to mention how pleasant everyone at Coastal Cottages was compared to others I talked to before coming. Fritz is as sweet and cute as he can be. Enjoyed dinner at Sign of the Mermaid and the Shrimp ‘n Grits at Waterfront are worth the hype! Loved Beach Bums for our golf cart, beach supplies, etc.
Guest Book entry by Jason and Hannah of West Decatur, Alabama, for their stay in 8/2012

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We really had a great time here. This was our first visit to the Island, and it sure is beautiful! The cottage made a perfect place for us to enjoy time together on our honeymoon!
Guest Book entry by Isaac and Heather of Unicoi, Tennessee, for their stay in 8/2012

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Oh, Anna Maria Island, how we adore thee! We loved every minute rain and shine! Kids especially loved the pool and riding bikes we rented from Beach Bums. Took a ride via Trolley to scope out our surroundings, ate at several places . . . my personal fav: The Waterfront—Shrimp and Grits were, as my husband says, “off the chain!” We South Carolinians love Shrimp and Grits—Yummo! Another great meal worth mentioning for sure . . . seafood at Sign of the Mermaid (may need a reservation-call ahead) . . . kids options are nice and worth every cent. Had Oma’s Pizza near Bridge Street midweek—Pizza is fantastic and so is their fried eggplant :) Two Scoops and Dips (ice cream) both are wonderful—nice staff too! Sandbar was nice and very convenient being right on the beach! We had lunch one day and dinner another there. Shopping on the island was fair—drove to St. Armands Circle one afternoon. Visited both piers and enjoyed watching all of the abundant wildlife! Weather was great low 90s most days, rain in late pm/early evenings—not bad. Went to beach in am, lunch @ the cottage, pool time, etc. very, very, very relaxing and had all we needed to make this trip a memorable one!
Guest Book entry by Russ, Laura, Aubrey and Landen of Anderson, South Carolina, for their stay in 7/2012

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My wife and I had an amazing time. The place was wonderful.
Guest Book entry by Tess and Ryan Berman of Columbus, Ohio, for their stay in 6/2012

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Family reunion we each had our own little spot on Pine and everyone agreed we had the best. We live in Bradenton, but did not want to have to drive beach and forth to visit family. This will be another stay-cation for us.
Guest Book entry by Don and Lois of Palma Sola Bay, Florida, for their stay in 6/2012

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This was our fifth time visiting the Island and our first stay at the Cottage. This has been our favorite vacation ever!
Guest Book entry by the Jones family of Pottsville, Pennsylvania, for their stay in 6/2012

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Our first time staying on AMI after it had been highly recommended to us by my parents who have stayed at Pineapple Cottage twice before! As soon as we set foot inside we loved it! So cozy and had everything we could need for our relaxing week in the sun. Beaches were fab! Best we have seen and we loved the Sandbar, especially the Grouper Tacos-yum! Sad to leave today but know we will be back!
Guest Book entry by Rhian and Alun Derrick of South Wales, United Kingdom, for their stay in 6/2012

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We had a great time at Pineapple Cottage. Really enjoyed the location and the kids especially loved walking to the pier. This was our first stay directly on Anna Maria and we would definitely visit again. We especially enjoyed the private backyard and the pool was well maintained. Thank you for such an enjoyable family vacation!
Submitted via VRBO for a stay in 4/2012

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We had a great time at the cottage and really enjoyed AMI! We will return again it is a lovely place for a family and their dog. Thanks for having everything we needed.
Guest Book entry by the Johnson family of Gahanna, Ohio, for their stay in 4/2012

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Another year at the cottage . . . another year of great times. Thanks again for offering such a great place for people vacationing with pets. See you next year!
Guest Book entry by Lisa, Val, Matilda, Molly and Oliver for their stay in 4/2012

This was our second year staying at the Pineapple Cottage . . . already booked for next year. Some of our family liked it so much while visiting, they will be renting An Island Place Cottage out front next year. What a wonderful vacation spot . . . great location, wonderful facilities, and a great place for our dogs! Just got back and can’t wait for next year!
Submitted via VRBO for a stay in 3/2012

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This is the place to stay in Anna Maria. Great heated pool and outdoor area. Owner and Gina were the best. We stayed a week and will return in the future.
Submitted via VRBO by Charles from Oregon for his stay in 1/2012

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We had a fabulous time. The place was perfect. Look forward to coming back. We appreciate your hospitality.
Guest Book entry by Kelli, John and the girls of Traverse City, Michigan, for their stay in 12/2011

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Thanks so much for making our time on “the island” memorable, fun, exciting, nerve racking and a joy! Your help was priceless in finding the perfect home for us. Our stay at your wonderful cottage was just what we needed. Enjoyed the pool, the quiet and the feel of the island. Looking forward to becoming seasonal islanders and getting to know you and the area. We will smile every time we think of Anna Maria.
Guest Book entry by Kathie Rice of Lake City, Michigan, for their stay in 9/2011

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Thank you, thank you, thank you! I am so excited and blessed that I was able to meet you and I thank you for all of your amazing help over the last few days! Your place here is awesome and Anna Maria Island truly feels like home! We are going to have wonderful memories of all our visits to the Island! Thank you again for helping my parents find their home and being so gracious to us all! Not only did we find the best realtor on the island we found a friend! Look forward to seeing you again soon!
Guest Book entry by Mollie Osborn for their stay in 9/2011

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Thanks so much for all of our help. You’re the best.
Guest Book entry by Jay Price of Lake City, Michigan, for their stay in 9/2011

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I want to say THANK YOU for the last four days and all you’ve done for my mom and dad. They are so thankful for such a caring and determined realtor they can trust here on the island. You’re the best! Thanks too for providing a place for us to stay while we were house shopping. Pineapple Cottage is cute and cozy and was very convenient for us. I loved and enjoyed the pool too! Looking forward to seeing you again in the spring.
Guest Book entry by Sue Yount for her stay in 9/2011

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Thank you very much for letting us rent the Pineapple Cottage to allow our friends to spend the night here in Anna Maria Island. We absolutely love this area and the place is very nice. The pool with the Jacuzzi jets was super relaxing. Thanks for all of your hospitality!! We want to come back next year for more than a few days.
Guest Book entry by the Beckwith family for their stay in 7/2009

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We had the best stay at the Pineapple Cottage. It’s the perfect cottage on the perfect island. The location couldn’t have been better either. The cottage was well stocked down to the smallest details! The pool was wonderful. We had the best time.
Guest Book entry by Tricia for her stay in 7/2009

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Pineapple Cottage is a lovely place to stay on Anna Maria Island. It is not only tastefully decorated, but it is also a very comfortable place to relax. We enjoy the quiet, private, and cheerful setting of the cottage. We also think the location of the cottage is perfect because we like the short walk down to the City Pier and shops. We are already looking forward to our next visit to Pineapple Cottage.
Guest Book entry by Joan DeKoker from New York for her stay in 5/2006

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Just wanted to let you know what a great time Marlene and I had during our recent stay at your charming Pineapple Cottage. The unit itself is everything we hoped for and more! The location is great (so close to Mamma Lo’s, the Waterfront Restaurant, the Anna Maria Pier and all those other great eateries! And you, Fritz, Mark, Adelle and all the other locals just added to the charm and experience! It should be obvious that we thoroughly enjoyed our stay at your lovely Pineapple Cottage, since we booked it for two future visits prior to our departure.
Guest Book entry by Mel & Marlene Lindauer from Daytona Beach Shores for their stay in 5/2006

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