This cottage is so clean and comfortable. Plenty of room - front porch, living area and backyard. It is right in the middle of Pine Ave - surrounded by shops and restaurants. The beds were comfortable, huge TV, pool is great and backyard is completely private. We loved The Cottage on pine and will definitely be back.

Thank you so much for this thoughtful review. We are so glad to hear how much you enjoyed your stay at The Cottage on Pine.

It is one of those special homes where everything just comes together. The location right in the heart of Pine Avenue, the comfort of the beds, the spacious indoor and outdoor areas, and that private backyard with the pool really make it easy to settle in and relax.

We truly appreciate you highlighting the cleanliness and comfort as well. That is something our team takes a lot of pride in, and it means a lot to hear it reflected in your experience.

We would absolutely love to host you again when you are ready to return. Your spot on Pine will be waiting.

Marlene - Posted: 4/26/2026

Beautiful 2-bed, 1-bath home on Pine in Anna Maria. The Cottage on Pine is gorgeous inside and out, with a small yard complete with a putting green and a pool. Once Upon A Beach takes great care of this property, ensuring guests have everything they need for a fun and relaxing stay. And, you can't beat the location on Pine - walking distance to the beach, general store, local restaurants, etc. Highly recommend this cute home for a couple or even a couple with 2 children.

Thank you so much for this thoughtful and detailed review!

We’re so happy you enjoyed The Cottage on Pine and everything it has to offer, from the putting green and pool to the walkable Pine Avenue location. It means a lot to hear that the home and experience came together for a fun and relaxing stay.

We truly appreciate your recommendation and would love to welcome you back again soon!

Colette - Posted: 3/27/2026

Very professional, helpful and friendly. Highly recommend this spot.

Thank you so much for the kind words! We are truly grateful you chose to stay with us and that your experience felt both professional and welcoming from start to finish.

It means a lot to hear that you found our team helpful and friendly. Creating a smooth, enjoyable stay is always our goal. We would absolutely love to host you again anytime the island calls you back. 🌴

Steve - Posted: 2/27/2026

We had a wonderful week staying at this charming little cottage over winter break with our kids. The location is fantastic—very close to the beach and within easy walking distance of all the cute boutiques and restaurants on Anna Maria Island. The backyard was a huge highlight for us: the pool and putting green made it such a fun and relaxing space for both adults and kids. Overall, we had a great experience and would absolutely stay here again. We made great memories with our kids, and are already looking forward to coming back again soon.

Thank you so much for sharing this lovely review! 🌴

We’re so happy to hear you had such a wonderful winter break at the cottage and that it was the perfect setting for making special memories with your kids. It’s great to know you enjoyed the convenient location near the beach, shops, and restaurants, and that the backyard truly stood out. The pool and putting green are favorites for a reason, and we love hearing how much fun your family had there.

Thank you again for choosing to stay with us. We’d absolutely love to welcome you back to Anna Maria Island for another memorable getaway in the future!

Kathleen - Posted: 1/5/2026

My husband and I had the opportunity to get away for a few days and the opportunity for us to stay here came up. We had never been to AMI so we had no idea of the location or things to do. As soon as we saw the Cottage we realized we were in the most amazing location. The coast was on one end of road and the beach the other end, both in walking distance. The choices for food, coffee, candy, ice cream and so much more were all in walking distance. The Cottage has everything you will need for your stay, in cooler weather the patio would be a nice area to BBQ and eat with friends. The back yard had a nice pool and 3 hole putting green to top off the evening. If you need any beach gear or golf carts for transportation all you need to do is get with Nikki or a member of her team. Thank you for suggesting the Cottage!

Thank you so much for your kind words! We’re thrilled to hear that you and your husband enjoyed your getaway and that The Cottage was the perfect spot for your first visit to AMI. It sounds like you were able to experience the best of everything — the beach, the coast, local treats, and relaxing by the pool. We’re so happy we could help make your stay even more enjoyable. We’d love to welcome you back for another visit whenever you’re ready for more island memories! 🌴✨

Mary Jean - Posted: 8/22/2025

Our family of 4 stayed in the Cottage on Pine and it was absolutely perfect! The house was spotless, beautifully decorated, and had everything we needed. This house is in the perfect location to access the beach along with great restaurants and shopping just steps away. Every interaction we had with the owners of the property was wonderful. They were very gracious and responded to any needs or questions we had very promptly. We will absolutely be back!

Thank you so much for your kind words! We’re thrilled to hear that your stay at the Cottage on Pine was perfect and that you enjoyed the home’s cleanliness, décor, and location. It means a lot to know you felt well taken care of—providing a seamless and memorable experience is always our goal. We truly appreciate you choosing to stay with us and can’t wait to welcome your family back again soon! 🌴☀️

Katie - Posted: 6/6/2025

Great place all around

Cassie - Posted: 5/16/2025

Thank you for the kind words! We're so glad you had a great experience all around. It means a lot to us, and we’d love to welcome you back for another stay anytime! 🌴😊

Once Upon a Beach staff

Posted: 5/16/2025

I cannot say enough good things about this adorable cottage on AMI! It had been over 20 years since our last visit, but this stay definitely put this vacation locale back on our list. Everything was exactly as advertised and even better in person. Furnishings were very nice, clean, stylish, and comfortable. Kitchen appliances and laundry facilities were spotless. Backyard with pool was just right for the two of us, but could have easily accommodated a larger family. The location can't be beat with many walkable options, but that didn't stop us from renting a golf cart from Once Upon a Beach as well! All questions to the welcoming hosts were answered promptly. Thanks for having us - this was the absolute perfect place to celebrate our 25th anniversary and we cannot wait to come back!

Thank you so much for your beautiful review! We're honored you chose to celebrate such a special milestone with us—congratulations again on 25 years! We're so glad the cottage exceeded your expectations and that everything from the furnishings to the backyard and location helped make your stay memorable. It’s always wonderful to hear when guests rediscover Anna Maria Island and fall in love all over again. We’d be absolutely thrilled to welcome you back anytime!

Jessica - Posted: 5/16/2025

This beautiful home was a perfect fit for our family, including our 18 and 16-year-old children, offering ample space for everyone. A fantastic bonus was the small pool in the backyard, providing a refreshing alternative when we wanted a break from the beach. Although the house is located on Pine Street, which is a lively area with coffee shops and boutiques, its position set back behind the main office ensures a surprisingly quiet and peaceful stay. While being on a busy street could be seen as a potential drawback, the tranquility of the house itself and its overall charm are not diminished.

Thank you so much for your kind words! We're absolutely thrilled to hear that the home was a great fit for your family and that everyone—from your teens to the adults—had the space and comfort they needed. It's wonderful to know that the pool added a fun and refreshing touch to your stay, and that you enjoyed the vibrant location while still appreciating the peace and quiet the house offers. Your thoughtful feedback truly means a lot, and we’re so glad the charm of the home shone through. We’d love to welcome you back anytime!

Delilah - Posted: 4/24/2025

This was our first time coming to AMI, and we could not have chosen a more perfect location to spend it. The cottage was just the right size for our family of 4 (our boys are 5 and 7). It was well-appointed, decorated beautifully, and had everything we needed for the week. We also rented a golf cart from Once Upon A Beach and would definitely recommend it! We went to Bean Point and the access at White Avenue most days, and the golf cart made the trip much more manageable! We had a tiny issue the first night upon arrival, but a quick text to Mike and it was resolved within 10 minutes. We will definitely book again!

Anonymous U from White Pine, TN - Posted: 3/23/2024

Thank you so much for your wonderful review! We’re thrilled to hear that your first visit to AMI was made perfect by staying at the cottage. It’s fantastic to know that the space was just right for your family and that you appreciated the beautiful decor and well-appointed amenities. We’re glad the golf cart rental made exploring Bean Point and White Avenue even more enjoyable! We truly appreciate your patience with the tiny issue and are happy that Mike could resolve it quickly for you. We can’t wait to welcome you back for another unforgettable stay! Thanks once again for choosing Once Upon A Beach!

Once Upon a Beach staff

Posted: 2/25/2025

Stayed for 6 nights for our nephew’s wedding. The Pineapple cottage was great. Very clean, nice pool, very quiet even though it’s on a busy street. Able to walk to the beach and the city pier. Lots of food options nearby. The gas grille was very clean and there is a nice covered table outside. Very nice small property. Hope to be back. Had a beach buggy and chairs.

Mike W - Posted: 6/19/2023

Thank you so much for your kind review! We’re so glad Pineapple Cottage was a great fit for your trip and gave you a comfortable, quiet place to relax during such a special occasion. 💛 It’s wonderful to hear that the cleanliness, pool, and outdoor setup—including the grill and covered dining area—helped make your stay even better. We’re also happy you could enjoy the easy walk to the beach, pier, and so many local favorites nearby. We’d love to welcome you back anytime and truly appreciate you choosing to stay with us!

Once Upon a Beach staff

Posted: 5/9/2025

We vacationed at Anna Maria Island (AMI) and stayed at "Pineapple Cottage" by Once Upon A Beach. The beach cottage was cozy, exceptionaly clean, and the interior woodwork was absolutely lovely! The private partially shaded inground pool was perfect for a refreashing afternoon swim and lighted during the evening. There was plenty of outdoor seating areas including a covered and shaded dining area. The location on Pine Ave was within walking distance of many local shops, eating establishments, Two Scoops Ice Cream (which has the best ice cream on the island), and the island pier. The owners of Once Upon A Beach are very attentive to their occupant's needs and add "special touches" such as a welcome gift bag. The cottage was stocked with everything we needed for a beach day such as chairs, umbrella, and even a wagon to carry them. We will definately be back to the tranquil and relaxing AMI. I highly recommend staying at one of Once Upon A Beach's lovely homes!

Celine P - Posted: 6/19/2023

Thank you so much for this beautiful and thoughtful review! 💛 We’re absolutely delighted that Pineapple Cottage was the perfect island retreat for your time on AMI. Cozy, clean, and full of charm—that’s exactly what we hope every guest experiences, and we’re so happy to hear the woodwork and poolside ambiance stood out for you! 🌴💦 It’s wonderful to know you enjoyed the convenience of Pine Ave and all the local favorites—especially Two Scoops (we couldn’t agree more about the ice cream 🍦). We’re also thrilled that the little touches, like the welcome gift and beach gear, helped make your stay feel easy and special. Your kind words mean the world to us, and we truly can’t wait to welcome you back to the island. Thank you for recommending us and being part of the Once Upon A Beach family!

Once Upon a Beach staff

Posted: 5/9/2025

We have been coming to AMI for over 10 years now this is by far my favorite place to stay ! Very clean and cozy ! Finally a place with comfortable beds !!! Perfect location this made our trip top shelf staying here ! Coming back in May ! Love the Pineapple Cottage !!!

Kimberly S - Posted: 6/19/2023

Thank you so much for your wonderful review! 🌟 It means the world to us to hear that after 10+ years of visiting AMI, Pineapple Cottage is your favorite stay yet! We’re especially glad you found it clean, cozy, and—yes!—with comfortable beds (we know how important that is for a truly restful vacation 💤). The location really is hard to beat, and we’re thrilled it helped make your trip feel “top shelf.” We can’t wait to welcome you back in May! Until then, thank you for choosing to stay with us and for the love you’ve shown our home. 💛🍍

Once Upon a Beach staff

Posted: 5/9/2025