Historic MamaDear House, Boca Grande Island w/private pool, 5min stroll to beach

We visit the island every year, and this is one of the best homes we’ve stayed in. The house was exceptionally clean, comfortable, and perfectly located—just a short block from downtown, making it easy to walk everywhere. The home is much more spacious than it appears in the photos and is thoughtfully designed with a great layout. One detail that really stood out was the comfort of the beds and pillows in every room, which is something we rarely find in vacation rentals. The owner reached out shortly after check-in and again during our stay to make sure everything was going well. That level of attentiveness was greatly appreciated and is not something we often experience. It’s clear she takes great pride in her home, and it shows in every detail.We highly recommend this property

We just returned from our third year at the Historic Mama Dear House, and it was just as magical as the first! The family home is meticulously furnished and stocked with all the amenities required for a wonderful family getaway. Owner, Deana, is responsive, helpful, and incredibly kind. Our vacation at the Mama Dear House was exceptional!

Wow! This home is an absolute gem on the island! We have had a home here for 30 years, but we needed extra space for overflow of family. It was so clean, so comfortable and SO perfect! It is located right downtown-across the street from Newlin’s (get the lobster roll!) and a short walk away from Hudson’s, the island grocery. Deana is very responsive and so helpful. We had a medical situation with a family member and not only was she helpful with resources, she was so kind and supportive! We are grateful for Deana and her beautiful home!!

Deana and the Mama Dear house is an excellent option for staying in BG. Location is incredible along with the house. 5 stars all day.

Love, love, love! This is our third year here and we can only again rave about the house, the pool, the location, the owners. What's not to love...thank you, MamaDear!

We had a great family trip. The house is absolutely wonderful. Will definitely want to come back.

Great location, great house

I love this house so much. It is beautifully appointed and so well maintained and loved.

This was our second year staying at the Historic Mama Dear Home in Boca Grande, and perfection best describes the home, the location, the activities, and the weather! The house is beautiful and well-appointed with high-quality furniture and amenities for maximum comfort. The well-equipped kitchen and dining area are functional and aesthetically pleasing, providing a very comfortable space for cooking and gathering. The lovely backyard pool and outdoor table offer yet another comfortable space to gather. The outdoor grill and shower are a bonus, as are the beach chairs and beach towels. The house is centrally located in Boca Grande's quaint and quiet village on Gasparilla Island. We walked, biked, and golf carted to all locations; our car sat parked for a week. The beach is 4 blocks from the home, and is lovely for swimming, sunbathing, and shelling. The fishing is fantastic, and there are numerous outfitters to take you out for the day. There are nice restaurants such as the Pink Elephant, South Beach Grille, and the Eagle Grille. And, we highly recommend Newlins for gourmet provisions such as lobster salad rolls and crab cakes! Deana, owner and host, is a delightful person and very responsive. She is one text away for questions. And, it is so apparent how much she loves and cares for her family home. Thank you, Deana!It was a wonderful vacation for my family, perfect actually! We have reservations for 2026 and cannot wait to return!

My family stayed here for our kids' spring break and had an excellent time. The home is beautiful, very well and comfortably furnished, and in a great location. I had a couple of questions while there that the owner promptly answered, including by text message and phone call. Highly recommend staying here!

Absolutely amazing house, location and management. We will 100% be renting this house again.

Our second year at Mama Dear and it was so much fun enjoying this special place with kids and grandkids. The house is so warm, welcoming, comfortable and well laid out! The pool was a big hit! And being only a short stroll from the beach and downtown, for us, it was the perfect location. We never used our car. Can't wait til next year! Thank you!

Great location and was great for our family!