Cottage holiday rentals in Gulfport

I’ve found my new favorite staycation spot and where I will enthusiastically recommend to friends and family visiting the area. The space was thoughtfully designed, clean, and comfortable. I will miss my morning coffee on the patio amongst all the plants and birds, my daily work sessions in the small quiet office, and the evening dips in the hot tub. Thanks for your thoughtfulness in creating this space!

Our cottage wasn’t ready when we arrived but Captain Al was very responsive and accommodating! He provided us another cottage in a timely manner and generously took care of our dinner tab while we waited. It was very chilly in Florida during our stay and Captain Al brought us an additional space heater to use during our stay. The location is amazing and the cottages are very unique! We’d definitely come back!

Beautiful home, nice & spacious kitchen, and all beach amenities provided. Our family really enjoy our stay, perfect location with really short walk to the beach. Paula was a great host and quick to response. Thank you for our wonderful stay and we will be back.

We had a wonderful day! It’s in walking distance to everything that we needed to do. We even were able to walk to safety Harbor spa where we had a lovely spa day! Everything was very clean and I loved the amenities from the bath soap to the Starbucks k cups. We enjoyed the hot tub and bird watching from the cute outdoor setup. Perfect location!

First time staying at Capt Al’s cottages and we had a fantastic time! We had everything we needed, easy walking distance to beach, restaurants, and waterfront. The cottage was clean and well supplied, the common area tiki bar vibe was fantastic! We appreciated the use of all the beach chairs, sand toys, ect. Perfect for a family beach vacation!

My friend and I recently stayed at Laura‘s place with our four kids under four years old. The house was not only super cute and clean, but also very comfortable, accommodating and kid friendly. Laura even made sure we had enough cribs/ floor beds to accommodate our specific sleeping needs for our young kiddos. Despite the chaos of juggling 4 kids, we felt right at home and welcomed by Laura. It was so nice to have plenty to “do” at the house when we chose to stay in and were within 15 minutes to beaches and shops on days we chose to venture out. Indian rocks beach was our favorite (less crowded than Clearwater - although parking took a little time to find mid day) and we had a blast at ZooTampa (~40 min away). We also walked around shops and ate lunch at Pelican Walk Plaza which was a fun change of pace. Ice cream and Walmart (and other grocery/ stores) were 2-5 minutes from the house which was super convenient as well. We highly recommend the house/ property, location and hostess!

Anna was extremely helpful and accommodating for our last-minute trip with the kids. Her place was super cute and very clean and well kept and we would be happy to recommend it to friends and family or return ourselves. Thank you so much, Anna!

Ame is a wonderful host! This is the cutest little house, stocked with everything you might need for a stay in sunny Florida! Clean as a whistle, too. Location was perfect, groceries, the beach, pizza and shopping all close by.

The cottage was very cozy and comfortable. Loved being able to walk down to bayshore for nightly walks. Also enjoyed the nice little back patio with sitting area. The weather was so nice and we ate out there many nights . Also nice to have your own driveway to park in. Would stay here again . :)

The Yachtsman is a charming cottage in a perfect location, with a lovely view of the ocean. Open the front door and you're right on the beach to go for a walk, sit on the patio and see a beautiful sunset every night. It was impressive how quickly and well the Management restored everything after the hurricanes. Staying at The Yachtsman was a special and unique experience; I would do it again in a heartbeat if I could.

Bob was very accommodating, easy to communicate with and very friendly. Everything went smoothly, from entry to instructions for leaving. Adorable place, all new appliances, nice bedrooms, even great water pressure in the shower! Can’t wait to come back!

Citrus Cottage 2 was the perfect size for my wife and I. The location can't be beat. Dunedin is a walkable town, and the cottage was right in the center of everything. We were a 5-minute walk to numerous restaurants and breweries and to the Pinellas Trail. Michael provided a clean and comfortable home for us to relax in. The shower was amazing and felt so good after a 13+ mile bike ride. We have been to Dunedin several times and this was, by far, the best place we've stayed in. We highly recommend Citrus Cottage 2, and we will definitely look to stay here again the next time we visit Dunedin!

We LOVED staying at Christopher’s. The apartment was exactly what we needed. The neighborhood is adorable and so close to downtown. Christopher was an absolute gem of a host who went above and beyond to make sure we had a great stay. So grateful! Would return.

The cottage was immaculately clean and comfortable. It was stocked with everything you would need such as kitchen necessities, toiletries, extra towels and beach items. The pool was beautiful and even lit up at night. It is a three minute walk to the beach and some of the bars and restaurants. It is a very quiet neighborhood. The host was extremely nice and responsive with everything. We would stay there again. And I loved the free library out front. I left a book in there ☺️If you are thinking about renting this cottage, you definitely should, you won't be disappointed.

Whenever I visit Gulfport, Uncle Finley’s is the first place I check for availability. The house is well situated with all the right touches to make you feel at home. There have been some recent improvements to the inside and outside of the home that add even more value to the stay.

We enjoyed our stay. The house was very clean and had everything we needed. It was very quiet and peaceful. Very easier to get everywhere we had to go. I highly, recommend Doug's place.

We really enjoyed our stay at Erin's place. First off, it was spotless! The location is great and within easy walking distance to Dunedin's delightful Main St. We found the space to be comfortable and quiet. Erin was very responsive and pleasure to deal with. We will stay here again when we return to Dunedin.

My husband and I enjoyed our stay at the cozy cottage. The location to Crystal Beach is great! We loved sitting on the screen porch. The house is just like the pictures. We had everything we needed to spend one month. Joni is a responsive host. We would be happy to stay again.

This place is very close to the beach and walkable to the local stores and restaurants. Beautiful place - had everything we needed! We hope to return again!

Very responsive, went above and beyond!

We really enjoyed our stay, walk to beach, comfortable deck, close access to restaurants and shops. We were a little apprehensive of the circular stairs at first but were no issue at all. Only downside was the spotty Wi-Fi which both Jude and Jenni tried to help with, but it was a Spectrum issue. Both were available and extremely accessible, helpful and friendly.(

Your cottage truly felt like a home away from home. I was charmed by its character & history – the beautiful wooden floors, the cozy fireplace – it all created such a welcoming atmosphere. Your place was the perfect base for our stay to visit with family. I had prepared all of our meals in advance, but, of course, forgot some basics like foil and storage bags. I was delighted to find your wonderfully stocked kitchen had everything we needed and more. We enjoyed every meal in the spacious dining room, with the fireplace adding a lovely touch of comfort. Every room in the cottage was big, and thoughtfully decorated. And the bathroom – with that incredible soaking tub – was the cherry on top. I treated myself to a long, relaxing soak on our second morning. Though we didn’t use the second bathroom, the large step in shower was a great option to have. The neighborhood felt very safe, which added to our sense of ease. Thank you for creating such a thoughtful, comfortable space.

Excellent experience! We loved everything about the cottage! Great location, lovely grounds, loved sitting on the porch and watch tv….highly recommend!

This super cute cottage is very clean with up-to-date appliances and beautifully decorated with well-thought-out use of space! We stayed for 10 weeks and slept soundly every night due to the comfortable mattress, peaceful & quiet safe neighborhood. The newer fixtures and large washer/dryer were so convenient. Communication with Mary Jane was fantastic. She’s very responsive to questions and even though she lives next door, never intrusive. She’s so gracious we’d be back in a heartbeat! 💗 Truly one of the best experiences we’ve had in the nearly decade of staying in Airbnbs. Location is a bonus as is very walkable to Bay/Beach or bicycle to the Pinellas Trail. This area has so much to offer with beaches, trails, restaurants, fairs, etc