Cottage holiday rentals in Hillsborough County

The Location was great, short walk to downtown Dunedin. There was some construction outside but didn't affect getting in or out of the property and sound wasn't an issue. 10/10 would stay again next time I'm in Dunedin.

Cozy, comfortable, yet two stories with plenty space to stretch out, scenic view with a hot tub, nice balcony view for coffee in the morning. Can’t go wrong.

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!

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 perfect for my stay. The area was clean and quiet. The common building was inviting with comfortable areas to relax and free coffee! I had a small issue with the lock and Antonia and her staff responded within seconds with a quick resolution. I could not be happier with my stay. You can’t go wrong staying here!!

Tim and Jeannie are the best hosts ever! Communication and local recommendations are top notch! If you are like us, you’ll be on the go because Saint Petersburg offers so much with arts, culture and outdoor recreation that most of the time was being out and about. However, when you get back, you’ll feel like you’re at home and everything you need is right there! Sleep in and eat breakfast at the cottage, come back early and watch a movie or hit the hot tub or just do another load of laundry and hit the beach one more time! It’s so convenient and the best location ever! Thank you Tim and Jeannie :)

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 had a great stay at Sandy Feet VR! The house is clean, comfortable, and located in a lovely, walkable neighborhood—perfect for morning strolls or quick trips to nearby spots. It’s a great place to relax and unwind. The home is well-appointed, though it could be stocked a little better for longer stays—just a small consideration for future guests. That said, it’s a wonderful place overall, and we’d definitely stay again. Highly recommend for a relaxing getaway!

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.

This house is an absolute gem! It had everything that we (and our dogs) needed and more! There are so many wonderful spaces to relax in. We enjoyed the main room, screened in back porch, beautiful front courtyard, and sipped coffee in the back yard each morning by the canal. We also had a blast paddling out to the bay in the canoe! The host is super friendly and quick to respond. She has put a lot of nice touches on the property that we really appreciated. We had the best time here and would love to come back! Highly recommend a stay here!

The Alafia River House did not disappoint. Check in was easy with helpful photos & directions. The neighborhood is pretty quiet but yet close to everything too. The house is tucked in right on the river, the yard is lush & Florida tropical, it is the perfect place to sit & read, eat a meal or take a nap. Watching the chickens and surrounding nature are an added bonus. The home is old with character, but so clean & refreshing. All the things you need and more are carefully stowed in antique furniture. Martha is easy to contact, but you shouldn’t need anything. The kitchen is up to date & has all of the extra things that you probably forgot to bring. My husband and I had a sweet trip & the Alafia River House was a gem. Thank you Martha.

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 arrived at night days late due to flight cancellations from home weather. Ashley and Josh were very understanding and welcoming. They were responsive and kind throughout our stay. Their daughter showed our kids around the property and shared her toys, making everyone feel welcome. The back house was comfortable, clean, and well stocked. The area is beautiful and we felt very safe with our small children. We enjoyed walks to feed the cows, playing with the dogs, finding frogs, watching lizard play, listening to birds, dipping out feet in the pool, and collecting eggs from the chickens. The location was convenient for getting to many locations in and around Tampa.

We cannot say enough about this Airbnb. It’s exactly like the pictures show. Beautiful, clean, peaceful place to stay close to everything you need and want to do. Easy to get in and out. Very reasonable on expectations. Extremely fast and communicative. Price is definitely worth every penny. If we visit this part of Florida again we will definitely see if this Airbnb is available first!

Karina was extremely communicative. The location was perfect - walkable to all downtown!

We stayed at Lisa’s place for a little over 2 months. We are from the area, however our home was unavailable. We liked walking the neighborhoods and to the lake each day. Downtown St Pete is about 1.5 miles away, so very nice walk or quick drive. Lots of great nightlife and restaurants there. A 4-5 block walk puts you on 4th with coffee shops, restaurants and breweries nearby. The cottage is also well equipped for making meals at home or relaxing in front of the TV. The patio area was beautiful and well maintained. It’s nice for coffee in the morning, or a glass of wine in the evening. King size bed! Big shower, laundry on premises. Everything we needed and at a great price!

We had a great time we walked down to the beach the peer was closed due to hurricanes that destroyed it but can still walk on sand over there very dog friendly area not far from Clearwater definitely recommend wish it had a grill to grill out but it was relaxing

Very responsive, went above and beyond!

Our stay at Mango Cottage was very relaxing. The house is very cheerful and bright. Nice beach house. The back yard is large, we enjoyed sitting outside. The bedrooms are nice and dark with the blinds and curtains. the beds are very comfy. There's an awesome fresh seafood store, Frenchie's that we picked up seafood to cook. The beach is small and "weedy" as the description says but offers beautiful sunsets for pictures. The neighborhood is quiet and nice to go for walks in. I would return, for sure!

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