Cottage vacation rentals in Hillsborough County

Very responsive, helpful hosts and a wonderful location with lots to offer.

Really enjoyed our stay at the Captain’s Cottage! Nicely kept, with thoughtful amenities. Hope to be back someday to explore more of Dunedin.

We absolutely loved it here. It was very clean and had everything we needed. Hot tub was a great amenity. The shed full of beach needs was amazing! Definitely would stay here again!

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 time staying here! The location is phenomenal and it was always quiet outside the home, day and night. You can walk to restaurants, bars, shops, and more in less than 2 minutes. Beach access is 15 or so minutes away as well. The home was clean and well appointed for 2 people and the host was always responsive and nice. We were also able to bring our dogs, which we appreciated. We love Safety Harbor and will definitely stay here again!

Capt Al and his crew were friends and attentive to all our needs! Great location with a great vibe that has easy access to the beach!

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!

The house was cute, cozy and beautifully decorated. Laura was very responsive when communicating. Our family of 4 stayed for 3 nights and enjoyed the outdoor space and game room a lot. Plenty to do and lacked nothing. Just be warned about the mosquitoes if you plan on spending long periods of time in back patio area. Bug repellent was provided, however we were still eaten alive. This however did not ruin our overall experience. I would totally recommend this location to anyone and would definitely like to visit again.

Lisa was a great host, and paradise by the beach is an awesome place to stay. My family of 4 (2 adults and our older teens) just loved being able to have a lot of space (compared to the hotel rooms on st Pete beach) and a full kitchen and a close walk to the beach. The kids loved riding the bikes to get an ice cream at night, and it was so easy and convenient to pack up the chairs and umbrella and walk over to the beach. The walk is actually shorter than the resorts we have stayed at on spb. It was kind of like settling into our home by the beach—very comfy and convenient with everything we needed. Lots of tvs, lots of space, easy to get around. I also liked having a fully equipped kitchen—only made dinner one night, but everything we needed was there! We’d definitely again and prefer it to the other resorts we have stayed at. It’s less expensive, more convenient, and a lot more space. Thank you so much, Lisa! We hope your space is available next time we come down!

Had a great stay ! Fishing was fun and right across the street Would stay again for sure !

The sweetest beach cottage which was perfect for my husband and I and our two kids. We loved how spacious it felt with high ceilings and open floor plan. The beach is a two minute walk and the pool in the backyard is beautiful! Would stay again! I also appreciated the convenience of providing a high chair and beach supplies. The small details were much appreciated. Highly recommended.

We absolutely love staying at this property! It is our third time booking. The cottage is always impeccably clean and in a very safe area. It is stocked with everything you need. We love Coral Cottage! And Barbara is very friendly and so responsive. Dunedin is an amazing, quaint little town with so many wonderful food choices. Cafe' Alfresco is our personal favorite. Barbara's cottage is just a couple blocks from downtown Dunedin and only a 15 minute drive to Honeymoon Island State Park or Clearwater beach. I always pick up a piece of jewelry as a memento when we go on a trip. Just kitty-corner from the Airbnb is a charming jewelry store filled with beautiful, unique pieces that are reasonably priced. Romantique Jewelers. Just ask for Kimber, she's a doll! Don't hesitate to book this property for your next trip!!!

Great stay!!! We stayed with our 4 year old here and it was awesome. Easy to walk to places/beach. It was extremely clean. I definitely would recommend this place. Eric was welcoming and helpful

Such a vibe! The location is perfect. Close enough to walk to downtown, but far enough to feel like you've got privacy.

Beautiful little house, only a 1 block walk to the beach. Many restaurants, bars, shopping areas all within walking distance. The sound of the pickle ball players and laughter in the park while sitting on the back patio was a very nice touch! Overall fantastic experience, we will be back!!

Absolutely perfect Airbnb in every way! The location could not be better. We laughed because we had dinner reservations at Pia’s Italian restaurant and realized it was right across the street. Talk about convenience! This was hands down the cleanest Airbnb we’ve ever stayed in. Uncle Finley left us a thoughtful welcome package with a bottle of wine, beer, water, orange juice, and more. It’s clear he’s put real care into every detail to make the stay extra comfortable. Phone chargers were exactly where you needed them (no hunting for outlets), there were doggie bowls and doggie bags for our pup, Uncle Finley was super responsive to questions and genuinely committed to taking care of both his guests and this beautiful home. We’d come back in a heartbeat. Don’t hesitate just book it! Tip: In addition to Pia’s homemade pasta with pesto sauce, I’d also highly recommend the restaurant Pearl by Chef Karim for an unforgettable meal! The Pearl is a testament to culinary excellence.

Couldn’t be happier with our stay. Nick and Anna were wonderful and went above and beyond to make sure we had a perfect experience. The home was clean, conveniently located, and appointed with everything we needed. We’d gladly stay again!

Gloria is a wonderful host. Easy to communicate with and had the place stocked with amenities. We loved the location on the water and used the available kayaks to access the water to fish and have some fun in the sun. 10/10 recommend. Thank you Gloria!

The house was perfect! Well stocked, beautiful space and great location.

This place was wonderful ! Martha was great and very responsive anytime ! Quiet and peaceful and very charming cottage ! Will definitely be returning

We needed to escape the busyness of Orlando, and Dean’s cottage was exactly what we were looking for—peaceful, quiet, and beautifully tucked away. The location was perfect for us, just a short distance from a Pinellas Trail access point, which made it easy to hop on our bikes and ride for miles. The cottage was clean, modern, and stocked with everything we needed—whether we were heading to the beach, relaxing on the patio, or winding down with a Netflix movie. The bed was incredibly comfortable—we seriously didn’t want to get up in the mornings! The grounds were a pleasant surprise—lush with flowers and shrubs, perfect for short strolls with our dogs. It felt like our own little sanctuary. And when the work week started, we appreciated having a peaceful place to work remotely. At the end of the day, we were just minutes from beaches, downtown St. Pete, and charming local spots. Dean’s place truly had everything!

We can't say enough good things about our stay. Morgan was so friendly upon our arrival and made us feel right at home. The cottage was very cozy, and it was literally on the beach. The view from the patio was amazing. We sat out there until after dark every night. We would definitely love to make a return visit.

Excellent accommodations. Very well maintained and comfortable with all the accomodations for a relaxing and enjoyable stay. Great location close to beaches, restaurants, ancd other attractions. I am looking forward to a return visit. Marie Karine was a friendly and responsive host.

Rick was such a kind helpful host! Checked on us to see if we needed anything. Had one request and he quickly fixed it! Upon entering, home was ready, music playing and a welcome note! He even had eggs and oatmeal available for breakfast! We would stay again.