Cottage holiday rentals in Treasure Island

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

Great old school beach cottage. Perfect for my Son and me. The Capt. and especially the First mate made it 5 stars!

Antonia hosts a modern, cozy property featuring three cottages (each have two themed guest suites with a kitchenette). We stayed in the "Captain" cottage and definitely enjoyed our stay! There are also five themed guest rooms attached to a main "house". With eleven possible parties staying at any given time, everything seems to run very smoothly...like an intimate inn. There is ample parking, a Keurig machine in the lounge area, a mini fridge with a selection of sodas, and even towels for the hot tub/pool. They thought of everything to make our stay enjoyable. It certainly is a fantastic property just a few blocks from restaurants and activities in Dunedin. Thank you so much. We will be back to visit again!

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!

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!

Awesome place! Captain Al and housekeeping were great and very hospitable. Great location. Will definitely go back.

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!

We had an amazing experience at Laura’s cottage. The property was exactly as described—clean, comfortable, and fully equipped with everything we needed. The location was perfect, close to beaches, shops, and restaurants, yet in a quiet and peaceful neighborhood. The host was incredibly responsive and made sure we felt welcome. Check-in and check-out were seamless, and we really appreciated the photo shoot areas around the house. We would definitely stay here again and highly recommend it to anyone visiting the area!

We really liked Bob’s place. So much we tried to book it for Christmas but it was already booked. We didn’t do any cooking as we were visiting with our boys and their family. Our pup loved exploring the backyard. Thank you again Bob for sharing your home.

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.

Everything about our stay was as near to perfection as possible.The cottage interior is decorated in a modern minimalistic way to make the small cottage feel more spacious. Everything was clean, and we thought Lisa had thought of everything detail. She quickly responded to our two questions. When I need a place in St. Pete again, hers will be the first choice. Yhanks for making it a very relaxing place to be.

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!!!

While staying in Indians Rock Beach, the apartment was just what we needed. It was a perfect size for the 3 of us. And so close to the beach. We took his recommendations and went to Cooky Coconut while the sun was setting. The neighborhood was quiet and peaceful. Great amenities for the beach we were grateful for. Overall great experience!! Hoping to visit again. Thank you Eric!

The location was great. Place was tidy and clean also checking in was super easy. Tons of things to do nearby. Neighborhood was quiet. Host was super responsive and made our stay perfect! Would book this again it’s just as you see!!!

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.

Coral cottage was the perfect place to get to our favorite locations on the suncoast - being 10 minutes from Hellas is a godsend

Extremely convenient. Exactly as described and pictured. Walls are paper-thin between units, so we did hear the other party come in late one night. That was not enough to deter me - I would book here again in a heartbeat. Very easy to walk to the beach, clean, cute, comfortable bed, very clean bathroom and kitchen - great stay. Close to good restaurants.

Amazing location & SUPER clean!! Quiet area, perfect for relaxing, biking, walking, restaurants & enjoying the cute town of Dunedin. Highly recommend & would book again next time we are in the area. Absolutely perfect!

I flew in from cold and gloomy Chicago and Shane’s place was exactly what I was looking for when my son who stayed with me sent the add to the perfect Beach House. It was a very short walking distance to the beach. Enjoyed a couple of gorgeous sunsets and my favorite, walking on the shore. The beach house was perfect the sun amazing and the perfect long weekend. Thanks Shane.

Great Airbnb and space for 2 couples. Everything was clean, updated and had everything we needed! So close to the beach- there is a lot of foot traffic as the house has direct access to the beach. The place was just what we hoped for! Very clean and comfortable and our host was communicative. We felt at ease here! Thanks for a great experience!

Very responsive, went above and beyond!

Lisa’s place was perfect for four of us attending graduation in Tampa. The house was clean, very comfortable, and the backyard was beautiful. The extra welcome gifts were a nice touch. Would definitely recommend!

Second time staying at the beautiful place! Will again!