Cottage holiday rentals in Clearwater

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

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.

I had a pleasant stay at Dallas’ little cottage. I was traveling alone with my medical foster and felt incredibly safe, even after arriving pretty late. There were guests in the house up front, but were quiet and respectful. The size is perfect for solo or a couple. The decor was tasteful, house was clean (no pet smell) and having a fence was convenient. Loved how walkable the neighborhood was too! It is an older house with typical character-filled imperfections, but I love that vibe and the warmth it gives. As a heads up to anyone unsteady on their feet, the floor does slope in some areas. The only star I knocked for description was for the additional pet rules posted in the house that weren’t in the online listing at the time of booking/stay. Biggest one to note is that pets are not permitted to be on the furniture (understandable, but a surprise). With a velcro dog, that put me in a predicament. If your needs match with the rules, it is a solid choice!

Really cute place! And close to everything in downtown Gulfport Florida. Great small flooring community with a great community vibe!

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.

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

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!

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.

Everything was more than the description! Beatiful cozy place on the outside, inside everything was almost new, a big surprise. Loved the location!

3 of us were down there on a golf trip. I found the whole experience seamless, from booking to access to leaving. Jen was extremely responsive (within 30 min most times). The place was spotless and uncluttered. Had the right amount of kitchen ware for what we were looking for and the beds and chairs were comfortable. We would definitely stay there again.

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!

My husband needed to be in town for work so I joined with the kids. This house provided everything we needed for the time we were there. The house was exactly as advertised, great location, spacious, comfortable beds and no issues with the hosts. The neighbor was also very friendly. No complaints and nothing lacking. I would recommend.

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.

clean, spacious. Beautiful location right on the bayou. Friendly neighbours.

Such a lovely cottage with an unbeatable oceanfront location. The beach is the backyard! We loved the Old Florida feel of the cottage, but it was also very clean and well-appointed. We also loved that there was plenty of beach gear, toys, and games available for the Scruggs Harbor guests to borrow. Morgan is a wonderful host — quick to respond and around if you need her. We most certainly would love to stay here again!

I absolutely adored this home! I live in Charleston and work remotely, but my corporate office is in Largo. I travel there quite often for work, and have always stayed in hotels. This time, I wanted to try something new and I will never be able to go back! I truly hope that I can stay in Chanel and Justin's place for ALL my future work trips and have already shared it with co-workers, as well. The photos are accurate and I would even say they don't do the place justice. It was spotless when I arrived, and I appreciated a soak in the tub after a long work day. I slept in the front bedroom and it was SO COZY! I really enjoyed the Florida room and ended up doing quite a bit of work out there on my laptop. Neighborhood was peaceful, quiet, and I felt safe. The beach was a quick 10-15 minute drive, allowing me to catch a sunset. There are plenty of DoorDash options for those that don't want to mess up the spotless kitchen. Highly recommend for business or pleasure. Will be back soon!

My husband, 3 kiddos and I had the best time at the bitchin beach house!!!! We felt right at home. Loved the private back yard..we all enjoyed squirrel watchin! 🤣 great host, great place, can’t wait to go back! Also, honeymoon island is a short 25 minute drive, $8 to park, beautiful natural beaches and less crowded than the public beach! <we spent most of our days there ❤️