Cottage holiday rentals in Longboat Key

Great home and location with all the amenities that we needed. We walked and rode our bikes all over, and enjoyed the local restaurants.

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.

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.

My boyfriend and I had a wonderful 5 night stay at Amy's for my first visit to Florida. The space was clean, the bed was comfortable, the kitchen was well stocked and the outside space was a peaceful area to spend our mornings. The hot tub in the evening was a perfect way to end the day of exploring. Short driving distance to the beach and other lovely neighbourhoods. We would absolutely recommend, and would be happy to stay 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.

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!

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!!!

You can truly tell that these owners put their all in to what they do. The suite was so clean and nicely decorated and they went the extra mile to include everything you might need. They even included a sweet treat at check in which we enjoyed. We will definitely be back again!

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!!!

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.

My son and I had a wonderful stay at this cute little cottage. Everything was clean and well-decorated, and we had everything we needed in the kitchen. We loved having the golf cart to run around in! The host also provided beach chairs and a kayak to use, which was very handy. The area is pleasant, situated in a quiet neighborhood with public tennis and basketball courts across the street. Anna Maria is a happy little island, with a lot of good food and entertainment, and a number of beach areas to choose from. Lynda was very responsive to any questions we had, and provided a lot of easy -to-follow instructions for the house, as well as lots of helpful tips about the area. We will definitely be back!

We had a wonderful week at Beach Boutique's Anna Maria Island Cottages. The cottage is very cute and tastefully decorated. The kitchen had the necessary supplies, although we also explored the local restaurant scene and used it mostly for breakfast. Despite being situated close to a street, it was quiet and peaceful. The small set of cottages that makes up the property also has several private nooks and a little fountain with more seating areas. We appreciated having access to laundry facilities on-site. The location is also pretty walkable to a few shops and restaurants. We 100% enjoyed a calm, relaxing week away from New England March weather, went for swims and long walks on the beach, enjoyed magnificent sunsets and recharged our batteries.

We stayed at this home for 2 weeks and the nature watching was fascinating. Alligators, turtles, birds and fish jumping out of the water. The home was comfortable and included everything one would need. The Wi-Fi was solid for zoom calls and remote work. The kitchen had every dish, pot, utensil for cooking. The AC worked great and the beds were super comfy. The host replied quickly to every question. I would stay here again. 5 stars. ⭐️ ⭐️⭐️⭐️⭐️

The cottage was comfortable and the setting lovely. A short walk to a beautiful beach . My sister and I loved sitting under the shade of the trees and gazing out at the ocean. On site office meant any questions or concerns were immediately taken care of.

We had a fantastic stay at Crysty’s place. The home was exactly as described—clean, cozy, and thoughtfully decorated. Check-in was seamless, and communication with the host was quick and helpful throughout the trip.

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.

This was our second summer in a row staying at the cottages. We always have a blast.

House was very cozy comfortable and relaxing , Choose from many beaches around area , would stay there again.