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.

Marc and Dave were incredible. They were responsive and proactive! I will definitely be back. We had a family of 7 and even though it was small, we were comfortable. The bikes were an added bonus and amazing to use for our trips to the Daiquiri Deck! Although the weather didn’t cooperate we still had an amazing time and would 10000% recommend this place. Traveling with 5 kids can be stressful and they made accommodations seamless!

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

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!

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!

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.

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.

Our family had a great stay! We traveled with a baby, toddler and two dogs and had plenty of space and everything we needed. Birgit was quick to respond when we had questions. The house is spacious and comfortable. We loved being able to walk across the street to the beach! And the convenience of having an outdoor shower to wash off the kids. There was lingering hurricane damage nearby, but Birgit’s place is pristine! We would definitely return in the future.

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.

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!

Cute spot!! Loved the lake! Actually caught a couple fish! Not a bad drive to the beach area. Would definitely stay again!

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.

We had a very pleasant stay. Sandra and Kim were great to deal with including special accommodations for a late night arrival. We really did feel like guests in every sense. I guess the best thing I can say is that we are back in Bradenton next week and looking forward to another stay.

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!

A week of absolute relaxation. Literally 20 steps to the beach. Wonderful sunsets. The community was great extremely friendly people. Will be back again soon.

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. ⭐️ ⭐️⭐️⭐️⭐️

Absolutely — here’s the updated version with that added: ⸻ Wonderful apartment. Very clean and nicely decorated. We didn’t cook more than coffee because the island’s restaurants were great, but the kitchen looked well equipped. The bed was very comfortable and there were plenty of soft towels. The private gardens and fountains were lovely. Walk right across the street to the beach and under a mile to good coffee and food. The management was quick, attentive, and detail-oriented with their responses to my questions. The beaches are very walkable, and the island is also super bike-friendly and you can easily reach beautiful, secluded beaches that way. Definitely try Mademoiselle’s Paris restaurant—great food, and Chuck played guitar the night we were there. I also liked Hurricane Hanks and The Sandbar. Really nice beach vacation. Great apartment in a beautiful location.

The one issue with this rental was the cleaning and service fees. Upon checking out they asked for guests to clean up, meaning taking out the trash and empty the trash throughout the house, which was partially why am I going through the house and cleaning up when I’ve paid a hefty amount for cleaning fees. When we cleaned with the broom, we found left over food crumbles and pills (medication). Overall tho, a great experience.

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.