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!

We enjoyed our stay, it was a very pleasant, clean, and a practical location. We give thanks to the host!

Beautiful home, nice & spacious kitchen, and all beach amenities provided. Our family really enjoy our stay, perfect location with really short walk to the beach. Paula was a great host and quick to response. Thank you for our wonderful stay and we will be back.

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.

Barbara was a great host. She responded so quickly to my questions. Her cottage was immaculate, organized and had everything you would need to feel like you were at home. Location was walking distance to downtown and the Pinellas County Trail was across the street. It was great to be able to have our dog with us. Fenced in area to let him out. Barbara even had dog treats!!

We brought two toddlers to the little pink house, and they just loved it. The kitchen was set up Perfect. The Murphy bed in the living room was a bonus and let us all spread out when it was time to sleep. Eric was nearby in a nearby apartment, and so helpful with everything. The best is he provided just the right amount of beach toys, and two wagons to get toddlers to the beach, which is just a block away. If we would’ve stayed longer, we would’ve Used the laundry, which was lovely We discovered night frogs at the fountain around the corner, and the nature park and playground also just a walk away . Great spot

Great stay and host!

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!!

This may be my one of favorite vacation rentals we’ve done! The owner is super attentive and quick with responding. The place itself is adorable. Amazing location, clean and so charmingly decorated. They have the fridge and cabinets stocked with essentials which is an amazing touch. Already thinking about booking again for a trip in the winter!

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.

If you're looking for a peaceful retreat, you'll find it here. We had an amazing experience at the Lazy Gator ! Cottage is equipped with everything you could need, including alligators that swim by and bass jumping out of the water. We would definitely return. Thanks Josh!

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.