Cottage vacation rentals in Longboat Key

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

The Yachtsman is a charming cottage in a perfect location, with a lovely view of the ocean. Open the front door and you're right on the beach to go for a walk, sit on the patio and see a beautiful sunset every night. It was impressive how quickly and well the Management restored everything after the hurricanes. Staying at The Yachtsman was a special and unique experience; I would do it again in a heartbeat if I could.

Excellent stay Excellent hosts Thank you for hosting us

Everything was awesome the cottage was very cozy. Perfect beach. The only inconvenience I would say we had was the fact that we booked for 5 guests and only received 2 parking passes, therefore some of our guests did not have parking passes and led to the worry of their cars being towed. They then had to pay for their own parking for their stay, other than that we had a wonderful time. We would love to come back and stay, everything else was beautiful. Thank you so much.!

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.

The Palmetto Cottage was a lovely getaway! We stayed for just under a week, and enjoyed our time there. It was great to be able to cook our own meals & swim in the pool, and still head to the beach & enjoy the ocean when we wanted to. And it’s close enough that we went into Tampa one evening for a nice dinner out. Thank you for such a lovely, cozy space!

This was our 3rd year staying at Kelly's cottage. We always have a wonderful time seeing our family. This cottage is the perfect size, big, roomy, and always squeaky clean !! It has everything you need for your stay. Looking forward to coming back next year !!

Fantastic location. One block from the beach and provided chairs and umbrella were very nice to have. When ready to be quiet the pool area at the house was perfect.

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.

We had the best time - it was everything we could've wanted in a rental! This was our first time staying in Holmes Beach and we loved it. The house is close to everything in town. We used and enjoyed all the wonderful amenities that Craig provides - the golf cart (a must!), beach cruisers, beach wagon, umbrella and chairs. The pool, hot tub and hammock were also a highlight for us. We can't wait to come back!

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.

Small but cozy place. Perfect location to walk to the beach or to get something to eat.

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!