Vacation rentals with a kayak in Longboat Key

Phillip was an amazing host. He thought of every little detail in the house for our comfort. Any questions that I had he replied to very quickly. The location was great and so close to the beach. The pool and barbecue were awesome. We would definitely stay there again and again.

We had an amazing week at this beautiful home just 10 minutes from Siesta Key. The house was spotless, super comfortable, and had everything we needed; the pool, boat dock, games, comfy beds, and a great TV setup. Everything was perfect. Jennifer was an amazing host as well; very responsive, respectful, and friendly. You can tell she puts a lot of care into keeping the place clean and welcoming. Definitely recommend!

This home in Port Charlotte is fantastic! The key to a great stay in an Airbnb is a good host. I don't care how good the house is, if you don't have a good host your trip can be ruined. Holli is a great host! We had a minor issue with the pool and texted her about it. We were pulling out of the driveway 15 minutes later and the pool service guy was pulling in. I have not had a more responsive and proactive host before. We had 3 ocean days and 3 kayaking days as our main activities on our trip. I feel like the kayaking is downplayed on the website. There are 4 kayaks to choose from with paddles and life vests. The canals and Myakka river are great places to explore and nature watch. We went in late May and only ran into one other kayaker on our journeys. Venice and Siesta Key were our favorite nearby beaches! White sand and clear water beaches. The house was really fun and modern. We loved the smart couches and very large kitchen. Every part of the home was taken care of with love!

very nice home, the hot tub and pool were fantastic. hot tub was nice and warm. my boys fished off the dock and had a little luck with some small ones. We used the kayaks and saw dolphins! Mike provided us with an amazing meal the night we arrived, which was really great after a long day of travel. The area was also nice, we enjoyed sand key park for fishing, beach and saw dolphins there also. highly recommend!!!

We definately enjoyed our week here and would return. The house was comfortable and had everything we needed. We really loved the outdoor pool area! The host was also wonderful and so helpful. Thank you for a great week!

The place was wonderful. it was very comfy. Big kitchen with lots of pans to cook in. big fridge and huge TV in all the rooms. AC is on point and works great. The yard, the water, the atmosfere is pretty awesome. Loved it

The property was extremely peaceful and equally accommodating!! Super comfortable beds, clean bathrooms and a kitchen with everything you need!! The water views and fishing we're amazing and we will definitely stay there when in the area!! Thank you guys for having us!!

The house was great. Trysten is a great host. Has a lot of things to use for the beach and stuff to use for your little ones. He is also really responsive when we had questions.

Great place right on Pass-A-Grille. Far enough from the restaurants to be quiet, but close enough to walk/stumble to. Beach access is very close. Parking as easy as possible. Rental was Clean and Plenty of Amenities. Would stay again.

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

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!

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.

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!

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 Alafia River House did not disappoint. Check in was easy with helpful photos & directions. The neighborhood is pretty quiet but yet close to everything too. The house is tucked in right on the river, the yard is lush & Florida tropical, it is the perfect place to sit & read, eat a meal or take a nap. Watching the chickens and surrounding nature are an added bonus. The home is old with character, but so clean & refreshing. All the things you need and more are carefully stowed in antique furniture. Martha is easy to contact, but you shouldn’t need anything. The kitchen is up to date & has all of the extra things that you probably forgot to bring. My husband and I had a sweet trip & the Alafia River House was a gem. Thank you Martha.

This super cute cottage is very clean with up-to-date appliances and beautifully decorated with well-thought-out use of space! We stayed for 10 weeks and slept soundly every night due to the comfortable mattress, peaceful & quiet safe neighborhood. The newer fixtures and large washer/dryer were so convenient. Communication with Mary Jane was fantastic. She’s very responsive to questions and even though she lives next door, never intrusive. She’s so gracious we’d be back in a heartbeat! 💗 Truly one of the best experiences we’ve had in the nearly decade of staying in Airbnbs. Location is a bonus as is very walkable to Bay/Beach or bicycle to the Pinellas Trail. This area has so much to offer with beaches, trails, restaurants, fairs, etc