
Vacation rentals with a kayak in Longboat Key
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Top-rated kayak rentals in Longboat Key
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Popular amenities for Longboat Key kayak rentals
House rentals with a kayak

Waterfront home with pool and Jacuzzi. Boat to bay
We enjoyed our stay in Tampa at Chris’s home. House was exactly as described and in pictures. The pool and hot tub was a great addition. Chris was very responsive and accommodating. We enjoyed our short visits from Joseph the cat and friend .

Summer House longboat key
Chris was a very responsive host. During our stay he spent a day working on his boat in the back. He was very friendly, but also respected our privacy. The house met all of our expectations and our kids loved the pool. The neighborhood was great to walk through and each house offered fantastic curb appeal. With 3 kids under the age of 6, the 10-12 minute walk to the beach was a little long, but Chris’ wagon and beach supplies helped! The golf cart would have been ideal, but without a place to park near the beach we didn’t have much use for it. We thoroughly enjoyed our stay and the entire family agrees we’d love to go back. Thanks Chris!

Rambling River Retreat on the Manatee River
What a Gorgeous and unique Airbnb. I loved the history behind the house and its tie to the Nitty Gritty Dirt Band. It truly felt like a little piece of history. The view out the kitchen window alone was worth the stay. Most peaceful cup of coffee I’ve had in a long time. The beds were comfy, the decor was modern yet meaningful. We partook in the kids game selection. We truly enjoyed our stay. I look forward to our next visit. We even meet and chatted with Wylan on the day of our departure and honestly couldn’t have been a nicer more welcoming host. A big thank you again for opening your home to us!

Water Front Home to Alafia River
House was clean with lots of things to do on property. Private area and relaxing. Accommodated my 10 guest.

Clean and Spacious Remodeled Home! Master Suite
Book this great house for the location alone! You will get a Superhost in Ryan, and a nicely appointed vacation home with easy access to a lovely nature park just across the street all while less than a 1.5 miles to the famous Sponge Docks and Greek section of Tarpon Springs. The nature park is a great spot to walk your dog or just enjoy the natural beauty of the area. Clean, comfortable and nicely remodeled home, great bed, and functional kitchen with plenty of storage for your items. Ryan is highly engaged and responsive; you won’t be disappointed with this Tarpon Springs home. We would book again without hesitation.

5 Bed/4 Bath Waterfront Pool Home in Apollo Beach
Beautiful, well maintained and stocked property(toilet paper, trash bags etc)!! We enjoyed fishing off the dock as well as relaxing in the hot tub while the kids played in the pool! The beds were comfy home was clean and comfortable! Didn’t hear a complaint from anyone! We loved that the home was located walking distance to restaurants!

Beautiful MidCentury Modern Home
Michael's home was beautiful! It was exceptionally quiet, perfect for sleeping. The kitchen is spotless, well stocked, very organized and inviting to use. My favorite space was the lanai. We enjoyed the outdoor space for coffee each morning, and a glass of wine in the evening. Neighborhood is safe, friendly, walkable, with beautiful sunsets by the water down the street. Michael was very helpful and immediately responsive when we had some travel issues due to weather.

A Riverview Hideaway
Super unique home, great location, close to everything, but also tucked away. The home had something for everyone, fishing, lots of space and very cool antiques. The home was very clean and inviting. Pete and Tammy were great, we look forward to visiting again. Thank you for everything!
Cottage rentals with a kayak

Pink Gulfside Cottage, Steps to Beach, Pets OK
Our cottage wasn’t ready when we arrived but Captain Al was very responsive and accommodating! He provided us another cottage in a timely manner and generously took care of our dinner tab while we waited. It was very chilly in Florida during our stay and Captain Al brought us an additional space heater to use during our stay. The location is amazing and the cottages are very unique! We’d definitely come back!

Anna Maria Cottage w/Golf Cart
Our stay was great. Having the Golf Cart was so handy we didn’t have to rent one. The house is nice and clean the bedding towels. Everything was nice and clean. We would definitely stay again.

BEACH! Sunny Escape! Steps 2 Famous Beach w/2 Bike
If you are looking for a historic, old-school Florida home, this is it. The only reason it isn’t a perfect score is that the hurricane closed most of the shops that make Pass-a-Grille quaint. We were able to support a few local restaurants, and the local traffic was very light. We wouldn’t have changed our trip, but it would have been good to know. It seems like businesses are working hard to get back on their feet. Overall a good experience. I appreciate Lisa’s great responsiveness.

2/2 Charming Riverfront Cottage w Deck & Kayaks
We love this little cottage! The view from the back is phenomenal - we even saw a couple gators. The set up is so good for pets. The cottage has everything you need and the primary bed is more comfortable than a hotel bed. 10/10 and would def stay here again!

Bay Lake Cottage
Kristin’s place is absolutely fantastic!!! I stayed almost 2 weeks and was sad to say goodbye! This cottage is such a relaxing little oasis! Kristin is on the ball with everything! Anything I needed she was on it! The cottage was clean, cozy, and I felt right at home! Next time I return to Tampa, I will absolutely book with Kristin!!

Happy Camper Cottage | Cozy Oasis with Hot Tub
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!

Alafia River Cottage
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.

Elegant Crystal Beach cottage within sea glimpse
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
Quick stats about vacation rentals with a kayak in Longboat Key
Total rentals
50 properties
Nightly prices starting at
ﺩ.ﺇ441 before taxes and fees
Total number of reviews
520 reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
40 properties have a pool
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- John's Pass
- Crescent Beach
- Bean Point Beach
- Cortez Beach
- Lido Key Beach
- Busch Gardens Tampa Bay
- Amalie Arena
- Raymond James Stadium
- North Beach
- Clearwater Beach
- Vinoy Park
- Coquina Beach
- Manasota Key Beach
- Fort De Soto Park
- Tampa Theatre
- Curtis Hixon Waterfront Park
- Jannus Live
- Streamsong Resort
- ZooTampa at Lowry Park
- Splash Harbour Water Park
- Adventure Island
- Myakka River State Park
- Englewood Beach
- Alafia River State Park