Vacation rentals with a kayak in Longboat Key

Find and book unique kayak rentals on Airbnb

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Popular amenities for Longboat Key kayak rentals

House rentals with a kayak

Guest favorite
Home in Tampa
4.88 out of 5 average rating, 26 reviews

Waterfront home with pool and Jacuzzi. Boat to bay

AmyRating, 5 stars4 weeks ago
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 .
Superhost
Home in Longboat Key
4.88 out of 5 average rating, 121 reviews

Summer House longboat key

DaneRating, 5 stars2 days ago
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!
Guest favorite
Home in Bradenton
4.93 out of 5 average rating, 81 reviews

Rambling River Retreat on the Manatee River

AleahRating, 5 stars1 week ago
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!
Superhost
Home in Brandon
4.81 out of 5 average rating, 32 reviews

Water Front Home to Alafia River

SeniquaRating, 5 stars2 weeks ago
House was clean with lots of things to do on property. Private area and relaxing. Accommodated my 10 guest.
Guest favorite
Home in Tarpon Springs
4.86 out of 5 average rating, 28 reviews

Clean and Spacious Remodeled Home! Master Suite

WayneRating, 5 stars2 months ago
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.
Top guest favorite
Home in Apollo Beach
4.98 out of 5 average rating, 135 reviews

5 Bed/4 Bath Waterfront Pool Home in Apollo Beach

MicheleRating, 5 stars1 week ago
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!
Top guest favorite
Home in Sarasota
4.95 out of 5 average rating, 21 reviews

Beautiful MidCentury Modern Home

PattyRating, 5 stars1 month ago
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.
Superhost
Home in Tarpon Springs
4.7 out of 5 average rating, 37 reviews

A Riverview Hideaway

MichelleRating, 5 stars26 months ago
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

Cottage in Clearwater Beach
4.76 out of 5 average rating, 146 reviews

Pink Gulfside Cottage, Steps to Beach, Pets OK

LoniRating, 5 stars3 months ago
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!
Guest favorite
Cottage in Holmes Beach
5 out of 5 average rating, 6 reviews

Anna Maria Cottage w/Golf Cart

AmandaRating, 5 stars1 day ago
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.
Guest favorite
Cottage in Pass-a-Grille Beach
4.87 out of 5 average rating, 166 reviews

BEACH! Sunny Escape! Steps 2 Famous Beach w/2 Bike

CindyRating, 5 stars4 months ago
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.
Top guest favorite
Cottage in Bradenton
5 out of 5 average rating, 28 reviews

2/2 Charming Riverfront Cottage w Deck & Kayaks

RenaeRating, 5 stars2 weeks ago
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!
Top guest favorite
Cottage in Tampa
4.97 out of 5 average rating, 196 reviews

Bay Lake Cottage

GinaRating, 5 stars3 days ago
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!!
Guest favorite
Cottage in Crystal Beach
4.83 out of 5 average rating, 90 reviews

Happy Camper Cottage | Cozy Oasis with Hot Tub

JasonRating, 5 stars7 months ago
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!
Guest favorite
Cottage in Riverview
4.93 out of 5 average rating, 84 reviews

Alafia River Cottage

Jessica MorrieRating, 5 stars2 weeks ago
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.
Superhost
Cottage in Crystal Beach
4.88 out of 5 average rating, 33 reviews

Elegant Crystal Beach cottage within sea glimpse

BernitaRating, 5 stars1 month ago
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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