
Holiday rentals with a kayak in Longboat Key
Find and book unique kayak rentals on Airbnb
Top-rated Accommodation with a Kayak in Longboat Key
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Longboat Key kayak rentals
Holiday House Rentals with a Kayak

Hibernate in our Bear Creek Home
The place is perfect for a short or long stay. The house has all the amenities you will need. The pool was amazing. Everything was clean and spotless. Short ride to the beach and a short ride to downtown. I hope we can go back again!

Renovated peaceful 2 Bed cottage with/hot tub.
The house is just like the pictures. The kitchen has everything we needed and more. I would definitely would recommend this place.

Historic Wares Creek 3 bedroom with dock access
Clean and beautiful home, we really enjoyed our stay! The host Lisa was extremely helpful! Definitely recommended 👌🏼

Stunning Home, Heated Pool and Boat Dock
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!

Oceanfront Home with Heated Pool in Fishers Haven
House is immaculate! Super clean and comfortable. Beds and linens were luxurious! Ceiling fans in entry room including the screened in porch. Nice touch! Backyard waterfront is amazing. We used pool and hot tub multiple times per day. We fished off the dock and caught a few catfish. Sergiy was a perfect host. Excellent communication and direction when needed. Highly recommend!

Peaceful waterfront home
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!

Piece of paradise in Indian Rocks Beach.
Fantastic home with a great host! Great location and everything needed was at the house. Dinner from a restaurant by the host was very generous

MCM Waterfront Getaway w/ Private Dock + 4 Kayaks
If you’re looking for the perfect Airbnb for fishermen and vacationers are alike, this is it. This Home is elegant and extremely clean. The host are responsive and so sweet and kind. It has everything you can need , and it’s in the perfect location. We loved relaxing and watching the rain in the Florida room. We really enjoyed all the nature outside and fishing from the dock so many memories were made with our family here.
Cottages with a kayak

Pink Gulfside Cottage, Steps to Beach, Pets OK
Great old school beach cottage. Perfect for my Son and me. The Capt. and especially the First mate made it 5 stars!

Anna Maria Cottage w/Golf Cart
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!

Hot tub, 2 floors riverfront, Bush Gardens, kajaks
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.

2/2 Charming Riverfront Cottage w Deck & Kayaks
We stayed at this home for 2 weeks and the nature watching was fascinating. Alligators, turtles, birds and fish jumping out of the water. The home was comfortable and included everything one would need. The Wi-Fi was solid for zoom calls and remote work. The kitchen had every dish, pot, utensil for cooking. The AC worked great and the beds were super comfy. The host replied quickly to every question. I would stay here again. 5 stars. ⭐️ ⭐️⭐️⭐️⭐️

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
This place was wonderful ! Martha was great and very responsive anytime ! Quiet and peaceful and very charming cottage ! Will definitely be returning

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

Cottage by the Bay - free charging, Level 2 EV
John did all he could to make our stay wonderful in his absence. He has a great caretaker who hosted us since John was on vacation, was willing to help us with kayak rentals since he wasn’t there for us to use his, had the nice bicycles ready to ride. Sorry we didn’t get to meet him and Carmen in person; they seem as wonderful as their caretaker! Had pastries and delicious bottle of wine for myself and a treat for my husband, who is not a wine drinker. Caretaker met us and gave us an orientation as soon as we arrived. Was available for anything we needed throughout our visit and had lots of connections and ideas for outings. Grateful for laundry, beach chairs, cooler, comfy bed, recliners, lanai, and all the help and generosity offered during our weeklong stay!
Quick stats about holiday rentals with a kayak in Longboat Key
Total rentals
50 properties
Nightly prices starting at
$198 NZD 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
Destinations to explore
- St Petersburg Holiday rentals
- Tampa Bay Holiday rentals
- Seminole Holiday rentals
- Tampa Holiday rentals
- Central Florida Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Orlando Holiday rentals
- Saint Johns River Holiday rentals
- Fort Lauderdale Holiday rentals
- Gold Coast Holiday rentals
- Miami Holiday rentals
- Kid-friendly rentals Longboat Key
- Rentals with outdoor seating Longboat Key
- Rentals with lake access Longboat Key
- Condo rentals Longboat Key
- Beach house rentals Longboat Key
- Beachfront rentals Longboat Key
- Family-friendly rentals Longboat Key
- Rentals with a hot tub Longboat Key
- Beach condo rentals Longboat Key
- House rentals Longboat Key
- Apartment rentals Longboat Key
- Rentals with beach access Longboat Key
- Rentals with an EV charger Longboat Key
- Villa rentals Longboat Key
- Townhouse rentals Longboat Key
- Rentals with a fireplace Longboat Key
- Rentals with a washing machine and dryer Longboat Key
- Rentals with a patio Longboat Key
- Rentals with pools Longboat Key
- Waterfront rentals Longboat Key
- Pet-friendly rentals Longboat Key
- Cottage rentals Longboat Key
- Rentals with a fire pit Longboat Key
- Fitness-friendly rentals Longboat Key
- Rentals with a kayak Manatee County
- Rentals with a kayak Florida
- Rentals with a kayak United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Dunedin Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Vinoy Park
- Jannus Live
- Streamsong Resort
- Tampa Theatre
- ZooTampa at Lowry Park