
Holiday rentals with a kayak in Longboat Key
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Longboat Key
Guests agree: these rentals with 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 kayak rentals in Longboat Key
House rentals with a kayak

The Pink Riverhouse- No damage from Hurricanes
Our stay at Katie's was a wonderful experience. So much to do within the house as well as the backyard. Katie & Terry were both prompt when needed throughout the trip and made us feel at home. Katie also have great recommendations for grocery shopping which made me fall in love with the Amisb Supermarket. Also, great proximty to many attractions. We will most definitely find more time to stay here again!

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!

5 Bed/4 Bath Waterfront Pool Home in Apollo Beach
Family drove in from all over for our son’s graduation from USF and everyone was extremely pleased with the accommodations. We really enjoyed the lower level game room, the kayaks, the pool area, and the local restaurants - notably the ice cream shop across the street! The elevator was a big plus as well. Everything ran smoothly, the house was well stocked with essentials, and everything we used worked perfectly fine. We thoroughly enjoyed our stay.

Florida Cove Cottage - 2BD/2BA in the heart of SRQ
We had an amazing stay at this fabulous beach house. Such a gorgeous property and even better than the photos! Would 100% return if we came back to Sarasota!

Perfect Family Getaway+ping pong, mini golf, bikes
We loved Lotte’s place:) we came down from Tampa for a quick getaway and it was incredibly comfortable and very well equipped with everything we needed. Lotte was very kind to let us bring our dog too. The home is located really close to all the fun things to do in Sarasota (smugglers mini golf, whimsy art galleries, lido beach, mote aquarium were our choices!) We were unfamiliar with the neighborhood but were blown away by how charming and lovely the immediate area is- stunning homes along the bay front- we had a really fun time strolling around with our dog- everyone was really friendly and the atmosphere was really relaxed and the foliage and gardens were beautiful. We even got to see a couple of neighborhood owls in the evening.

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.

Luxe 3BR Siesta Key Home Pool, Hot Tub, Near Beach
Beautiful place on a quiet road. The little touches around the place made it even better and everything was so well stocked. Felt we didn't have to worry about anything and could just relax. Host very responsive and pro-active ahead of time, during and afterwards. Can't wait to go back
Cottage rentals with a kayak

Sunny PaG Island rental w/bikes-just steps2beach
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.

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
Quick stats about holiday rentals with a kayak in Longboat Key
Total rentals
50 properties
Nightly prices starting at
₹10,339 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
- House rentals Longboat Key
- Rentals with lake access Longboat Key
- Beachfront rentals Longboat Key
- Apartment rentals Longboat Key
- Beach apartment rentals Longboat Key
- Family-friendly rentals Longboat Key
- Villa rentals Longboat Key
- Rentals with pools Longboat Key
- Pet-friendly rentals Longboat Key
- Fitness-friendly rentals Longboat Key
- Flat rentals Longboat Key
- Rentals with beach access Longboat Key
- Family-friendly rentals Longboat Key
- Rentals with a fireplace Longboat Key
- Rentals with a washing machine and dryer Longboat Key
- Rentals with an EV charger Longboat Key
- Townhouse rentals Longboat Key
- Rentals with a patio Longboat Key
- Beach house rentals Longboat Key
- Rentals with outdoor seating Longboat Key
- Waterfront rentals Longboat Key
- Rentals with a hot tub Longboat Key
- Cottage rentals Longboat Key
- Rentals with a firepit 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
- Dunedin Beach
- Anna Maria Public Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Cortez Beach
- Lido Key Beach
- Amalie Arena
- Coquina Beach
- Gulfport Beach Recreation Area
- Vinoy Park
- North Beach
- Fort De Soto Park
- Manasota Key Beach
- Streamsong Resort
- Tampa Theatre
- Jannus Live
- Curtis Hixon Waterfront Park