Holiday 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

Holiday House Rentals with a Kayak

Guest favourite
Home in St. Petersburg
4.89 out of 5 average rating, 126 reviews

Hibernate in our Bear Creek Home

AnthonyRating, 5 stars1 day ago
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!
Superhost
Home in Palm Harbor
4.9 out of 5 average rating, 121 reviews

Renovated peaceful 2 Bed cottage with/hot tub.

KrishaRating, 5 stars3 weeks ago
The house is just like the pictures. The kitchen has everything we needed and more. I would definitely would recommend this place.
Top Guest favourite
Home in Bradenton
4.95 out of 5 average rating, 128 reviews

Historic Wares Creek 3 bedroom with dock access

AssemgulRating, 5 stars8 months ago
Clean and beautiful home, we really enjoyed our stay! The host Lisa was extremely helpful! Definitely recommended 👌🏼
Guest favourite
Home in Sarasota
5 out of 5 average rating, 26 reviews

Stunning Home, Heated Pool and Boat Dock

GinaRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Sarasota
4.91 out of 5 average rating, 58 reviews

Oceanfront Home with Heated Pool in Fishers Haven

DinaRating, 5 stars1 month ago
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!
Top Guest favourite
Home in Port Charlotte
4.88 out of 5 average rating, 16 reviews

Peaceful waterfront home

CurtisRating, 5 stars3 weeks ago
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!
Top Guest favourite
Home in Indian Rocks Beach
5 out of 5 average rating, 167 reviews

Piece of paradise in Indian Rocks Beach.

SamanthaRating, 5 stars4 days ago
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
Guest favourite
Home in Venice
4.95 out of 5 average rating, 141 reviews

MCM Waterfront Getaway w/ Private Dock + 4 Kayaks

KatieRating, 5 stars1 week ago
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

Cottage in Clearwater Beach
4.77 out of 5 average rating, 149 reviews

Pink Gulfside Cottage, Steps to Beach, Pets OK

MarkRating, 5 stars1 week ago
Great old school beach cottage. Perfect for my Son and me. The Capt. and especially the First mate made it 5 stars!
Guest favourite
Cottage in Holmes Beach
5 out of 5 average rating, 7 reviews

Anna Maria Cottage w/Golf Cart

SarahRating, 5 stars1 week ago
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!
Guest favourite
Cottage in Tampa
4.94 out of 5 average rating, 125 reviews

Hot tub, 2 floors riverfront, Bush Gardens, kajaks

HanselRating, 5 stars1 month ago
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.
Top Guest favourite
Cottage in Bradenton
5 out of 5 average rating, 31 reviews

2/2 Charming Riverfront Cottage w Deck & Kayaks

KellyRating, 5 stars2 days ago
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. ⭐️ ⭐️⭐️⭐️⭐️
Guest favourite
Cottage in Crystal Beach
4.83 out of 5 average rating, 90 reviews

Happy Camper Cottage | Cozy Oasis with Hot Tub

JasonRating, 5 stars8 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 favourite
Cottage in Riverview
4.93 out of 5 average rating, 86 reviews

Alafia River Cottage

AngelaRating, 5 stars3 weeks ago
This place was wonderful ! Martha was great and very responsive anytime ! Quiet and peaceful and very charming cottage ! Will definitely be returning
Superhost
Cottage in Crystal Beach
4.88 out of 5 average rating, 34 reviews

Elegant Crystal Beach cottage within sea glimpse

BernitaRating, 5 stars3 months 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
Guest favourite
Cottage in Sarasota
4.96 out of 5 average rating, 77 reviews

Cottage by the Bay - free charging, Level 2 EV

AmyRating, 5 stars1 month ago
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