Holiday rentals with a kayak in Longboat Key

Find and book unique kayak rentals on Airbnb

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Popular amenities for kayak rentals in Longboat Key

House rentals with a kayak

Top guest favourite
Home in Ellenton
5 out of 5 average rating, 41 reviews

The Pink Riverhouse- No damage from Hurricanes

ArianeRating, 5 stars1 week ago
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!
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 Apollo Beach
4.98 out of 5 average rating, 137 reviews

5 Bed/4 Bath Waterfront Pool Home in Apollo Beach

LesleyRating, 5 stars1 month ago
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.
Guest favourite
Home in Laurel Park
4.83 out of 5 average rating, 29 reviews

Florida Cove Cottage - 2BD/2BA in the heart of SRQ

CharlotteRating, 5 stars3 weeks ago
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!
Guest favourite
Home in Indian Beach-Sapphire Shores
4.96 out of 5 average rating, 54 reviews

Perfect Family Getaway+ping pong, mini golf, bikes

JenniferRating, 5 stars3 weeks ago
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.
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.
Guest favourite
Home in Sarasota
4.91 out of 5 average rating, 11 reviews

Luxe 3BR Siesta Key Home Pool, Hot Tub, Near Beach

DavidRating, 5 stars3 weeks ago
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

Superhost
Cottage in Pass-a-Grille Beach
4.81 out of 5 average rating, 277 reviews

Sunny PaG Island rental w/bikes-just steps2beach

ChristopherRating, 5 stars3 weeks ago
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.
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 stars1 day 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

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