
Holiday rentals with a kayak in Longboat Key
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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.
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Popular amenities for Longboat Key kayak rentals
Holiday House Rentals with a Kayak

Waterfront home with pool and Jacuzzi. Boat to bay
We enjoyed our stay in Tampa at Chrisâs 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 .

Rambling River Retreat on the Manatee River
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 Iâve 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 couldnât have been a nicer more welcoming host. A big thank you again for opening your home to us!

Water Front Home to Alafia River
Was great for what we needed it for rent around the corner from the event nice peaceful clean everything was said it was it was

Clean and Spacious Remodeled Home! Master Suite
We had an absolutely fantastic week at Ryanâs place. It was clean with comfortable beds. Some of the extra amenities we enjoyed: Brita water filter, beach chairs, games, and a large garage, which we used to store our kayak trailer when not in use. The location is perfect if youâre looking to explore Tarpon Springs, and a great base for kayaking spring fed rivers within an hour or two drive. Having the nature trail across the street was perfect for morning dog walks.

5 Bed/4 Bath Waterfront Pool Home in Apollo Beach
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! Didnât hear a complaint from anyone! We loved that the home was located walking distance to restaurants!

Beautiful MidCentury Modern Home
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.

A Riverview Hideaway
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!

Boat house on the gulf 4B/3B
Joey was outstanding when it came to any questions we had for the house, very responsive. House is exactly as described and the views are outstanding. Joey even had some extras for our arrival.
Cottages with a kayak

Anna Maria Cottage w/Golf Cart
Our stay was great. Having the Golf Cart was so handy we didnât have to rent one. The house is nice and clean the bedding towels. Everything was nice and clean. We would definitely stay again.

BEACH! Sunny Escape! Steps 2 Famous Beach w/2 Bike
If you are looking for a historic, old-school Florida home, this is it. The only reason it isnât 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 wouldnât 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 Lisaâs great responsiveness.

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. Canât go wrong.

2/2 Charming Riverfront Cottage w Deck & Kayaks
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!

Bay Lake Cottage
We had such a great stay at Kristinâs place! It was super cute, really clean, and had everything we needed. Kristin was amazing â super responsive and helpful with all of my questions. The AC worked perfectly, which was such a relief with the April heat, and the shower was awesome too. There was a little construction nearby, but honestly, we barely even noticed it, and Kristin made sure to let us know about it ahead of time. The private dock felt so peaceful and tucked away, and the gazebo made the perfect spot for our wedding ceremony â it was seriously magical. Kristin made us feel so welcome and at home, and we couldnât have asked for a better place to have our special day. Weâre so grateful and would definitely stay here again!

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!

Sandy/Salty- Sleep 16 - 2 homes connected by yards
Great gathering place for an extended family to get together. Very short walk to a stunning beach Great for kids. Perfectly located next to a park as well which was great.

Alafia River Cottage
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 shouldnât 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.
Quick stats about holiday rentals with a kayak in Longboat Key
Total rentals
50 properties
Nightly prices starting at
$184Â AUD 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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- Anna Maria Island
- Siesta Beach
- Anna Maria Public Beach
- Dunedin Beach
- Crescent Beach
- John's Pass
- Turtle Beach
- Caspersen Beach
- Bean Point Beach
- Cortez Beach
- Lido Key Beach
- Busch Gardens Tampa Bay
- Amalie Arena
- Raymond James Stadium
- Gulfport Beach Recreation Area
- Clearwater Beach
- North Beach
- Coquina Beach
- Vinoy Park
- Manasota Key Beach
- Fort De Soto Park
- Tampa Theatre
- Curtis Hixon Waterfront Park
- Streamsong Resort