Vacation rentals with a kayak in Longboat Key

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Popular amenities for Longboat Key kayak rentals

House rentals with a kayak

Guest favorite
Home in Tampa
4.88 out of 5 average rating, 26 reviews

Waterfront home with pool and Jacuzzi. Boat to bay

AmyRating, 5 stars1 month ago
We enjoyed our stay in Tampa at Chris’s 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 .
Superhost
Home in Longboat Key
4.88 out of 5 average rating, 121 reviews

Summer House longboat key

DaneRating, 5 stars1 week ago
Chris was a very responsive host. During our stay he spent a day working on his boat in the back. He was very friendly, but also respected our privacy. The house met all of our expectations and our kids loved the pool. The neighborhood was great to walk through and each house offered fantastic curb appeal. With 3 kids under the age of 6, the 10-12 minute walk to the beach was a little long, but Chris’ wagon and beach supplies helped! The golf cart would have been ideal, but without a place to park near the beach we didn’t have much use for it. We thoroughly enjoyed our stay and the entire family agrees we’d love to go back. Thanks Chris!
Superhost
Home in Brandon
4.82 out of 5 average rating, 33 reviews

Water Front Home to Alafia River

SeniquaRating, 5 stars2 weeks ago
House was clean with lots of things to do on property. Private area and relaxing. Accommodated my 10 guest.
Guest favorite
Home in Tarpon Springs
4.86 out of 5 average rating, 29 reviews

Clean and Spacious Remodeled Home! Master Suite

JanelleRating, 5 stars2 months ago
We had an absolutely fantastic week at Ryan’s 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 you’re 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.
Guest favorite
Home in Brandon
4.89 out of 5 average rating, 53 reviews

On the Alafia River, private yard, hottub & kayaks

Patricia ColleenRating, 5 stars6 days ago
Two families stayed at the house for a soccer tournament. The location was great, just 20 minutes from the fields. The house was well equipped and a perfect set up with bedrooms and bathrooms. Kids had fun fishing in the canal. Rebecca was as amazing host!! She was quick to respond to questions. Had a wonderful stay!!
Top guest favorite
Home in Sarasota
4.95 out of 5 average rating, 21 reviews

Beautiful MidCentury Modern Home

PattyRating, 5 stars1 month ago
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.
Superhost
Home in Tarpon Springs
4.7 out of 5 average rating, 37 reviews

A Riverview Hideaway

MichelleRating, 5 stars26 months ago
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!
Superhost
Home in St. Petersburg
4.8 out of 5 average rating, 251 reviews

Bungalow near the sea

DonnaRating, 5 starstoday
Very nice place. Felt at home. We enjoyed walking around the neighborhood and to the bay.

Cottage rentals with a kayak

Guest favorite
Cottage in Holmes Beach
5 out of 5 average rating, 6 reviews

Anna Maria Cottage w/Golf Cart

AmandaRating, 5 stars6 days ago
Our stay was great. Having the Golf Cart was so handy we didn’t have to rent one. The house is nice and clean the bedding towels. Everything was nice and clean. We would definitely stay again.
Guest favorite
Cottage in Pass-a-Grille Beach
4.87 out of 5 average rating, 166 reviews

BEACH! Sunny Escape! Steps 2 Famous Beach w/2 Bike

CindyRating, 5 stars4 months ago
If you are looking for a historic, old-school Florida home, this is it. The only reason it isn’t 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 wouldn’t 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 Lisa’s great responsiveness.
Guest favorite
Cottage in Tampa
4.95 out of 5 average rating, 122 reviews

Hot tub, 2 floors riverfront, Bush Gardens, kajaks

Kemp Signs & ServiceRating, 5 stars1 week ago
Hosts was accommodating and quick to respond. Nice, quiet, hidden, place to kick back and relax after a long day!
Top guest favorite
Cottage in Bradenton
5 out of 5 average rating, 28 reviews

2/2 Charming Riverfront Cottage w Deck & Kayaks

RenaeRating, 5 stars3 weeks ago
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!
Top guest favorite
Cottage in Tampa
4.97 out of 5 average rating, 197 reviews

Bay Lake Cottage

Michelle AnnRating, 5 stars6 days ago
We had such a great stay at Kristin’s place! It was super cute, really clean, and had everything we needed. Kristin was amazing — 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 — it was seriously magical. Kristin made us feel so welcome and at home, and we couldn’t have asked for a better place to have our special day. We’re so grateful and would definitely stay here again!
Guest favorite
Cottage in Crystal Beach
4.83 out of 5 average rating, 90 reviews

Happy Camper Cottage | Cozy Oasis with Hot Tub

JasonRating, 5 stars7 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 favorite
Cottage in Riverview
4.93 out of 5 average rating, 84 reviews

Alafia River Cottage

Jessica MorrieRating, 5 stars2 weeks ago
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 shouldn’t 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.
Superhost
Cottage in Crystal Beach
4.88 out of 5 average rating, 33 reviews

Elegant Crystal Beach cottage within sea glimpse

BernitaRating, 5 stars1 month 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

Cabin rentals with a kayak

Top guest favorite
Cabin in Port Charlotte
4.97 out of 5 average rating, 38 reviews

Unique loft experience for motorcycle enthusiasts

IvanRating, 5 stars1 month ago
Awesome and fun place to stay, especially if you're big into bikes or drag racing! Would recommend!
Superhost
Cabin in Sarasota
4.87 out of 5 average rating, 480 reviews

Private Charming Cottage w/ Kayaks

JenniferRating, 5 stars5 months ago
This is the third time we’ve stayed at Bridget’s tropical cabin oasis and we just love it! Bridget is always welcoming and communicative with every visit. She leaves a welcome basket with delicious treats, snacks and wine along with breakfast staples including coffee cream, eggs, cream cheese and bagels which we always enjoy! The kitchen is fully stocked with everything you need. A large great room with skylights and windows let in the gorgeous tropical foliage. The master bedroom has an adjoining bathroom and a very comfy bed with a beautiful skylight above to enjoy the stars. We choose to stay at this beautiful cabin as it offers quiet, restful old Florida charm and is around the corner from the airport, The Ringling Museum, Asolo Theatre, restaurants, shopping and a short drive to St. Armand’s Circle with more restaurants and shopping on Lido Key and our absolute favorite beach. We are so lucky to have found this wonderful airbnb! Highly recommend!
Superhost
Cabin in Odessa
4.9 out of 5 average rating, 21 reviews

LakeHouse Cabin Getaway

AlejandroRating, 5 stars1 month ago
Cozy and beautiful place, the views of the lake are amazing, can’t wait to come back
Guest favorite
Cabin in Riverview
4.9 out of 5 average rating, 10 reviews

Alafia River Waterfront Tranquil Cabin Home

ClintonRating, 5 stars1 week ago
We appreciate home because it offers plenty of space for the family to hang out. This includes a spacious Florida room, two separate outdoor sitting areas for BBQ, and access to the Alafia River for fishing and kayaking. Plus, Gisselle was very responsive to any issues that we had.

Quick stats about vacation rentals with a kayak in Longboat Key

  • Total rentals

    50 properties

  • Nightly prices starting at

    $120 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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