Vacation rentals with a kayak in Osceola County

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Osceola County

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Lake Wales

4.96 out of 5 average rating, 27 reviews

Lake Rosalie Getaway

Escape the hustle and bustle of life and enjoy a relaxing vacation at our newly remodeled lakefront home in beautiful Lake Wales! Located on peaceful Lake Rosalie, our residence is the perfect isolated getaway, yet still close to popular attractions such as Bok Tower Gardens, Legoland, Lake Kissimmee Park, Westgate River Ranch Rodeo and more! Unique amenities: - Large, upper-story wooden deck - 2 kayaks - Outdoor games, fishing poles - Exercise bike - Office room with printer - New kitchen

Superhost

Condo in Kissimmee

4.85 out of 5 average rating, 186 reviews

Disney 4 miles NEW * Heated LazyRiver & Pool*2B/2B

Discover luxurious comfort at the beautiful Sunset Paradise Condo. For your vacation we provide the best family friendly tropical getaway. The entire Condo is crafted with intentional love. We have faith that your vacation will have you feeling right at home, enhanced with our amazing amenities that exude an all inclusive resort like experience: waterpark, beach volleyball, basketball, hammocking, full service for our poolside restaurant and bar, Kayaking, and mini golf. It's magical here.

Guest favorite

Townhouse in Kissimmee

4.92 out of 5 average rating, 138 reviews

Fall Superhost Special, Dogs OK

Escape to a whimsical wonderland at Bullseye's Disney Ranch! Located just minutes away from amazing theme parks & adventures, this home away from home was designed with families in mind. Mickey and Toy Story-themed bedrooms will delight kids of all ages while parents can relax by the private heated pool or take advantage of resort amenities. Is this home already booked? Check out our Vacation Alchemy Profile and choose from over a dozen magical properties suited for every group size!

Superhost

Guesthouse in Lake Wales

4.83 out of 5 average rating, 23 reviews

Cozy Cottage on Peaceful Lake

Property is on a beautiful pristine lake, with lake access and free amenities, to provide a wonderful experience on the lake. However, you can not view lake from the cottage window. It is a 1 minute walk from cottage to the lake edge. Chairs, fire pit and grill may be provided at lake edge or at unit. If you prefer a unit with a lake view from window, we do have another unit to rent that does have a lake view from window. Please message me if you need help locating this listing.

Superhost

Condo in Kissimmee

4.83 out of 5 average rating, 126 reviews

Modern Storey Lake Resort Disney Orlando 3171-107

Relax in our Stylish & Modern 2Bed/2bath fully equipped apartment for up to 7 guests, located in the family friendly Storey Lake Resort. Minutes from DISNEY World Theme Parks in Orlando Florida. Close to UNIVERSAL STUDIOS & SEAWORLD. Enjoy our lake view from the balcony. Close to restaurants, supermarkets, outlet malls & retail stores. Great amenities: Heated Pools, Kids Splash Zone, Water Slides, Lazy River, Gym, Mini Golf, Kayak, Tiki Bar & Ice Cream Shop, security guard!

Guest favorite

Home in Babson Park

4.97 out of 5 average rating, 110 reviews

Authentic "Old Florida" on Crooked Lake!

Authentic "Old Florida" on Crooked Lake! Surrounded by palmettos and Florida foliage, our 1930's rustic lakehouse is serene, private, and exceptionally relaxing. Spring-fed Crooked Lake is designated an "Outstanding Florida Waters" lake and is great for swimming, paddle boarding, kayaking, fishing, and waterskiing. Huge screen porch, ping pong table, fully-equipped kitchen, dining room table for 12, spacious living area (great for games) -- you won't want to leave!

Guest favorite

Condo in Kissimmee

4.9 out of 5 average rating, 119 reviews

NEW APT WITH WATER PARK AND NEAR DISNEY

Enjoy a carefree vacation at Storey Lake Resort. Located just minutes from Disney, Falcon's Fire Golf Club, Universal, Epic Universal, SeaWorld, Orange County Convention, Premium Outlets. Within 1 mile Walmart, Target and restaurants, your family will have everything they need. Water Park, Gym, and all the FREE amenities. Free parking, 24/7 security at this gated resort and with an automatic check in with direct access key and elevator available

Guest favorite

Condo in Kissimmee

4.88 out of 5 average rating, 101 reviews

Modern 2Bed Condo Lake View Near Disney 3151

Indulge in our magical vacation homes, fully equipped for your comfort. With spacious bedrooms & full equiped kitchens, just minutes from Disney's theme parks. Book your stay for 7 days or more and unlock an exclusive 5% discount! Craft unforgettable memories with loved ones at Disney World. For extended stays of a month or more, enjoy an even greater 10% discount as part of our long-stay offer. Reserve now! we would love to be your host!

Guest favorite

Condo in Kissimmee

4.89 out of 5 average rating, 111 reviews

D-Gated Resort-5 miles to Disney-2 FREE Water Park

Is this home booked? We have more! Click on the circular profile image, then scroll down till you see James's Listings. Gated/24 hour security. Resort living with 2 main clubhouses and a few other extra quieter pools, playground and a soccer field. 10 min to Disney 15 min to Universal 10 min to the Convention Center Within a 5 min drive: Publix Grocery Walmart Target 10-15 restaurants

Guest favorite

Guest suite in St. Cloud

4.93 out of 5 average rating, 327 reviews

LAKE FRONT Suite with FREE USE of Kayaks & Canoes

Private Master Suite with it's own exclusive entry. It has a convenient kitchenette complete with mini refrigerator, microwave, toaster, toaster oven and an outside grill. Comfy Queen size bed with overhead ceiling fan. Private Bathroom and shower. Lake view from the front of property, unit is in the back overlooking wetlands. Plenty of parking, with enough room to bring a boat.

Guest favorite

Vacation home in Kissimmee

4.88 out of 5 average rating, 143 reviews

Lazy River Oasis Near Disney - Best Clubhouse!

Enjoy this comfortable, lovely, peaceful, pet friendly and centrally-located place just minutes away from Disney World, Sea World. and all other fun attractions of Orlando, Florida. The house is next to a beautiful quiet lake that you can enjoy every evening after a busy day playing. Enjoy the different pools and the amazing club house with your family; gym included.

Superhost

Condo in Kissimmee

4.89 out of 5 average rating, 121 reviews

SL106 - Mickey's Hideaway - Resort Access included

Welcome to Your Dream Vacation at Storey Lake Resort! Step into this stylish and spacious 2-bedroom, 2-bathroom condo, designed to comfortably accommodate up to seven guests. Nestled in the heart of Storey Lake Resort in Kissimmee, FL, this vacation rental offers the perfect blend of luxury, comfort, and convenience for an unforgettable getaway.