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

4.94 out of 5 average rating, 17 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

Sep 12 – 19

G$40,066 GYD per night

Guest favorite

Condo in Kissimmee

4.87 out of 5 average rating, 164 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.

Oct 16 – 23

G$35,931 GYD per night

Guest favorite

Condo in Kissimmee

4.89 out of 5 average rating, 47 reviews

The Summer Apt (5 Beds/2 Bdrm) Sleeps 6 Full Kitch

You and your family will be staying in our lovely home, and the whole place will be just for you. You will be less than 10 minutes away from many local fun places like, bowling course, hiking trails, roller skating, kayak paddling, shopping, movie theaters, dining and many more, staying in a clean and relaxing apartment that you can enjoy and rest as if you were at home. Places near: Shopping mall, Restaurants, Old Town, Disney Parks, Fun Spot, Universal Studios, SeaWorld, and many more!

Jun 20 – 27

G$22,450 GYD per night

Guest favorite

Condo in Kissimmee

4.94 out of 5 average rating, 124 reviews

Modern Storey Lake Resort Disney Orlando 3161-305

Minutes from Disney, stylish & modern 2bed/2bath fully equipped apartment for up to 6 guests, located in the family friendly Storey Lake Resort. Enjoy our pool view from the balcony. Master suite has a King bed. Second bedroom has 2 Twin beds. Living room with sofa bed. The open floor plan blends Kitchen, Dining and Living room. Close to outlet malls & retail stores. Great amenities: Pools, Kids Splash Zone, Water Slides, Lazy River, Gym, Mini Golf, Kayak, Tiki Bar & Ice Cream Shop.

Aug 15 – 22

G$31,226 GYD per night

Guest favorite

Townhouse in Kissimmee

4.93 out of 5 average rating, 122 reviews

Storey Lake, Themes, Dogs OK, Free Heated Pool!

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!

May 31 – Jun 7

G$45,735 GYD per night

Guest favorite

Home in Lake Wales

4.92 out of 5 average rating, 88 reviews

Lake house 3/2 Fish 4 Monster Bass! Kayak & Canoe

This 3/2 lake house is located in Central Florida just off US 27 in South Lake Wales. It is 60 min. south of Disney World Orlando , 25 min. south of Legoland in Winter Haven, 60 min. west of Busch Gardens in Tampa, and 2 minutes to Warner College. It is situated on a fresh water canal with a dock out back across from 6000 acre Crooked Lake. Boating, tubing, swimming, fishing, kayaking, jet skiing, are popular in the lake. The lake is so big, it is never crowded. Great fishing.

Oct 7 – 14

G$31,457 GYD per night

Guest favorite

Home in Babson Park

4.97 out of 5 average rating, 108 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!

May 14 – 21

G$60,893 GYD per night

Guest favorite

Tiny home in Avon Park

5.0 out of 5 average rating, 19 reviews

Back to Nature!

Reconnect with nature at this unforgettable escape. There are acres of beautiful Hammock land to explore and enjoy nature. We also raise USDA grass finished beef for purchase to enjoy while you stay or take home! You can also purchase our beef at the Highlands FARMERSmarket held on our property most Sundays from 11-3pm. Our tiny house is the perfect getaway to recharge your batteries! We are looking forward to sharing our property with you! NO HUNTING ALLOWED!

Nov 8 – 15

G$21,567 GYD per night

Guest favorite

Condo in Kissimmee

4.89 out of 5 average rating, 111 reviews

SL106 - Mickey's Hideaway - Resort Access included

Experience the unparalleled thrills and adventure of Mickey's Hideaway - SL106! Perfect for a family getaway, this rental includes ALL of the amenities and fun of a water park, right in your own backyard. Enjoy delights like a water slide, full kitchen, two spacious bedrooms, and plenty of outdoor space to play and explore. Immerse yourself and your family in a vacation experience of a lifetime, without ever leaving the sanctuary of your home away from home.

Apr 1 – 8

G$56,781 GYD per night

Superhost

Townhouse in Kissimmee

4.84 out of 5 average rating, 157 reviews

Luxury townhome with private pool

Brand new fully furnished townhome with private pool in gated community. Spacious living and dining rooms ideal for large family gatherings. Free parking situated in front of house. Walking distance from lake and short drive from attractions, malls, and golf course. The unit has fast Wi-Fi, and many smart devices can be connected to the Wi-Fi. Extra charges will be added to your reservation for pool heating, BBQ and others.

Aug 12 – 19

G$38,316 GYD per night

Guest favorite

Condo in Kissimmee

4.91 out of 5 average rating, 115 reviews

O-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

Jul 29 – Aug 5

G$34,797 GYD per night

Guest favorite

Guest suite in St. Cloud

4.93 out of 5 average rating, 293 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.

Nov 19 – 26

G$20,157 GYD per night