Vacation rentals with a kayak in Osceola County

Find and book unique kayak rentals on Airbnb

Top-rated accommodations with a kayak in Osceola County

Guests agree: these accommodations with a kayak are highly rated for location, cleanliness, and more.

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Guest favourite

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

Aug. 4 – 11

$314 CAD per night

Guest favourite

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.

Aug. 16 – 23

$283 CAD per night

Guest favourite

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!

Sep. 19 – 26

$371 CAD per night

Guest favourite

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. 22 – 29

$265 CAD per night

Guest favourite

Condo in Kissimmee

4.94 out of 5 average rating, 104 reviews

Modern Storey Lake Resort Disney Orlando 3191-106

Minutes from Disney, stylish & modern 2bed/2bath fully equipped apartment for up to 8 guests, located in the family friendly Storey Lake Resort. Enjoy our pond view from the balcony. Master suite has a King bed. Second bedroom has a Full bed & a Twin bunk 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.

Sep. 29 – Oct. 6

$235 CAD per night

Guest favourite

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!

Jun. 3 – 10

$487 CAD per night

Guest favourite

Tiny homes in Avon Park

5.0 out of 5 average rating, 20 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. 10 – 17

$163 CAD per night

Guest favourite

Condo in Kissimmee

4.89 out of 5 average rating, 112 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.

Mar. 1 – 8

$370 CAD 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.

Jan. 22 – 29

$307 CAD per night

Guest favourite

Condo in Kissimmee

4.92 out of 5 average rating, 144 reviews

Dolce vita at Storey Lake only 5 miles to Disney

Welcome to Dolce Vita, my place is located near the heart of the Walt Disney World Resort area, shop, outlets, major parks and restaurants. We are ready to invite our valued guests back to their home-away-from-home for family Orlando vacations. We look forward to providing you and your loved ones with world-class service and a spacious environment to spread out and create lasting memories.

May 30 – Jun. 6

$240 CAD per night

Guest favourite

Condo in Kissimmee

4.87 out of 5 average rating, 123 reviews

P-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

Sep. 11 – 18

$244 CAD per night

Guest favourite

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.

Dec. 29 – Jan. 5

$149 CAD per night