Ski-in/Ski-out holiday rentals in Osceola County

Find and book unique ski-in/out homes on Airbnb

Top-rated ski-in/out rentals in Osceola County

Guests agree: these ski-in/out homes are highly rated for location, cleanliness and more.

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Top guest favourite

Home in Kissimmee

4.96 out of 5 average rating, 84 reviews

“Casa Del Sol”

"Casa Del Sol" is an exquisitely clean stay. We have all NEW furniture. And never forgetting our four legged friends,we have some toys and a comfortable and clean yard. "Casa Del Sol" has security cameras, although it is peacefully quiet to rest.PLUS there is what you like near you.Located minutes from the attractions.*Disney Springs -2.4 Miles *Magic Kingdom -7.4 *Animal Kingdom *Hollywood Studios -4.2 *Epcot -4.1 *Universal Studios and Universal CityWalk -9*SeaWorld Orlando-4.8 *Walmart 1 min

Top guest favourite

Home in Kissimmee

4.93 out of 5 average rating, 60 reviews

Ultimate Townhome Oasis with Pool: Sleeps 13!

2489 RT - Ultimate Townhome Oasis with Pool 🏠 Entire Place – Experience the ultimate in comfort and privacy in our spacious 4-bedroom, 3-bathroom home, accommodating up to 13 guests. Your dream vacation starts here. 🔐 Self Check-In – Enjoy a seamless arrival with our keyless entry system. You'll receive a personalized door code for convenient, stress-free access. 📌 House Rules ✅ Check-in: 4:00 PM ✅ Check-out: 10:00 AM 🚫 No pets, parties, or smoking 👤 Minimum booking age: 21 years old

Superhost

Apartment in Kissimmee

4.77 out of 5 average rating, 30 reviews

MARBELLA beautiful residential complex

Diviértete con toda la familia en este alojamiento Have fun with the whole family in this accommodation with style and a lot of comfort for your vacations, located in the center of kissimme just 15 minutes from the most fun parks of Disney world, restaurants, shops, recreational parks and much more in one place, the community has a swimming pool, picnic area, Gin, lake, free parking, 24 hour security and much more you will not regret choosing this beautiful quiet and crowded place

Townhouse in Kissimmee

4.74 out of 5 average rating, 27 reviews

Luxury home at windsor Resort | 15 min to Disney

This is a brand new LUXURY home at Windsor at westside resort, 5bedroom/ 4.5bathroom, Private and resort pool. * Community: Windsor At Westside * 5 Bedrooms/ 4.5 Bathrooms * Disney (8 min) Sea World (21 min) Universal (30 min) • Convention Center (18 min) Legoland (40 min) • Location: Dubai Street, Kissimmee FL 34747 * Kissimmee FL 34747 Don't wait! Book with us now and give you and your family/friends the vacation you all deserve. We can't wait to welcome you!!

Townhouse in Kissimmee

5 out of 5 average rating, 3 reviews

Near Disney, comfortable house,10 min to the parks

Stay just 10 minutes from Disney, Epcot, and Hollywood Studios at our "Near Disney Wonderful House Spa Pool Resort." Relax in your private spa and pool, and enjoy 3 cozy bedrooms (1 king, 1 queen, and 2 twins), each with a TV, plus 2.5 bathrooms. The fully equipped kitchen and in-home laundry make your stay hassle-free. Close to SeaWorld, outlets, and restaurants, our home is the perfect retreat for family fun and relaxation. Book now and create magical memories!

Home in Davenport

4.42 out of 5 average rating, 19 reviews

Spacious Pool Home w/ 2 Masters, Games Room

Mickey’s Holiday Home has everything you could want in a vacation rental home. You'll love the feeling of spaciousness in this home, the two master suites, the pool and spa, the privacy, the quiet neighborhood, and the wonderful view from the pool deck. It's also close to Disney and other Orlando attractions, restaurants and shops. As you enter the home, you find yourself in the spacious living room which features comfortable seating and a large flat screen TV.

Home in Kissimmee

8848 BC - 8Bds Windsor At Westside

🏠 Entire Place – Experience the ultimate in comfort and privacy in our spacious 8-bedroom, 6-bathroom home, accommodating up to 18 guests. Your dream vacation starts here. 🔐 Self Check-In – Enjoy a seamless arrival with our keyless entry system. You'll receive a personalized door code for convenient, stress-free access. 📌 House Rules ✅ Check-in: 4:00 PM ✅ Check-out: 10:00 AM 🚫 No pets, parties, or smoking 👤 Minimum booking age: 21 years old

Home in Kissimmee

8848 BC - 8Bds Windsor At Westside

Home in Kissimmee

4.5 out of 5 average rating, 4 reviews

4701-Lake Berkley villa- Renovated 3 bed

This homes location is convenient to everything- just off Hwy 192 at Marker 14. Less than 10 minutes away from Disney and about 15 minutes away from Universal Studios & Sea World. 3 bedrooms and 2 bathrooms with a private pool facing a lake. What can be better? Fish at the lake in the afternoons after a long day at parks or relax at the pool and cook homemade meals in the fully equipped kitchen.

Superhost

Home in Kissimmee

4.83 out of 5 average rating, 6 reviews

Great Value 3BR Villa w/ Private Pool & Game Room

Elegant 3BR Villa with Private Pool & Game Room in Emerald Island Resort Welcome to your dream vacation home! This luxurious 3-bedroom, 2-bathroom villa is located in the prestigious Emerald Island Resort in Kissimmee. Perfect for families and large groups, this spacious home offers top-notch amenities and a prime location just minutes from Disney World and other top attractions.

Superhost

Flat in Davenport

4.76 out of 5 average rating, 17 reviews

17 minutes to Disney

Welcome to Disney Dream Retreat ,at the exclusive tuscana resort at the gates of champion gate,Modern apartment that offers luxury and comfort,enjoy a refreshing relaxing pool in The Jacuzzi keep fit in El gimnacio savor cocktails and food in bar and restaurant ,shops and attractions in Pocos Pasos as well as access to Golf camps this in the place Perfect for your vacations !!

Home in Kissimmee

4 out of 5 average rating, 5 reviews

Storey Lake Home W/ Game Room,Pool and near Disney

Experience luxury at our stunning 9-bedroom, 5-bathroom villa in Kissimmee, just 30 minutes from Orlando. Perfect for families, this spacious villa features a private pool, game room, and modern amenities. Enjoy a movie theatre, heated pools, lazy river, and more within the secure, gated community with 24-hour security. Book now for easy access to Orlando’s top attractions.