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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Home in Kissimmee

4.33 out of 5 average rating, 3 reviews

Stylish Family Villa with Game Room & Pool

Escape to our luxurious villa, perfect for families and groups. Enjoy modern amenities, a spacious living room, a fully equipped kitchen, and themed bedrooms. Relax by the private pool or have fun in the game room. Conveniently located near Disney, Universal, and other top attractions, it's your ideal vacation home. A maximum of five vehicles is permitted for this property. Resort features include a state-of-the-art clubhouse, heated pool, lazy river, splash park, gym, and more. Book now for an

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

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Apartment in Kissimmee

4.76 out of 5 average rating, 29 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,

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.

Apartment in Kissimmee

4.75 out of 5 average rating, 4 reviews

8507 Retreat 3 Bedroom Condo near Disney

Relax into the nature with this amazing unit backed by trees and serene view. Located only 15 minutes to Disney and 5 minutes to any other place you would ever imagine or need. Enjoy the club house amenities, pool, jacuzzi, game room, courts and tiki bar and grab your favorite drink. Here you have easy and convenient access to shopping and restaurants. Closet all major Kissimmee attractions. You can't miss out on this condo a 3/2 to impress.

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.

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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 !!

Guest favourite

Home in Kissimmee

4.93 out of 5 average rating, 15 reviews

Lake Berkley Home: Pool, Lakefront & near Disney

Located in secure Lake Berkley Resort with access to a clubhouse, gym, heated pool, spa, sports courts, and fishing pier. Just 10 minutes to Disney and close to Orlando’s top attractions. This lakefront home features a private pool and peaceful natural surroundings. Ideal for families or groups seeking relaxation and adventure in a tranquil, secure community.

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Home in Kissimmee

4.83 out of 5 average rating, 6 reviews

Lakeview Home in Terra Verde:Pool&Resort Perks

Located at Terra Verde Resort. Just 15–30 minutes from Disney.Private patio with grill and outdoor seating. Fully equipped kitchen, TV, and Wi-Fi. Resort amenities include a hot tub, mini-golf, fitness center, playground, and more. Ideal for families or groups seeking comfort and convenience near top attractions.