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

4.5 out of 5 average rating, 4 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

Guest favourite

The exterior of the single-family home is illuminated at night, highlighting the garage and front entrance. Soft lighting accentuates the landscaped garden and driveway, creating a welcoming entrance. The home's design features a combination of stone and stucco, framed by a well-maintained lawn.

Home in Kissimmee

4.95 out of 5 average rating, 109 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

Flat in Kissimmee

New place to stay

Live your best dream in a Disney-like resort.

Leve toda a família a este ótimo lugar com muito espaço para se divertir. Consiga mais 2 colchões infláveis e podem ficar 6 no Ap. Berço nos fornecemos. Apart. de alto padrão com infraestrutura de Resort de luxo. Tem cozinha completa, maquina de lavar pratos, lavadora e secadora, pratos, copos talheres e panelas, Apart. possui sofa cama confortável. O Resort possui 14 piscinas, parque de água completo de 2 andares, 3 restaurantes, arcade de jogos eletrônicos, boliche, bicicletas e mini golf.

A game room is showcased with vibrant green artificial turf flooring. A poker table with four black chairs occupies one side, while a foosball table and a basketball arcade game are present. The walls are adorned with sports-themed graphics, creating an engaging atmosphere for leisure activities.

Home in Kissimmee

4.72 out of 5 average rating, 46 reviews

510 BS - 5BD Cozy Family Haven with Pool

510 BS - 5BD Elegant Escape: Private Haven 🏠 Entire Place – Experience the ultimate in comfort and privacy in our spacious 5-bedroom, 5-bathroom home, accommodating up to 14 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

Summer 35% Off 4BR Pool Villa/Game Room

Welcome to our charming new Villa in the heart of Kissimmee, Florida. This beautiful 4-bedroom, 2-bathroom Villa is nestled in the desirable Oak Hill community. Immaculate and cozy, this home invites you to experience Florida living at its finest. Centrally located, it offers quick convenience to shopping at outlets, supermarkets, dining, and all the wonderful Orlando Parks. Major roadways are easily accessible, ensuring a quick commute to all the greater Orlando area have to offer.

Superhost

A swimming pool and a spa are shown, surrounded by a paved area with lounge chairs. Lush greenery and colorful buildings are visible in the background, adding to the inviting atmosphere. The pool features clear blue water, with a gentle gradient from shallow to deep.

Apartment in Kissimmee

4.76 out of 5 average rating, 33 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

Guest favourite

A cozy living area features a comfortable sofa with light cushions and a coffee table at its center. A ceiling fan is positioned above, while a television is mounted on the wall. Natural light enters through glass doors that lead to a balcony with greenery visible outside.

Apartment in Davenport

4.86 out of 5 average rating, 35 reviews

Tuscana Resort,Disney a 17 minutos

Welcome to Disney's Tuscana Resort at the exclusive Champion Gate Resort.Modern apartment offerings Luxury & Comfort enjoy a refreshing pool,Relax in the hot tub,stay fit in the gym,sip delicious cocktails and beverages at the Tiki bar,enjoy some delicious and flavorful dining at the restaurant open late! shops and attractions within walking distance! Attractions like Disney World are only 7 miles away! The perfect family getaway unforgettable memories and fun.

A vibrant game room features a Super Mario theme, with colorful murals of Mario characters on blue walls. An air hockey table occupies the foreground, while a large screen television is mounted on the wall. Bright red pendant lights hang from the ceiling, enhancing the playful atmosphere.

Home in Kissimmee

5 out of 5 average rating, 3 reviews

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

Superhost

Home in Kissimmee

Storey Lake Home:Pool, Gym, Lazy River&near Disney

Escape to this beautiful home in the secure Storey Lake Resort, just minutes from Disney. Enjoy a private pool, modern kitchen, spacious living and dining areas, and stylish decor. Resort amenities include a clubhouse, heated pool, lazy river, waterslides, gym, and more. Perfect for families or groups, this home offers comfort, convenience, and easy access to Orlando’s top attractions. Book now for an unforgettable stay!

Guest favourite

Four inviting bedrooms are displayed, each featuring distinct color themes and decor. Comfortable beds with accent pillows are complemented by nightstands with lamps. Large windows provide natural light, enhancing the cozy ambiance in each space, perfect for restful stays.

Home in Kissimmee

4.95 out of 5 average rating, 41 reviews

Brand-new home with Reunion Village amenities

This home features 3 bedrooms and 2 bathrooms with an open-concept layout, including a fully equipped kitchen, dining area, and spacious living room perfect for family gatherings. Enjoy the ping pong table and kids' play area for added fun. The community offers a variety of amenities, including seven pools, a fitness center, playgrounds, gift shop and access to resort restaurants. Just a few minutes from Disney.

Home in Kissimmee

4.64 out of 5 average rating, 14 reviews

25% Off 8BR Villa. Private Pool/Spa/ Game Room

You won't regret to choose this house for your Orlando vacation, this well equipped home is just 15 min away from all the Disney parks and a few miles away from most convenient restaurants, markets and fun areas of Kissimmee and Orlando. Our private pool and spa adds to the whole fun in this gated neighborhood. A property like this is rare to find. Speak Portuguese, Spanish, Turkish and English.

The exterior of the villa showcases a modern design with a welcoming entrance featuring a large door and decorative windows. Lush landscaping surrounds the home, including well-maintained shrubs and palm trees. A spacious driveway leads to the attached garage, providing ample parking.

Home in Kissimmee

4.57 out of 5 average rating, 7 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.