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

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

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

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

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A private pool is surrounded by a screened enclosure, enhancing the outdoor space. The pool features a light green hue, with stepped entry points visible. Lush greenery is present around the perimeter, while the sky displays a colorful sunset in the background.

Home in Kissimmee

Luxurious Retreat near Disney: Pool & Game Room

Welcome to our exquisite 7-bedroom villa nestled in the prestigious Windsor at Westside Resort! Ideal for large families or groups, this luxurious home boasts a private pool, expansive living room, and a fully equipped kitchen. Revel in the fun of the in-house game room with a pool table, and stay comfortable with air conditioning. A maximum of four vehicles is permitted for this property. The nearby clubhouse offers a resort-style pool with a waterslide, a lazy river, a fitness center, volleyba

Top 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

4.97 out of 5 average rating, 88 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

Home in Davenport

4.58 out of 5 average rating, 12 reviews

Luxury home with Heated Pool near Disney!#2

Nuestro espacio en Airbnb es único y especial por varias razones. En primer lugar, nuestra ubicación es excepcional. Estamos situados en un tranquilo vecindario, lejos del bullicio de la ciudad, pero lo suficientemente cerca como para acceder fácilmente a todas las atracciones principales. Además, ofrecemos vistas impresionantes de la naturaleza circundante, lo que brinda a nuestros huéspedes una sensación de paz y tranquilidad. En cuanto al diseño, hemos creado un espacio acogedor y elegante.

Condo in Kissimmee

4.6 out of 5 average rating, 15 reviews

8102 Vacation getaway at Windsor

Introducing your dream Disney vacation rental at Winsdor Palms Resort, fully furnished and beautifully remodeled for your ultimate comfort and enjoyment. Step inside to discover a newly renovated kitchen featuring sleek cabinets, modern appliances, and stunning quartz countertops, perfect for preparing delicious meals and snacks with family. The bathrooms have undergone a complete transformation with stylish vanities and quartz countertops, offering a touch of luxury and elegance. No Carpets.

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.

Condo in Kissimmee

4.77 out of 5 average rating, 31 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

A large outdoor swimming pool is surrounded by a spacious deck, featuring several lounge chairs arranged on either side. Two cabana structures provide shaded areas for relaxation. Lush green landscaping is visible in the background under a clear blue sky with scattered clouds.

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!

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.

Condo in Davenport

4.82 out of 5 average rating, 28 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 serene pool area is showcased, featuring a crystal-clear oval pool and a connected spa. Comfortable lounge chairs are positioned around the pool, all set under a protective screen enclosure. A grassy retention area is visible in the background, enhancing the tranquil atmosphere.

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

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

8848 BC - 8Bds Windsor At Westside

Superhost

Home in Davenport

4.58 out of 5 average rating, 12 reviews

Luxurious house near Disney

Our space on Airbnb is unique and special for several reasons. First of all, our location is exceptional. We are located in a quiet neighborhood, away from the hustle and bustle of the city, but close enough to easily access all the main attractions. In addition, we offer stunning views of the surrounding nature, which gives our guests a feeling of peace and tranquility. As for the design, we have created a cozy and elegant space

Superhost

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

4.83 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.