Ski-in/Ski-out vacation 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

4.75 out of 5 average rating, 4 reviews

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

Guest favorite

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, 107 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 favorite

A private splash pool is highlighted, featuring a serene aqua color surrounded by a safety fence. Two modern lounge chairs are positioned nearby, and a small dining table with four chairs is set on the patio, ready for relaxation and enjoyment.

Home in Kissimmee

4.94 out of 5 average rating, 68 reviews

Spacious Townhome 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

Apartment in Kissimmee

New place to stay

Experience the ultimate dream in a Disney quasi-resort.

Bring the whole family to this great place with plenty of room to have fun. Get 2 more inflatable mattresses, and 6 people can stay in the apartment. We provide a crib. High-end apartment with luxury resort amenities. It has a full kitchen, dishwasher, washer and dryer, dishes, glasses, cutlery, and pots and pans. The apartment has a comfortable sofa bed. The resort has 14 swimming pools, a full 2-story water park, 3 restaurants, an electronic game arcade, bowling, bicycles, and mini golf.

Superhost

Home in Kissimmee

4.86 out of 5 average rating, 7 reviews

Encantada Resort:Pool Gym Clubhouse 10mi to Disney

Welcome to your vacation haven at Encantada Resort, a secure and gated community just minutes from Disney! This 3-bedroom villa comfortably sleeps up to 7 guests and features a private pool, spacious living and dining areas, and a fully-equipped kitchen with modern amenities. Relax in this stylish retreat with convenient parking and access to resort amenities like a clubhouse, gym, and heated pools. Perfect for a memorable family getaway close to all the excitement Orlando has 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.

Condo 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 favorite

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

4.86 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 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

4.38 out of 5 average rating, 21 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.

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

Condo in Kissimmee

4.63 out of 5 average rating, 16 reviews

25% Off Stylish Disney Condo Near Parks! Pool/Arca

Welcome to your perfect family getaway near Disney! This beautifully renovated 3-bedroom condo in the sought-after Windsor Palms Resort was designed with comfort, convenience, and fun in mind — making it the ideal home base for young families, moms traveling with kids, couples, and Disney lovers alike. Just minutes from Walt Disney World®, this bright and modern vacation home combines resort-style amenities with all the comforts of home.

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 favorite

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

4.97 out of 5 average rating, 39 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.