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

Summer 35% Off 4BR Pool Villa/Game Room

Escape to the sunshine and make unforgettable memories at this beautifully maintained 4-bedroom, 2-bathroom vacation home in the desirable Oak Hill community of Kissimmee. Perfect for families, couples, and small groups, this inviting villa offers the ideal blend of comfort, entertainment, and an unbeatable location just minutes from Walt Disney World® and Orlando's world-famous attractions. Whether you're spending the day at the theme parks, shopping the premium outlets, or relaxing by your ow

Hospitality · Cleanliness · Pool

“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

Family · Location · Cleanliness

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

Location · Value · Indoor spaces

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.

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

Value · Family · Quiet

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.

Family · Location · Amenities

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.

Location · Family · Hot tub

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

Cozy 2-Bed Studio with Pool & A/C

Relax in this charming retreat at the Heritage Inn, featuring pool views and modern amenities. Perfect for couples or solo travelers, this room offers two plush double beds, a spacious bathroom, flat-screen TV, mini fridge, microwave, and high-speed WiFi. Enjoy your morning coffee on the private balcony overlooking the pool and lush greenery. Located close to beaches, dining, shopping, and outdoor activities. ​​​​​​​Book your stay today!

Value · Bathroom · Cleanliness

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!

Location · Outdoor spaces · Comfort

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.

Value · Family · Amenities

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.

Location · Value · Nearby