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

Pool · Hospitality · Cleanliness

“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 · Value · Pets

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 · Walkability

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.

Location · Family · Hospitality

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.

Value · Location · Getting around

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

4812 BR - Luxe Getaway Retreat

Storey Lake Escape: Dreamy 4BR Pool Home Near Disney in Storey Lake Resort 🏠 Entire Place – Enjoy complete comfort and privacy with the entire home exclusively for your group. 👥 Capacity – Accommodates up to 10 guests comfortably. 🔐 Self Check-In – Easy arrival with keyless entry and your personalized door code. 📌 House Rules ✅ Check-in: 4:00 PM ✅ Check-out: 10:00 AM 🚫 No pets, parties, or smoking 👤 Minimum booking age: 21 years old

Pool · Air conditioning · Accuracy

Cozy 3BR Retreat at The Hub

The Hub Retreat: Modern 3 Bedroom Home Near Disney 🏠 Entire Home – Enjoy complete comfort and privacy with the entire property exclusively for your group. 👥 Capacity – Comfortably accommodates up to 8 guests. 🔐 Self Check-In – Enjoy an easy arrival with keyless entry and your personalized door code. 📌 House Rules ✅ Check-in: 4:00 PM ✅ Check-out: 10:00 AM 🚫 No pets, parties, or smoking allowed 👤 Minimum booking age: 21 years old

Family · Location · Amenities

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 · Accuracy · Hospitality

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 · Location · Checkout

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.

Family · Location · Walkability

Modern 3BR Near Disney|Private Pool&Ensuite Luxury

Just minutes from Disney!!! Relax in this 3 bedroom, 3 bath townhouse with your Own private pool. Cook in a full kitchen, unwind in ensuite bedrooms, and enjoy Windsor Palms resort perks: community pool, spa, movie theater, and sports courts. Perfect for families or friends looking for comfort, fun, and a true home away from home near Orlando’s top attractions!

Location · Value · Indoor spaces