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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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

HospitalityCleanlinessPool

Top Guest favourite

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

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

LocationFamilyParks

4.94 out of 5 average rating, 70 reviews

Apartment in Kissimmee

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

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

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

FamilyValueParks

4.76 out of 5 average rating, 33 reviews

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

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.

ValueLocationGetting around

4.86 out of 5 average rating, 35 reviews

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

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.

FamilyLocationQuiet

4.36 out of 5 average rating, 22 reviews

Home in Kissimmee

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 children's bedroom features vibrant Mickey Mouse-themed wallpaper, showcasing iconic characters against a bright backdrop. A white dresser is positioned against the wall, and a cozy bunk bed is visible with colorful bedding. Large windows allow natural light, enhancing the playful atmosphere.

Villa in Kissimmee

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

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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

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.

ValueLocationHospitality

4.95 out of 5 average rating, 43 reviews

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

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.

LocationFamilyHospitality

4.57 out of 5 average rating, 7 reviews

Guest favourite

Townhouse in Kissimmee

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!

ValueLocationNearby

4.82 out of 5 average rating, 28 reviews

Home in Kissimmee

Golden Star Heaven

Golden Star Heaven is a stylish and cozy Florida retreat perfect for families and groups. With 6 comfortable beds, space for 8 guests, and a private screened-in pool, there’s room to relax, unwind, and make unforgettable memories. Enjoy a fully equipped modern kitchen, comfortable living spaces, fun games, and a playful Super Mario-themed bedroom.

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