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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Top guest favorite

Home in Kissimmee

4.97 out of 5 average rating, 76 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!

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

4.85 out of 5 average rating, 13 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.

Condo in Kissimmee

4.73 out of 5 average rating, 26 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

Townhouse in Kissimmee

4.73 out of 5 average rating, 26 reviews

Luxury home at windsor Resort | 15 min to Disney

This is a brand new LUXURY home at Windsor at westside resort, 5bedroom/ 4.5bathroom, Private and resort pool. * Community: Windsor At Westside * 5 Bedrooms/ 4.5 Bathrooms * Disney (8 min) Sea World (21 min) Universal (30 min) • Convention Center (18 min) Legoland (40 min) • Location: Dubai Street, Kissimmee FL 34747 * Kissimmee FL 34747 Don't wait! Book with us now and give you and your family/friends the vacation you all deserve. We can't wait to welcome you!!

Superhost

Condo in Davenport

4.82 out of 5 average rating, 17 reviews

Tuscana Resort Disney

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.

Superhost

Home in Kissimmee

4.75 out of 5 average rating, 4 reviews

Lakeview Home in Terra Verde:Pool&Resort Perks

Adventure, comfort, and memories start here at this beautifully appointed property offers lake and garden views, a fully equipped kitchen, private outdoor seating with a grill, and entertainment options like TV and Wi-Fi. The resort features a heated pool, hot tub, mini-golf, fitness center, playground, and more. Located just 15-30 minutes from Disney and Orlando's top attractions, it’s the perfect spot for families or groups. Book now for a memorable stay!

Home in Davenport

4.55 out of 5 average rating, 11 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

Top guest favorite

Home in Kissimmee

5 out of 5 average rating, 15 reviews

Brand New 3 Bedrooms Close to Disney

**Entire place** You’ll have the house to yourself. 3 Bedrooms/3 Bathrooms/Sleeps 6 **Self-Check-in** Keyless check-in, you’ll get a unique door code. **House rules** - Check-in time is 4:00 pm. - Check-out time is 10:00 am. - No pets, parties, or smoking allowed. - Minimum age is 21 years old. -A selfie and a valid government-issued ID (e.g., Driver's License or Passport) are required for all reservations.

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What guests are saying

510 BS - 5BD Cozy Family Haven with Pool

4.72 out of 5 average rating, 25 reviews1 month ago

Beautiful house and very comfortable. Everyone had their own bathroom which made it a breeze getting everyone to the parks in the morning. Loved all the core memories our family made on this trip and having a comfy place close to the parks allowed us to unwind after a long day in the parks and enjoy being with grandparents and aunts and uncles.

Home in Kissimmee

What guests are saying

Luxury 8BR Villa-Private Pool and Themed Bedrooms

4.82 out of 5 average rating, 11 reviews2 weeks ago

We had a wonderful weekend stay in Orlando with our family! The place was very clean, well-maintained, and had a warm, welcoming feel from the moment we arrived. It’s clearly designed with families in mind—fun, comfortable, and full of thoughtful touches that made our stay easy and enjoyable. The location was perfect, close to great attractions and dining, but still peaceful and relaxing. Edy, the host, was very responsive and helpful throughout our stay, which made the experience even better. Highly recommend this spot for anyone looking for a family-friendly getaway. We’d definitely stay here again!

Home in Kissimmee

What guests are saying

Disney Dreams: 5BR Luxury Retreat, Poolside Paradi

4.72 out of 5 average rating, 25 reviews3 months ago

We had an excellent stay!! Eddy was very responsive and helpful! House is exactly as described and location is great! Only 25 minutes from Disney and the resort amenities were excellent. Would highly recommend the home for your future stay! It was super easy to check in and accessible for arriving in the early hours of the morning and checking out was simple. Thank you Eddy!

Home in Davenport

What guests are saying

7462 Themed Villa 6BD - Pool & Spa-Game room

4.79 out of 5 average rating, 19 reviews4 months ago

Everything was exactly like the listing photos, beautiful place. Had everything we needed while we were there. We did have an issue with security, the truck was too long for the driveway and they almost towed but gave a warning and allowed us to move so we weren’t in violation. Other than that was an enjoyable trip.

Home in Kissimmee

What guests are saying

4812 BR - Dreamscape Villa

4.9 out of 5 average rating, 10 reviews1 month ago

My family and I had an amazing stay. The home was exactly as described in the listing. The location was beautiful and close to Disney World . The host was welcoming and responsive, making sure I had everything I needed for a comfortable stay. I would stay here again and highly recommend it to anyone visiting the area!

Home in Kissimmee

What guests are saying

Brand New 3 Bedrooms Close to Disney

4.92 out of 5 average rating, 13 reviews1 week ago

Our stay was absolutely amazing! The home was spotless, beautifully maintained, and had everything we needed for a comfortable and relaxing trip. The location was perfect, and every detail felt thoughtfully prepared. The host was incredibly responsive and went above and beyond to make sure we had a great experience — from quick communication to thoughtful touches that made us feel right at home. We couldn’t have asked for a better stay and would absolutely book again. Highly recommend!

Home in Kissimmee

What guests are saying

Windsor at Westside - Amazing 5bd Villa

5 out of 5 average rating, 3 reviews3 weeks ago

I will say the space for parking is kind of tight all the way around the community but edy was an amazing host and handled everything very well was upset about the pool and really wish that was working regardless of the refund lol but again thank you Edy and Airbnb for allowing us to stay

Townhouse in Kissimmee

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