
Ski-in/Ski-out holiday rentals in Kissimmee
Find and book unique ski-in/out homes on Airbnb
Top-rated ski-in/out rentals in Kissimmee
Guests agree: these ski-in/out homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Kissimmee ski-in/out rentals
Ski-in/out house rentals

Pet-Friendly Home w/Pool near Disney&ChampionsGate
Stayed for 5 nights with one other person and a dog and the house was clean and spacious. Great location for a calm relaxing getaway. The pool and pool area was great for the most part but the first night we arrived, we noticed a decent amount of debris in the pool. We communicated the issue with Alex and Luis; They were responsive and quickly rectified the issue by having the pool guy stop by the next day at 8am. We didn’t experience any other issues during our stay after that. The neighborhood was also great. It was quiet for most of our stay and the house is located in a convienant area. Would definitely stay here again!

Encantada Resort:Pool,Gym,Clubhouse,10mi to Disney
Great place to stay at . Alex is a wonderful host. This location was conveniently near shopping centers and all amazing food spots.

Windsor Hills Home w/Arcade Game Room|Near Disney
Very reasonable price for a four bedroom home with a very cool game room. The Harry Potter themed room was over the top fun. The neighborhood pool was enjoyed by all and the food we got at the pool was well done for a small café.

Family Home w/ Pool & Resort Perks Near Disney
it was a good place to stay but couldn't throw out trash out in the cans we had to know where else to put them but other then that they was awesome

Resort home, Lakeview, private pool (4417AC)
My family enjoyed every minute of our vacation. Home was absolutely beautiful and everything we could have wanted and needed. Will definitely be back.

Sunny Storey Lake Oasis w/ Pool & near disney

Luxury Storey Lake 10 Bedroom HM

Bedroom #3 double
Ski-in/out apartment rentals

Penthouse Level! Disney! Ensuite king-bed/bathroom
Ruth is an Amazing and Friendly Host.She is very responsive.Our stay at Ruth's home is a beautiful memory.The place can make you see a beautiful sunrise.The amenities there are really stress-free and the view makes you feel peaceful.Happy to stay again in this home. Thank you Ruth for a happy Stay 😀

Lake Buena Vista Condo facing Disney Fireworks
Great location and the apartment was updated, clean and spacious. Will book again.

8507 Retreat 3 Bedroom Condo near Disney
I would 100% recommend Omar’s townhome. The furniture is very comfortable, and the place is clean and spacious. The checking in was a bit confusing but we managed to get it done. Neighborhood is beautiful, quiet and peaceful. Very responsive host. My family loved the place as well.

1802 Cozy Condo 3 min Universal
I booked this Airbnb on behalf of two colleagues, and the location was perfect for visiting Universal Studios. They really enjoyed their stay and found the location very convenient. The only minor issue was that they couldn’t find a broom at the property, but it wasn’t a big deal. Overall, they had a great experience!” Thank you .

2701 Enclave Condo near Univesal-Lakeview
Great stay!

Tuscana Resort,Disney a 17 minutos
This is the first time where I actually am overly satisfied, not only was this home beautiful but it felt like a home away from home. My family and I watched movies and played board games. This home was not only in a super local area we also drove maybe 30 minutes to the nearest outlet mall and had a great time. We also enjoyed the universal themes parks as well !! Great stay would definitely recommend 10/10

8102 Vacation getaway at Windsor
Casatima for a visit to Orlando. With good restaurants and parks nearby.

Club Wyndham Cypress Palms Resort (Deluxe)
Quick stats about holiday rentals that are ski-in/out in Kissimmee
Total rentals
20 properties
Nightly prices starting at
₹5,995 before taxes and fees
Total number of reviews
380 reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Universal Studios Florida
- Orange County Convention Center
- Universal's Volcano Bay
- Old Town Kissimmee
- Discovery Cove
- Disney's Animal Kingdom Theme Park
- SeaWorld Orlando
- Universal Orlando Resort
- Disney Springs
- ESPN Wide World of Sports
- Amway Center
- Epcot
- Reunion West
- Magic Kingdom Park
- Aquatica
- ChampionsGate Golf Club
- Disney's Hollywood Studios
- Kissimmee Lakefront Park
- Universal's Islands of Adventure
- Island H2O Water Park
- Walt Disney World Resort Golf
- Blue Spring State Park
- ICON Park
- Universal CityWalk