Ski-in/Ski-out holiday rentals in Kissimmee

Find and book unique ski-in/ski-out homes on Airbnb

Top-rated ski-in/ski-out rentals in Kissimmee

Guests agree: These ski-in/ski-out homes are highly rated for location, cleanliness and more.

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Top Guest favourite

Home in Kissimmee

4.97 out of 5 average rating, 77 reviews

“Casa Del Sol”

AndrewRating, 5 stars2 weeks ago

Javier was great to work with. He was very responsive to requests and quick to reply. He came by to help me with something in the garage and gave me a brief walk through of things while there. The house was very nice, clean, comfortable and the AC worked great. Beds were comfy, TV's and fans in the two larger bedrooms. The back yard was great to relax and play with the dog. We crated our dog when not at the house, but the dog door was a nice added touch that allowed ours to go in and out as she pleased when we were at the house. We brought an air fryer with us, however, the kitchen had one when we arrived. For our activities, the location was perfect between where our Daughter was staying with her team and the Orange County Convention Center. Walmart is right around the corner and Publix across the street. Wawa convenience store right down the street with excellent Blueberry Cobbler Coffee. We had a great stay.

Condo in Kissimmee

4.73 out of 5 average rating, 26 reviews

MARBELLA beautiful residential complex

MaryRating, 5 stars4 months ago

Very well located and very cozy house. Supermarket and nearby restaurants. Sterling was very kind, it quickly answered a problem that we had with the Internet and allowed us to anticipate the time of entry and exit of the property for a few hours. I recommend

Apartment in Orlando

4.8 out of 5 average rating, 5 reviews

2BR-King Bed-Hot Tub-Spa-Pools-Water Park

StanRating, 5 stars3 weeks ago

Daniela’s description was accurate, she was very responsive and helpful . Super easy to work with and always willing to make the stay perfect , highly recommended and will definitely be back . Couldn’t have picked a more suitable place , it was a blessing

Condo in Florida Center

4.76 out of 5 average rating, 17 reviews

1802 Cozy Condo 3 min Universal

DonnaRating, 5 stars2 months ago

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 .

Top Guest favourite

Home in Kissimmee

5 out of 5 average rating, 15 reviews

Brand New 3 Bedrooms Close to Disney

MarthaRating, 5 stars2 weeks ago

The home is exceptional—straight out of a magazine. It was incredibly serene, creating the perfect environment for relaxation. The kids loved having their own space and, for the first time, even slept on their own! We really enjoyed the pool, and Edy was very responsive and helpful throughout our stay. I’m looking forward to coming back!

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Kissimmee ski-in/ski-out rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Ski-in/ski-out house rentals

Superhost

Home in Kissimmee

4.33 out of 5 average rating, 3 reviews

Storey Lake Home:Pool, Gym, Lazy River&near Disney

AndreRating, 5 stars5 months ago

This day was great nice and comfortable. No complaints here …… if I’m ever in the area again I wouldn’t hesitate to book this Airbnb again

Superhost

Home in Kissimmee

4.67 out of 5 average rating, 3 reviews

Encantada Resort:Pool,Gym,Clubhouse,10mi to Disney

ShaunRating, 5 stars1 week ago

Great place to stay at . Alex is a wonderful host. This location was conveniently near shopping centers and all amazing food spots.

Home in Davenport

4.55 out of 5 average rating, 11 reviews

Luxurious house near Disney

davidRating, 5 stars4 months ago

our stay was quiet and peaceful which is what we were looking for to celebrate New Years, the house was in a nice community, we had more than enough space to relax!

Superhost

Home in Kissimmee

4.67 out of 5 average rating, 3 reviews

Windsor Hills Home w/Arcade Game Room|Near Disney

SuzanneRating, 5 stars1 month ago

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.

Home in Davenport

4 out of 5 average rating, 5 reviews

Resort home, Lakeview, private pool (4417AC)

FatariRating, 5 stars11 months ago

My family enjoyed every minute of our vacation. Home was absolutely beautiful and everything we could have wanted and needed. Will definitely be back.

Home in Davenport

3.78 out of 5 average rating, 9 reviews

4 Bed Davenport home

MarioRating, 5 stars41 months ago

very nice house it’s clean i would definitely say here again there was a lazy river,pool and water slide which was nice publix was right around the corner if you need to get anything for your stay

Guest favourite

Home in Kissimmee

5 out of 5 average rating, 9 reviews

Lake Berkley Home: Pool, Lakefront & near Disney

FrankRating, 5 stars1 week ago

Would highly recommend this place to anyone traveling to Orlando. Gated community so always felt safe. Private pool over looking the lake was exactly what we were looking for, and the kids had a great time in the pool. Plenty of space in the house and sleeping arrangements for 4 adults and 5 kids. Quick 20-25 minute ride/Uber to both City Walk and Disney Springs. Alex and Luis were always responsive and addressed any questions we had in minutes. Would recommend to anyone traveling to the area! A+

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Ski-in/ski-out condo rentals

Guest favourite

Private room in Orlando

4.85 out of 5 average rating, 60 reviews

Penthouse Level! Disney! Ensuite king-bed/bathroom

KarthikRating, 5 stars3 months ago

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 😀

Condo in Orlando

New place to stay

Lake Buena Vista Condo facing Disney Fireworks

WaleskaRating, 5 stars2 weeks ago

Great location and the apartment was updated, clean and spacious. Will book again.

Condo in Kissimmee

4.75 out of 5 average rating, 4 reviews

8507 Retreat 3 Bedroom Condo near Disney

NicoleRating, 5 stars2 months ago

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.