Ski-in/Ski-out vacation 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 favorite

The exterior of the single-family home is illuminated at night, highlighting the garage and front entrance. Soft lighting accentuates the landscaped garden and driveway, creating a welcoming entrance. The home's design features a combination of stone and stucco, framed by a well-maintained lawn.

Home in Kissimmee

4.97 out of 5 average rating, 76 reviews

“Casa Del Sol”

AndrewRating, 5 stars4 days 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.

Superhost

The spacious bedroom features a large bed with turquoise bedding, complemented by natural light from a nearby window. An open-concept living area is furnished with comfortable seating and a large television. A game area includes arcade games, while a private pool is enclosed with a clear screen.

Home in Clermont

5 out of 5 average rating, 3 reviews

Family Home w/ Pool & Resort Perks Near Disney

LynnRating, 5 stars4 months ago

We had a wonderful time! The kitchen was well equipped and the living area was comfortable. Owners were very attentive. It should be noted that instead of 2 king beds and 2 twins, there was just 1 king, 1 queen and 2 twins. Also, 5 miles to Disney equates to about a 30 minute drive. Overall, a great 5star review! 🌟

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

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

A vibrant water park is featured, showcasing colorful water slides and a large pool surrounded by sun loungers. Lush landscaping adds to the leisure area, including a thatched-roof structure nearby. Multiple buildings are visible in the background, contributing to a welcoming resort atmosphere.

Apartment in Orlando

4.8 out of 5 average rating, 5 reviews

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

StanRating, 5 stars2 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

The image shows a panoramic view of a vibrant resort area with tall buildings reflecting on a serene lake under clear blue skies. Also depicted are cozy living and sleeping spaces with stylish furniture and bright natural light filtering through the windows.

Condo in Florida Center

4.76 out of 5 average rating, 17 reviews

1802 Cozy Condo 3 min Universal

DonnaRating, 5 stars1 month 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 favorite

A creatively decorated bedroom features a spacious bed adorned with a light blue quilt. Accents include two colorful cushions and a playful mural with abstract shapes reminiscent of iconic characters. Soft lighting is provided by modern fixtures flanking the bed.

Home in Kissimmee

5 out of 5 average rating, 15 reviews

Brand New 3 Bedrooms Close to Disney

MarthaRating, 5 stars1 week 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!

Vacation rentals for every style

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

Kitchen

Wifi

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 stars4 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

ChellezRating, 5 stars2 weeks ago

Great location Quick response would stay again

A bright and inviting bedroom features a white bunk bed with vibrant yellow bedding and pillows. A modern dresser with a light wood finish sits against the wall, accompanied by a stylish lamp. Artwork is displayed above the dresser, adding a touch of personality.

Home in Davenport

4.55 out of 5 average rating, 11 reviews

Luxurious house near Disney

davidRating, 5 stars3 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!

The open living area features a sectional sofa and a large ottoman. A smart TV is mounted on the wall, and light enters through sliding glass doors that lead to an outdoor space, creating a bright and airy feel.

Home in Davenport

4 out of 5 average rating, 5 reviews

Resort home, Lakeview, private pool (4417AC)

FatariRating, 5 stars10 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

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Ski-in/ski-out condo rentals

Guest favorite

Two tall condominium towers stand side by side near a large body of water. The buildings feature multiple balconies and layered terraces, surrounded by lush greenery and trees. A clear sky with scattered clouds complements the serene water view.

Private room in Orlando

4.85 out of 5 average rating, 60 reviews

Penthouse Level! Disney! Ensuite king-bed/bathroom

KarthikRating, 5 stars2 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 😀

An aerial view of the iconic Pirate Ship pool highlights the expansive turquoise water, with loungers arranged around the edges. A pirate ship structure is featured, alongside a peaceful surrounding landscape that includes palm trees and a nearby fountain, providing a serene setting.

Condo in Orlando

New place to stay

Lake Buena Vista Condo facing Disney Fireworks

WaleskaRating, 5 stars4 days ago

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

A dining area features a wooden table set with colorful plates and a vase of flowers, surrounded by textured chairs. An exterior view captures the house's façade with palm trees framing the entrance, while a cozy living space is depicted with a plush sofa and a wall-mounted TV.

Condo in Kissimmee

4.75 out of 5 average rating, 4 reviews

8507 Retreat 3 Bedroom Condo near Disney

NicoleRating, 5 stars1 month 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.