Ski-in/out vacation rentals in Osceola County

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.

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

Top guest favourite

5 out of 5 average rating, 15 reviews

Brand New 3 Bedrooms Close to Disney

MarthaRating, 5 stars3 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!

Guest favourite

5 out of 5 average rating, 9 reviews

Lake Berkley Home: Pool, Lakefront & near Disney

FrankRating, 5 stars2 weeks 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+

Vacation rentals for every style

Get the amount of space that is right for you.

Houses

A space that's all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Villas

Luxurious estates for the ultimate escape

Popular amenities for Osceola County ski-in/out rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Ski-in/out house rentals

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

Home in Davenport

4.39 out of 5 average rating, 18 reviews

Spacious Pool Home w/ 2 Masters, Games Room

MichaelRating, 5 stars1 month ago

The place was ideal for the four of us. Local attractions were 20-25 min away (add 15 min for morning traffic). Plenty of places to eat nearby. Neighborhood was quiet. Got to see rocket launch from backyard.

4.75 out of 5 average rating, 4 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.

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.

Private room in Kissimmee

New place to stay

Bedroom #3 double

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Ski-in/out condo rentals

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

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.

4.82 out of 5 average rating, 17 reviews

Condo in Davenport

Tuscana Resort Disney

CamiloRating, 5 stars3 weeks ago

We had a great time in the hosdaje, the apartment is very nice and the host was very friendly. We had a great time. 100% RECOMMENDED

4.62 out of 5 average rating, 52 reviews

4901 RC - Storey Lake - Luxury 4 Bed Villa

JordynRating, 5 stars22 months ago

This place is very spacious and extremely close to Disney World! It’s well stocked with things you need for your stay. When we contacted the owner about a couple of things that needed to be fixed, they were done so very quickly. The only complaint I would have to have is that maintenance will come into your rental while you are not there and the pool cleaners entered the back patio without making anyone aware. My daughters were outside and it felt a little uncomfortable. Other than that we really enjoyed this house and we would rent from Adriana again when we come back.