Find ski hotels & lodging in Kissimmee, FL

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Pick from 21 Kissimmee Ski Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

Luxury Condo, Gated Resort, Unbeatable Location, Steps to Disney, ESPN Universal
Property grounds
Luxury Condo, Gated Resort, Unbeatable Location, Steps to Disney, ESPN Universal
10.0 out of 10, Exceptional, 39 reviews
"We had a wonderful stay at Windsor Palms. This location is located just steps from a huge pool and club house. The owners were very kind and responsive to all messages. The unit is as described. Everything we needed for a nice vacation. We had a car and the Disney parks, resorts, and so many restaurants are within 10-20 minute drive. Windsor Palms is a gated community and very quiet (for the most part) during the day and at night. We enjoyed nightly walks around the neighborhood. Hope to return...
Luxury Condo, Gated Resort, Unbeatable Location, Steps to Disney, ESPN Universal
Windsor Hills Condo! No Resort Fees!
A heated pool
Windsor Hills Condo! No Resort Fees!
9.4 out of 10, Exceptional, 51 reviews
"This property is great for a family vacay. Close to the parks and the resort was a great place to hang out on days we didn’t visit WDW. Would definitely stay again"
Windsor Hills Condo! No Resort Fees!
Renovated, Windsor Hills Resort Upgraded Fireworks View Condo! Granite!
A heated pool
Renovated, Windsor Hills Resort Upgraded Fireworks View Condo! Granite!
9.2 out of 10, Wonderful, 42 reviews
"The property was everything we expected and more. Clean, comfortable, and the rooms were just what our family needed. The themes in the apartment were nice. The pool and waterslide were clean, refreshing and a great vibe. The shop, arcade and entertainment areas were all fun. The location to the parks was perfect. The communitiy was all welcoming during our stay. We loved it."
Renovated, Windsor Hills Resort Upgraded Fireworks View Condo! Granite!
Brand New, Completely Renovated, South Facing w/ Luxurious Finishes & Updates
Pool
Brand New, Completely Renovated, South Facing w/ Luxurious Finishes & Updates
9.2 out of 10, Wonderful, 58 reviews
"We enjoyed the stay we stayed in Windsor before the only thing I would say about this property is that the pool and the area around the pool needed cleaning so we could not use a pool. The entryway was hard to get out of because the landscape was not as trimmed up as it should’ve been. The bathroom upstairs seat did not drain adequately and the stairs were squeaky so they tend to wake people up"
Brand New, Completely Renovated, South Facing w/ Luxurious Finishes & Updates
FULLY REMODELED! Windsor Hills 402! A Must See, 2 Bedroom Condo!
A heated pool
FULLY REMODELED! Windsor Hills 402! A Must See, 2 Bedroom Condo!
9.0 out of 10, Wonderful, 39 reviews
"We had an amazing time at Windsor resorts. My family and I have been coming down to Florida for the last 8 years and Windsor by far has been our favorite place to stay. This particular condo was nicely updated and was conveniently located to just about every amenity imaginable."
FULLY REMODELED! Windsor Hills 402! A Must See, 2 Bedroom Condo!
Windsor Hills 205! No Resort Fees! New Water-Park! Great Value!
A heated pool
Windsor Hills 205! No Resort Fees! New Water-Park! Great Value!
8.8 out of 10, Excellent, 41 reviews
"The condo we rented was extremely clean when we arrived! We were also pleasantly surprised with the amount of room this condo offered; the pictures didn't do it justice. It was the perfect location, surrounded by the theme parks and right around the corner from Walmart. The pool and waterslides in this gated community were a favorite attraction for our 4 kids. We definitely wouldn't hesitate to stay here again!"
Windsor Hills 205! No Resort Fees! New Water-Park! Great Value!
Your "home away from home": Windsor Hills Resort near Disney!
Outdoor pool, a heated pool
Your "home away from home": Windsor Hills Resort near Disney!
8.0 out of 10, Very Good, 5 reviews
"This condo was once a luxury condo, but unfortunately it no longer is. The couches you see in the picture are there; however the vinyl is peeling off of the one on the left. It is so bad that little pieces stick to your clothes and skin when you sit on it. It is still a comfortable couch, but in desperate need of at least a couch cover. The other couch is only peeling slightly, but very uncomfortable. It looked to be a fold out, but even so there was no support on the bottom for anyone to sit...
Your "home away from home": Windsor Hills Resort near Disney!
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotels with ski-in / ski out

Windsor Hills 205! No Resort Fees! New Water-Park! Great Value!

Windsor Hills 205! No Resort Fees! New Water-Park! Great Value!

Kissimmee
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8.6/10 Excellent! (29 reviews)

Hotels with ski lift privileges

Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/Spa/WiFI

Tropical Oasis - Windsor at Westside - NEW 7 Bedroom, 5.5 Bath, Pool/Spa/WiFI

Kissimmee
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8.6/10 Excellent! (50 reviews)

Kissimmee Ski Hotels information

 

Ski Hotels in Kissimmee

21

Highest price
Cheapest price
Number of guest reviews
61
Total number of hotels in Kissimmee
32,255

 

Frequently asked questions

Are there any family-friendly ski hotels in Kissimmee?
You bet there are! After a fun day in the snowy outdoors, unwind at Marriotts Cypress Harbour Villas, a family-friendly ski hotel in Kissimmee. This 4-star property features amenities such as a sauna and childcare services. You can also hit the pistes with your team at Marriotts Lakeshore Reserve. With conveniences such as a waterslide and a nearby theme park, this 3.5-star stay makes an ideal base for your ski getaway in Kissimmee. Once you’ve checked in and unpacked, there’s a host of family-friendly attractions to discover around Kissimmee. Discovery Cove and Aquatica guarantee fun for young and old.
Why book your ski hotel in Kissimmee with Expedia?
Expedia is your one-stop shop for arranging the ultimate ski trip. We have the widest range of accommodations to choose from, search filters that make it a breeze to find the perfect stay for you and the best prices on the market. Join Expedia Rewards free of charge and access even more bargains on your Kissimmee ski hotel and other bonuses.
How can I find cheap ski hotels in Kissimmee?
First off, make your way to our convenient filters. Then, choose your preferred hotel rating — they range from basic (1 star) to luxe (5 star). You can also sort your search results by price so that the most affordable stays appear at the top of the list. Booking a ski hotel in Kissimmee at a terrific price couldn’t be easier!
What is there to do near my ski hotel in Kissimmee?
Kissimmee has enough sights and activities to keep you busy for weeks, starting with Discovery Cove. Aquatica, Disneys Typhoon Lagoon Water Park and Gatorland® are other awesome attractions. If you have more time, Medieval Times and Fun Spot America are great additions to your itinerary.