Title: Key West Ski Vacations 2026 | Expedia.com ![](https://images.trvl-media.com/place/1187/a7c3fad3-5f12-4d91-8996-ed0e1b61b0a3.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Key West Ski Vacations ## Book a Ski Hotel + Flight or Car together to unlock savings ## Planning your Key West ski vacation #### What are some things I should consider when booking a Key West ski trip package? Yes, you want pristine powder and perfect runs, but take a moment to consider how close you want to be to the slopes, what extras you want from your resort, and—of course—how much après ski you intend to indulge in. #### How can I find cheap Key West ski packages? Right now, ski trips start at just . Prices and availability are subject to change. Additional terms may apply. #### Can I book a beginner ski package in Key West? Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Key West. Book lessons so you can gear up to take on the rest of the mountain with confidence. Après awaits for all after an eventful day in the snow. #### How much does a ski trip to Key West cost? Sensational ski trips to Key West start from . Use the budget filter to find powder at your perfect price. As always, prices and availability are subject to change. Additional terms may apply. #### When’s the best time of year to plan a ski trip to Key West? The best time to hit the slopes in Key West depends on what you’re looking for. If you’re all about powder-packed pistes and brilliant blue-sky skiing conditions, aim for the middle of the season. Alternatively, if you’re willing to take a chance on start or end of season snow, you’ll bag much cheaper prices —just make sure there’s a spa or après bar to shelter in on white-out days. #### Can I book Key West ski packages with airfare? Save money on your snow time by booking your accommodation, airfare, and car rental in a brilliant bundle. It’s both convenient and cash-flow friendly. #### Can I book a Key West ski trip with free cancellation and/or flexible dates? Flexibility is always a bonus when you’re flying down the slopes—and it makes for an easier booking process, too. Check the payment option filter to find trips with free cancellation as well as buy now, pay later options. #### Why should I book a ski package in Key West with Expedia? Simple search and fantastic filters make it easy to find, build, and book your dream Key West ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy. ## Top Ski Key West Hotels ![Direct Ocean View from Your Condo-No Contact Check-In](https://images.trvl-media.com/lodging/19000000/19000000/18993500/18993405/743f9aeb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Direct Ocean View from Your Condo-No Contact Check-In Key West FL - 29 min walk from Duval Street Stay at this condo in Key West. Enjoy laundry facilities, tennis courts, and balconies. Our guests praise the property condition in our reviews. Popular attractions ... 9.4/10 Exceptional! (169 reviews) Came to Key West for our son’s wedding. It was a perfect place for us. Very clean and Roberta was very prompt responding to questions I had. Even willing to go above and beyond to help us. I would definitely recommend. Reviewed on Feb 1, 2026 [](https://expedia.com/Key-West-Hotels-Direct-Ocean-View-From-Your-Condo-No-Contact-Check-In.h18993405.Hotel-Information) ![ Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach](https://images.trvl-media.com/lodging/19000000/19000000/18993100/18993026/29971ddf_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach Key West FL - 5 min walk from Duval Street Stay at this condo in Key West. Enjoy free WiFi, laundry facilities, and balconies. Popular attractions Duval Street and Ernest Hemingway Home and Museum are ... 9.6/10 Exceptional! (133 reviews) The pool was nice. The location could not be beat. It was within walking distance to everything for tourists. Reviewed on Jan 21, 2026 [](https://expedia.com/Key-West-Hotels-Historic-District-Pool-View-Duval-Street-Beach-Nearby-No-Contact-Check-In.h18993026.Hotel-Information) ![Spacious Waterfront 4 Bedroom Home](https://images.trvl-media.com/lodging/19000000/18770000/18765700/18765661/55e380c9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Spacious Waterfront 4 Bedroom Home Key West FL - 5 min drive from Duval Street Stay at this vacation home in Key West. Enjoy free WiFi, private pools, and laundry facilities. Popular attractions Duval Street and Smathers Beach are located ... 9.6/10 Exceptional! (91 reviews) We loved everything about this place. Reviewed on Mar 12, 2026 [](https://expedia.com/Key-West-Hotels-Spacious-Waterfront-4-Bedroom-Home-With-Private-Heated-Pool.h18765661.Hotel-Information) [See all 2,714 properties in Key West](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=1187) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. 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Rentals in Key West ](https://expedia.com/Car-Rentals-In-Key-West.d1187.Car-Rental-Guide)[ Key West Vacations ](https://expedia.com/Key-West.d1187.Destination-Travel-Guides)[ Things to do in Key West ](https://expedia.com/Things-To-Do-In-Key-West.d1187.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.