Title: Ski Vacations in Key West 2026 | Expedia.ca ![](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 Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Plan the ultimate ski vacation in Key West #### What are some benefits when booking ski vacations in Key West? If you're interested in skiing, there's nothing quite like a ski vacation. These trips are designed to allow you to enjoy being on the slopes and relax in tranquil and convenient accommodations at the end of the day. Amenities on ski trips can be pretty upscale, so it's easy to relax in a hot tub or at a spa in between your skiing excursions. Plus, they can put you right next to the slopes. You'll even find a variety of different vacation types available whether you're looking for family friendly, cheap, or even last minute ski vacations. #### How can I book the best ski vacation in Key West? It is most important to implement the ski filter in your search when trying to find a ski vacation that will make you happy. Using the filter will automatically remove any entries that don't offer the skiing opportunities you want. After that, you'll need to think about what specifically you want from Key West, and think about the time of year that's best to visit. #### How can I find cheap ski vacations? Cheap ski vacations are readily available in Key West with some as cheap as . You can see the cheapest options by sorting your accommodation choices by price, which automatically puts the least-expensive results at the top of the list. You may also want to consider an accommodation with a kitchen, so you can cook instead of eating out. #### Can I book ski packages? Yes, ski packages are readily available throughout Key West. All you have to do is put in your travel dates and see what's available. When you book a ski package, you may be able to enjoy discounts with savings of up to when you book your accommodation and your flight together. #### What should I consider when booking family ski vacations? The key to a successful family ski vacation is ensuring that your family is kept happy and entertained. Consider what your family members are interested in and the kind of vacation they want. If they have little skiing experience, for example, you may want to opt for an accommodation that offers ski lessons or a kid's club. Various slope difficulties may be essential in providing opportunities for everyone at Key West. #### Can I book all-inclusive ski vacations in Key West? Yes, all-inclusive ski trips are available and may be precisely what you're looking for. All you have to do is include the filter for all-inclusive stays, and your search results will only show the accommodations that provide this handy feature that allows you to plan your entire trip to Key West in advance. #### What's the best time of year to plan a ski trip? The apparent answer to when you should plan a ski trip is in winter, but other details are important too. If you book for Key West's high season around January and February, you'll likely find increased prices. It's generally best to opt for the early or late season in December and April, as prices tend not to be quite as high. #### How can I find the best deals on ski packages in Key West? When you're looking for cheap ski vacations, there are a few factors you can take advantage of to help get the best deals. Travelling during the off-season can be cheaper since there's more availability. However, the beginning and end of the season tend to be the most affordable for skiing. #### Can I book a ski vacation that's fully refundable? Being fully refundable is a feature you'll find on several accommodation packages in Key West. You can even search for it explicitly using a filter for full refundability. #### Why should I book a ski vacation package with Expedia? When you book with Expedia, you'll find everything you need for cheap ski vacations, luxury ski vacations and everything in between in one central location. You may even be able to enjoy discounts for booking your accommodation and your flight together with savings of up to . With Expedia Rewards, you can earn points towards your next booking. ## Ski Hotels in Key West ![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.ca/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.ca/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! (90 reviews) Sunshine in KeyWest Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had a lovely stay in February for five nights. ... Reviewed on Mar 6, 2026 [](https://expedia.ca/Key-West-Hotels-Spacious-Waterfront-4-Bedroom-Home-With-Private-Heated-Pool.h18765661.Hotel-Information) [See all 2,708 properties in Key West](https://expedia.ca/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. Additional terms may apply. ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Top Ski Vacation Destinations > - [Ski vacations in Whistler ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/4115/Whistler) > - [Ski vacations in Banff ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/4332/Banff) > - [Ski vacations in Mont Tremblant ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/55374/Mont-Tremblant) > - [Ski vacations in Jasper ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/8028/Jasper) > - [Ski vacations in Jackson ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/180006/Jackson) > - [Ski vacations in France ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/59/France) > - [Ski vacations in Quebec ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/180017/Quebec) > - [Ski vacations in Queenstown ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/3611/Queenstown) > - [Ski vacations in Lake Louise ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/10115/Lake-Louise) > - [Ski vacations in Nelson ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/6194600/Nelson) > - [Ski vacations in Kitzbuhel ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/6346453/Kitzbuehel) > - [Ski vacations in Switzerland ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/174/Switzerland) > - [Ski vacations in La Plagne ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/6034464/La-Plagne) > - [Ski vacations in St Gervais ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/3000402612/St-Gervais-Sur-Mare) > - [Ski vacations in Austria ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/11/Austria) > - [Ski vacations in Germany ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/64/Germany) > - [Ski vacations in Wengen ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/6186871/Wengen) > - [Ski vacations in Ontario ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/2680/Ontario) > - [Ski vacations in Colorado ](https://www.expedia.ca/lp/theme-vacations/ski-vacations/207/Colorado) ## More Vacations Ideas [Flights to Key West ](https://expedia.ca/Cheap-Flights-To-Key-West.d1187.Travel-Guide-Flights)[ Key West Hotels ](https://expedia.ca/Key-West-Hotels.d1187.Travel-Guide-Hotels)[ Key West Vacation Rentals ](https://expedia.ca/Key-West-Vacation-Rentals.d1187.Travel-Guide-VacationRentals)[ Key West Car Rentals ](https://expedia.ca/Car-Rentals-In-Key-West.d1187.Car-Rental-Guide)[ Key West Vacations ](https://expedia.ca/Key-West.d1187.Destination-Travel-Guides)[ Things to do in Key West ](https://expedia.ca/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. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app