Title: Ski Vacations in Windley Key 2026 | Expedia.ca ![](https://images.trvl-media.com/place/553248635997958830/30b22f53-286f-436b-ae7a-d035c9062e6c.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Windley Key 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 ## Flight and Ski hotel deals in Windley Key Price found within the past 48 hours. Click for updated prices. ![Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton](https://images.trvl-media.com/lodging/2000000/1170000/1169600/1169583/16bbce87_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Faro Blanco Resort & Yacht Club Marathon, Curio by Hilton CA $1,618 per person Feb 18 - Feb 25 found 18 hours ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8.8/10 Excellent! (1,275 reviews) Very nice resort. All the staff was friendly and helpful. The pool bar was great and the bartender was friendly. Our favorite place to stay in Marathon. Reviewed on Dec 14, 2025 ![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/b1845555_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hawks Cay Resort CA $2,061 per person Feb 18 - Feb 25 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Miami (MIA) 8/10 Very Good! (1,003 reviews) The resort was beautiful, the room was nice and clean although the day after we arrived housekeeping did not come to our room to empty garbages and give us fresh towels and had to ask at front desk. But after that it was not a problem. Also 1 morning we woke up to no water in our room and had to call front desk and eventually was turned back on. Other than those things we had a nice time. Reviewed on Dec 14, 2025 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/dffb9d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach CA $9,622 per person Mar 2 - Mar 6 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Miami (MIA) 8/10 Very Good! (1 review) ![The Shelborne By Proper, a Member of Design Hotels](https://images.trvl-media.com/lodging/1000000/30000/25500/25451/e49031f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Shelborne By Proper, a Member of Design Hotels South Beach CA $2,017 per person Jan 15 - Jan 19 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Miami (MIA) 9.4/10 Exceptional! (56 reviews) Really great spot. Love the low key aesthetic and cool design. The tiles in the bar area are great. Nice breakfast spot by pool, and beach club is outstanding. Only small issue is there were a bunch of loud little kids shouting and cannon-balling into the pool. Super disruptive to the peaceful setting and zero was done to ask the kids to chill just a bit. Overall - super spot and renovation has made it a gem again. Reviewed on Dec 14, 2025 ![Villas At Hawks Cay Resort](https://images.trvl-media.com/lodging/100000000/99930000/99920100/99920083/8638cc9f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Villas At Hawks Cay Resort CA $2,709 per person Mar 7 - Mar 14 found 24 hours ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 8.4/10 Very Good! (145 reviews) great trip. Clean, easy to get around. Good amenities for a family trip. Reviewed on Nov 16, 2025 Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-16/2026-01-23/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Ski holidays in Windley Key Price found within the past 48 hours. Click for updated prices. ![1 Hotel South Beach](https://images.trvl-media.com/lodging/2000000/1800000/1790100/1790087/w4800h3297x0y3-ab24f575_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 1 Hotel South Beach South Beach CA $2,943 per person Mar 2 - Mar 6 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Miami (MIA) 9.4/10 Exceptional! (1,365 reviews) We love the 1 hotel! Staff are friendly and helpful and the facilities are immaculate. Room was gorgeous and the food on property was phenomenal. We loved being on the beach and having access to lounge chairs and towels- also so nice to have waiter service on the beach and at the pools! Reviewed on Dec 13, 2025 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/dffb9d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach CA $9,622 per person Mar 2 - Mar 6 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Miami (MIA) 8/10 Very Good! (1 review) ![EAST Miami Residences](https://images.trvl-media.com/lodging/79000000/78580000/78570600/78570563/dca879fa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### EAST Miami Residences Brickell CA $3,199 per person Mar 8 - Mar 15 found 1 day ago Roundtrip non-stop flight included Ottawa (YOW) to Miami (MIA) 9/10 Wonderful! (84 reviews) Great location and hotel. Reviewed on Dec 8, 2025 Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-16/2026-01-23/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Ski holidays in Windley Key Price found within the past 48 hours. Click for updated prices. ![EAST Miami Residences](https://images.trvl-media.com/lodging/79000000/78580000/78570600/78570563/dca879fa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### EAST Miami Residences Brickell CA $1,602 per person Feb 26 - Mar 1 found 1 day ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 9/10 Wonderful! (84 reviews) Great location and hotel. Reviewed on Dec 8, 2025 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/dffb9d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach CA $8,702 per person Jan 26 - Jan 29 found 8 hours ago Roundtrip non-stop flight included Ottawa (YOW) to Miami (MIA) 8/10 Very Good! (1 review) ![The Shelborne By Proper, a Member of Design Hotels](https://images.trvl-media.com/lodging/1000000/30000/25500/25451/e49031f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Shelborne By Proper, a Member of Design Hotels South Beach CA $1,630 per person Feb 19 - Feb 22 found 1 day ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 9.4/10 Exceptional! (56 reviews) Really great spot. Love the low key aesthetic and cool design. The tiles in the bar area are great. Nice breakfast spot by pool, and beach club is outstanding. Only small issue is there were a bunch of loud little kids shouting and cannon-balling into the pool. Super disruptive to the peaceful setting and zero was done to ask the kids to chill just a bit. Overall - super spot and renovation has made it a gem again. Reviewed on Dec 14, 2025 Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-16/2026-01-23/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Ski holidays in Windley Key Price found within the past 48 hours. Click for updated prices. ![Bay Breeze Premium Apartments By Eskape Collection](https://images.trvl-media.com/lodging/28000000/27610000/27603500/27603405/c37fc122_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bay Breeze Premium Apartments By Eskape Collection CA $927 per person Jan 15 - Jan 19 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Miami (MIA) 8.6/10 Excellent! (189 reviews) From the very efficient and effective check in, courteous customer service, and spotless room, our stay was great from the beginning. The place was spacious and modern. There was a big wrap around balcony (we had the two bedroom), and large kitchen. Even a washer and dryer. The only cons were the water pressure in the bathroom sink, and after a certain time, you cannot get more towels. House cleaning is "ask if you want", its not every day. For us we liked our privacy, so this worked for us. Another thing we loved was the quiet. The views were ok. Go ahead and book, you will not regret. Reviewed on Dec 8, 2025 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/dffb9d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach CA $9,622 per person Mar 2 - Mar 6 found 1 day ago Roundtrip non-stop flight included Montreal (YMQ) to Miami (MIA) 8/10 Very Good! (1 review) ![The Shelborne By Proper, a Member of Design Hotels](https://images.trvl-media.com/lodging/1000000/30000/25500/25451/e49031f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Shelborne By Proper, a Member of Design Hotels South Beach CA $2,017 per person Jan 15 - Jan 19 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Miami (MIA) 9.4/10 Exceptional! (56 reviews) Really great spot. Love the low key aesthetic and cool design. The tiles in the bar area are great. Nice breakfast spot by pool, and beach club is outstanding. Only small issue is there were a bunch of loud little kids shouting and cannon-balling into the pool. Super disruptive to the peaceful setting and zero was done to ask the kids to chill just a bit. Overall - super spot and renovation has made it a gem again. Reviewed on Dec 14, 2025 Don't see what you're looking for? See all available trips from Columbus to Windley Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-01-16/2026-01-23/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the ultimate ski vacation in Windley Key #### What are some benefits when booking ski vacations in Windley Key? 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 Windley Key? 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 Windley Key, 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 Windley Key with some as cheap as CA $927\. 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 Windley Key. 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 48 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 Windley Key. #### Can I book all-inclusive ski vacations in Windley Key? 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 Windley Key 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 Windley Key'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 Windley Key? 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 Windley Key. 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 48\. With Expedia Rewards, you can earn points towards your next booking. ## 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 Windley Key ](https://expedia.ca/Cheap-Flights-To-Windley-Key.d553248635976197663.Travel-Guide-Flights)[ Windley Key Hotels ](https://expedia.ca/Windley-Key-Hotels.d553248635976197663.Travel-Guide-Hotels)[ Windley Key Vacation Rentals ](https://expedia.ca/Windley-Key-Vacation-Rentals.d553248635976197663.Travel-Guide-VacationRentals)[ Windley Key Car Rentals ](https://expedia.ca/Car-Rentals-In-Windley-Key.d553248635976197663.Car-Rental-Guide)[ Windley Key Vacations ](https://expedia.ca/Windley-Key.d553248635976197663.Destination-Travel-Guides)[ Things to do in Windley Key ](https://expedia.ca/Things-To-Do-In-Windley-Key.d553248635976197663.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