Title: Ski Vacations in Upper Matecumbe Key 2026 | Expedia.ca ![](https://images.trvl-media.com/place/10768/414c55a9-82b2-4829-857c-fd7c26e0bd48.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Upper Matecumbe Key Ski Vacations ## Book a Hotel + Flight or Car together to unlock savings Photo by Cameron Abbott - ## 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 Upper Matecumbe Key Price found within the past 48 hours. Click for updated prices. ![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 $1,264 per person Feb 8 - Feb 14 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8/10 Very Good! (1,003 reviews) Overall the resort was great! The only criticism I can add is that the villa showed some wear and tear. Reviewed on Dec 30, 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 $7,088 per person Feb 8 - Feb 11 found 10 hours ago Roundtrip flight included Hamilton (YHM) to Miami (MIA) 8/10 Very Good! (1 review) ![Miami Downtown Condos](https://images.trvl-media.com/lodging/110000000/109790000/109784700/109784697/w2048h1535x0y1-af4622e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Miami Downtown Condos Downtown Miami CA $2,100 per person Mar 21 - Mar 28 found 18 hours ago Roundtrip non-stop flight included Montreal (YMQ) to Miami (MIA) 8.6/10 Excellent! (72 reviews) Amazing customer service! Always there when you need them, no matter the time, or iinquiry! I had an amazing stay, and I’d highly recommend you stay! Reviewed on Dec 28, 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 $2,551 per person Feb 3 - Feb 10 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8.4/10 Very Good! (145 reviews) Resort is lovely. Food is expensive. “Premium” villas are subpar for $1000 a night over the holiday. Paid for 3 bedroom that was supposed to have per our reservation 1 king and 3 queen beds plus pull out. Received a room with one true bedroom with a king bed, 2 closet size rooms one with a hard queen bed, and 1 room with no closet, laundry in it, no dresser and two twin beds. No where for our kids to sleep because I can’t sleep in the middle of the living room on Christmas. Had to sleep on the floor, management brought broken air matress after them sleeping on the floor first night. That deflated middle of night. They gave us a discount after complaints but it was still not what we paid for and stressful for all. Beautiful pool and other grounds. Would probably try a hotel room if we went back. Reviewed on Dec 27, 2025 ![Pelican Hotel](https://images.trvl-media.com/lodging/1000000/60000/55100/55046/22b81b04_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pelican Hotel South Beach CA $1,764 per person Mar 12 - Mar 19 found 1 day ago Roundtrip flight included Hamilton (YHM) to Miami (MIA) 9.2/10 Wonderful! (394 reviews) Perfect location! Cool room designs! Older building but well maintained. Reviewed on Dec 23, 2025 Don't see what you're looking for? See all available trips from Columbus to Upper Matecumbe Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-03/2026-02-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 5\* Ski holidays in Upper Matecumbe Key Price found within the past 48 hours. Click for updated prices. ![Miami Downtown Condos](https://images.trvl-media.com/lodging/110000000/109790000/109784700/109784697/w2048h1535x0y1-af4622e2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Miami Downtown Condos Downtown Miami CA $2,100 per person Mar 21 - Mar 28 found 18 hours ago Roundtrip non-stop flight included Montreal (YMQ) to Miami (MIA) 8.6/10 Excellent! (72 reviews) Amazing customer service! Always there when you need them, no matter the time, or iinquiry! I had an amazing stay, and I’d highly recommend you stay! Reviewed on Dec 28, 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 $7,088 per person Feb 8 - Feb 11 found 10 hours ago Roundtrip flight included Hamilton (YHM) 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 $2,101 per person Mar 12 - Mar 16 found 12 hours ago Roundtrip flight included Toronto (YTO) 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 Upper Matecumbe Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-03/2026-02-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 3 Night Ski holidays in Upper Matecumbe Key Price found within the past 48 hours. Click for updated prices. ![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 $1,059 per person Mar 28 - Mar 31 found 13 hours ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8/10 Very Good! (1,003 reviews) Overall the resort was great! The only criticism I can add is that the villa showed some wear and tear. Reviewed on Dec 30, 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 $7,088 per person Feb 8 - Feb 11 found 10 hours ago Roundtrip flight included Hamilton (YHM) 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 $1,220 per person Mar 23 - Mar 26 found 13 hours ago Roundtrip flight included Toronto (YYZ) to Miami (MIA) 9.4/10 Exceptional! (56 reviews) Excellent amenities and great location Reviewed on Dec 31, 2025 Don't see what you're looking for? See all available trips from Columbus to Upper Matecumbe Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-03/2026-02-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## 4 Night Ski holidays in Upper Matecumbe Key Price found within the past 48 hours. Click for updated prices. ![Cavalier Hotel South Beach](https://images.trvl-media.com/lodging/1000000/20000/13600/13579/c0c3faa8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cavalier Hotel South Beach South Beach CA $685 per person Mar 29 - Apr 2 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8.4/10 Very Good! (1,001 reviews) Perfect location and great bonus with beach towels and two free chairs on the beach. Reviewed on Dec 27, 2025 ![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/5e43c05b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Creekside Inn CA $823 per person Feb 16 - Feb 20 found 1 day ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 8/10 Very Good! (1,004 reviews) There was a sign in the bathroom saying not to flush toilet paper down the toilet, the door was glass and was not completely covered, The fridge and the coffee maker could not be plugged in at the same time. Otherwise it was okay Reviewed on Jan 3, 2026 ![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 $2,125 per person Feb 11 - Feb 15 found 3 hours ago Roundtrip flight included Toronto (YTO) to Miami (MIA) 9.4/10 Exceptional! (56 reviews) Excellent amenities and great location Reviewed on Dec 31, 2025 Don't see what you're looking for? See all available trips from Columbus to Upper Matecumbe Key [View all trips](https://expedia.ca/go/package/search/FlightHotel/2026-02-03/2026-02-10/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=MIA&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ## Plan the ultimate ski vacation in Upper Matecumbe Key #### What are some benefits when booking ski vacations in Upper Matecumbe 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 Upper Matecumbe 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 Upper Matecumbe 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 Upper Matecumbe Key with some as cheap as CA $685\. 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 Upper Matecumbe 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 Upper Matecumbe Key. #### Can I book all-inclusive ski vacations in Upper Matecumbe 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 Upper Matecumbe 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 Upper Matecumbe 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 Upper Matecumbe 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 Upper Matecumbe 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 Upper Matecumbe Key ](https://expedia.ca/Cheap-Flights-To-Upper-Matecumbe-Key.d553248635975749648.Travel-Guide-Flights)[ Upper Matecumbe Key Hotels ](https://expedia.ca/Upper-Matecumbe-Key-Hotels.d553248635975749648.Travel-Guide-Hotels)[ Upper Matecumbe Key Vacation Rentals ](https://expedia.ca/Upper-Matecumbe-Key-Vacation-Rentals.d553248635975749648.Travel-Guide-VacationRentals)[ Upper Matecumbe Key Car Rentals ](https://expedia.ca/Car-Rentals-In-Upper-Matecumbe-Key.d553248635975749648.Car-Rental-Guide)[ Upper Matecumbe Key Vacations ](https://expedia.ca/Upper-Matecumbe-Key.d553248635975749648.Destination-Travel-Guides) \* 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