Florida Keys Ski Vacations
Book a Ski Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Planning your Florida Keys ski vacation
What are some things I should consider when booking a Florida Keys 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 Florida Keys 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 Florida Keys?
Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Florida Keys. 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 Florida Keys cost?
Sensational ski trips to Florida Keys 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 Florida Keys?
The best time to hit the slopes in Florida Keys 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 Florida Keys 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 Florida Keys 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 Florida Keys with Expedia?
Simple search and fantastic filters make it easy to find, build, and book your dream Florida Keys ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy.
Top Ski Florida Keys Hotels
Direct Ocean View from Your Condo-No Contact Check-In
"Location was great to go downtown and had alot of neighborhood places close..Sunrise 's were amazing from the balcony...pool and hot tub were great...Our host was top notch...responding quickly and thoroughly to our questions..Would recommend and would stay there again.."
Reviewed on Jun 3, 2026
Weekly Rentals Allowed 2026/2027-Pool View-Gated-Duval Street-Beach
"We stayed 4 nites. Excellent location, walkable to the ocean and downtown. Very nice complex. The only real issue we had was no A/C the first 20 hrs. The A/C guys fixed it on the 3rd try. Not a great start of our vacation. Roberta was excellent dealing with us and the A/C guys. It was 91f and 95% ..."
Reviewed on Jun 6, 2026
Spacious Waterfront 4 Bedroom Home
"The house was beautiful. Our trip was 2 couples, one single. The house layout was great , one bedroom on the first floor and three on the second floor, all with their own bathroom. The pool was great , porches all spacious. It was a great space and none of us ever felt cramped or closed in. It's ..."
Reviewed on Jun 9, 2026
Things to do
Miami to Key West Day Trip with Activity Options
Key West Half-Day Fishing Charter
