Florida Keys Ski Vacations

Book a Ski Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 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

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

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! (152 reviews)
Very nice stay

Reviewed on Oct 15, 2025

Direct Ocean View from Your Condo-No Contact Check-In
Grandfathered Unit Weekly Rentals Allowed-Pool View-Duval Street-Beach

Grandfathered Unit Weekly Rentals Allowed-Pool View-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 ...
9.4/10 Exceptional! (118 reviews)
Roberta was wonderful I left something important behind and she mailed it to me the next day. The location is great. We LOVE the Annex. Would stay here again.

Reviewed on Oct 28, 2025

Grandfathered Unit Weekly Rentals Allowed-Pool View-Duval Street-Beach
Spacious Waterfront 4 Bedroom Home

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! (44 reviews)
Great house. Loved the pool. Quiet area. Would stay again.

Reviewed on Jun 12, 2025

Spacious Waterfront 4 Bedroom Home
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

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.