Key Haven Ski Vacations

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

Top Ski vacation packages in Key Haven

Price found within the past 48 hours. Click for updated prices.
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
$1,394
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,004 reviews)
The Gardens Hotel

The Gardens Hotel

Old Town Key West
Save 100% on your flight
$2,137
per person
Dec 4 - Dec 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,003 reviews)
Eden House

Eden House

Key West Historic District
Save 100% on your flight
$2,136
per person
Dec 4 - Dec 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,003 reviews)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
$1,744
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,003 reviews)
Always solid

Reviewed on Sep 26, 2026

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
$1,501
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (3,560 reviews)
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3 Night Ski vacations in Key Haven

Price found within the past 48 hours. Click for updated prices.
The Gardens Hotel

The Gardens Hotel

Old Town Key West
$789
per person
Oct 27 - Oct 30
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,003 reviews)
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

New Town
$916
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (2,652 reviews)
Genial

Reviewed on Sep 26, 2026

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
$1,864
per person
Nov 6 - Nov 9
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (3,560 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Key Haven
View all trips

4 Night Ski vacations in Key Haven

Price found within the past 48 hours. Click for updated prices.
Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

Old Town Key West
Save 100% on your flight
$1,153
per person
Nov 27 - Dec 1
just found
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,005 reviews)
The Key West Hotel

The Key West Hotel

Key West Historic District
Save 100% on your flight
$2,029
per person
Dec 9 - Dec 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (562 reviews)
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

Save 100% on your flight
$1,161
per person
Nov 27 - Dec 1
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,226 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Key Haven
View all trips

Planning your Key Haven ski vacation

What are some things I should consider when booking a Key Haven 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 Key Haven ski packages?

Right now, ski trips start at just $789. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Key Haven?

Yes! Head for the green runs—wide, sweeping slopes—for a gentle introduction to snow life in Key Haven. 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 Key Haven cost?

Sensational ski trips to Key Haven start from $789. 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 Key Haven?

The best time to hit the slopes in Key Haven 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 Key Haven 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 Key Haven 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 Key Haven with Expedia?

Simple search and fantastic filters make it easy to find, build, and book your dream Key Haven ski vacation in just a few clicks. It’s ‘snow’ joke, it really is that easy.

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