Stock Island Ski Vacations

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Top Ski vacation packages in Stock Island

Price found within the past 48 hours. Click for updated prices.
Eden House

Eden House

Key West Historic District
$1,369
per person
Oct 28 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,002 reviews)
The Gardens Hotel

The Gardens Hotel

Old Town Key West
Save 100% on your flight
$2,221
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,000 reviews)
Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
$1,961
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,004 reviews)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
$2,158
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,016 reviews)
Always solid

Reviewed on Sep 26, 2026

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

New Town
$1,472
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (2,652 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Stock Island
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3 Night Ski vacations in Stock Island

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

The Gardens Hotel

Old Town Key West
$1,105
per person
Dec 2 - Dec 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,000 reviews)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
$1,282
per person
Dec 2 - Dec 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,016 reviews)
Always solid

Reviewed on Sep 26, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
$1,140
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,004 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Stock Island
View all trips

4 Night Ski vacations in Stock Island

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West

Old Town Key West
Save 100% on your flight
$1,880
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (419 reviews)
The Key West Hotel

The Key West Hotel

Key West Historic District
Save 100% on your flight
$2,490
per person
Dec 23 - Dec 27
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
$1,947
per person
Dec 23 - Dec 27
found 1 day ago
Roundtrip 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 Stock Island
View all trips

Planning your Stock Island ski vacation

What are some things I should consider when booking a Stock Island 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 Stock Island ski packages?

Fly down the slopes during low or shoulder season, either side of , for a ski package to please your purse. Right now, ski trips start at just $1,105. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Stock Island?

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

Sensational ski trips to Stock Island start from $1,105. 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 Stock Island?

The best time to hit the slopes in Stock Island 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 Stock Island 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 Stock Island 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 Stock Island with Expedia?

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

Things to do

Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

$79
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
Key West Champagne Sunset Sail

Champagne and Sunsets: A Key West Catamaran Adventure

$59
per adult
94% of travellers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
Combo image of activity in Key West

Key West Rum & Reggae: Snorkel & Sunset Sail Combo

$61
per adult
88% of travellers recommend
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
See all activities in Stock Island

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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.