Stock Island Ski Vacations 2026

Top Ski vacation packages in Stock Island

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

The Perry Hotel & Marina Key West

$835

per person

May 17 - May 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.4/10 Exceptional! (1,234 reviews)

We really enjoyed our time at the Perry. We ate at the two restaurants and the pool. The shuttle service was very good. We plan to go back.

Reviewed on Apr 13, 2026

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$856

per person

Jun 18 - Jun 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,848 reviews)

Our once-in-a-lifetime family trip was deeply disappointing because of our experience with the restaurant staff at Oceans Edge Resort & Marina Key West. Their rude and unprofessional behavior had a major negative impact on what should have been a special vacation. We chose to eat most of our meals at the resort for convenience, but unfortunately, each interaction left us feeling unwelcome and frustrated. We did our best not to let it ruin our trip, but it was hard to overlook given how often we had to deal with the restaurant staff. The property itself has potential, but management needs to take a serious look at the employees representing the dining experience. Because of this experience, we will not be returning to this property on our next trip to Key West. If I could rate the restaurant staff lower, I would.

Reviewed on Apr 11, 2026

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

Save 100% on your flight

$924

per person

Jun 18 - Jun 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,230 reviews)

Winslow’s Bungalows offers a delightful stay for guests. It is centrally located for exploring Key West. The staff were very helpful.

Reviewed on Apr 10, 2026

The Reach Key West, Curio Collection by Hilton

Old Town Key West

$1,100

per person

May 16 - May 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.6/10 Excellent! (1,002 reviews)

The dining/room bar on the beach was great!

Reviewed on Apr 11, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

$1,012

per person

May 17 - May 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.8/10 Excellent! (3,162 reviews)

Beautiful balcony view

Reviewed on Apr 13, 2026

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3 Night Ski vacations in Stock Island

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

Oceans Edge Key West Resort, Hotel & Marina

$623

per person

Jun 29 - Jul 2

found 13 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,848 reviews)

Reviewed on Apr 11, 2026

Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

$689

per person

Jun 9 - Jun 12

found 23 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.4/10 Very Good! (595 reviews)

We had a great time. The hotel is beautiful and in a great location. The beach and two pools are perfectly located. A easy walk to Duval st. The rooms are nice but not much storage or closet space for clothing. The showers could use some shelving for personal shower products. The food and drinks are outrageously expensive, so you may wa t to think about dinner and drinks elsewhere. Overall we really loved the place. The staff was amazing. We will come back next year.

Reviewed on Apr 11, 2026

Winslow's Bungalows - Key West Historic Inns

Old Town Key West

$712

per person

Jun 29 - Jul 2

found 13 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (1,230 reviews)

Winslow’s Bungalows offers a delightful stay for guests. It is centrally located for exploring Key West. The staff were very helpful.

Reviewed on Apr 10, 2026

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See all available trips from Columbus to Stock Island

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4 Night Ski vacations in Stock Island

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

Oceans Edge Key West Resort, Hotel & Marina

Save 100% on your flight

$856

per person

Jun 18 - Jun 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9/10 Wonderful! (1,848 reviews)

Reviewed on Apr 11, 2026

The Key West Hotel

Key West Historic District

Save 100% on your flight

$1,273

per person

Jun 18 - Jun 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (542 reviews)

Great location! We were very impressed with Chris! He told us where to park and was very welcoming when we arrived. The loft room setup was perfect for us and the Bali Bar did not disappoint! We will be back!!

Reviewed on Apr 5, 2026

Hyatt Vacation Club at Sunset Harbor, Key West

Old Town Key West

Save 100% on your flight

$1,384

per person

May 19 - May 23

found 14 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Key West (EYW)

8.6/10 Excellent! (345 reviews)

No bottled water for drinking. They had water and paper cups at the front desk. We had to leave the property and drive to get bottled waters.

Reviewed on Apr 12, 2026

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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?

Right now, ski trips start at just $623. 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 $623. 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.