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.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,710 reviews)
The front desk help were excellent. Told me about the amenities, they texted me to see if we needed anything. We had a bit of rain and I received another text letting me know about things to do In the rain at the resort and in town . So thoughtful. I would recommend this resort highly . I definitely will go stay any.

Reviewed on Aug 17, 2025

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Save 100% on your flight
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,055 reviews)
The bed was pretty good, but definitely not the best I’ve stayed in for the price. The view of the room was great. The internet was good, but would drop every 2-3 hours or so. The first night I stayed there, the room was equipped with only 2 towels when the reservation was made for 2 adults and 2 kids. I had to ask for more. After that, the general room service was good. Parking was pretty far and the cost of self parking, (which is the only option,) was pretty high. The noise level at night coming from the hallway was pretty loud and crazy. The parking fees and hotels fees definitely don’t match and are quite off from what’s on Expedia as opposed to what’s charged at the hotel. In summary, I would stay again at The Perry if I go back to Key West in the future, but for the cost, there are better options out there.

Reviewed on Aug 14, 2025

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
Save 100% on your flight
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,007 reviews)
Bed and pillows - super confortable! Hotel, gardens, trees, pools, bars, five stars! Service and love like home!!

Reviewed on Aug 17, 2025

Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
New Town
Save 100% on your flight
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (1,756 reviews)
The shuttle to the downtown area was very convenient. And the pool was great!

Reviewed on Aug 16, 2025

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Save 100% on your flight
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (2,662 reviews)
Food and drinks are expensive but good. Not much in terms of entertainment at the resort but there are multiple pools to explore.

Reviewed on Aug 17, 2025

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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

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
per person
Oct 27 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,710 reviews)
The front desk help were excellent. Told me about the amenities, they texted me to see if we needed anything. We had a bit of rain and I received another text letting me know about things to do In the rain at the resort and in town . So thoughtful. I would recommend this resort highly . I definitely will go stay any.

Reviewed on Aug 17, 2025

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Save 100% on your flight
per person
Oct 27 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,055 reviews)
The bed was pretty good, but definitely not the best I’ve stayed in for the price. The view of the room was great. The internet was good, but would drop every 2-3 hours or so. The first night I stayed there, the room was equipped with only 2 towels when the reservation was made for 2 adults and 2 kids. I had to ask for more. After that, the general room service was good. Parking was pretty far and the cost of self parking, (which is the only option,) was pretty high. The noise level at night coming from the hallway was pretty loud and crazy. The parking fees and hotels fees definitely don’t match and are quite off from what’s on Expedia as opposed to what’s charged at the hotel. In summary, I would stay again at The Perry if I go back to Key West in the future, but for the cost, there are better options out there.

Reviewed on Aug 14, 2025

Pier House Resort & Spa

Pier House Resort & Spa

4 out of 5
Key West Historic District
Save 100% on your flight
per person
Oct 27 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,014 reviews)
We live Pier House. Have stayed before. Unfortunately we were stuck in a "Junior Spa Suite" in rear spa building this time. Our "patio" was in the rear parking lot. Literally. Loud at night and in am with cars, workers. Patio walls rusted . Room small amd cramped. Will say it was very clean . Mattress a bit hard . Fees upon fees upon fees added plus ridiculous drink prices . Was not worth what I paid ...should have had an oceanfront suite for what I paid instead had ghetto suite

Reviewed on Aug 17, 2025

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4 Night Ski vacations in Stock Island

Price found within the past 48 hours. Click for updated prices.
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Save 100% on your flight
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,055 reviews)
The bed was pretty good, but definitely not the best I’ve stayed in for the price. The view of the room was great. The internet was good, but would drop every 2-3 hours or so. The first night I stayed there, the room was equipped with only 2 towels when the reservation was made for 2 adults and 2 kids. I had to ask for more. After that, the general room service was good. Parking was pretty far and the cost of self parking, (which is the only option,) was pretty high. The noise level at night coming from the hallway was pretty loud and crazy. The parking fees and hotels fees definitely don’t match and are quite off from what’s on Expedia as opposed to what’s charged at the hotel. In summary, I would stay again at The Perry if I go back to Key West in the future, but for the cost, there are better options out there.

Reviewed on Aug 14, 2025

Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
Save 100% on your flight
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Key West (EYW)
9.2/10 Wonderful! (1,004 reviews)
The place was nice, quite clean and very spacious. But I tink there are some things that need remodeling like kitchen cabinets .They’re a bit bare, meaning they need paint. I think it’s a bit outdated. The parking was a bit uncomfortable.The pool was super clean, and the atmosphere was peaceful for relaxing .

Reviewed on Aug 16, 2025

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

3.5 out of 5
Old Town Key West
Save 100% on your flight
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (768 reviews)
Room was tight but more importantly dirty. The floor in the bathroom was grimy and the shower moldy.

Reviewed on Aug 13, 2025

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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 $325. 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 $325. 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.

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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.