Raccoon Key Ski Vacations

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Top Ski vacation packages in Raccoon Key

Price found within the past 48 hours. Click for updated prices.
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

Northside Resort
$842
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,460 reviews)
Wonderful stay with my family. Fantastic location. Friendly staff. Large, clean rooms.

Reviewed on Sep 11, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
Save 100% on your flight
$1,610
per person
Oct 30 - Nov 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
The Gardens Hotel

The Gardens Hotel

Old Town Key West
Save 100% on your flight
$1,095
per person
Nov 22 - Nov 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,003 reviews)
Wonderful property and staff! Annette, Luna and George, our pool bartenders and breakfast staff were outstanding. Front desk staff very helpful and pleasant as well. Beautiful gardens and grounds, clean rooms, love that the pool is open all night for swimming. Live music every afternoon. Great location centrally located in old town, convenient to everything! Will definitely book here again!

Reviewed on Sep 12, 2026

Lighthouse Suites Collection

Lighthouse Suites Collection

Old Town Key West
$1,059
per person
Nov 22 - Nov 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
No reviews
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

Save 100% on your flight
$1,334
per person
Oct 30 - Nov 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,328 reviews)
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3 Night Ski vacations in Raccoon Key

Price found within the past 48 hours. Click for updated prices.
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

Northside Resort
$1,039
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,460 reviews)
Wonderful stay with my family. Fantastic location. Friendly staff. Large, clean rooms.

Reviewed on Sep 11, 2026

The Gardens Hotel

The Gardens Hotel

Old Town Key West
Save 100% on your flight
$1,095
per person
Nov 22 - Nov 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (1,003 reviews)
Wonderful property and staff! Annette, Luna and George, our pool bartenders and breakfast staff were outstanding. Front desk staff very helpful and pleasant as well. Beautiful gardens and grounds, clean rooms, love that the pool is open all night for swimming. Live music every afternoon. Great location centrally located in old town, convenient to everything! Will definitely book here again!

Reviewed on Sep 12, 2026

Lighthouse Suites Collection

Lighthouse Suites Collection

Old Town Key West
$1,059
per person
Nov 22 - Nov 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
No reviews
Don't see what you're looking for?
See all available trips from Columbus to Raccoon Key
View all trips

4 Night Ski vacations in Raccoon Key

Price found within the past 48 hours. Click for updated prices.
Heron House - Adult Only

Heron House - Adult Only

Old Town Key West
$836
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,158 reviews)
The Key West Hotel

The Key West Hotel

Key West Historic District
Save 100% on your flight
$2,020
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (562 reviews)
Great place to stay - highly recommend.

Reviewed on Aug 20, 2026

Coconut Beach Resort

Coconut Beach Resort

Old Town Key West
Save 100% on your flight
$1,177
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (219 reviews)
Maintenance people were so nice and helpful Place was clean Blanket on the bed was paper thin like a sheet Could not get both TVs to work said no service Room was on Third floor all stairs no elevator a bit difficult with luggage

Reviewed on Sep 11, 2026

Don't see what you're looking for?
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Planning your Raccoon Key ski vacation

What are some things I should consider when booking a Raccoon Key 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 Raccoon Key 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 $836. Prices and availability are subject to change. Additional terms may apply.

Can I book a beginner ski package in Raccoon Key?

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

Sensational ski trips to Raccoon Key start from $836. 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 Raccoon Key?

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

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

Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

$42
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
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 Half-Day Fishing Charter

Key West Half-Day Fishing Charter

$102
per adult
92% of travellers recommend
Key West Half-Day Fishing Charter
See all activities in Raccoon Key

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.