Lower Florida Keys Ski Vacations

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Flight and Ski hotel deals in Lower Florida Keys

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

The Gardens Hotel

Old Town Key West
Save 100% on your flight
CA $1,895
per person
Dec 13 - Dec 17
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.8/10 Exceptional! (1,000 reviews)
It is a GREAT property in Key West, right in the center of the action.

Reviewed on Sep 28, 2026

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
CA $1,958
per person
Oct 31 - Nov 4
found 1 hour ago
Roundtrip flight included
Buffalo (BUF) to Key West (EYW)
9.2/10 Wonderful! (1,016 reviews)
Friendly staff, nice grounds, Great location

Reviewed on Sep 28, 2026

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
CA $3,267
per person
Nov 5 - Nov 9
found 21 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Key West (EYW)
8.6/10 Excellent! (3,560 reviews)
A+

Reviewed on Sep 28, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
CA $2,850
per person
Nov 5 - Nov 9
found 21 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Key West (EYW)
9.4/10 Exceptional! (1,004 reviews)
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

New Town
CA $2,309
per person
Nov 5 - Nov 9
found 21 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Key West (EYW)
8.6/10 Excellent! (2,652 reviews)
No breakfast that da

Reviewed on Sep 28, 2026

Don't see what you're looking for?
See all available trips from Columbus to Lower Florida Keys
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3 Night Ski holidays in Lower Florida Keys

Price found within the past 48 hours. Click for updated prices.
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

New Town
CA $1,693
per person
Nov 7 - Nov 10
found 6 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Key West (EYW)
8.6/10 Excellent! (2,652 reviews)
No breakfast that da

Reviewed on Sep 28, 2026

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
CA $2,447
per person
Nov 7 - Nov 10
found 6 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Key West (EYW)
8.6/10 Excellent! (3,560 reviews)
A+

Reviewed on Sep 28, 2026

Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive

Old Town Key West
CA $2,283
per person
Nov 7 - Nov 10
found 6 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) 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 Lower Florida Keys
View all trips

4 Night Ski holidays in Lower Florida Keys

Price found within the past 48 hours. Click for updated prices.
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
CA $1,958
per person
Oct 31 - Nov 4
found 1 hour ago
Roundtrip flight included
Buffalo (BUF) to Key West (EYW)
9.2/10 Wonderful! (1,016 reviews)
Friendly staff, nice grounds, Great location

Reviewed on Sep 28, 2026

The Key West Hotel

The Key West Hotel

Key West Historic District
Save 100% on your flight
CA $3,908
per person
Nov 5 - Nov 9
found 21 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Key West (EYW)
9.2/10 Wonderful! (562 reviews)
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Old Town Key West
CA $3,267
per person
Nov 5 - Nov 9
found 21 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Key West (EYW)
8.6/10 Excellent! (3,560 reviews)
A+

Reviewed on Sep 28, 2026

Don't see what you're looking for?
See all available trips from Columbus to Lower Florida Keys
View all trips

Plan the ultimate ski vacation in Lower Florida Keys

What are some benefits when booking ski vacations in Lower Florida Keys?

If you're interested in skiing, there's nothing quite like a ski vacation. These trips are designed to allow you to enjoy being on the slopes and relax in tranquil and convenient accommodations at the end of the day. Amenities on ski trips can be pretty upscale, so it's easy to relax in a hot tub or at a spa in between your skiing excursions. Plus, they can put you right next to the slopes. You'll even find a variety of different vacation types available whether you're looking for family friendly, cheap, or even last minute ski vacations.

How can I book the best ski vacation in Lower Florida Keys?

It is most important to implement the ski filter in your search when trying to find a ski vacation that will make you happy. Using the filter will automatically remove any entries that don't offer the skiing opportunities you want. After that, you'll need to think about what specifically you want from Lower Florida Keys, and think about the time of year that's best to visit.

How can I find cheap ski vacations?

Cheap ski vacations are readily available in Lower Florida Keys with some as cheap as CA $1,693. You can see the cheapest options by sorting your accommodation choices by price, which automatically puts the least-expensive results at the top of the list. You may also want to consider an accommodation with a kitchen, so you can cook instead of eating out.

Can I book ski packages?

Yes, ski packages are readily available throughout Lower Florida Keys. All you have to do is put in your travel dates and see what's available. When you book a ski package, you may be able to enjoy discounts with savings of up to 20 when you book your accommodation and your flight together.

What should I consider when booking family ski vacations?

The key to a successful family ski vacation is ensuring that your family is kept happy and entertained. Consider what your family members are interested in and the kind of vacation they want. If they have little skiing experience, for example, you may want to opt for an accommodation that offers ski lessons or a kid's club. Various slope difficulties may be essential in providing opportunities for everyone at Lower Florida Keys.

Can I book all-inclusive ski vacations in Lower Florida Keys?

Yes, all-inclusive ski trips are available and may be precisely what you're looking for. All you have to do is include the filter for all-inclusive stays, and your search results will only show the accommodations that provide this handy feature that allows you to plan your entire trip to Lower Florida Keys in advance.

What's the best time of year to plan a ski trip?

The apparent answer to when you should plan a ski trip is in winter, but other details are important too. If you book for Lower Florida Keys's high season around January and February, you'll likely find increased prices. It's generally best to opt for the early or late season in December and April, as prices tend not to be quite as high.

How can I find the best deals on ski packages in Lower Florida Keys?

When you're looking for cheap ski vacations, there are a few factors you can take advantage of to help get the best deals. Travelling during the off-season can be cheaper since there's more availability. However, the beginning and end of the season tend to be the most affordable for skiing.

Can I book a ski vacation that's fully refundable?

Being fully refundable is a feature you'll find on several accommodation packages in Lower Florida Keys. You can even search for it explicitly using a filter for full refundability.

Why should I book a ski vacation package with Expedia?

When you book with Expedia, you'll find everything you need for cheap ski vacations, luxury ski vacations and everything in between in one central location. You may even be able to enjoy discounts for booking your accommodation and your flight together with savings of up to 20. With Expedia Rewards, you can earn points towards your next booking.

Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $59
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

CA $78
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Key West Champagne Sunset Sail

Champagne and Sunsets: A Key West Catamaran Adventure

CA $82
per adult
94% of travellers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
See all activities in Lower Florida Keys

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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.