Raccoon Key Ski Vacations

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Flight and Ski hotel deals in Raccoon Key

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

Blue Flamingo Resort Key West

New Town

CA $1,765

per person

Dec 14 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

8.6/10 Excellent! (2,681 reviews)

The Gardens Hotel

Old Town Key West

Save 100% on your flight

CA $3,467

per person

Dec 18 - Dec 23

found 18 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.8/10 Exceptional! (1,000 reviews)

The Marker Key West Harbor Resort

Key West Historic District

Save 100% on your flight

CA $2,963

per person

Dec 14 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.2/10 Wonderful! (1,016 reviews)

Clean.helpful staff.good a/c.good location.will definitely stay here again.

Reviewed on Oct 1, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $2,603

per person

Dec 14 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

8.6/10 Excellent! (3,606 reviews)

Southernmost House - Adult Exclusive

Old Town Key West

CA $2,554

per person

Dec 14 - Dec 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.4/10 Exceptional! (1,001 reviews)

We arrived at Key West just after 12 noon on a Sunday. I was planning to just leave our luggage’s at the hotel since check in time was at 4pm. Catherine was the one that greeted us and help us out on our check in process. She was very professional and very friendly. We got our room ready right away and we didn’t have to wait until check in time at 4PM. Our room was right by the pool, it was clean, has a full size fridge and small microwave, some kitchen amenities (plates, cups, silverware’s) and a dehumidifier. The bathroom is clean and very spacious (shower area). We thought it will be loud since it’s close to the pool and the bar but the whole time we were there it was nice and quiet. There’s are near by restaurants, shops and coffee shops but I suggest to rent a scooter to get to the port area if you have any plans on going to any boating trips (it’s a good 20-30 mins walk from the hotel). We met dean on our 2nd day and he was very friendly and make sure to give us our parking pass for the scooter that we rented. Dean and Catherine definitely made our stay special. And we will definitely come back to stay at this facility on our next trip to Key West. I highly recommend this place if you want a relaxing, laidback stay at Key West.

Reviewed on Oct 1, 2026

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3 Night Ski holidays in Raccoon Key

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

The Gardens Hotel

Old Town Key West

CA $1,924

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

9.8/10 Exceptional! (1,000 reviews)

Eden House

Key West Historic District

CA $2,537

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

9/10 Wonderful! (1,002 reviews)

Great stay with friendly staff

Reviewed on Oct 2, 2026

The Marker Key West Harbor Resort

Key West Historic District

CA $2,162

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

9.2/10 Wonderful! (1,016 reviews)

Clean.helpful staff.good a/c.good location.will definitely stay here again.

Reviewed on Oct 1, 2026

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4 Night Ski holidays in Raccoon Key

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

Hyatt Vacation Club at Windward Pointe, Key West

Save 100% on your flight

CA $1,888

per person

Dec 9 - Dec 13

found 12 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.4/10 Exceptional! (1,285 reviews)

We would definitely stay again, it was a beautiful resort..

Reviewed on Sep 30, 2026

The Key West Hotel

Key West Historic District

Save 100% on your flight

CA $2,443

per person

Nov 1 - Nov 5

found 6 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.2/10 Wonderful! (563 reviews)

Orchid Key Inn - Adults Only

Old Town Key West

CA $3,417

per person

Dec 26 - Dec 30

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

9.8/10 Exceptional! (1,001 reviews)

We stayed for five days and we thoroughly enjoyed the property would highly recommend and would love to come back Kim and Maili from Seattle

Reviewed on Oct 1, 2026

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What are some benefits when booking ski vacations in Raccoon Key?

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 Raccoon Key?

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 Raccoon Key, 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 Raccoon Key with some as cheap as CA $1,765. 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 Raccoon Key. 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 21 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 Raccoon Key.

Can I book all-inclusive ski vacations in Raccoon Key?

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 Raccoon Key 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 Raccoon Key'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 Raccoon Key?

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 Raccoon Key. 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 21. With Expedia Rewards, you can earn points towards your next booking.