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.

The Perry Hotel & Marina Key West

CA $1,274

per person

Sep 26 - Oct 3

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.4/10 Exceptional! (1,314 reviews)

Great Staff and nice environment, rooms, and amenities. The only shortcoming is that the hotel is about a 15-minute drive from where all the attractions are, but the staff and food were amazing

Reviewed on Aug 17, 2026

Southernmost House - Adult Exclusive

Old Town Key West

CA $2,295

per person

Nov 3 - Nov 7

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.4/10 Exceptional! (1,002 reviews)

Excellent place to stay and will absolutely stay there again! The staff was so helpful and friendly! The restaurant on the property has delicious food! I highly recommend staying at he Southern Most House, great pool, great location, great vacation!

Reviewed on Aug 16, 2026

Parrot Key Hotel & Villas

Northside Resort

CA $1,602

per person

Nov 3 - Nov 7

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9/10 Wonderful! (1,438 reviews)

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $2,247

per person

Nov 3 - Nov 7

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

8.8/10 Excellent! (3,469 reviews)

Part of the reason I booked this hotel was it had beach access? Well, the beach was completely covered in 3 to 6 feet of seaweed. No mention of it when booking the hotel. Or I would have made other arrangements The staff was excellent. The rooms were a little dated the room was clean, but some of the furniture had small rips In them

Reviewed on Aug 18, 2026

The Marker Key West Harbor Resort

Key West Historic District

CA $1,877

per person

Sep 26 - Oct 3

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.2/10 Wonderful! (1,002 reviews)

I enjoyed the location. The staff was friendly and helpful. The room was clean. The pool was a little too warm for my taste.

Reviewed on Aug 18, 2026

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5* Ski holidays in Raccoon Key

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

The Porch on Frances Inn

Old Town Key West

CA $1,588

per person

Nov 1 - Nov 5

found 8 hours ago

Roundtrip flight included

Detroit (DTW) to Key West (EYW)

9.8/10 Exceptional! (137 reviews)

Great value

Reviewed on Aug 13, 2026

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3 Night Ski holidays in Raccoon Key

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

The Perry Hotel & Marina Key West

CA $1,177

per person

Oct 9 - Oct 12

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Key West (EYW)

9.4/10 Exceptional! (1,314 reviews)

Great Staff and nice environment, rooms, and amenities. The only shortcoming is that the hotel is about a 15-minute drive from where all the attractions are, but the staff and food were amazing

Reviewed on Aug 17, 2026

Pier House Resort & Spa

Key West Historic District

CA $1,625

per person

Sep 21 - Sep 24

found 16 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

9/10 Wonderful! (1,258 reviews)

Beautiful hotel with a great sand beach. Perfect location, right on Duval, but a quiet garden resort. The showers are to die for. Would stay here again.

Reviewed on Aug 18, 2026

Southernmost Beach Resort and Guesthouses

Old Town Key West

CA $2,829

per person

Nov 5 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

8.8/10 Excellent! (3,469 reviews)

Reviewed on Aug 18, 2026

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4 Night Ski holidays in Raccoon Key

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

Coconut Beach Resort

Old Town Key West

CA $1,758

per person

Sep 17 - Sep 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

8.8/10 Excellent! (212 reviews)

The Key West Hotel

Key West Historic District

CA $3,533

per person

Nov 3 - Nov 7

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.2/10 Wonderful! (561 reviews)

This is the best place to stay in Key West! It is a hotel but it has the quaint B&B vibes. The tiki bar by the pool is amazing and they are adding food soon which makes it literally perfect. Close to everything you’d want to do- walk or scooter. 10/10 recommend!

Reviewed on Jul 27, 2026

Ridley House - Key West Historic Inns

Key West Historic District

CA $2,109

per person

Nov 3 - Nov 7

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.2/10 Wonderful! (946 reviews)

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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 $1,177. 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 27 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 27. With Expedia Rewards, you can earn points towards your next booking.