Keewaydin Island Ski Vacations

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Flight and Ski hotel deals in Keewaydin Island

Price found within the past 48 hours. Click for updated prices.
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

CA $1,141
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Fort Myers (RSW)
9.2/10 Wonderful! (3,389 reviews)
The Perry Hotel Naples

The Perry Hotel Naples

Save 100% on your flight
CA $1,963
per person
Nov 15 - Nov 22
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (1,163 reviews)
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

Vanderbilt Beach
Save 100% on your flight
CA $3,158
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9/10 Wonderful! (1,004 reviews)
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

Save 100% on your flight
CA $1,492
per person
Nov 1 - Nov 7
found 14 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Fort Myers (RSW)
9.2/10 Wonderful! (1,006 reviews)
Wiggins Pass Chalet

Wiggins Pass Chalet

CA $1,288
per person
Nov 15 - Nov 22
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (291 reviews)
Such a hidden gem in Naples! I’ve stayed here three weekends in a row and already have my next stay planned in two weeks. The rooms are incredibly clean, modern, comfortable and have everything you need. The staff is always friendly and welcoming, and it truly feels more like staying in a beautiful little condo than a hotel. I’m so happy I found this place — it has officially become my go-to whenever I’m in Naples. Highly recommend! ⭐️⭐️⭐️⭐️⭐️

Reviewed on Oct 1, 2026

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5* Ski holidays in Keewaydin Island

Price found within the past 48 hours. Click for updated prices.
Sundial Beach Resort & Spa

Sundial Beach Resort & Spa

Mid Island
Save 100% on your flight
CA $2,408
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Fort Myers (RSW)
8.6/10 Excellent! (2,700 reviews)
Tiki bar and restaurants were excellent and very good prices for excellent food. All staff were so helpful. So much to do. Rooms were spacious and comfy

Reviewed on Oct 1, 2026

Naples Beach Club, A Four Seasons Resort

Naples Beach Club, A Four Seasons Resort

Coquina Sands
Save 100% on your flight
CA $6,143
per person
Nov 15 - Nov 22
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.6/10 Exceptional! (38 reviews)
The Ritz-Carlton, Naples

The Ritz-Carlton, Naples

Pelican Bay
CA $5,697
per person
Nov 15 - Nov 22
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.2/10 Wonderful! (519 reviews)
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3 Night Ski holidays in Keewaydin Island

Price found within the past 48 hours. Click for updated prices.
Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

CA $976
per person
Dec 4 - Dec 7
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9/10 Wonderful! (2,580 reviews)
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

CA $1,231
per person
Dec 4 - Dec 7
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to Fort Myers (RSW)
9.2/10 Wonderful! (1,006 reviews)
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

Punta Rassa
CA $1,015
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
8.6/10 Excellent! (1,002 reviews)
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4 Night Ski holidays in Keewaydin Island

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Coconut Cove, Bonita Springs

Hyatt Vacation Club at Coconut Cove, Bonita Springs

CA $873
per person
Dec 12 - Dec 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Fort Myers (RSW)
9.2/10 Wonderful! (1,006 reviews)
The Perry Hotel Naples

The Perry Hotel Naples

Save 100% on your flight
CA $1,337
per person
Dec 4 - Dec 8
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
9.6/10 Exceptional! (1,163 reviews)
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

Punta Rassa
CA $898
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Fort Myers (RSW)
8.6/10 Excellent! (1,002 reviews)
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Plan the ultimate ski vacation in Keewaydin Island

What are some benefits when booking ski vacations in Keewaydin Island?

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 Keewaydin Island?

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 Keewaydin Island, 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 Keewaydin Island with some as cheap as CA $873. 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 Keewaydin Island. 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 26 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 Keewaydin Island.

Can I book all-inclusive ski vacations in Keewaydin Island?

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 Keewaydin Island 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 Keewaydin Island'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 Keewaydin Island?

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 Keewaydin Island. 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 26. With Expedia Rewards, you can earn points towards your next booking.

Things to do

Naples Sightseeing Boat Tour

Naples Sightseeing Boat Tour

CA $93
per adult
96% of travellers recommend
Naples Sightseeing Boat Tour
Naples Florida: Downtown Electric Trike Tour

Naples Florida: Downtown Electric Trike Tour - Family Fun

CA $69
per adult
100% of travellers recommend
Naples Florida: Downtown Electric Trike Tour - Family Fun
Gulf of Mexico Sunset Cruise from Naples

Gulf of Mexico Sunset Cruise from Naples

CA $103
per adult
88% of travellers recommend
Gulf of Mexico Sunset Cruise from Naples
See all activities in Keewaydin Island

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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.