Kahoolawe Ski Vacations

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Flight and Ski hotel deals in Kahoolawe

Price found within the past 48 hours. Click for updated prices.
Maui Vista – Maui Condo & Home

Maui Vista – Maui Condo & Home

South Kihei
CA $2,034
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
8.6/10 Excellent! (54 reviews)
Everything was great

Reviewed on Feb 1, 2026

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

Wailea
Save 100% on your flight
CA $5,454
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
9.6/10 Exceptional! (1,002 reviews)
Hotel Wailea Maui

Hotel Wailea Maui

Wailea
Save 100% on your flight
CA $5,992
per person
Nov 14 - Nov 21
found 16 hours ago
Roundtrip flight included
Edmonton (YEG) to Kahului (OGG)
9.4/10 Exceptional! (1,002 reviews)
Everything was excellent, form the location to the incredible food!

Reviewed on Sep 22, 2026

The Residences at Kamaole Sands Resort

The Residences at Kamaole Sands Resort

South Kihei
CA $2,590
per person
Nov 29 - Dec 5
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Kahului (OGG)
10/10 Exceptional! (5 reviews)
Bonus was there were beach chairs, towels and an umbrella. We only used two chairs as our family were busy snorkeling or boarding away while 1-2 sat out and rested. Clean, right down from beach park 3...stocked pantry got some add-ons and pots and pans enough to allow us making most of our meals. Great times and great communication from host. Thanks! Lucas

Reviewed on Aug 30, 2026

AC Hotel by Marriott Maui Wailea

AC Hotel by Marriott Maui Wailea

Wailea
CA $2,680
per person
Nov 29 - Dec 5
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Kahului (OGG)
9.2/10 Wonderful! (283 reviews)
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5* Ski holidays in Kahoolawe

Price found within the past 48 hours. Click for updated prices.
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

Wailea
Save 100% on your flight
CA $5,003
per person
Nov 29 - Dec 5
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Kahului (OGG)
9.6/10 Exceptional! (1,000 reviews)
Incredible service and high end property. The rooms are updated with a nice balcony. 3 pools and direct beach access makes it easy.

Reviewed on Sep 24, 2026

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

Wailea
Save 100% on your flight
CA $5,454
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
9.6/10 Exceptional! (1,002 reviews)
Hotel Wailea Maui

Hotel Wailea Maui

Wailea
Save 100% on your flight
CA $5,992
per person
Nov 14 - Nov 21
found 16 hours ago
Roundtrip flight included
Edmonton (YEG) to Kahului (OGG)
9.4/10 Exceptional! (1,002 reviews)
Everything was excellent, form the location to the incredible food!

Reviewed on Sep 22, 2026

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

Price found within the past 48 hours. Click for updated prices.
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

Wailea
CA $1,912
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kahului (OGG)
9.2/10 Wonderful! (1,004 reviews)
Hotel Wailea Maui

Hotel Wailea Maui

Wailea
Save 100% on your flight
CA $2,475
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kahului (OGG)
9.4/10 Exceptional! (1,002 reviews)
Everything was excellent, form the location to the incredible food!

Reviewed on Sep 22, 2026

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

Wailea
Save 100% on your flight
CA $2,868
per person
Dec 13 - Dec 16
found 14 hours ago
Roundtrip flight included
Vancouver (YVR) to Kahului (OGG)
9.6/10 Exceptional! (1,002 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Kahoolawe
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4 Night Ski holidays in Kahoolawe

Price found within the past 48 hours. Click for updated prices.
Maui Beach Vacation Club

Maui Beach Vacation Club

North Kihei
CA $1,328
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Kahului (OGG)
8.4/10 Very good! (956 reviews)
Hotel Wailea Maui

Hotel Wailea Maui

Wailea
Save 100% on your flight
CA $5,476
per person
Dec 24 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Kahului (OGG)
9.4/10 Exceptional! (1,002 reviews)
Everything was excellent, form the location to the incredible food!

Reviewed on Sep 22, 2026

Maui Banyan Vacation Club

Maui Banyan Vacation Club

South Kihei
CA $1,355
per person
Dec 15 - Dec 19
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Kahului (OGG)
8/10 Very good! (392 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Kahoolawe
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Plan the ultimate ski vacation in Kahoolawe

What are some benefits when booking ski vacations in Kahoolawe?

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 Kahoolawe?

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 Kahoolawe, 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 Kahoolawe with some as cheap as CA $1,328. 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 Kahoolawe. 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 18 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 Kahoolawe.

Can I book all-inclusive ski vacations in Kahoolawe?

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 Kahoolawe 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 Kahoolawe'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 Kahoolawe?

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 Kahoolawe. 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 18. With Expedia Rewards, you can earn points towards your next booking.

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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.