Kahoolawe Luxury Vacations

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence
Better together
Save up to CA $4,200 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Flight and Luxury hotel deals in Kahoolawe

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

AC Hotel by Marriott Maui Wailea

Wailea

CA $1,887

per person

Dec 14 - Dec 18

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Kahului (OGG)

9.2/10 Wonderful! (283 reviews)

Hotel Wailea Maui

Wailea

Save 100% on your flight

CA $4,437

per person

Dec 1 - Dec 8

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

Wailea

Save 100% on your flight

CA $5,454

per person

Dec 12 - Dec 19

found 19 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Kahului (OGG)

9.6/10 Exceptional! (1,002 reviews)

Great experience and would highly recommend.

Reviewed on Sep 27, 2026

Maui Vista – Maui Condo & Home

South Kihei

CA $1,908

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to Kahului (OGG)

8.6/10 Excellent! (54 reviews)

Everything was great

Reviewed on Feb 1, 2026

Grand Wailea Maui, A Waldorf Astoria Resort

Wailea

CA $2,619

per person

Dec 14 - Dec 18

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Kahului (OGG)

8.8/10 Excellent! (1,002 reviews)

Everything was just FANTASTIC. Please don't laugh. The only thing that we can think of that for you guys to do something about, and only if you are allowed to do something about it, is too many black bees at the smoking hut areas.

Reviewed on Sep 27, 2026

Don't see what you're looking for?

See all available trips from Columbus to Kahoolawe

View all trips

5* Luxury holidays in Kahoolawe

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

Grand Wailea Maui, A Waldorf Astoria Resort

Wailea

CA $2,619

per person

Dec 14 - Dec 18

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Kahului (OGG)

8.8/10 Excellent! (1,002 reviews)

Reviewed on Sep 27, 2026

Hotel Wailea Maui

Wailea

Save 100% on your flight

CA $4,437

per person

Dec 1 - Dec 8

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

Wailea

Save 100% on your flight

CA $5,454

per person

Dec 12 - Dec 19

found 19 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Kahului (OGG)

9.6/10 Exceptional! (1,002 reviews)

Great experience and would highly recommend.

Reviewed on Sep 27, 2026

Don't see what you're looking for?

See all available trips from Columbus to Kahoolawe

View all trips

3 Night Luxury holidays in Kahoolawe

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

Wailea Beach Resort - Marriott, Maui

Wailea

CA $1,912

per person

Nov 1 - Nov 4

found 20 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Kahului (OGG)

9.2/10 Wonderful! (1,004 reviews)

Beautiful resort, nice ground, very clean property, quite. Has a lot of things, few infinity pools, good restaurant.

Reviewed on Sep 28, 2026

Hotel Wailea Maui

Wailea

Save 100% on your flight

CA $2,475

per person

Nov 1 - Nov 4

found 20 hours 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

Wailea

Save 100% on your flight

CA $2,985

per person

Nov 1 - Nov 4

found 20 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Kahului (OGG)

9.6/10 Exceptional! (1,002 reviews)

Great experience and would highly recommend.

Reviewed on Sep 27, 2026

Don't see what you're looking for?

See all available trips from Columbus to Kahoolawe

View all trips

4 Night Luxury holidays in Kahoolawe

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

Maui Banyan Vacation Club

South Kihei

CA $1,308

per person

Dec 14 - Dec 18

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Kahului (OGG)

8/10 Very good! (392 reviews)

We were pleasantly surprised how nice and how large the unit was. We loved the view of the path and gardens from the balcony. The only glitch was that when we arrived, the door code we were given didn't work. But this was quickly resolved - the lady at the front desk just reset it to a new code and we were in.

Reviewed on Sep 25, 2026

Maui Beach Vacation Club

North Kihei

Save 100% on your flight

CA $1,647

per person

Dec 14 - Dec 18

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Kahului (OGG)

8.4/10 Very good! (937 reviews)

The only problem with the resort was the rooms do not have AC and it got a little bit hot!

Reviewed on Sep 28, 2026

Fairmont Kea Lani Maui

Wailea

Save 100% on your flight

CA $3,361

per person

Dec 14 - Dec 18

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Kahului (OGG)

9.6/10 Exceptional! (1,002 reviews)

Great experience and would highly recommend.

Reviewed on Sep 27, 2026

Don't see what you're looking for?

See all available trips from Columbus to Kahoolawe

View all trips

What are some benefits when booking luxury Kahoolawe vacations?

When you book a luxury Kahoolawe vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax.

How can I find all-inclusive luxury vacations in Kahoolawe?

If you're looking for something luxurious in Kahoolawe, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together.

Can I book a cheap luxury vacation?

While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $1,308, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 17. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first.

Are there luxury spa vacations?

Yes, luxury spa vacations are available and quite popular in Kahoolawe. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search.

What should I look for in a luxury family vacation in Kahoolawe?

When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Kahoolawe.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in Kahoolawe. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces.

What can help me find the best luxury vacation deals in Kahoolawe?

You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Kahoolawe or travelling to more obscure destinations altogether can often lead to lower prices.

Can I book a luxury vacation that is fully refundable?

Yes, fully refundable reservations are sometimes available on luxury vacation packages in Kahoolawe. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking.

Why should I book my luxury vacation with Expedia?

When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings.