Luxury Vacations in Hawaii Island 2026

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Flight and Luxury hotel deals in Hawaii Island

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

Royal Kona Resort

Historic Kailua Village

CA $1,974

per person

Dec 18 - Dec 24

found 5 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Kailua-Kona (KOA)

8.4/10 Very good! (3,006 reviews)

Restaurant and bar on property had amazing views and the food was great! Especially breakfast. Hotel rooms sufficient and clean, just need an update eventually. Room views incredible.

Reviewed on Oct 13, 2026

Fairmont Orchid

CA $3,784

per person

Dec 19 - Dec 24

found 11 hours ago

Roundtrip flight included

Vancouver (YVR) to Kailua-Kona (KOA)

9.2/10 Wonderful! (1,006 reviews)

The Islands at Mauna Lani - CoralTree Residence Collection

CA $3,669

per person

Jan 2 - Jan 7

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Kailua-Kona (KOA)

9.4/10 Exceptional! (124 reviews)

Slept, had breakfast and left didn’t use amenities.

Reviewed on Apr 15, 2026

Castle Hali'i Kai at Waikoloa

CA $3,647

per person

Dec 24 - Dec 31

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Kailua-Kona (KOA)

9/10 Wonderful! (755 reviews)

This property was absolutely beautiful! Our "condo" had just about everything we needed! Cooking and eating utensils, shampoo, conditioner body wash...we went to the store for a few things, but the majority of what we needed was already there. The layout of the condo was simple and there was lots of storage space! We loved eating on the back patio, and listening to the birds. The whole place was pretty quiet- and occasional yard worker, but nothing unsettling. There were lots of things to do close by, including multiple beaches and grocery stores. This property was a great choice for our first time stay in Hawaii- I would highly recommend this property!

Reviewed on Oct 10, 2026

Four Seasons Resort Hualalai

Kaupulehu

Save 100% on your flight

CA $7,469

per person

Jan 2 - Jan 7

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Kailua-Kona (KOA)

9.6/10 Exceptional! (505 reviews)

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5* Luxury holidays in Hawaii Island

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

Mauna Kea Beach Hotel, Autograph Collection

CA $3,189

per person

Nov 13 - Nov 16

found 21 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Kailua-Kona (KOA)

9.4/10 Exceptional! (479 reviews)

Four Seasons Resort Hualalai

Kaupulehu

Save 100% on your flight

CA $7,469

per person

Jan 2 - Jan 7

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Kailua-Kona (KOA)

9.6/10 Exceptional! (505 reviews)

Mauna Lani, Auberge Collection

CA $4,531

per person

Jan 2 - Jan 7

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Kailua-Kona (KOA)

9.4/10 Exceptional! (1,002 reviews)

This place was absolutely beautiful! The snorkeling was fantastic! And Manny on the beach was very attentive.

Reviewed on Oct 12, 2026

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3 Night Luxury holidays in Hawaii Island

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

Grand Naniloa Hotel Hilo - a Doubletree by Hilton

Keaukaha

CA $1,244

per person

Nov 13 - Nov 16

found 21 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Kailua-Kona (KOA)

8.2/10 Very good! (1,383 reviews)

Fairmont Orchid

CA $2,947

per person

Nov 13 - Nov 16

found 21 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Kailua-Kona (KOA)

9.2/10 Wonderful! (1,006 reviews)

Kanaloa at Kona by OUTRIGGER

Keauhou

CA $1,712

per person

Nov 13 - Nov 16

found 21 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Kailua-Kona (KOA)

8.6/10 Excellent! (564 reviews)

Beautiful condo and convenient washer and dryer inside the condo itself. We had a partial ocean view and it was absolutely breathtaking. Very close to so many places and only 30min from the airport

Reviewed on Oct 2, 2026

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4 Night Luxury holidays in Hawaii Island

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

Royal Kona Resort

Historic Kailua Village

CA $1,549

per person

Nov 18 - Nov 22

found 8 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Kailua-Kona (KOA)

8.4/10 Very good! (3,006 reviews)

Restaurant and bar on property had amazing views and the food was great! Especially breakfast. Hotel rooms sufficient and clean, just need an update eventually. Room views incredible.

Reviewed on Oct 13, 2026

Fairmont Orchid

CA $2,623

per person

Nov 18 - Nov 22

found 8 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Kailua-Kona (KOA)

9.2/10 Wonderful! (1,006 reviews)

Kona Coast Resort

Keauhou

CA $1,824

per person

Nov 18 - Nov 22

found 8 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Kailua-Kona (KOA)

9.2/10 Wonderful! (1,490 reviews)

Clean, quiet and very private.

Reviewed on Oct 13, 2026

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What are some benefits when booking luxury Hawaii Island vacations?

When you book a luxury Hawaii Island 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 Hawaii Island?

If you're looking for something luxurious in Hawaii Island, 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 $1,244, 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 Hawaii Island. 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 Hawaii Island?

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 Hawaii Island.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in Hawaii Island. 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 Hawaii Island?

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 Hawaii Island 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 Hawaii Island. 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.

Luxury Hotels in Hawaii Island

Mauna Lani, Auberge Collection

68-1400 Mauna Lani Dr Kamuela HI

2 hours drive from Hawaii Volcanoes National Park

Book a stay at this luxury resort in Kamuela. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...

9.4/10 Exceptional! (1,004 reviews)

"This place was absolutely beautiful! The snorkeling was fantastic! And Manny on the beach was very attentive."

Reviewed on Oct 12, 2026

Fairmont Orchid

1 North Kaniku Drive Kohala Coast HI

2 hours drive from Hawaii Volcanoes National Park

Book a stay at this luxury resort in Kamuela. Enjoy free WiFi, a full-service spa, and 5 restaurants. Our guests praise the pool and the helpful staff in our ...

Mauna Kea Beach Hotel, Autograph Collection

62-100 Mauna Kea Beach Dr Kamuela HI

2 hours drive from Hawaii Volcanoes National Park

Book a stay at this luxury resort in Kamuela. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...

See all 7,280 properties in Hawaii Island

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.