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.

Grand Naniloa Hotel Hilo - a Doubletree by Hilton

Keaukaha

CA $1,697

per person

Nov 7 - Nov 14

found 1 day ago

Roundtrip flight included

Calgary (YYC) to Kailua-Kona (KOA)

8.2/10 Very good! (1,392 reviews)

The room was literally falling apart. The cabinet was hanging off the wall and the door had a hole in it and was difficult to close. The air unit was terribly loud.

Reviewed on Sep 2, 2026

Kanaloa at Kona by OUTRIGGER

Keauhou

CA $2,172

per person

Nov 7 - Nov 14

found 1 day ago

Roundtrip flight included

Calgary (YYC) to Kailua-Kona (KOA)

8.6/10 Excellent! (560 reviews)

I enjoyed the property. We got there at 10:30 pm, security explained everything to us and was very friendly. The resort interior was like Golden Girls decor style(1970’s beachy) it was great. The handle on the dryer popped off but talked to the property mgr and he mentioned it happens, response time was really quick too. A great place to stay and the location was perfect for what we needed.

Reviewed on Sep 1, 2026

Fairmont Orchid

CA $3,635

per person

Oct 8 - Oct 15

found 1 day ago

Roundtrip flight included

Edmonton (YEG) to Kailua-Kona (KOA)

9.2/10 Wonderful! (1,005 reviews)

The staff, food and view were incredible. The room could be cleaner we were upgraded to a suite for an extra cost and the sink knobs were rusted, the tub was growing mold in small areas and glass doors and closer mirror doors were not clean. We stayed for 5 nights and used the dining table often it was never cleaned the entire time we were there. We also encounter large cockroaches at the gift shop and near the room. Made staff aware right before checking out and their response was thank you we will pass it on to management,

Reviewed on Sep 1, 2026

Castle Hali'i Kai at Waikoloa

CA $2,680

per person

Nov 24 - Nov 29

just found

Roundtrip flight included

Seattle (SEA) to Kailua-Kona (KOA)

9/10 Wonderful! (749 reviews)

We had a great stay in condo 4E. Very roomy very clean. The grounds are beautiful. One of the best sunsets of my trip was by the pool. Asked for someone to come fix my patio light but that didn't happen. Overall great time and would recommend.

Reviewed on Aug 12, 2026

The Islands at Mauna Lani - CoralTree Residence Collection

CA $3,675

per person

Nov 13 - Nov 20

found 5 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Kailua-Kona (KOA)

9.4/10 Exceptional! (124 reviews)

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

Reviewed on Apr 15, 2026

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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 $4,029

per person

Nov 6 - Nov 10

found 1 day ago

Roundtrip flight included

Calgary (YYC) to Kailua-Kona (KOA)

9.4/10 Exceptional! (477 reviews)

This is the best hotel that we have stayed at. The amenities, staff, rooms, the spa, the adult pool, the food, the beach…all 5 stars! Swam with manta rays and did the longest running luau that was well done. Have been coming here since the 80’s and it only keeps getting better. We love the Mauna Kea and the Big Island of Hawaii.

Reviewed on Aug 8, 2026

Four Seasons Resort Hualalai

Kaupulehu

CA $9,900

per person

Oct 8 - Oct 15

found 1 day ago

Roundtrip flight included

Edmonton (YEG) to Kailua-Kona (KOA)

9.6/10 Exceptional! (501 reviews)

Went there everything is beautiful but the most amazing thing is the people!!!!!

Reviewed on Aug 11, 2026

Mauna Lani, Auberge Collection

CA $6,167

per person

Nov 4 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to Kailua-Kona (KOA)

9.4/10 Exceptional! (1,009 reviews)

Room was clean and had turn down service. All the staff were friendly and helpful. Pool and beach were beautiful and well kept.

Reviewed on Sep 2, 2026

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3 Night Luxury holidays in Hawaii Island

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

Royal Kona Resort

Historic Kailua Village

CA $1,053

per person

Nov 13 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to Kailua-Kona (KOA)

8.4/10 Very good! (2,997 reviews)

Centrally located. Easy walk to restaurants and shops. Pool and lagoon clean and comfortable.Restaurant food very good. Bar good and friendly. Good for female travelers. Hotel under renovation but did not inconvenience us at all. Family owned. Highly recommend

Reviewed on Sep 1, 2026

The Westin Hapuna Beach Resort

CA $2,477

per person

Oct 17 - Oct 20

found 20 hours ago

Roundtrip flight included

Winnipeg (YWG) to Kailua-Kona (KOA)

9.2/10 Wonderful! (1,003 reviews)

An absolutely beautiful property. The staff was very friendly and helpful. The only challenge was finding enough child friendly food options, as the property is quite isolated and no restaurants offer delivery there. There are only so many times you can eat the same food at the same restaurant with kids.

Reviewed on Sep 2, 2026

The Islands at Mauna Lani - CoralTree Residence Collection

CA $2,468

per person

Oct 17 - Oct 20

found 20 hours ago

Roundtrip flight included

Winnipeg (YWG) to Kailua-Kona (KOA)

9.4/10 Exceptional! (124 reviews)

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

Reviewed on Apr 15, 2026

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4 Night Luxury holidays in Hawaii Island

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

Castle Waimea Country Lodge

CA $1,495

per person

Nov 26 - Nov 30

found 5 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Kailua-Kona (KOA)

7.4/10 Good! (573 reviews)

Paniolo Greens At Waikoloa

CA $1,566

per person

Nov 26 - Nov 30

found 5 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Kailua-Kona (KOA)

9.4/10 Exceptional! (1,004 reviews)

Staff were very friendly from the moment you walk into their office to check in. Rooms were clean and met our needs. I didnt know the gameroom could be reserved and their was a birthday party the day we tried to use it but its ok we still used the pool and now know in advance we can book a reservation for it. Mahalo

Reviewed on Sep 1, 2026

Kanaloa at Kona by OUTRIGGER

Keauhou

CA $2,005

per person

Nov 26 - Nov 30

found 5 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Kailua-Kona (KOA)

8.6/10 Excellent! (560 reviews)

Reviewed on Sep 1, 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 $1,053, 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! (1,005 reviews)

"Room was clean and had turn down service. All the staff were friendly and helpful. Pool and beach were beautiful and well kept."

Reviewed on Sep 2, 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 ...

9.2/10 Wonderful! (1,000 reviews)

"The staff, food and view were incredible. The room could be cleaner we were upgraded to a suite for an extra cost and the sink knobs were rusted, the tub was growing mold in small areas and glass doors and closer mirror doors were not clean. We stayed for 5 nights and used the dining table often ..."

Reviewed on Sep 1, 2026

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 ...

9.4/10 Exceptional! (477 reviews)

"This is the best hotel that we have stayed at. The amenities, staff, rooms, the spa, the adult pool, the food, the beach…all 5 stars! Swam with manta rays and did the longest running luau that was well done. Have been coming here since the 80’s and it only keeps getting better. We love the Mauna ..."

Reviewed on Aug 8, 2026

See all 7,342 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.