Hawaii Island 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 Hawaii Island

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

Royal Kona Resort

Historic Kailua Village
CA $619
per person
Nov 20 - Nov 22
found 7 hours ago
Roundtrip flight included
Honolulu (HNL) to Kailua-Kona (KOA)
8.4/10 Very good! (3,006 reviews)
Nice

Reviewed on Oct 17, 2026

Fairmont Orchid

Fairmont Orchid

Save 100% on your flight
CA $5,296
per person
Dec 19 - Dec 26
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to Kailua-Kona (KOA)
9.2/10 Wonderful! (1,006 reviews)
Excellent

Reviewed on Oct 17, 2026

Four Seasons Resort Hualalai

Four Seasons Resort Hualalai

Kaupulehu
Save 100% on your flight
CA $8,601
per person
Jan 5 - Jan 12
found 2 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Kailua-Kona (KOA)
9.6/10 Exceptional! (505 reviews)
Mauna Lani, Auberge Collection

Mauna Lani, Auberge Collection

CA $9,928
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Kailua-Kona (KOA)
9.4/10 Exceptional! (1,002 reviews)
Everything is excellent!

Reviewed on Oct 14, 2026

Castle Hali'i Kai at Waikoloa

Castle Hali'i Kai at Waikoloa

CA $804
per person
Nov 20 - Nov 22
found 7 hours ago
Roundtrip flight included
Honolulu (HNL) to Kailua-Kona (KOA)
9/10 Wonderful! (755 reviews)
The building itself is very old and unattractive. Although the property looks very spacious in the photos, the actual interior is disappointingly small and unimpressive. The female receptionist seemed to be very familiar with the local residents and appeared to give them rooms as she pleased. I also felt that she showed a strong sense of hostility toward people from outside the area, which made me feel very uncomfortable during my stay.

Reviewed on Oct 17, 2026

Don't see what you're looking for?
See all available trips from Columbus to Hawaii Island
View all trips

5* Luxury holidays in Hawaii Island

Price found within the past 48 hours. Click for updated prices.
Mauna Kea Beach Hotel, Autograph Collection

Mauna Kea Beach Hotel, Autograph Collection

CA $2,931
per person
Nov 20 - Nov 22
found 2 hours ago
Roundtrip flight included
Honolulu (HNL) to Kailua-Kona (KOA)
9.4/10 Exceptional! (479 reviews)
Four Seasons Resort Hualalai

Four Seasons Resort Hualalai

Kaupulehu
Save 100% on your flight
CA $8,601
per person
Jan 5 - Jan 12
found 2 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Kailua-Kona (KOA)
9.6/10 Exceptional! (505 reviews)
Mauna Lani, Auberge Collection

Mauna Lani, Auberge Collection

CA $9,928
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Kailua-Kona (KOA)
9.4/10 Exceptional! (1,002 reviews)
Everything is excellent!

Reviewed on Oct 14, 2026

Don't see what you're looking for?
See all available trips from Columbus to Hawaii Island
View all trips

3 Night Luxury holidays in Hawaii Island

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

Royal Kona Resort

Historic Kailua Village
CA $1,617
per person
Nov 22 - Nov 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Kailua-Kona (KOA)
8.4/10 Very good! (3,006 reviews)
Nice

Reviewed on Oct 17, 2026

Fairmont Orchid

Fairmont Orchid

CA $2,894
per person
Nov 22 - Nov 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Kailua-Kona (KOA)
9.2/10 Wonderful! (1,006 reviews)
Excellent

Reviewed on Oct 17, 2026

Castle Hali'i Kai at Waikoloa

Castle Hali'i Kai at Waikoloa

CA $2,116
per person
Nov 22 - Nov 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Kailua-Kona (KOA)
9/10 Wonderful! (755 reviews)
The building itself is very old and unattractive. Although the property looks very spacious in the photos, the actual interior is disappointingly small and unimpressive. The female receptionist seemed to be very familiar with the local residents and appeared to give them rooms as she pleased. I also felt that she showed a strong sense of hostility toward people from outside the area, which made me feel very uncomfortable during my stay.

Reviewed on Oct 17, 2026

Don't see what you're looking for?
See all available trips from Columbus to Hawaii Island
View all trips

4 Night Luxury holidays in Hawaii Island

Price found within the past 48 hours. Click for updated prices.
Castle Waimea Country Lodge

Castle Waimea Country Lodge

CA $2,419
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Kailua-Kona (KOA)
7.4/10 Good! (576 reviews)
The staff in the main office were not the friendliest. We ran out of liquid soap in the shower the second day. We left our used towels in the laundry bag outside our door…no one came to replace it. We had to personally take it to the office and then found new towels outside our room.

Reviewed on Oct 9, 2026

Royal Kona Resort

Royal Kona Resort

Historic Kailua Village
CA $2,420
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Kailua-Kona (KOA)
8.4/10 Very good! (3,006 reviews)
Nice

Reviewed on Oct 17, 2026

Kona Coast Resort

Kona Coast Resort

Kahaluu-Keauhou
CA $2,474
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Kailua-Kona (KOA)
9.2/10 Wonderful! (1,490 reviews)
We had a wonderful experience!

Reviewed on Oct 17, 2026

Don't see what you're looking for?
See all available trips from Columbus to Hawaii Island
View all trips

Plan the perfect luxury Hawaii Island vacation with Expedia

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 $619, 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 13. 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

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! (1,000 reviews)
"Everything is excellent!"

Reviewed on Oct 14, 2026

Mauna Lani, Auberge Collection
Fairmont Orchid

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! (1,006 reviews)
"Excellent"

Reviewed on Oct 17, 2026

Fairmont Orchid
Mauna Kea Beach Hotel, Autograph Collection

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 ...
Mauna Kea Beach Hotel, Autograph Collection
See all 7,261 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.

Things to do

Deluxe Snorkel & Dolphin Watch

4.5hr Snorkel & Dolphin Watch includes breakfast & Lunch plus a 20ft slide

CA $181
per adult
96% of travellers recommend
4.5hr Snorkel & Dolphin Watch includes breakfast & Lunch plus a 20ft slide
Kona Catamaran Sail aboard Spirit of Aloha from Honokohau Harbor

Kona Catamaran Day or Sunset Sail aboard Spirit of Aloha

CA $124
per adult
96% of travellers recommend
Kona Catamaran Day or Sunset Sail aboard Spirit of Aloha
Young girl holding a sea urchin on the glass bottom boat in the Pacific Ocean near the Big Island of Hawaii

Glass-Bottom Boat Tour in Waikoloa

CA $70
per adult
94% of travellers recommend
Glass-Bottom Boat Tour in Waikoloa
See all activities in Hawaii Island

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.