Luxury Vacations in Hawaii 2026

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Flight and Luxury hotel deals in Hawaii

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

OUTRIGGER Kauaʻi Beach Resort & Spa

CA $1,671

per person

Nov 28 - Dec 4

found 22 hours ago

Roundtrip non-stop flight included

Winnipeg (YWG) to Lihue (LIH)

8.4/10 Very good! (1,141 reviews)

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea

CA $3,832

per person

Nov 19 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Kahului (OGG)

9.4/10 Exceptional! (1,000 reviews)

My husband and I had an incredible honeymoon stay. We couldn't recommend Hotel Wailea enough!! The team are all so lovely and attentive and all went out their way to give us the best experience. Shannon was an absolute star organising an itinerary prior to arrival so everything was so smooth and easy. Would definitely recommend the in-room Lomi Lomi couples massage and hiring e-bikes with Bear. Shoutout to Sunny also for her help on the front desk and assistance with our postcards! Our hotel room was spacious, comfortable and had a breathtaking ocean view and sofa balcony loungers. We were also very grateful to the valet team for all their assistance chauffeuring us around Wailea and the beaches. The food was utterly divine, in particular the Bird Cage was a highlight, superb menu and sake. The breakfasts also were so fresh! Not to mention the moreish cocktail menu and bites by the pool! The ariel and flow yoga with Andrea and outrigger canoe experience were also fantastic. We couldn't fault it and was the most perfect honeymoon. Thank you all so so much again. We look forward to returning one day X

Reviewed on Sep 6, 2026

1 Hotel Hanalei Bay

CA $7,096

per person

Nov 19 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Lihue (LIH)

9.2/10 Wonderful! (381 reviews)

Grand Wailea Maui, A Waldorf Astoria Resort

Wailea

CA $21,065

per person

Nov 19 - Nov 26

found 4 hours ago

Roundtrip flight included

Vancouver (YVR) to Kahului (OGG)

8.6/10 Excellent! (1,008 reviews)

Some of the best customer service we’ve ever had. Room was gorgeous, grounds were stunning, views were amazing

Reviewed on Sep 14, 2026

Ko'a Kea Resort on Po'ipu Beach

Poipu

CA $2,866

per person

Nov 19 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Lihue (LIH)

9.4/10 Exceptional! (1,004 reviews)

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5* Luxury holidays in Hawaii

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

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea

CA $3,832

per person

Nov 19 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Kahului (OGG)

9.4/10 Exceptional! (1,000 reviews)

Reviewed on Sep 6, 2026

1 Hotel Hanalei Bay

CA $7,096

per person

Nov 19 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Lihue (LIH)

9.2/10 Wonderful! (381 reviews)

Grand Wailea Maui, A Waldorf Astoria Resort

Wailea

CA $21,065

per person

Nov 19 - Nov 26

found 4 hours ago

Roundtrip flight included

Vancouver (YVR) to Kahului (OGG)

8.6/10 Excellent! (1,008 reviews)

Some of the best customer service we’ve ever had. Room was gorgeous, grounds were stunning, views were amazing

Reviewed on Sep 14, 2026

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See all available trips from Columbus to Hawaii

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3 Night Luxury holidays in Hawaii

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

Halekulani

Waikiki

CA $1,846

per person

Oct 31 - Nov 3

found 2 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Honolulu (HNL)

9.8/10 Exceptional! (1,001 reviews)

Excellent experience

Reviewed on Sep 10, 2026

1 Hotel Hanalei Bay

CA $3,524

per person

Oct 19 - Oct 22

found 21 hours ago

Roundtrip flight included

San Francisco (SFO) to Lihue (LIH)

9.2/10 Wonderful! (381 reviews)

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea

CA $3,892

per person

Oct 25 - Oct 28

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Kahului (OGG)

9.4/10 Exceptional! (1,000 reviews)

Reviewed on Sep 6, 2026

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4 Night Luxury holidays in Hawaii

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

Stay Hotel Waikiki

Waikiki

CA $705

per person

Nov 16 - Nov 20

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Honolulu (HNL)

8.2/10 Very good! (1,994 reviews)

Service was very accommodating and kind

Reviewed on Sep 15, 2026

1 Hotel Hanalei Bay

CA $5,621

per person

Oct 27 - Oct 31

found 19 hours ago

Roundtrip flight included

Winnipeg (YWG) to Lihue (LIH)

9.2/10 Wonderful! (381 reviews)

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea

CA $3,223

per person

Oct 28 - Nov 1

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Kahului (OGG)

9.4/10 Exceptional! (1,000 reviews)

Reviewed on Sep 6, 2026

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See all available trips from Columbus to Hawaii

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What are some benefits when booking luxury Hawaii vacations?

When you book a luxury Hawaii 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?

If you're looking for something luxurious in Hawaii, 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 $705, 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 34. 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. 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?

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.

Can I book last-minute luxury vacations?

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

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 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. 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

The Royal Hawaiian, a Luxury Collection Resort, Waikiki

2259 Kalakaua Avenue Honolulu HI

7 min walk from Waikiki Beach

CA $573

CA $765 total

Oct 17 - Oct 18

includes taxes & fees

Book a stay at this luxury resort in Honolulu. Enjoy 2 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the helpful staff in our reviews. ...

9.2/10 Wonderful! (1,217 reviews)

"Historic and magical location on the beach. Amazing bed but A/C super noisy. No real milk for tea in the room! Had to buy our own at the ABC store. The facilities for dining and bars are great."

Reviewed on Sep 15, 2026

The Kahala Hotel & Resort

5000 Kahala Ave Honolulu HI

6 min drive from Waikiki Beach

CA $559

CA $664 total

Oct 17 - Oct 18

includes taxes & fees

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

9.4/10 Exceptional! (1,004 reviews)

"We loved the dolphin lagoon the beach and amenities. Restaurants were very good."

Reviewed on Sep 15, 2026

Hilton Vacation Club The Modern Honolulu

1775 Ala Moana Boulevard Honolulu HI

21 min walk from Waikiki Beach

CA $170

CA $260 total

Sep 29 - Sep 30

includes taxes & fees

Book a stay at this business-friendly hotel in Honolulu. Enjoy 2 outdoor pools, a marina, and a 24-hour fitness center. Our guests praise the pool and the helpful ...

8.8/10 Excellent! (1,691 reviews)

"Tranquil, exceptionally clean, great service. Wish they had a restaurant."

Reviewed on Sep 15, 2026

See all 35,187 properties in Hawaii

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.