Luxury Vacations in Maui 2026

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Flight and Luxury hotel deals in Maui

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

Wailea Beach Resort - Marriott, Maui

Wailea

CA $2,778

per person

Nov 8 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Kahului (OGG)

9.2/10 Wonderful! (1,008 reviews)

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea

CA $3,753

per person

Nov 9 - Nov 13

found 7 hours ago

Roundtrip flight included

Toronto (YTO) 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

Fairmont Kea Lani Maui

Wailea

CA $6,708

per person

Nov 8 - Nov 15

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Kahului (OGG)

9.6/10 Exceptional! (1,003 reviews)

Four Seasons Resort Maui at Wailea

Wailea

CA $6,383

per person

Nov 13 - Nov 20

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Kahului (OGG)

9.6/10 Exceptional! (1,001 reviews)

Loved every moment we spent there! Best decision to stay at Four Seasons for our honeymoon trip :)

Reviewed on Aug 25, 2026

Wailea Beach Villas

Wailea

CA $5,134

per person

Nov 9 - Nov 12

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Kahului (OGG)

9.8/10 Exceptional! (199 reviews)

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5* Luxury holidays in Maui

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

Wailea Beach Resort - Marriott, Maui

Wailea

CA $2,778

per person

Nov 8 - Nov 13

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to Kahului (OGG)

9.2/10 Wonderful! (1,008 reviews)

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea

CA $3,753

per person

Nov 9 - Nov 13

found 7 hours ago

Roundtrip flight included

Toronto (YTO) to Kahului (OGG)

9.4/10 Exceptional! (1,000 reviews)

Reviewed on Sep 6, 2026

Fairmont Kea Lani Maui

Wailea

CA $6,708

per person

Nov 8 - Nov 15

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Kahului (OGG)

9.6/10 Exceptional! (1,003 reviews)

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3 Night Luxury holidays in Maui

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

Wailea Beach Resort - Marriott, Maui

Wailea

CA $1,943

per person

Nov 13 - Nov 16

found 5 hours ago

Roundtrip flight included

Edmonton (YEA) to Kahului (OGG)

9.2/10 Wonderful! (1,008 reviews)

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea

CA $4,020

per person

Oct 9 - Oct 12

found 1 day ago

Roundtrip flight included

Vancouver (YVR) to Kahului (OGG)

9.4/10 Exceptional! (1,000 reviews)

Reviewed on Sep 6, 2026

Andaz Maui at Wailea Resort - a concept by Hyatt

Wailea

CA $2,037

per person

Oct 29 - Nov 1

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to Kahului (OGG)

9.2/10 Wonderful! (1,002 reviews)

An amazing experience over all.

Reviewed on Sep 5, 2026

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4 Night Luxury holidays in Maui

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

Castle Kama'ole Sands

South Kihei

CA $1,358

per person

Oct 8 - Oct 12

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to Kahului (OGG)

8/10 Very good! (2,346 reviews)

We had everything we needed.

Reviewed on Sep 1, 2026

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea

CA $3,753

per person

Nov 9 - Nov 13

found 7 hours ago

Roundtrip flight included

Toronto (YTO) to Kahului (OGG)

9.4/10 Exceptional! (1,000 reviews)

Reviewed on Sep 6, 2026

Aston Maui Hill

South Kihei

CA $1,729

per person

Oct 8 - Oct 12

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to Kahului (OGG)

9/10 Wonderful! (964 reviews)

Clean room. Staff were pleasant. 10-15 minutes walk to beach.

Reviewed on Sep 6, 2026

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What are some benefits when booking luxury Maui vacations?

When you book a luxury Maui 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 Maui?

If you're looking for something luxurious in Maui, 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 $1,358, 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 14. 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 Maui. 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 Maui?

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 Maui.

Can I book last-minute luxury vacations?

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

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 Maui 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 Maui. 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 Maui

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive Kihei HI

43 min drive from Kaanapali Beach

Book a stay at this luxury resort in Kihei. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...

9.6/10 Exceptional! (1,001 reviews)

"Loved every moment we spent there! Best decision to stay at Four Seasons for our honeymoon trip :)"

Reviewed on Aug 25, 2026

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr Kihei HI

43 min drive from Kaanapali Beach

Book a stay at this luxury resort in Kihei. Enjoy 3 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property ...

Andaz Maui at Wailea Resort - a concept by Hyatt

3550 Wailea Alanui Dr Kihei HI

41 min drive from Kaanapali Beach

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

9.2/10 Wonderful! (1,001 reviews)

"An amazing experience over all."

Reviewed on Sep 5, 2026

See all 13,559 properties in Maui

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.