Maui 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 Maui

Price found within the past 48 hours. Click for updated prices.
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

Wailea
CA $1,998
per person
Oct 26 - Oct 29
found 6 hours ago
Roundtrip non-stop flight included
Prince George (YXS) to Kahului (OGG)
9.2/10 Wonderful! (1,005 reviews)
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea
CA $3,021
per person
Oct 29 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Kelowna (YLW) to Kahului (OGG)
9.4/10 Exceptional! (1,004 reviews)
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

Wailea
CA $2,726
per person
Oct 26 - Oct 29
found 6 hours ago
Roundtrip non-stop flight included
Prince George (YXS) to Kahului (OGG)
9.4/10 Exceptional! (1,018 reviews)
I booked this for my son and daughter in-laws honeymoon. They had a great time and loved this resort. While it was on the reservation and I called the day before to tell them the couple was on their honeymoon, it was only recognized as they were settling up their fees at the end of the visit. The breakfast buffet was reportedly superb. They were able to rent a jeep very easily at the nearby Avis and enjoyed touring the island.

Reviewed on Aug 23, 2026

Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea

Wailea
CA $8,045
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kahului (OGG)
9.6/10 Exceptional! (50 reviews)
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

Wailea
CA $6,068
per person
Oct 29 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Kelowna (YLW) to Kahului (OGG)
9.6/10 Exceptional! (1,001 reviews)
Four hours waiting for hotel check in is unacceptable. Sorry.

Reviewed on Aug 20, 2026

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

5* Luxury holidays in Maui

Price found within the past 48 hours. Click for updated prices.
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

Wailea
CA $1,998
per person
Oct 26 - Oct 29
found 6 hours ago
Roundtrip non-stop flight included
Prince George (YXS) to Kahului (OGG)
9.2/10 Wonderful! (1,005 reviews)
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea
CA $3,021
per person
Oct 29 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Kelowna (YLW) to Kahului (OGG)
9.4/10 Exceptional! (1,004 reviews)
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

Wailea
CA $2,726
per person
Oct 26 - Oct 29
found 6 hours ago
Roundtrip non-stop flight included
Prince George (YXS) to Kahului (OGG)
9.4/10 Exceptional! (1,018 reviews)
I booked this for my son and daughter in-laws honeymoon. They had a great time and loved this resort. While it was on the reservation and I called the day before to tell them the couple was on their honeymoon, it was only recognized as they were settling up their fees at the end of the visit. The breakfast buffet was reportedly superb. They were able to rent a jeep very easily at the nearby Avis and enjoyed touring the island.

Reviewed on Aug 23, 2026

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

3 Night Luxury holidays in Maui

Price found within the past 48 hours. Click for updated prices.
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

Wailea
CA $2,272
per person
Sep 25 - Sep 28
found 15 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
9.2/10 Wonderful! (1,005 reviews)
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

Wailea
CA $2,726
per person
Oct 26 - Oct 29
found 6 hours ago
Roundtrip non-stop flight included
Prince George (YXS) to Kahului (OGG)
9.4/10 Exceptional! (1,018 reviews)
I booked this for my son and daughter in-laws honeymoon. They had a great time and loved this resort. While it was on the reservation and I called the day before to tell them the couple was on their honeymoon, it was only recognized as they were settling up their fees at the end of the visit. The breakfast buffet was reportedly superb. They were able to rent a jeep very easily at the nearby Avis and enjoyed touring the island.

Reviewed on Aug 23, 2026

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea
CA $2,806
per person
Sep 25 - Sep 28
found 15 hours ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
9.4/10 Exceptional! (1,004 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Maui
View all trips

4 Night Luxury holidays in Maui

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

Aston Maui Hill

South Kihei
CA $1,321
per person
Sep 24 - Sep 28
found 5 hours ago
Roundtrip flight included
Vancouver (YVR) to Kahului (OGG)
9/10 Wonderful! (950 reviews)
Dennis and the entire staff made our trip so enjoyable. We will forever have a special place in our hearts for this place. Celebrated our 10 year wedding anniversary here!

Reviewed on Aug 21, 2026

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea
CA $4,880
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kahului (OGG)
9.4/10 Exceptional! (1,004 reviews)
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

Wailea
CA $3,736
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Kahului (OGG)
9.4/10 Exceptional! (1,018 reviews)
I booked this for my son and daughter in-laws honeymoon. They had a great time and loved this resort. While it was on the reservation and I called the day before to tell them the couple was on their honeymoon, it was only recognized as they were settling up their fees at the end of the visit. The breakfast buffet was reportedly superb. They were able to rent a jeep very easily at the nearby Avis and enjoyed touring the island.

Reviewed on Aug 23, 2026

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

Plan the perfect luxury Maui vacation with Expedia

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 $1,321, 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 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

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)
"Four hours waiting for hotel check in is unacceptable. Sorry."

Reviewed on Aug 20, 2026

Four Seasons Resort Maui at Wailea
Fairmont Kea Lani Maui

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 ...
9.6/10 Exceptional! (1,022 reviews)
"I booked this for my son and daughter in-laws honeymoon. They had a great time and loved this resort. While it was on the reservation and I called the day before to tell them the couple was on their honeymoon, it was only recognized as they were settling up their fees at the end of the visit. The ..."

Reviewed on Aug 23, 2026

Fairmont Kea Lani Maui
Andaz Maui at Wailea Resort - a concept by Hyatt

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! (1,002 reviews)
"Landscaping needs improvement"

Reviewed on Aug 24, 2026

Andaz Maui at Wailea Resort - a concept by Hyatt
See all 13,270 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.

Things to do

Myths of Maui Luau at the Royal Lahaina Resort

Myths of Maui Luau at the Royal Lahaina Resort

CA $238
per adult
86% of travellers recommend
Myths of Maui Luau at the Royal Lahaina Resort
Xpress Snorkel

2.5hr Express Catamaran Snorkel from Ka'anapali

CA $201
per adult
100% of travellers recommend
2.5hr Express Catamaran Snorkel from Ka'anapali
Trio of fire twirlers at Drums of the Pacific Luau

Drums of the Pacific Luau at the Hyatt Regency Resort

CA $296
per adult
86% of travellers recommend
Drums of the Pacific Luau at the Hyatt Regency Resort
See all activities in Maui

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.