A lush green mountain range with a clear blue sky.

Maui Luxury Vacations

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Top Luxury vacation packages in Maui

Price found within the past 48 hours. Click for updated prices.
  • Sept 4 - Sept 10

    Grand Wailea Maui, A Waldorf Astoria Resort + Flight

    Wailea
    6 nights
    5.0 star property
    8.8/10 - Excellent (1,003 reviews)
    "There is an overall lack of genuine service. You feel very rushed and staff is just looking to charge everything to your room. Lack of food options for families with young kids. The pool is not as nice as advertised, the lazy river is small and the slides only open for a limited time each day, the water elevator was broken and the snorkeling is just putting on equipment no fishes. Extra charge for umbrellas at the beach. $80 daily charge for valet is excessive with the car just sitting there for..."
    Reviewed August 3, 2026
    Roundtrip Toronto (YTO) - Maui (OGG)
    YYZ - OGG1 stop OGG - YKF2 stops
    CA $4,677
    CA $3,752
    per traveller
    found 1 day ago
    Grand Wailea Maui, A Waldorf Astoria Resort
  • Sept 4 - Sept 10

    Hotel Wailea, Relais & Chateaux - Adults Only + Flight

    Wailea
    6 nights
    5.0 star property
    9.4/10 - Exceptional (1,000 reviews)
    "This is a super nice adult only hotel. Nice and quiet. Staff is wonderful. On point. Hotel car service is excellent with luxury cars available. The room is nice. Large and spacious. My only critique is that the restaurant has a limited menu. But selection is great. Highly recommend."
    Reviewed July 25, 2026
    Roundtrip Toronto (YTO) - Maui (OGG)
    YYZ - OGG1 stop OGG - YKF2 stops
    CA $7,222
    CA $3,762
    per traveller
    found 1 day ago
    Hotel Wailea, Relais & Chateaux - Adults Only
  • Sept 4 - Sept 10

    Fairmont Kea Lani Maui + Flight

    Wailea
    6 nights
    5.0 star property
    9.4/10 - Exceptional (1,006 reviews)
    "We had a wonderful stay at the Fairmont Kea Lani and would absolutely return in the future. Our suite was beautiful, spacious, and very comfortable. The rooms were always clean and well maintained, and the entire property was spotless and clearly very well cared for. The amenities were excellent, and we especially enjoyed spending time at the beach. The water was amazing, clean, and beautiful. We also really appreciated that the hotel provided chairs and an umbrella for our family each day...."
    Reviewed August 4, 2026
    Roundtrip Toronto (YTO) - Maui (OGG)
    YYZ - OGG1 stop OGG - YKF2 stops
    CA $5,571
    CA $4,090
    per traveller
    found 1 day ago
    Fairmont Kea Lani Maui
  • Sept 13 - Sept 19

    Fairmont Kea Lani Maui Villa Experience + Flight

    Wailea
    6 nights
    5.0 star property
    9.8/10 - Exceptional (7 reviews)
    Roundtrip Toronto (YTO) - Maui (OGG)
    YYZ - OGG1 stop OGG - YKF2 stops
    CA $17,056
    CA $15,368
    per traveller
    found 19 hours ago
    Fairmont Kea Lani Maui Villa Experience
  • Sept 13 - Sept 19

    Four Seasons Resort Maui at Wailea + Flight

    Wailea
    6 nights
    5.0 star property
    9.6/10 - Exceptional (1,001 reviews)
    "Our stay was amazing. The staff and service were absolutely off the charts. The newly opened spa was the nicest I have ever been in. The food at the adult pool and service by the bar staff was impeccable. The main thing that stuck out to me was the genuine kindness and pride that the staff puts into their work. They make you feel special and valued. The canoe experience with the beach staff was so fun. We hated leaving :(. We will be back as this is truly paradise. Thanks for making our stay so..."
    Reviewed July 22, 2026
    Roundtrip Toronto (YTO) - Maui (OGG)
    YYZ - OGG1 stop OGG - YKF2 stops
    CA $7,205
    CA $6,530
    per traveller
    found 19 hours ago
    Four Seasons Resort Maui at Wailea

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Top Luxury Maui Hotels

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.

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 $3,752, 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 19. 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.