Wailea Vacations from ¥281,872

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The Latest Wailea Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Kahana Falls Maui by VRI Americas
Napili Kai Beach Resort
Aston Mahana at Kaanapali
Fairmont Kea Lani Maui
Aston Kaanapali Shores

Wailea Hotel Deals

Grand Wailea Maui, A Waldorf Astoria Resort
Grand Wailea Maui, A Waldorf Astoria Resort
5 out of 5
3850 Wailea Alanui Drive, Kihei, HI
The price is ¥94,734 per night from Oct 2 to Oct 3
¥94,734
per night
Oct 2 - Oct 3
8.8/10 Excellent! (1,009 reviews)
"The price is high because very few properties can have such luxury. There are many great properties nearby but this is the penultimate with a tiki meets art deco neo classical architecture/styling. My only disappointment is that they no longer have a (walnut) lei upon arrival. I’d assume after the ..."

Reviewed on Sep 23, 2024

Grand Wailea Maui, A Waldorf Astoria Resort
Four Seasons Resort Maui at Wailea
Four Seasons Resort Maui at Wailea
5 out of 5
3900 Wailea Alanui Drive, Kihei, HI
The price is ¥115,005 per night from Oct 6 to Oct 7
¥115,005
per night
Oct 6 - Oct 7
9.6/10 Exceptional! (999 reviews)
"Best place to relax and have a great time"

Reviewed on Sep 19, 2024

Four Seasons Resort Maui at Wailea
Fairmont Kea Lani Maui
Fairmont Kea Lani Maui
4.5 out of 5
4100 Wailea Alanui Dr, Kihei, HI
The price is ¥108,350 per night from Oct 26 to Oct 27
¥108,350
per night
Oct 26 - Oct 27
9.2/10 Wonderful! (1,006 reviews)
"It wasn’t perfect! We reserved the suite for 3 person, for 4 nights, but they had everything in the suite for 2 people and we had to ask them every day to provide us extra towels, cups, etc."

Reviewed on Sep 24, 2024

Fairmont Kea Lani 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.

Frequently asked questions

How much does a Wailea vacation package cost?
The most affordable Wailea package is ¥281,872, so your dream vacation can become a reality — without it costing a fortune. Combine flights, hotels, car rentals and more to custom build a package that matches your traveling style.
How do I get a cheap travel package to Wailea?
Crafting your own Wailea vacation package with Expedia is the easiest way to save. We have access to more than 550 airlines and 1,000,000 properties across the globe. With such an extensive range to select from, you’ll have no trouble pulling together your ideal escape.
Where should I stay in Wailea?
A vacation in Wailea isn’t complete without checking out Wailea Beach, Kamaole Beach Park and Makena State Park Beach. Spend your nights close to these top sights and make sightseeing easy.
What are the top hotels in Wailea?
Lock in a room at Ocean And Golf Course View 3 Bed. It’s one of this area’s most sought-after hotels. Another top-rated option in Wailea is Wailea Ekahi 36b One Of The Best Locations In Wailea.
How far in advance should I book my Wailea vacation?
While prices change from time to time, we generally recommend booking your spot as soon as possible. Most international fares can be compared on Expedia up to a year in advance. If you’re booking last minute, you might still be in luck. Discount prices to Wailea occasionally appear in the weeks prior to departure.
What does an Expedia Wailea travel package include?
Car rentals, hotels and flights — we connect you to the very best deals. All you’ll have to do is decide on your preferred combination. Once you’ve made your booking, you can add on the fun stuff like experiences and tours. Our travel packages make it simple to craft an awesome Wailea getaway.
What should I know before booking a Wailea travel package?
You’ll pick up amazing savings when you bundle your flights, hotels and rental cars into a package. Plus, booking everything in one spot makes trip planning much easier. So why waste time or money? Whether you’re organizing an upscale romantic escape or a budget family adventure, browse our vacation packages today.
If I'm not able to travel, can I cancel my Wailea vacation package?
Yes, you can. We realize life doesn’t always go to plan, so we’re here to help if you need to make changes to your Wailea vacation package. It may be possible to cancel or change your itinerary for free if you’ve booked within 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for further information. Also, check your itinerary for the finer details on change fees.

Discover the most popular places to visit in Wailea

Things to do

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