Wailea Holidays

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Top hotels in Wailea

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 HK$5,471 per night from 2 May to 3 May
HK$5,471
HK$6,453 total
includes taxes & fees
2 May - 3 May
9.6/10 Exceptional! (1,000 reviews)
"A good hotel. The free upgrade was nice though I suspect because they weren’t filled. The beach was somewhat mediocre for the price, you’re better off in the North near Kaanapali. The breakfast involved a lot of waiting for someone who there was no clear reason for him helping. It was a buffet, adding ..."

Reviewed on 17 Apr 2025

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 HK$7,829 per night from 7 May to 8 May
HK$7,829
HK$9,693 total
includes taxes & fees
7 May - 8 May
9.4/10 Exceptional! (987 reviews)
"Our stay here was absolutely incredible. The property is stunningly gorgeous and all the staff are wonderful. My daughter and I both have Celiac Disease, which can be tricky to travel with, however we were very Well taken care of and had many options to safely eat. Highly recommend"

Reviewed on 22 Apr 2025

Fairmont Kea Lani Maui
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 HK$6,588 per night from 1 May to 2 May
HK$6,588
HK$8,198 total
includes taxes & fees
1 May - 2 May
8.8/10 Excellent! (1,000 reviews)
"This is by far the best property on Maui, especially for families. Pool was great and only steps away from the beach. Highly recommend!"

Reviewed on 21 Apr 2025

Grand Wailea Maui, A Waldorf Astoria Resort
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 , 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 holiday 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 holiday 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 holiday?
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 organising an upscale romantic escape or a budget family adventure, browse our holiday 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.

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