Wailea Holidays & Package Deals

Q: 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 .

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Your Wailea Holiday

Lose yourself in the magic of this picturesque neighbourhood with a Wailea holiday package. From its surfing and coastal beaches to its views, there's something here for every traveller. Not sure what to do and see during your trip to Wailea? Nearby attractions such as Wailea Beach, Kamaole Beach Park and Keawakapu Beach North are good places to start. Whatever your travel plans or budget, booking your dream Wailea holiday is quick and easy with Expedia.

Our guide on where to stay in Wailea

Find the best Wailea areas and neighborhoods for the activities you enjoy most. Learn more about Wailea

A sunset over a beach with palm trees and a few people walking.

South Kihei

4 out of top 10 points of interest in this area

While visiting South Kihei, you might make a stop by sights like Kamaole Beach Park 2 and Kamaole Beach Park 3.

Our pick of the best Wailea Hotel Deals

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

AU$1,254

30 Nov - 1 Dec

includes taxes & fees

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive Kihei HI

AU$1,739

28 Nov - 29 Nov

includes taxes & fees

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr Kihei HI

AU$1,752

27 Nov - 28 Nov

includes taxes & fees

9.6/10 Exceptional! (1,002 reviews)

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Reviewed on 30 Oct 2026

See all 1,231 properties in Wailea

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 holiday package cost?

The most affordable Wailea package is , so your dream holiday can become a reality — without it costing a fortune. Combine flights, hotels, car rentals and more to custom build a package that matches your travelling 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 holiday package?

Yes, you can. We realise life doesn't always go to plan, so we're here to help if you need to make changes to your Wailea holiday 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.