Wailea Holidays from NZ$2,926

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Top Holiday Package Deals in Wailea

Price found within the past 48 hours. Click for updated prices.
Kahana Beach Vacation Club
Mana Kai Maui- Official Onsite Rental
Sands of Kahana
The Ritz-Carlton Maui, Kapalua
Maui Beach Vacation Club

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

Our pick of the best 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 NZ$1,490 per night from 23 Feb to 24 Feb
NZ$1,490
23 Feb - 24 Feb
includes taxes & fees
8.8/10 Excellent! (1,013 reviews)
The entire staff is soooo kind! Absolutely beautiful grounds and rooms. We ate at all the restaurants there. While pricey, everything was delicious. Pools are very fun, including the pool bar. And, very easy beach access.

Reviewed on 25 Jan 2026

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 NZ$1,843 per night from 10 Feb to 11 Feb
NZ$1,843
10 Feb - 11 Feb
includes taxes & fees
9.6/10 Exceptional! (999 reviews)
The Four Seasons Wailea was, once again, exceptional. All the staff, from the front desk to the pool to the outrigger crew to housekeeping, all helped make our stay one we will never forget. We were sad to leave and hope to return soon!

Reviewed on 26 Jan 2026

Four Seasons Resort Maui at Wailea
Andaz Maui at Wailea Resort - a concept by Hyatt

Andaz Maui at Wailea Resort - a concept by Hyatt

4.5 out of 5
3550 Wailea Alanui Dr Kihei HI
The price is NZ$1,765 per night from 1 Mar to 2 Mar
NZ$1,765
1 Mar - 2 Mar
includes taxes & fees
9.2/10 Wonderful! (999 reviews)
Pools were excellent, and the service was fantastic.

Reviewed on 30 Jan 2026

Andaz Maui at Wailea Resort - a concept by Hyatt
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 NZ$2,926, 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.

Discover the most popular places to visit in Wailea

Activities

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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.