Wailea Holidays from NZ$5,975

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Top Holiday Package Deals in Wailea

Price found within the past 48 hours. Click for updated prices.
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
Wailea
Price was NZ$7,006, price is now NZ$5,975 per person
NZ$5,975
per person
11 Sept - 17 Sept
found 1 day ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
8.8/10 Excellent! (1,000 reviews)

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.

Find hotels in South Kihei

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$1,617 per night from 27 Aug to 28 Aug
NZ$1,617
27 Aug - 28 Aug
includes taxes & fees
Grand Wailea Maui, A Waldorf Astoria Resort
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
The price is NZ$2,094 per night from 17 Aug to 18 Aug
NZ$2,094
17 Aug - 18 Aug
includes taxes & fees
Fairmont Kea Lani Maui
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$1,803 per night from 24 Aug to 25 Aug
NZ$1,803
24 Aug - 25 Aug
includes taxes & fees
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 ..."

Reviewed on 22 July 2026

Four Seasons Resort Maui at Wailea
See all 1,192 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 NZ$5,975, 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.

Stay near popular Wailea attractions

A tropical beach with palm trees, a sandy shore, and the ocean.

Wailea Beach

9.4/10 (4,138 reviews)
With its smooth sandy shoreline, temperate waters and fantastic sporting facilities, it’s little wonder that Wailea Beach is one of Maui’s most popular destinations.
See properties

Activities

South Maui: Snorkel to Coral Gardens or Molokini Crater

South Maui: Snorkel to Coral Gardens or Molokini Crater

NZ$176
per adult
88% of travellers recommend
South Maui: Snorkel to Coral Gardens or Molokini Crater
Maui Premium Dinner Cruise: Four Course Dining Experience

Maui Premium Dinner Cruise: Four Course Dining Experience

NZ$300
per adult
94% of travellers recommend
Maui Premium Dinner Cruise: Four Course Dining Experience
Authentic Polynesian experience, Maui's only luau on the water

Maui Sunset Dinner Cruise - A Hawaiian Hula Experience

NZ$296
per adult
94% of travellers recommend
Maui Sunset Dinner Cruise - A Hawaiian Hula Experience
See all activities in Kihei

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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.