Wailea Holidays from NZ$1,755

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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
OUTRIGGER Kaanapali Beach Resort
Sands of Kahana
Aston Mahana at Kaanapali
Hotel Wailea, Relais & Chateaux - Adults Only

Our pick of the best Wailea Hotel Deals

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$1,839 per night from 7 Mar to 8 Mar
NZ$1,839
includes taxes & fees
7 Mar - 8 Mar
9.6/10 Exceptional! (999 reviews)
"Very enjoyable experience, we stayed on the Club Level and felt the perks were worth it."

Reviewed on 10 Feb. 2025

Four Seasons Resort Maui at Wailea
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$1,935 per night from 27 Feb to 28 Feb
NZ$1,935
includes taxes & fees
27 Feb - 28 Feb
8.8/10 Excellent! (1,003 reviews)
"The property is very big which leads to a lot of walking. They charge $150.00 a day for beach chairs.and one umbrella No other alternative available. No umbrellas available in the adult section. Not a five star hotel."

Reviewed on 20 Feb. 2025

Grand Wailea Maui, A Waldorf Astoria Resort
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$1,944 per night from 27 Feb to 28 Feb
NZ$1,944
includes taxes & fees
27 Feb - 28 Feb
9.2/10 Wonderful! (1,000 reviews)
Amazing!
"Went for conference with my wife. Outstanding resort in every way."

Reviewed on 17 Feb. 2025

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$1,755, 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

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