Wailea Holidays from NZ$2,042

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Top Holiday Package Deals in Wailea

Price found within the past 48 hours. Click for updated prices.
AEI at Maui Kaanapali Villas Resort

AEI at Maui Kaanapali Villas Resort

3.5 out of 5
Price was NZ$2,836, price is now NZ$2,042 per person
NZ$2,042
per person
10 Nov - 17 Nov
found 1 day ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
9.2/10 Wonderful! (187 reviews)
Staff was friendly. Place was really nice.

Reviewed on 4 Sep. 2025

Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
Save 100% on your flight
Price was NZ$4,348, price is now NZ$2,488 per person
NZ$2,488
per person
10 Nov - 17 Nov
found 1 day ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
8.4/10 Very Good! (1,425 reviews)
This review is mostly related to the Towers since I did not stay in the bungalows. The tower room is a bit old. You can see the scratches on everything and the rust stains in the bathroom which makes it appear not clean but it is. Once you accept this is not a major modern resort, it is perfectly fine. I really have no complaints, these observations were all just aesthetics. The resort is very low key. I recommend this resort as a home base for all other off resort activities. There is also a complimentary trolley which will take you to the Whaler Village, etc... The staff was great. They were very pleasant and helpful. I travelled alone with no car rental so I had a lot of questions. The food was delicious. The drinks were also superb.

Reviewed on 2 Sep. 2025

Aston Kaanapali Shores

Aston Kaanapali Shores

3.5 out of 5
Price was NZ$2,864, price is now NZ$2,177 per person
NZ$2,177
per person
10 Nov - 17 Nov
found 1 day ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
8.6/10 Excellent! (3,684 reviews)
Most beautiful sunset I've ever seen. Saw a giant turtle, large ray & seal right off the beach. Happy hour food was delicious & drinks were amazing. The pools were also alot of fun & are well maintained. I recommend this place to anyone!

Reviewed on 4 Sep. 2025

Montage Kapalua Bay Collection by KBM - 2 Units (6301/6401)

Montage Kapalua Bay Collection by KBM - 2 Units (6301/6401)

4.5 out of 5
Save 100% on your flight
Price was NZ$41,400, price is now NZ$33,714 per person
NZ$33,714
per person
10 Nov - 17 Nov
found 1 day ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
No reviews
Kapalua Golf Villas Collection by KBM - 2 Units in same building (24p7/24p2)

Kapalua Golf Villas Collection by KBM - 2 Units in same building (24p7/24p2)

4 out of 5
Price was NZ$8,372, price is now NZ$7,077 per person
NZ$7,077
per person
10 Nov - 17 Nov
found 1 day ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
No reviews

Our pick of the best Wailea Hotel Deals

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr, Kihei, HI
The price is NZ$1,788 per night from 26 Sept to 27 Sept
NZ$1,788
26 Sept - 27 Sept
includes taxes & fees
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 NZ$1,507 per night from 10 Sept to 11 Sept
NZ$1,507
10 Sept - 11 Sept
includes taxes & fees
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$1,623 per night from 5 Oct to 6 Oct
NZ$1,623
5 Oct - 6 Oct
includes taxes & fees
Andaz Maui at Wailea Resort - a concept by Hyatt
See all 1,196 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$2,042, 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

Wailea Beach showing a sandy beach, tropical scenes and swimming

Wailea Beach

4.5/5(32 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.

Wailea Beach
Maluaka Beach which includes rocky coastline, mountains and a pebble beach

Maluaka Beach

4/5(3 reviews)

Packed with native marine life, Maluaka Beach is a prime spot for catching sight of Hawaiian green turtles and majestic hump-backed whales.

Maluaka Beach
Makena Beach State Park showing a beach

Makena State Park Beach

4.5/5(7 reviews)

The three beaches and soaring volcano which make up Makena Beach State Park provide something for everyone to enjoy.

Makena State Park Beach

Activities

Guided Turtle Town Snorkeling Tour with Underwater Photos

Snorkel with Turtles and Free Underwater Photos - Turtle Town

NZ$219
per adult
100% of travellers recommend
Snorkel with Turtles and Free Underwater Photos - Turtle Town
Book Your Unfogetable Adventure Now

Road to Hana Adventure with Farm to Table Lunch in Town of Hana

NZ$430
per adult
88% of travellers recommend
Road to Hana Adventure with Farm to Table Lunch in Town of Hana
Morning views at Haleakalā National Park

Haleakala National Park Sunrise Tour

NZ$408
per adult
92% of travellers recommend
Haleakala National Park Sunrise Tour
See all activities in Kihei
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.