Wailea Holidays from NZ$2,934

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Top Holiday Package Deals in Wailea

Price found within the past 48 hours. Click for updated prices.
Kahana Villa

Kahana Villa

3 out of 5
Price was NZ$4,430, price is now NZ$2,934 per person
NZ$2,934
per person
1 Apr - 8 Apr
found 1 day ago
Return direct flight included
Christchurch (CHC) to Kahului (OGG)
8/10 Very Good! (351 reviews)
This place was absolutely amazing! The location was fantasic, the view was beautiful and the two bedroom villa far exceeded my expectations! I will be back and I know exactly where I want to stay!

Reviewed on 6 Jan 2026

Kahana Beach Vacation Club

Kahana Beach Vacation Club

3 out of 5
Save 100% on your flight
Price was NZ$5,298, price is now NZ$3,000 per person
NZ$3,000
per person
1 Apr - 8 Apr
found 1 day ago
Return direct flight included
Christchurch (CHC) to Kahului (OGG)
8.4/10 Very Good! (744 reviews)
Great location. Quiet area and incredible views. Not the fanciest place but fantastic all the same. Comfortable room with plenty of space for the two of us.

Reviewed on 16 Jan 2026

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
Wailea
Save 100% on your flight
Price was NZ$7,853, price is now NZ$5,441 per person
NZ$5,441
per person
2 Mar - 8 Mar
found 3 hours ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
9.4/10 Exceptional! (1,001 reviews)
Everything was exceptional! Great property, quiet and peaceful

Reviewed on 6 Jan 2026

Montage Kapalua Bay

Montage Kapalua Bay

5 out of 5
Save 100% on your flight
Price was NZ$18,574, price is now NZ$13,654 per person
NZ$13,654
per person
1 Apr - 8 Apr
found 1 day ago
Return direct flight included
Christchurch (CHC) to Kahului (OGG)
9.6/10 Exceptional! (204 reviews)
I liked everything except the dining service. The staff was unfriendly and rude. They should not work there.- they kept us in the bar in excess of 15 minutes even after 4 tables had been open We had to walk over to tell them that tables had been open.

Reviewed on 4 Mar 2025

Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
Price was NZ$4,290, price is now NZ$3,265 per person
NZ$3,265
per person
1 Apr - 8 Apr
found 1 day ago
Return direct flight included
Christchurch (CHC) to Kahului (OGG)
8.4/10 Very Good! (1,548 reviews)
The resort was wonderful, the beach is so close and the location is near many points of interest

Reviewed on 16 Jan 2026

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
Keawakapu Beach showing landscape views, tropical scenes and a sandy beach

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

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$1,754 per night from 18 Jan to 19 Jan
NZ$1,754
18 Jan - 19 Jan
includes taxes & fees
9.6/10 Exceptional! (999 reviews)
Service was good

Reviewed on 8 Jan 2026

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$1,574 per night from 30 Jan to 31 Jan
NZ$1,574
30 Jan - 31 Jan
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
This property is amazing and you should definitely experience it! Only downside is that every single thing is paid. They have made it so that you can’t experience ever unless you book 3 days in any case so your research and be prepared to pay extra fees for all experiences

Reviewed on 14 Jan 2026

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$1,684 per night from 17 Feb to 18 Feb
NZ$1,684
17 Feb - 18 Feb
includes taxes & fees
9.2/10 Wonderful! (998 reviews)
I love the vibe of the hotel. Very family friendly and every one was courteous. The room was definitely not 5star condition though and Ocean view room was just a partial ocean view with very small sofa. I also did not like $60 mandatory valet parking per each time you take out my rental car. Over ...

Reviewed on 8 Jan 2026

Andaz Maui at Wailea Resort - a concept by Hyatt
See all 1,232 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$2,934, 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

Molokini Island

Maui Snorkeling Adventure to Molokini and Turtle Town

NZ$275
per adult
90% of travellers recommend
Maui Snorkeling Adventure to Molokini and Turtle Town
South Maui: Snorkel to Coral Gardens or Molokini Crater

South Maui: Snorkel to Coral Gardens or Molokini Crater

NZ$155
per adult
90% of travellers recommend
South Maui: Snorkel to Coral Gardens or Molokini Crater
Turtle Town Snorkel with Photo and Video

Turtle Town Snorkel with Photo and Video

NZ$222
per adult
100% of travellers recommend
Turtle Town Snorkel with Photo and Video
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.