Wailea Holidays from NZ$2,909

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Top Holiday Package Deals in Wailea

Price found within the past 48 hours. Click for updated prices.
Kahana Falls Maui by VRI Americas

Kahana Falls Maui by VRI Americas

3.5 out of 5
Price was NZ$3,257, price is now NZ$2,909 per person
NZ$2,909
per person
26 Mar - 31 Mar
found 3 hours ago
Return flight included
Auckland (AKL) to Kahului (OGG)
8/10 Very Good! (959 reviews)
Hotel was okay … ac doesn’t work well… but good location

Reviewed on 15 Feb 2026

Montage Kapalua Bay

Montage Kapalua Bay

5 out of 5
Save 100% on your flight
Price was NZ$23,156, price is now NZ$17,129 per person
NZ$17,129
per person
26 Mar - 31 Mar
found 3 hours ago
Return flight included
Auckland (AKL) to Kahului (OGG)
9.6/10 Exceptional! (204 reviews)
Staff was great. Some maintenance issues, leaking water dispenser on fridge leading to pooling and warping of floor. Same on large lanai. Otherwise, great

Reviewed on 14 Feb 2026

Kapalua Villas Maui

Kapalua Villas Maui

4 out of 5
Price was NZ$4,472, price is now NZ$3,385 per person
NZ$3,385
per person
26 Mar - 31 Mar
found 3 hours ago
Return flight included
Auckland (AKL) to Kahului (OGG)
8.8/10 Excellent! (957 reviews)
Incredible water view. Whales everywhere

Reviewed on 31 Jan 2026

Aston Kaanapali Shores

Aston Kaanapali Shores

3.5 out of 5
Price was NZ$4,414, price is now NZ$4,049 per person
NZ$4,049
per person
26 Mar - 31 Mar
found 3 hours ago
Return flight included
Auckland (AKL) to Kahului (OGG)
8.6/10 Excellent! (3,865 reviews)
Friendly staff Only wish we were warned about the power outage. All our food in the fridge had to be thrown out as such a long period of no power.

Reviewed on 16 Feb 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
Aloha state of mind #lifeatexpedia

South Kihei

3 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$1,499 per night from 3 Mar to 4 Mar
NZ$1,499
3 Mar - 4 Mar
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
Everything was fantastic from the room to the friendly staff and nearby surroundings. We had a great time

Reviewed on 16 Feb 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$1,673 per night from 3 Mar to 4 Mar
NZ$1,673
3 Mar - 4 Mar
includes taxes & fees
9.6/10 Exceptional! (1,002 reviews)
When I arrived, renovations were underway. I was placed in a section of the hotel where the noise associated with said renovations was pervasive and quite audible. I was not informed in advance that I would be subjected to noise that is incompatible with the rest and relaxation that

Reviewed on 13 Feb 2026

Four Seasons Resort Maui at Wailea
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

4.5 out of 5
3700 Wailea Alanui Dr Kihei HI
The price is NZ$1,352 per night from 20 Mar to 21 Mar
NZ$1,352
20 Mar - 21 Mar
includes taxes & fees
9.2/10 Wonderful! (1,006 reviews)
nice room and location. Love everything here - especially the early yoga/meditation class we took under the big tree.

Reviewed on 17 Feb 2026

Wailea Beach Resort - Marriott, Maui
See all 1,222 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$2,909, 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

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

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

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$267
per adult
90% of travellers recommend
Maui Snorkeling Adventure to Molokini and Turtle Town
Snorkeling Cruise to Molokini Crater & Turtle Town

Snorkeling Cruise to Molokini Crater & Turtle Town (Small Group)

NZ$298
per adult
96% of travellers recommend
Snorkeling Cruise to Molokini Crater & Turtle Town (Small Group)
Waterslide fun for all ages

Maui: Molokini & Turtle Town Snorkel & Waterslide Adventure

NZ$332
per adult
94% of travellers recommend
Maui: Molokini & Turtle Town Snorkel & Waterslide Adventure
See all activities in Kihei

Explore a world of travel with Expedia

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