Wailea Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • 4 outdoor pools, pool umbrellas, pool loungers
    Aug 12 - Aug 30

    Wailea Beach Resort - Marriott, Maui + Flight

    Wailea
    18 nights
    4.5 star property
    9.2/10 - Wonderful (1,004 reviews)
    "Good"
    Reviewed June 8, 2026
    Return • Auckland (AKL) - Oahu (HNL)
    AKL - HNL • 1 stop HNL - AKL • 1 stop
    Save 100% on your flight
    NZ$14,902
    NZ$10,422
    per traveller
    found 1 day ago
    Wailea Beach Resort - Marriott, Maui
  • 9 outdoor pools, pool cabanas (surcharge), pool loungers
    Jul 21 - Aug 4

    Grand Wailea Maui, A Waldorf Astoria Resort + Flight

    Wailea
    14 nights
    5.0 star property
    8.8/10 - Excellent (1,014 reviews)
    "Loved the view!"
    Reviewed June 8, 2026
    Return • Auckland (AKL) - Oahu (HNL)
    AKL - HNL • 2 stops HNL - AKL • 2 stops
    Save 100% on your flight
    NZ$15,040
    NZ$10,485
    per traveller
    found 1 day ago
    Grand Wailea Maui, A Waldorf Astoria Resort

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 coastal landscape with palm trees and a grassy area.

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$1,767 per night from 9 July to 10 July
NZ$1,767
9 July - 10 July
includes taxes & fees
8.8/10 Excellent! (1,014 reviews)
"Loved the view!"

Reviewed on 8 June 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$2,044 per night from 7 July to 8 July
NZ$2,044
7 July - 8 July
includes taxes & fees
9.6/10 Exceptional! (1,001 reviews)
"Absolutely beautiful! Staff were all friendly and attentive. We really appreciated the cleanliness, amenities, and high level of service."

Reviewed on 25 May 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$1,639 per night from 7 July to 8 July
NZ$1,639
7 July - 8 July
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"Good"

Reviewed on 8 June 2026

Wailea Beach Resort - Marriott, Maui
See all 1,226 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 , 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

Wailea Beach

4.5/5(33 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

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 State Park Beach

Makena State Park Beach

4.5/5(8 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

Maui: Molokini & Turtle Town Snorkel & Waterslide Adventure

Maui: Molokini & Turtle Town Snorkel & Waterslide Adventure

NZ$330
per adult
94% of travellers recommend
Maui: Molokini & Turtle Town Snorkel & Waterslide Adventure
Wailea Wildlife Tour with Snorkeling

Wailea Wildlife Experience: Snorkel With Sea Turtles

NZ$166
per adult
Wailea Wildlife Experience: Snorkel With Sea Turtles
Kayaking Adventure

Makena Turtle Town Eco Adventure in Maui

NZ$166
per adult
88% of travellers recommend
Makena Turtle Town Eco Adventure in Maui
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.