Wailea Holidays

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Price found within the past 48 hours. Click for updated prices.
  • Studio Suite, 1 Queen Bed | Terrace/patio
    Aug 17 - Aug 23

    Maui Banyan Vacation Club + Flight

    South Kihei
    6 nights
    3.0 star property
    8.0/10 - Very good (371 reviews)
    "Room is clean with full kitchen, nice beaches just across the road"
    Reviewed May 28, 2026
    Return • Auckland (AKL) - Oahu (HNL)
    AKL - HNL • 1 stop HNL - AKL • 1 stop
    NZ$3,324
    NZ$2,275
    per traveller
    found 9 hours ago
    Maui Banyan Vacation Club
  • Suite, 2 Bedrooms | Living area
    Aug 17 - Aug 23

    Maui Beach Vacation Club + Flight

    North Kihei
    6 nights
    2.5 star property
    8.4/10 - Very good (877 reviews)
    "Nice and relaxing experience. We just stayed here for 7 nights and our kids and our family enjoyed the pool multiple times with rarely any disturbance by other guests or residents. Our condo was well appointed, clean, well stocked with the basics for our stay. No a/c but it was not needed, open doors and windows and the ocean breeze is more than enough. The ceiling fans are mighty and they make air circulate well. All appliances, dinner and cooking ware were basically unused. The beach only..."
    Reviewed May 28, 2026
    Return • Auckland (AKL) - Oahu (HNL)
    AKL - HNL • 1 stop HNL - AKL • 1 stop
    NZ$3,332
    NZ$2,288
    per traveller
    found 9 hours ago
    Maui Beach Vacation Club
  • Courtyard
    Aug 17 - Aug 23

    Maui Schooner Resort + Flight

    Central Kihei
    6 nights
    3.5 star property
    9.2/10 - Wonderful (519 reviews)
    "Clean spacious 2 bedroom, 2 bathroom, 2 floor suite with all the amenities. Nice size lanai with view of pool, beach and sunset. No complaints! Loved it!"
    Reviewed May 19, 2026
    Return • Auckland (AKL) - Oahu (HNL)
    AKL - HNL • 1 stop HNL - AKL • 1 stop
    NZ$3,685
    NZ$2,832
    per traveller
    found 9 hours ago
    Maui Schooner Resort
  • Studio | Beach
    Aug 17 - Aug 23

    Lahaina Shores #218 Condo + Flight

    Lahaina
    6 nights
    3.0 star property
    Return • Auckland (AKL) - Oahu (HNL)
    AKL - HNL • 1 stop HNL - AKL • 1 stop
    NZ$3,458
    NZ$3,167
    per traveller
    found 9 hours ago
    Lahaina Shores #218 Condo

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
South Kihei

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$1,966 per night from 14 June to 15 June
NZ$1,966
14 June - 15 June
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Clean huge rooms with a great view, very friendly staff, lot of pool access, spa treatment was phenomenal."

Reviewed on 26 May 2026

Grand Wailea Maui, A Waldorf Astoria Resort
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
The price is NZ$2,298 per night from 27 June to 28 June
NZ$2,298
27 June - 28 June
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
"Great time and wonderful staff, restaurants were very good. Only thing that could have been better is alittle cleaner like the halls going to the rooms but other than that everything was great!"

Reviewed on 29 May 2026

Fairmont Kea Lani Maui
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$1,890 per night from 27 June to 28 June
NZ$1,890
27 June - 28 June
includes taxes & fees
9.6/10 Exceptional! (1,000 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
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

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

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

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

Makena State Park Beach

Activities

Sunrise Tour to Haleakala Includes Breakfast

Haleakala Sunrise Tour w/ Breakfast

NZ$384
per adult
88% of travellers recommend
Haleakala Sunrise Tour w/ Breakfast
Three tethered snorkelers diving in the ocean in Maui

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

NZ$301
per adult
96% of travellers recommend
Snorkeling Cruise to Molokini Crater & Turtle Town (Small Group)
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
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.