Wailea Holidays from NZ$1,982

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Top Holiday Package Deals in Wailea

Price found within the past 48 hours. Click for updated prices.
The Gardens at West Maui

The Gardens at West Maui

3 out of 5
Save 100% on your flight
Price was NZ$3,985, price is now NZ$1,982 per person
NZ$1,982
per person
19 Feb - 24 Feb
found 1 day ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
8.4/10 Very Good! (512 reviews)
This is a great stay on the usually outrageously priced west side of Maui! The kitchen had every amenity you could ask for, plus a washer/dryer in the room itself with complimentary detergent. Bed was comfy enough, and it felt more like an apartment than a hotel…very spacious The downside was general room cleanliness upon arrival (you could feel the sand on the sheets and on your feet if you walked barefoot before we even went to the beach on our first day). We were also traveling with an infant/young toddler and were offered virtually no accommodations but knew this prior to rental. Overall, a great value for one of the most pristine areas on the island.

Reviewed on 13 Dec 2025

Kahana Villa

Kahana Villa

3 out of 5
Save 100% on your flight
Price was NZ$3,917, price is now NZ$2,120 per person
NZ$2,120
per person
19 Feb - 24 Feb
found 1 day ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
8/10 Very Good! (351 reviews)
Hot water ran out within 5 minutes besides that good hotel and location

Reviewed on 30 Sept 2025

Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
South Kihei
Save 100% on your flight
Price was NZ$3,689, price is now NZ$2,033 per person
NZ$2,033
per person
19 Feb - 24 Feb
found 1 day ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
8/10 Very Good! (351 reviews)
All the workers were so nice

Reviewed on 2 Dec 2025

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$7,237, price is now NZ$4,237 per person
NZ$4,237
per person
19 Feb - 24 Feb
found 1 day ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
9.4/10 Exceptional! (1,001 reviews)
Great resort with great amenities! Very convenient to downtown wailea and the beaches and the staff are super friendly and attentive!

Reviewed on 27 Aug 2025

OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Save 100% on your flight
Price was NZ$4,562, price is now NZ$2,714 per person
NZ$2,714
per person
19 Feb - 24 Feb
found 1 day ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
9/10 Wonderful! (1,465 reviews)
Everything and everyone was nice and clean and the staff so friendly and helpful. Only thing i wish there was kids playgrounds or pool area for the kids. And pool has to much chlorine in the water. Other then that i love it and it is very hawaiian hotel

Reviewed on 18 Dec 2025

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

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$1,518 per night from 11 Jan to 12 Jan
NZ$1,518
11 Jan - 12 Jan 2026
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Everything was great. We would totally stay again.

Reviewed on 7 Dec 2025

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$1,544 per night from 19 Dec to 20 Dec
NZ$1,544
19 Dec - 20 Dec
includes taxes & fees
9.6/10 Exceptional! (999 reviews)
This property has long been one of my global Four Seasons favorites, and I remain truly grateful for the warm hospitality I always receive. I was also very appreciative of the wonderful upgrade to an ocean-view room — mahalo for that thoughtful gesture. I’ve been visiting this resort regularly since ...

Reviewed on 2 Dec 2025

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$1,424 per night from 9 Jan to 10 Jan
NZ$1,424
9 Jan - 10 Jan 2026
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
It was a great place to stay with my family for my 4-year-old twin's birthday, and there were a lot of activities to do such as yoga, pilates, kids activities, and among all other things. Not to mention the road trip that we’ve taken to Hana, which was very nice and fun.

Reviewed on 12 Dec 2025

Wailea Beach Resort - Marriott, Maui
See all 1,209 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$1,982, 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$249
per adult
90% of travellers recommend
Maui Snorkeling Adventure to Molokini and Turtle Town
Road to Hana Tour- Book your unforgettable Maui Adventure now and take home memories for a lifetime!

Maui: Road to Hana Adventure with Farm to Table Lunch

NZ$403
per adult
90% of travellers recommend
Maui: Road to Hana Adventure with Farm to Table Lunch
Beautiful views

Maui Premium Dinner Cruise: Four Course Dining Experience

NZ$303
per adult
94% of travellers recommend
Maui Premium Dinner Cruise: Four Course Dining Experience
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.