Wailea Holidays from NZ$2,775

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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$3,321, price is now NZ$2,775 per person
NZ$2,775
per person
23 Apr - 27 Apr
found 20 hours ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
8.2/10 Very Good! (1,020 reviews)
Great pool, clean room and property. I got lucky and my condo overlooked the pool. Overall it was a great experience. There was some issues with finding a parking spot and some occupants parking in a manner that took two spots, but the front desk made a space available in the front lobby lot for me. It would have been even better if the condo had some of the basics for a tropical vacation-beach chairs, beach towels, umbrella or even some basic snorkel gear. Sadly, I had to access the beach without a towel or something to sit on.

Reviewed on 12 Mar 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$7,980, price is now NZ$5,466 per person
NZ$5,466
per person
17 Apr - 22 Apr
found 1 day ago
Return 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

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
Wailea
Save 100% on your flight
Price was NZ$7,716, price is now NZ$5,605 per person
NZ$5,605
per person
17 Apr - 22 Apr
found 1 day ago
Return flight included
Auckland (AKL) to Kahului (OGG)
9.4/10 Exceptional! (1,012 reviews)
Our housekeeping staff did an amazing job. Every I ne was so friendly.

Reviewed on 12 Mar 2026

Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea

5 out of 5
Wailea
Save 100% on your flight
Price was NZ$12,592, price is now NZ$9,921 per person
NZ$9,921
per person
17 Apr - 22 Apr
found 1 day ago
Return flight included
Auckland (AKL) to Kahului (OGG)
9.6/10 Exceptional! (45 reviews)
Womderful home, terrific service, access to hotel amenities was key.

Reviewed on 28 Feb 2026

The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua

5 out of 5
Price was NZ$5,936, price is now NZ$5,184 per person
NZ$5,184
per person
17 Apr - 22 Apr
found 1 day ago
Return flight included
Auckland (AKL) to Kahului (OGG)
9.2/10 Wonderful! (1,007 reviews)
Partial ocean view as promised. Food good but not outstanding and food prices were ridiculously high ( $60) for breakfast buffet. It was nice but very busy and noisy at times because of so many people. Nice luxury hotel but didnt always feel like the relaxed pace we have expected from Hawaii.

Reviewed on 12 Mar 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$1,471 per night from 11 Apr to 12 Apr
NZ$1,471
11 Apr - 12 Apr
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
The property is a true gem boasting expansive lush flora and fauna with multiple pools creating a swimmer's paradise. The various coves and levels including a waterpark and adult pool add to its allure. The expansive beach offers breathtaking views shared with the Four Seasons. Our room was exquisitely ...

Reviewed on 11 Mar 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$2,354 per night from 17 Mar to 18 Mar
NZ$2,354
17 Mar - 18 Mar
includes taxes & fees
9.6/10 Exceptional! (1,000 reviews)
Staff

Reviewed on 28 Feb 2026

Four Seasons Resort Maui at Wailea
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
The price is NZ$2,478 per night from 30 Mar to 31 Mar
NZ$2,478
30 Mar - 31 Mar
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
Didn’t have an ocean view but still a very wonderful 2week stay. Such a beautiful place! Staff was amazing

Reviewed on 14 Mar 2026

Fairmont Kea Lani Maui
See all 1,224 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$2,775, 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
Waterslide fun for all ages

Maui: Molokini & Turtle Town Snorkel & Waterslide Adventure

NZ$328
per adult
94% of travellers recommend
Maui: Molokini & Turtle Town Snorkel & Waterslide Adventure
Sail Maui 'Alihilani Sunset Sail

Akialoa Sunset Sail with Open Bar & Delicious Appetizers from Ma'alaea

NZ$173
per adult
96% of travellers recommend
Akialoa Sunset Sail with Open Bar & Delicious Appetizers from Ma'alaea
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.