Wailea Holidays from AU$788

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Your Wailea Holiday

Lose yourself in the magic of this picturesque neighbourhood with a Wailea holiday package. From its surfing and coastal beaches to its views, there's something here for every traveller. Not sure what to do and see during your trip to Wailea? Nearby attractions such as Wailea Beach, Kamaole Beach Park and Keawakapu Beach North are good places to start. Whatever your travel plans or budget, booking your dream Wailea holiday is quick and easy with Expedia.

Top Holiday Package Deals in Wailea

Price found within the past 48 hours. Click for updated prices.
AEI at Kaanapali Shores

AEI at Kaanapali Shores

4 out of 5
Price was AU$1,081, price is now AU$788 per person
AU$788
per person
29 Oct - 1 Nov
found 1 day ago
Return flight included
San Diego (SAN) to Kahului (OGG)
8.8/10 Excellent! (454 reviews)
Room was very nice and staff was helpful all around. Parking is very reasonably priced. Just wish daily room service was included, you can request however with a fee.

Reviewed on 17 Sept 2025

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

4 out of 5
Save 100% on your flight
Price was AU$1,798, price is now AU$1,139 per person
AU$1,139
per person
29 Oct - 1 Nov
found 1 day ago
Return flight included
San Diego (SAN) to Kahului (OGG)
9.6/10 Exceptional! (237 reviews)
Property was excellent.

Reviewed on 18 Sept 2025

Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
Save 100% on your flight
Price was AU$1,291, price is now AU$875 per person
AU$875
per person
29 Oct - 1 Nov
found 1 day ago
Return flight included
San Diego (SAN) to Kahului (OGG)
8.4/10 Very Good! (1,448 reviews)
Great location and friendly staff. Only downside is no microwave in the rooms.

Reviewed on 18 Sept 2025

Wailea Beach Villas

Wailea Beach Villas

4.5 out of 5
Wailea
Save 100% on your flight
Price was AU$3,560, price is now AU$2,604 per person
AU$2,604
per person
29 Oct - 1 Nov
found 1 day ago
Return flight included
San Diego (SAN) to Kahului (OGG)
9.8/10 Exceptional! (177 reviews)
NOT QUIET. Maintance makes lots of noise right below our balcony.

Reviewed on 3 Sept 2025

AEI at The Mahana Kaanapali Resort

AEI at The Mahana Kaanapali Resort

4 out of 5
Price was AU$1,320, price is now AU$1,011 per person
AU$1,011
per person
29 Oct - 1 Nov
found 1 day ago
Return flight included
San Diego (SAN) to Kahului (OGG)
8.8/10 Excellent! (278 reviews)
easygoing to the beach

Reviewed on 6 Sept 2025

Our pick of the best Wailea Hotel Deals

Andaz Maui at Wailea Resort - a concept by Hyatt

Andaz Maui at Wailea Resort - a concept by Hyatt

4.5 out of 5
3550 Wailea Alanui Dr, Kihei, HI
The price is AU$1,300 per night from 12 Oct to 13 Oct
AU$1,300
12 Oct - 13 Oct
includes taxes & fees
9.2/10 Wonderful! (998 reviews)
"Amazing location and service. Very beautiful"

Reviewed on 1 Sept 2025

Andaz Maui at Wailea Resort - a concept by Hyatt
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 AU$1,295 per night from 28 Sept to 29 Sept
AU$1,295
28 Sept - 29 Sept
includes taxes & fees
8.8/10 Excellent! (1,011 reviews)
"Stunning resort!"

Reviewed on 15 Sept 2025

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 AU$1,960 per night from 1 Oct to 2 Oct
AU$1,960
1 Oct - 2 Oct
includes taxes & fees
9.4/10 Exceptional! (1,010 reviews)
"I like how they had a gift in our room to congratulate us on our wedding"

Reviewed on 18 Sept 2025

Fairmont Kea Lani Maui
See all 1,197 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.
All Inclusive Holidays
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beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Wailea holiday package cost?
The most affordable Wailea package is AU$788, 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

4.5/5(32 reviews)

Make friends with the local marine life at this popular beach resort where luxury comes as standard.

Wailea Beach
Maluaka Beach which includes rocky coastline, mountains and a pebble beach

Maluaka Beach

4/5(3 reviews)

This sandy, tree-lined stretch of coast is one of the best spots on Maui for viewing Hawaiian green turtles.

Maluaka Beach
Makena Beach State Park showing a beach

Makena State Park Beach

4.5/5(7 reviews)

Choose from three different beaches, each with its own character, along this unspoilt stretch of Maui’s southern shoreline.

Makena State Park Beach

Activities

Book Your Unfogetable Adventure Now

Road to Hana Adventure with Farm to Table Lunch in Town of Hana

AU$388
per adult
88% of travellers recommend
Road to Hana Adventure with Farm to Table Lunch in Town of Hana
Guided Turtle Town Snorkeling Tour with Underwater Photos

Snorkel with Turtles and Free Underwater Photos - Turtle Town

AU$197
per adult
100% of travellers recommend
Snorkel with Turtles and Free Underwater Photos - Turtle Town
Maui Family and Couple Beach Photo Session

Maui Family and Couple Beach Photo Session

AU$151
per adult
100% of travellers recommend
Maui Family and Couple Beach Photo Session
See all activities in Kihei

Explore a world of travel with Expedia

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.