Wailea Holidays from AU$1,837

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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.
The Gardens at West Maui

The Gardens at West Maui

3 out of 5
Save 100% on your flight
per person
21 Jun - 27 Jun
just found
Return direct flight included
Melbourne (MEL) to Kahului (OGG)
8.4/10 Very Good! (461 reviews)
It is in a great location for whatever we were looking to do. The rooms are nice but the studio one is very tight for a family of 4 but we made it work. Our Murphy beds headboard was completely broken. We also kept finding huge dead cockroaches. Yikes.

Reviewed on 26 Apr. 2025

Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
Save 100% on your flight
per person
21 Jun - 27 Jun
just found
Return direct flight included
Melbourne (MEL) to Kahului (OGG)
8.2/10 Very Good! (1,282 reviews)
Great location, comfortable beds and great AC. Lahaina Noon restaurant was good. Nice pool and excellent beach out front. Great coffee in the room, which is always appreciated. A little weird service checking in. The bellman weren't super helpful at the beginning. We booked this hotel through Expedia because it was a VIP hotel, usually meaning extra perks and we got nothing. Our room and view was nice on the 10th floor, but we were told an upgrade wasnt available. Too bad they dont have a hot tub anymore. Overall a good experience.

Reviewed on 29 Apr. 2025

Aston Maui Hill

Aston Maui Hill

3 out of 5
Save 100% on your flight
per person
13 Jul - 19 Jul
found 1 day ago
Return direct flight included
Sydney (SYD) to Kahului (OGG)
9/10 Wonderful! (786 reviews)
Nice landscape and large suite

Reviewed on 13 Apr. 2025

OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Save 100% on your flight
per person
21 Jun - 27 Jun
just found
Return direct flight included
Melbourne (MEL) to Kahului (OGG)
9.2/10 Wonderful! (1,019 reviews)
Beautiful friendly staff convenient all the way around!

Reviewed on 29 Apr. 2025

Aston at The Whaler on Kaanapali Beach

Aston at The Whaler on Kaanapali Beach

4 out of 5
Save 100% on your flight
per person
13 Jul - 19 Jul
found 1 day ago
Return direct flight included
Sydney (SYD) to Kahului (OGG)
9.2/10 Wonderful! (1,459 reviews)
Didn’t get the room I asked for when I scheduled the trip. 3 coffee makers. 1 didn’t have a carafe, 1 had a broken carafe. Didn’t see housekeeping the 9 days we were there.

Reviewed on 25 Apr. 2025

Our pick of the best Wailea Hotel Deals

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 AU$1,293 per night from 2 May to 3 May
AU$1,293
includes taxes & fees
2 May - 3 May
9.6/10 Exceptional! (1,002 reviews)
"One of the best resorts in Hawaii"

Reviewed on 26 Apr. 2025

Four Seasons Resort Maui at Wailea
Fairmont Kea Lani Maui
Fairmont Kea Lani Maui
4.5 out of 5
4100 Wailea Alanui Dr, Kihei, HI
The price is AU$1,814 per night from 11 May to 12 May
AU$1,814
includes taxes & fees
11 May - 12 May
9.4/10 Exceptional! (1,001 reviews)
"NA"

Reviewed on 25 Apr. 2025

Fairmont Kea Lani Maui
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$1,643 per night from 1 May to 2 May
AU$1,643
includes taxes & fees
1 May - 2 May
8.8/10 Excellent! (1,004 reviews)
"Very nice stay-grounds are beautiful. Staff at adult only pool 7/10-ran into many staff being short in their language to enforce wrist bands. For the price of resort it would be nice to have better customer service. Rest of staff very helpful and kind."

Reviewed on 23 Apr. 2025

Grand Wailea Maui, A Waldorf Astoria Resort
See all 1,179 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

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Wailea holiday package cost?
The most affordable Wailea package is AU$1,837, 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

Deluxe Molokini & Turtle Snorkel Luxury Sail Tour with Meals

Luxury Molokini & Turtle Snorkel Sail with Breakfast, Lunch & Open Bar

AU$453
per adult
96% of travellers recommend
Luxury Molokini & Turtle Snorkel Sail with Breakfast, Lunch & Open Bar
Guided Turtle Town Snorkeling Tour with Underwater Photos

Guided Turtle Town Snorkeling Tour with Underwater Photos

AU$180
per adult
100% of travellers recommend
Guided Turtle Town Snorkeling Tour with Underwater Photos
Wailea Beach: Guided Sea Scooter Snorkeling Tour

Wailea Beach: Guided Sea Scooter Snorkeling Tour

AU$234
per adult
100% of travellers recommend
Wailea Beach: Guided Sea Scooter Snorkeling Tour
See all activities in Kihei
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.