Wailea Holidays from AU$2,731

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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.
Sands of Kahana

Sands of Kahana

3 out of 5
Save 100% on your flight
Price was AU$4,405, price is now AU$2,731 per person
AU$2,731
per person
25 Dec - 1 Jan
just found
Return flight included
Sydney (SYD) to Kahului (OGG)
8.2/10 Very Good! (450 reviews)
The condo we stayed in was nice and it was massive. The restaurant on site is so good and the pools and beach access was nice! I didn’t have a problem with this because of the time of year, but there isn’t A/C in the units, so keep that in mind if you’re looking for that or your trip is in the warmer months.

Reviewed on 30 Oct 2025

Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
Save 100% on your flight
Price was AU$6,771, price is now AU$3,683 per person
AU$3,683
per person
25 Dec - 1 Jan
just found
Return flight included
Sydney (SYD) to Kahului (OGG)
8.4/10 Very Good! (1,500 reviews)
Everything was wonderful

Reviewed on 3 Nov 2025

OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Save 100% on your flight
Price was AU$7,660, price is now AU$4,291 per person
AU$4,291
per person
25 Dec - 1 Jan
just found
Return flight included
Sydney (SYD) to Kahului (OGG)
9/10 Wonderful! (1,384 reviews)
The property is beautiful and quiet.

Reviewed on 3 Nov 2025

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

4 out of 5
Save 100% on your flight
Price was AU$9,027, price is now AU$5,587 per person
AU$5,587
per person
25 Dec - 1 Jan
just found
Return flight included
Sydney (SYD) to Kahului (OGG)
9.6/10 Exceptional! (264 reviews)
Located on Kaanapali Beach, centrally located. The suite had a large bedroom, living area and 2 bathrooms, the carpet was a bit dated but everything else has great

Reviewed on 3 Nov 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 AU$8,060, price is now AU$5,472 per person
AU$5,472
per person
9 Jan - 15 Jan
found 18 hours ago
Return flight included
Sydney (SYD) to Kahului (OGG)
9.4/10 Exceptional! (1,002 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

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 AU$1,139 per night from 16 Nov to 17 Nov
AU$1,139
16 Nov - 17 Nov
includes taxes & fees
8.8/10 Excellent! (1,014 reviews)
Wonderful place can’t wait to go back great value

Reviewed on 2 Nov 2025

Grand Wailea Maui, A Waldorf Astoria Resort
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

4.5 out of 5
3700 Wailea Alanui Dr, Kihei, HI
The price is AU$1,051 per night from 1 Dec to 2 Dec
AU$1,051
1 Dec - 2 Dec
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
Really enjoyed our week here, nice room and extremely helpful and attentive staff. Location is great.

Reviewed on 29 Oct 2025

Wailea Beach Resort - Marriott, Maui
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$1,391 per night from 3 Dec to 4 Dec
AU$1,391
3 Dec - 4 Dec
includes taxes & fees
9.2/10 Wonderful! (998 reviews)
This place is not for the average traveller. Plan on a large budget. The breakfast buffet for two with one mimosa each ran roughly $160 after tip. Dinner for two was a little over $400, after tip. The Luao for two was around $850. It was our 10-year anniversary, and I was well prepared and fully ...

Reviewed on 9 Oct 2025

Andaz Maui at Wailea Resort - a concept by Hyatt
See all 1,181 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.
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Frequently asked questions

How much does a Wailea holiday package cost?
The most affordable Wailea package is AU$2,731, 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

Molokini Island

Molokini and Turtle Town Snorkeling Adventure Aboard the Malolo

AU$243
per adult
88% of travellers recommend
Molokini and Turtle Town Snorkeling Adventure Aboard the Malolo
Encounter Hawaii's Marine Life

Maui Ocean Center All Day Admission Ticket

AU$84
per adult
90% of travellers recommend
Maui Ocean Center All Day Admission Ticket
South Maui: PM Snorkel to Coral Gardens or Molokini Crater

South Maui: Snorkel to Coral Gardens or Molokini Crater

AU$137
per adult
90% of travellers recommend
South Maui: Snorkel to Coral Gardens or Molokini Crater
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.