Wailea Holidays from AU$2,893

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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.
Guava Suite

Guava Suite

3 out of 5
per person
28 Jun - 5 Jul
found 1 day ago
Return flight included
Sydney (SYD) to Kahului (OGG)
9.6/10 Exceptional! (5 reviews)
This property was perfect! Friendly staff and very clean room. We loved all the snacks! They had so many amenities! They had a cooler, chairs, towels, and an umbrella for the beach. All we needed was our clothes for our vacation! We will be back! Mahalo!

Reviewed on 30 Jun. 2024

OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Save 100% on your flight
per person
28 Jun - 5 Jul
found 1 day ago
Return flight included
Sydney (SYD) to Kahului (OGG)
9.2/10 Wonderful! (1,019 reviews)
Absolutely amazing resort! From the friendly staff all around the resort to the complimentary cultural activities guests could take part it. It made our first visit to Hawai’i one of the most amazing vacations we have had. Our room was amazing with double sliding doors opening to an ocean view. Highly recommend!

Reviewed on 14 Apr. 2025

The Historic Wailuku Inn

The Historic Wailuku Inn

3 out of 5
per person
28 Jun - 5 Jul
found 1 day ago
Return flight included
Sydney (SYD) to Kahului (OGG)
9.2/10 Wonderful! (20 reviews)
There is no on site staff. Communication is bad. Due to the traveling, we missed the email on the door code. So when we arrived, we called 3 times and emailed 2 times but no answer and that was between 3pm to 4pm. We asked around and figured out via Expedia, your website and searched all our emails. Finally we were able to get into the property - an hour and half after arriving. The shower room did not have a hand rail - concerning the safety.

Reviewed on 13 Apr. 2025

Hyatt Regency Maui Resort & Spa

Hyatt Regency Maui Resort & Spa

4 out of 5
per person
28 Jun - 5 Jul
found 1 day ago
Return flight included
Sydney (SYD) to Kahului (OGG)
9.2/10 Wonderful! (1,013 reviews)
Most gorgeous resort I’ve ever seen. Wonderful comfortable rooms as well

Reviewed on 14 Apr. 2025

Residence Inn by Marriott Maui Wailea

Residence Inn by Marriott Maui Wailea

3.5 out of 5
Wailea
per person
28 Jun - 5 Jul
found 1 day ago
Return flight included
Sydney (SYD) to Kahului (OGG)
9.2/10 Wonderful! (939 reviews)
Excellent service! Very polite and easy going staff. Our 2 kids enjoyed the pool.

Reviewed on 28 Mar. 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$1,322 per night from 2 May to 3 May
AU$1,322
includes taxes & fees
2 May - 3 May
9.6/10 Exceptional! (999 reviews)
"This must be the most beautiful and welcoming property in Maui. Yes, it is expensive but they do everything right. Cultural experiences, sporting experiences, poolside retreats, etc, etc all included. It is also on the best beach on the island. We loved our entire trip. Thank you very much to all ..."

Reviewed on 5 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$1,986 per night from 7 May to 8 May
AU$1,986
includes taxes & fees
7 May - 8 May
9.4/10 Exceptional! (1,007 reviews)
"The hotel and grounds are meticulous. The Fairmont has truly thought of every detail big and small. What a wonderful experience for the entire family. Highly recommend!"

Reviewed on 11 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$1,680 per night from 1 May to 2 May
AU$1,680
includes taxes & fees
1 May - 2 May
8.8/10 Excellent! (1,001 reviews)
"loved it lots of families tho"

Reviewed on 11 Apr. 2025

Grand Wailea Maui, A Waldorf Astoria Resort
See all 1,169 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$2,893, 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$460
per adult
96% of travellers recommend
Luxury Molokini & Turtle Snorkel Sail with Breakfast, Lunch & Open Bar
Wailea Beach: Guided Sea Scooter Snorkeling Tour

Wailea Beach: Guided Sea Scooter Snorkeling Tour

AU$237
per adult
100% of travellers recommend
Wailea Beach: Guided Sea Scooter Snorkeling Tour
Morning views at Haleakalā National Park

Haleakala National Park Sunrise Tour

AU$383
per adult
92% of travellers recommend
Haleakala National Park Sunrise 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.