Wailea Holidays from AU$799
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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.
Lahaina Shores Beach Resort By Castle
AU$1,074
per person
9 Nov - 15 Nov
found 4 hours ago
Return flight included
Honolulu (HNL) to Kahului (OGG)
9/10 Wonderful! (2 reviews)
Its a great place w great big rooms, super clean, the view is great too you get both beach and mountains view.
Reviewed on 15 Sept 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
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.
Central Kihei
1 out of top 10 points of interest in this area
While visiting Central Kihei, you might make a stop by sights like Kihei Regional Park and Kihei Town Center Shopping Center.
Makena
A noteworthy feature of Makena is its stunning beaches. While you're in town, be sure to stop and check out Makena State Park Beach and Maluaka Beach.
North Kihei
If you're spending some time in North Kihei, Hawaiian Islands Humpback Whale National Marine Sanctuary Headquarters and Kalepolepo Beach Park are top sights worth seeing.
Halama Street
While visiting Halama Street, you might make a stop by sights like Kihei Town Center Shopping Center and Coast Guard Beach.
Our pick of the best Wailea Hotel Deals
Grand Wailea Maui, A Waldorf Astoria Resort
3850 Wailea Alanui Drive Kihei HI
AU$1,307
2 Oct - 3 Oct
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
"Some of the best customer service we’ve ever had. Room was gorgeous, grounds were stunning, views were amazing"
Reviewed on 14 Sept 2026
Wailea Beach Resort - Marriott, Maui
3700 Wailea Alanui Dr Kihei HI
AU$1,171
5 Oct - 6 Oct
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"great ocean view"
Reviewed on 15 Sept 2026
Four Seasons Resort Maui at Wailea
3900 Wailea Alanui Drive Kihei HI
AU$1,463
19 Sept - 20 Sept
includes taxes & fees
9.6/10 Exceptional! (1,000 reviews)
"Loved every moment we spent there! Best decision to stay at Four Seasons for our honeymoon trip :)"
Reviewed on 25 Aug 2026
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 AU$799, 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.
Stay near popular Wailea attractions
Wailea Beach
9.4/10 (4,138 reviews)
Make friends with the local marine life at this popular beach resort where luxury comes as standard.
Maluaka Beach
9.4/10 (731 reviews)
This sandy, tree-lined stretch of coast is one of the best spots on Maui for viewing Hawaiian green turtles.
Makena State Park Beach
9.4/10 (1,787 reviews)
Choose from three different beaches, each with its own character, along this unspoilt stretch of Maui’s southern shoreline.
Makena Beaches
9.0/10 (18 reviews)
Why not spend a lazy afternoon at Makena Beaches during your trip to Kihei? Stroll along the seaside or discover the beautiful sunsets in this romantic area.
Photo by Torrey Kwok
Polo Beach
9.2/10 (186 reviews)
If a restful holiday is part of your travel plans, Polo Beach might be the perfect place to visit during your trip to Kihei. Wander the seaside or discover the beautiful sunsets in this romantic area.
Photo by Quintin Doroquez
Shops at Wailea
9.2/10 (381 reviews)
You can enjoy retail therapy at Shops at Wailea during your stay in Kihei. Wander the beautiful beaches or discover the beautiful sunsets in this romantic area.
Photo by Kathie Mercier
Ulua Beach
8.8/10 (53 reviews)
Why not spend a care-free afternoon at Ulua Beach during your travels in Kihei? Discover the beautiful sunsets in this romantic area or enjoy its snorkelling spots.
Mokapu Beach
10.0/10 (2 reviews)
Why not spend a care-free afternoon at Mokapu Beach during your travels in Kihei? Amble around this relaxing area's seaside or seek out the snorkelling spots.
Activities
Akialoa Sunset Sail with Open Bar & Delicious Appetizers from Ma'alaea
AU$145
per adult
96% of travellers recommend
Sunset Dinner Cruise aboard Quicksilver: Prime Rib, Fish, Chicken or Pasta
AU$185
per adult
84% of travellers recommend
Award-winning Dinner Cruise: Four Course Dining Experience
AU$237
per adult
90% of travellers recommend
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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.