Wailea Vacations from ₩493,759

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The Latest Wailea Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Kahana Villa

Kahana Villa

3 out of 5
Save 100% on your flight
per person
Sep 5 - Sep 7
found 1 day ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
8/10 Very Good! (341 reviews)
I’ve been trying to reach this property since I’ve checked out. I left behind in the room a Nikon camera and have not been able to get a hold of them to retrieve my item. Communication is difficult. Please contact me.

Reviewed on Aug 1, 2025

Mana Kai Maui- Official Onsite Rental

Mana Kai Maui- Official Onsite Rental

3.5 out of 5
Save 100% on your flight
per person
Oct 6 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Seoul (ICN) to Kahului (OGG)
8.8/10 Excellent! (1,001 reviews)
Beautiful property for a great price

Reviewed on Aug 3, 2025

OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Save 100% on your flight
per person
Sep 5 - Sep 7
found 1 day ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
9/10 Wonderful! (1,242 reviews)
Clean and comfortable, great staff

Reviewed on Aug 4, 2025

Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
per person
Oct 6 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Seoul (ICN) to Kahului (OGG)
8.4/10 Very Good! (1,385 reviews)
Amazing place with an amazing beach. Lots to do. Miss it already

Reviewed on Aug 5, 2025

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

4 out of 5
Save 100% on your flight
per person
Sep 5 - Sep 7
found 1 day ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
9.6/10 Exceptional! (210 reviews)
I highly recommend this resort. Its prime location near the beach makes it incredibly convenient for guests, and it’s just a short distance from all the main coral reef tour departures. The proximity to local attractions and activities adds great value to the stay, especially for those looking to explore the natural beauty of the area.

Reviewed on Aug 4, 2025

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 ₩973,662 per night from Aug 17 to Aug 18
₩973,662
₩1,238,408 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"The rooms were comfortable. Shower was great! Kids loved the giant bathtub! Pools were nice. Tarzan swing was fun. Staff was friendly"

Reviewed on Aug 2, 2025

Grand Wailea Maui, A Waldorf Astoria Resort
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 ₩976,404 per night from Sep 5 to Sep 6
₩976,404
₩1,151,786 total
Sep 5 - Sep 6
includes taxes & fees
9.6/10 Exceptional! (1,000 reviews)
Best hotel ever…
"Everything was top rate! Can’t wait to go back."

Reviewed on Aug 3, 2025

Four Seasons Resort Maui at Wailea
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 ₩993,023 per night from Aug 12 to Aug 13
₩993,023
₩1,252,702 total
Aug 12 - Aug 13
includes taxes & fees
9.2/10 Wonderful! (999 reviews)
"It was ok"

Reviewed on Aug 3, 2025

Andaz Maui at Wailea Resort - a concept by Hyatt
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.

Frequently asked questions

How much does a Wailea vacation package cost?
The most affordable Wailea package is ₩493,759, so your dream vacation can become a reality — without it costing a fortune. Combine flights, hotels, car rentals and more to custom build a package that matches your traveling style.
How do I get a cheap travel package to Wailea?
Crafting your own Wailea vacation 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 vacation 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 vacation?
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 organizing an upscale romantic escape or a budget family adventure, browse our vacation packages today.
If I'm not able to travel, can I cancel my Wailea vacation package?
Yes, you can. We realize life doesn't always go to plan, so we're here to help if you need to make changes to your Wailea vacation 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

Keawakapu Beach which includes tropical scenes, general coastal views and a hotel

Keawakapu Beach North

Enjoy the peace and quiet at one of Maui’s less crowded and wider beaches, where kids can wander around the rock pools, and divers can explore the artificial reef.

Keawakapu Beach North

Kihei Regional Park

Enjoy the beautiful sunsets and explore Kihei Regional Park, a lovely green space in Kihei. Stroll along the seaside in this romantic area, or check out its top-notch restaurants.

Kihei Regional Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.