Wailea Vacations from ￥684,415

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The Latest Wailea Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
Save 100% on your flight
Price was ￥1,137,204, price is now ￥684,415 per person
￥684,415
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
16.8/10 Exceptional! (1,548 reviews)
That’s a really nice place

Reviewed on Nov 26, 2025

Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea

5 out of 5
Wailea
Save 100% on your flight
Price was ￥4,059,356, price is now ￥2,669,272 per person
￥2,669,272
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
19.2/10 Exceptional! (44 reviews)
We stayed in Villa 99-5. . To sum it up quickly, the price to experience was in our opinion way too high. Also as a member an elite member, I did not get the discounts on the Cabana rentals and beach chair. The restaurant staff and food was very good. For the price we believe that there should be more comps than provided. Also on checking out the elevator was not working to allow the upstairs to bring their luggage down conveniently. The other complaint which was an ongoing complaint was the TVs not that you need to watch him when you're on such a beautiful island but if kids were staying they would need some entertainment at the evening I would believe. Again the cost to the experience was too expensive. For what you got. I would look at other opportunities or options for lodging where there was more bang for the buck.

Reviewed on Oct 22, 2025

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

4 out of 5
Price was ￥1,170,628, price is now ￥789,398 per person
￥789,398
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
19.2/10 Exceptional! (292 reviews)
Extremely clean with a fantastic location!

Reviewed on Nov 25, 2025

OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Price was ￥1,005,076, price is now ￥694,236 per person
￥694,236
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
18/10 Exceptional! (1,465 reviews)
Beautiful location. Staff was fantastic. View was stunning. Breakfast was good. Housekeeping was fabulous.

Reviewed on Nov 25, 2025

OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa

4 out of 5
Price was ￥1,237,592, price is now ￥901,533 per person
￥901,533
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
17.6/10 Exceptional! (2,864 reviews)
Loved it. Great for families

Reviewed on Nov 19, 2025

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 a sandy beach, landscape views and tropical scenes

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

Frequently asked questions

How much does a Wailea vacation package cost?
The most affordable Wailea package is ￥684,415, 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

Wailea Beach showing tropical scenes, swimming and a sandy beach

Wailea Beach

This stretch of powdery sand is part of an upscale resort community and is an ideal place to sunbathe, snorkel, and dive with Hawaiian green turtles and manta rays.

Wailea Beach
Makena Beach State Park showing a beach

Makena State Park Beach

Three distinct, undeveloped beaches and a dormant volcano crater form this scenic southern region of Maui.

Makena State Park Beach
Little Beach featuring general coastal views

Little Beach

Why not spend a carefree afternoon at Little Beach during your travels in Kihei? Wander the seaside or discover the beautiful sunsets in this relaxing area.

Little Beach

Things to do

Te Au Moana Luau at the Wailea Beach Marriott Resort

Te Au Moana Luau at the Wailea Beach Marriott Resort

￥33,843
per adult
92% of travellers recommend
Te Au Moana Luau at the Wailea Beach Marriott Resort
Lahaina Sunset Dinner Cruise

From Ma'alaea Harbor: Sunset Dinner Cruise Aboard the Quicksilver

￥22,030
per adult
80% of travellers recommend
From Ma'alaea Harbor: Sunset Dinner Cruise Aboard the Quicksilver
South Maui: PM Snorkel to Coral Gardens or Molokini Crater

South Maui: Snorkel to Coral Gardens or Molokini Crater

￥14,159
per adult
90% of travellers recommend
South Maui: Snorkel to Coral Gardens or Molokini Crater
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.