Wailea Vacations from ￥236,965

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    Better together
    Save up to ￥45,448 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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The Latest Wailea Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Maui Banyan - Maui Condo & Home

Maui Banyan - Maui Condo & Home

3 out of 5
per person
Sep 7 - Sep 14
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
7.6/10 Good! (61 reviews)
Montage Kapalua Bay

Montage Kapalua Bay

5 out of 5
Save 100% on your flight
per person
Sep 6 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
9.6/10 Exceptional! (200 reviews)
I liked everything except the dining service. The staff was unfriendly and rude. They should not work there.- they kept us in the bar in excess of 15 minutes even after 4 tables had been open We had to walk over to tell them that tables had been open.

Reviewed on Mar 4, 2025

Kamaole Sands - Maui Condo & Home

Kamaole Sands - Maui Condo & Home

3 out of 5
per person
Sep 7 - Sep 14
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
8.2/10 Very Good! (302 reviews)
Maui Kamaole - Maui Condo & Home

Maui Kamaole - Maui Condo & Home

3 out of 5
per person
Sep 6 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
8.8/10 Excellent! (393 reviews)
Castle Kama'ole Sands

Castle Kama'ole Sands

3 out of 5
per person
Sep 6 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
8/10 Very Good! (2,236 reviews)
Was nice and clean and decorated nicely. Best of all it’s in Maui ❤️❤️

Reviewed on Jun 19, 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 ￥139,525 per night from Jul 15 to Jul 16
￥139,525
￥172,589 total
Jul 15 - Jul 16
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"We had the best time! The property is absolutely gorgeous and the weather was perfect."

Reviewed on Jun 17, 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 ￥108,837 per night from Jul 14 to Jul 15
￥108,837
￥128,387 total
Jul 14 - Jul 15
includes taxes & fees
9.6/10 Exceptional! (999 reviews)
"Amazing service"

Reviewed on Jun 9, 2025

Four Seasons Resort Maui at Wailea
Wailea Beach Resort - Marriott, Maui
Wailea Beach Resort - Marriott, Maui
4.5 out of 5
3700 Wailea Alanui Dr, Kihei, HI
The price is ￥89,331 per night from Jun 23 to Jun 24
￥89,331
￥113,670 total
Jun 23 - Jun 24
includes taxes & fees
9/10 Wonderful! (994 reviews)
"Everything was great. Service was very good...everyone happy and willing to be of service. Adult pool area was awesome....very quiet..great music, service, enough towels and bar location was perfect. Will stay there again..."

Reviewed on Jun 18, 2025

Wailea Beach Resort - Marriott, Maui
See all 1,193 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 ￥236,965, 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

4.5/5(1,614 reviews)

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

4.5/5(438 reviews)

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

4.5/5(14 reviews)

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

Little Beach

Things to do

Guided Turtle Town Snorkeling Tour with Underwater Photos

Snorkel with Turtles and Free Underwater Photos - Turtle Town

￥18,653
per adult
100% of travellers recommend
Snorkel with Turtles and Free Underwater Photos - Turtle Town
Deluxe Molokini & Turtle Snorkel Luxury Sail Tour with Meals

Luxury Molokini & Turtle Snorkel Sail with Breakfast, Lunch & Open Bar

￥41,789
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

￥21,545
per adult
100% of travellers recommend
Wailea Beach: Guided Sea Scooter Snorkeling 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.