Wailea Vacations from ￥190,228

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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
per person
Aug 24 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
8/10 Very Good! (336 reviews)
The room was great, we had an ocean view with everything we needed for the week, we will be going back!

Reviewed on May 29, 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
Aug 24 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
8.8/10 Excellent! (1,002 reviews)
Beautiful beach right near hotel and great room with lots of AC. definitely recommend renting a car

Reviewed on Jun 17, 2025

Hono Koa Vacation Club

Hono Koa Vacation Club

3 out of 5
Save 100% on your flight
per person
Sep 7 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
8.8/10 Excellent! (188 reviews)
It was easily accessible to the ocean.

Reviewed on Jun 14, 2025

Sands of Kahana

Sands of Kahana

3 out of 5
per person
Aug 11 - Aug 18
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Kahului (OGG)
8.2/10 Very Good! (436 reviews)
Love the close proximity to the beach, pool and hot tub!

Reviewed on Apr 25, 2025

Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
per person
Aug 24 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
8.2/10 Very Good! (1,337 reviews)
Beautiful resort. Comfortable beds. The yoga classes in the morning were great. The instructors were great. It would be nice to have some bathrooms near the pools. A little variation on the breakfast buffet would be nice. Scrambled eggs every morning gets old.

Reviewed on Jun 16, 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 ￥139,055 per night from Jul 15 to Jul 16
￥139,055
￥172,008 total
Jul 15 - Jul 16
includes taxes & fees
8.8/10 Excellent! (1,004 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 ￥108,390 per night from Jul 14 to Jul 15
￥108,390
￥127,858 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 ￥100,920 per night from Jun 21 to Jun 22
￥100,920
￥127,314 total
Jun 21 - Jun 22
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 1,194 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 ￥190,228, 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

Snorkeling Cruise to Molokini Crater & Turtle Town

Snorkeling Cruise to Molokini Crater & Turtle Town

￥28,412
per adult
96% of travellers recommend
Snorkeling Cruise to Molokini Crater & Turtle Town
Male swing fire in the Te Au Moana Luau performance in Maui

Te Au Moana Luau at the Wailea Beach Marriott Resort

￥41,356
per adult
92% of travellers recommend
Te Au Moana Luau at the Wailea Beach Marriott Resort
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
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.