Wailea Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩1,660,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Where to stay in Wailea

Find the best Wailea areas and neighborhoods for the activities you enjoy most. Learn more about Wailea
South Kihei

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

Wailea Hotel Deals

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 ₩1,472,442 per night from Jun 26 to Jun 27
₩1,472,442
₩1,747,964 total
Jun 26 - Jun 27
includes taxes & fees
9.6/10 Exceptional! (1,001 reviews)
"Absolutely beautiful! Staff were all friendly and attentive. We really appreciated the cleanliness, amenities, and high level of service."

Reviewed on May 25, 2026

Four Seasons Resort Maui at Wailea
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 ₩1,212,280 per night from Jun 26 to Jun 27
₩1,212,280
₩1,540,213 total
Jun 26 - Jun 27
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"The grounds are stunning, the valet staff were amazing! The rooms are about average, the staff working the resort pool and beach were hit or miss. Cleaning staff was kind and thorough as were the staff at the desk at check in. The $55 resort charge, additional taxes and fees added up quickly. The ..."

Reviewed on Jun 4, 2026

Grand Wailea Maui, A Waldorf Astoria Resort
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
The price is ₩1,743,559 per night from Jun 27 to Jun 28
₩1,743,559
₩2,162,304 total
Jun 27 - Jun 28
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
"The resort was excellent and made for a great trip!"

Reviewed on May 31, 2026

Fairmont Kea Lani Maui
See all 1,226 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 , 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

Palauea Beach

Palauea Beach

If a restful vacation is part of your travel plans, Palauea Beach might be the perfect place to seek out during your trip to Kihei. Amble around this relaxing area's seaside, or seek out the snorkeling spots.

Palauea Beach
Keawakapu Beach North

Keawakapu Beach North

4.5/5(86 reviews)

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

4.5/5(80 reviews)

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.