Wailea Packages (Flight + Hotel)

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Where to stay in Wailea

Find the best Wailea areas and neighborhoods for the activities you enjoy most. Learn more about Wailea
A sunset over a beach with palm trees and a few people walking.

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

Top hotels in 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 ฿24,602 per night from 27 Aug to 28 Aug
฿24,602
฿31,388 total
27 Aug - 28 Aug
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"The hotel amenities were nice; however, the hotel was not that clean. For two days, we saw the same dirty spot on the floor (it looked like a dried drink), and it wasn’t until the day before we departed that they finally mopped the floors. We also saw a few roaches inside the room. They told us that ..."

Reviewed on 27 Jul 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 ฿36,629 per night from 18 Aug to 19 Aug
฿36,629
฿45,838 total
18 Aug - 19 Aug
includes taxes & fees
Fairmont Kea Lani Maui
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 ฿27,749 per night from 24 Aug to 25 Aug
฿27,749
฿35,137 total
24 Aug - 25 Aug
includes taxes & fees
9.6/10 Exceptional! (1,001 reviews)
"Our stay was amazing. The staff and service were absolutely off the charts. The newly opened spa was the nicest I have ever been in. The food at the adult pool and service by the bar staff was impeccable. The main thing that stuck out to me was the genuine kindness and pride that the staff puts into ..."

Reviewed on 22 Jul 2026

Four Seasons Resort Maui at Wailea
See all 1,182 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 holiday package cost?
The most affordable Wailea package is , so your dream holiday can become a reality — without it costing a fortune. Combine flights, hotels, car rentals and more to custom build a package that matches your travelling style.
How do I get a cheap travel package to Wailea?
Crafting your own Wailea holiday 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 holiday 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 holiday?
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 organising an upscale romantic escape or a budget family adventure, browse our holiday packages today.
If I'm not able to travel, can I cancel my Wailea holiday package?
Yes, you can. We realise life doesn't always go to plan, so we're here to help if you need to make changes to your Wailea holiday 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.

Stay near popular Wailea attractions

A tropical beach with palm trees, a sandy shore, and the ocean.

Wailea Beach

9.4/10 (4,138 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.
See properties

Things to do

Lahaina Sunset Dinner Cruise

Sunset Dinner Cruise aboard Quicksilver: Prime Rib, Fish, Chicken or Pasta

฿4,450
per adult
84% of travellers recommend
Sunset Dinner Cruise aboard Quicksilver: Prime Rib, Fish, Chicken or Pasta
Calypso Sunset Dinner Cruise

Sunset Dinner Cruise aboard Calypso: Prime Rib, Fish, Chicken or Pasta

฿5,019
per adult
90% of travellers recommend
Sunset Dinner Cruise aboard Calypso: Prime Rib, Fish, Chicken or Pasta
Waterslide fun for all ages

Small Group Coral Gardens Snorkel & Waterslide Adventure

฿4,763
per adult
86% of travellers recommend
Small Group Coral Gardens Snorkel & Waterslide Adventure
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.