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
Keawakapu Beach featuring tropical scenes, a beach and landscape views

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 ฿21,514 per night from 7 Jan to 8 Jan
฿21,514
฿27,577 total
7 Jan - 8 Jan 2026
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Everything was great. We would totally stay again.

Reviewed on 7 Dec 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 ฿24,969 per night from 4 Jan to 5 Jan
฿24,969
฿29,642 total
4 Jan - 5 Jan 2026
includes taxes & fees
9.6/10 Exceptional! (1,000 reviews)
This property has long been one of my global Four Seasons favorites, and I remain truly grateful for the warm hospitality I always receive. I was also very appreciative of the wonderful upgrade to an ocean-view room — mahalo for that thoughtful gesture. I’ve been visiting this resort regularly since ...

Reviewed on 2 Dec 2025

Four Seasons Resort Maui at Wailea
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
The price is ฿26,937 per night from 4 Jan to 5 Jan
฿26,937
฿33,830 total
4 Jan - 5 Jan 2026
includes taxes & fees
9.4/10 Exceptional! (1,005 reviews)
Room n staff was good, room getting a bit worn out, had a premium ocean view room

Reviewed on 13 Dec 2025

Fairmont Kea Lani Maui
See all 1,228 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.

Things to do

Lahaina Sunset Dinner Cruise

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

฿4,530
per adult
84% of travellers recommend
From Ma'alaea Harbor: Sunset Dinner Cruise Aboard the Quicksilver
Calypso Sunset Dinner Cruise

Ma'alaea Sunset Dinner Cruise - Prime Rib, Island Fish, Chicken or Pasta

฿4,854
per adult
90% of travellers recommend
Ma'alaea Sunset Dinner Cruise - Prime Rib, Island Fish, Chicken or Pasta
Molokini Island

Maui Snorkeling Adventure to Molokini and Turtle Town

฿5,177
per adult
88% of travellers recommend
Maui Snorkeling Adventure to Molokini and 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.