Wailea Holidays

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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 which includes landscape views, a beach and tropical scenes

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 S$987 per night from 17 Dec to 18 Dec
S$987
17 Dec - 18 Dec
includes taxes & fees
8.8/10 Excellent! (1,012 reviews)
Awesome place to stay with kids

Reviewed on 2 Dec, 2025

Grand Wailea Maui, A Waldorf Astoria Resort
Andaz Maui at Wailea Resort - a concept by Hyatt

Andaz Maui at Wailea Resort - a concept by Hyatt

4.5 out of 5
3550 Wailea Alanui Dr Kihei HI
The price is S$1,342 per night from 5 Dec to 6 Dec
S$1,342
5 Dec - 6 Dec
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
Honestly, a little bit of everything stood out. The room was spotless, the staff was incredibly warm and welcoming, and the overall property and amenities were beautiful. The location right by the shops and restaurants was also a huge plus. It all came together to make the stay amazing.

Reviewed on 28 Nov, 2025

Andaz Maui at Wailea Resort - a concept by Hyatt
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

4.5 out of 5
3700 Wailea Alanui Dr Kihei HI
The price is S$929 per night from 12 Dec to 13 Dec
S$929
12 Dec - 13 Dec
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
Amazing hotel and views , everything

Reviewed on 28 Nov, 2025

Wailea Beach Resort - Marriott, Maui
See all 1,204 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.

Popular places to visit

Makena Beach State Park which includes a sandy beach

Makena State Park Beach

3/5(1 review)

Choose from three different beaches, each with its own character, along this unspoilt stretch of Maui’s southern shoreline.

Makena State Park Beach

Shops at Wailea

You can enjoy retail therapy at Shops at Wailea during your stay in Kihei. Wander the beautiful beaches or discover the beautiful sunsets in this romantic area.

Shops at Wailea

Things to do

Te Au Moana Luau at the Wailea Beach Marriott Resort

Te Au Moana Luau at the Wailea Beach Marriott Resort

S$281
per adult
92% of travellers recommend
Te Au Moana Luau at the Wailea Beach Marriott Resort
Road to Hana Tour- Book your unforgettable Maui Adventure now and take home memories for a lifetime!

Maui: Road to Hana Adventure with Farm to Table Lunch

S$318
per adult
90% of travellers recommend
Maui: Road to Hana Adventure with Farm to Table Lunch
Lahaina Sunset Dinner Cruise

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

S$183
per adult
80% of travellers recommend
From Ma'alaea Harbor: Sunset Dinner Cruise Aboard the Quicksilver
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.