Wailea Holidays

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    Save up to S$134 when you book a flight and hotel together*
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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$1,522 per night from 14 Jul to 15 Jul
S$1,522
14 Jul - 15 Jul
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"We had the best time! The property is absolutely gorgeous and the weather was perfect."

Reviewed on 17 Jun, 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 S$1,128 per night from 14 Jul to 15 Jul
S$1,128
14 Jul - 15 Jul
includes taxes & fees
9.6/10 Exceptional! (1,000 reviews)
"Amazing stay and service. Four Seasons always exceeded our expectations. Beautiful resort with nice beaches and pools. Family loved it."

Reviewed on 18 Jun, 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 S$1,037 per night from 26 Jun to 27 Jun
S$1,037
26 Jun - 27 Jun
includes taxes & fees
9/10 Wonderful! (995 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 18 Jun, 2025

Wailea Beach Resort - Marriott, Maui
See all 1,193 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

Guided Turtle Town Snorkeling Tour with Underwater Photos

Snorkel with Turtles and Free Underwater Photos - Turtle Town

S$166
per adult
100% of travellers recommend
Snorkel with Turtles and Free Underwater Photos - Turtle Town
Male swing fire in the Te Au Moana Luau performance in Maui

Te Au Moana Luau at the Wailea Beach Marriott Resort

S$368
per adult
92% of travellers recommend
Te Au Moana Luau at the Wailea Beach Marriott Resort
Deluxe Molokini & Turtle Snorkel Luxury Sail Tour with Meals

Luxury Molokini & Turtle Snorkel Sail with Breakfast, Lunch & Open Bar

S$372
per adult
96% of travellers recommend
Luxury Molokini & Turtle Snorkel Sail with Breakfast, Lunch & Open Bar
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.