Wailea Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

Top hotels in Wailea

Fairmont Kea Lani Maui
Fairmont Kea Lani Maui
4.5 out of 5
4100 Wailea Alanui Dr, Kihei, HI
The price is S$1,049 per night from 17 Dec to 18 Dec
S$1,049
includes taxes & fees
17 Dec - 18 Dec
9.2/10 Wonderful! (1,003 reviews)
"Nice location"

Reviewed on 29 Nov,2024

Fairmont Kea Lani Maui
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$1,320 per night from 9 Dec to 10 Dec
S$1,320
includes taxes & fees
9 Dec - 10 Dec
8.8/10 Excellent! (1,006 reviews)
"5 pm is to early to close the pool bar"

Reviewed on 28 Nov,2024

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$1,261 per night from 17 Dec to 18 Dec
S$1,261
includes taxes & fees
17 Dec - 18 Dec
9.6/10 Exceptional! (1,000 reviews)
"The staff is very friendly and dining options are amazing! The resort has so many complimentary activities to participate, would be visiting again."

Reviewed on 24 Nov,2024

Four Seasons Resort Maui at Wailea
See all 1,166 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

Snorkeling Cruise to Molokini Crater & Turtle Town

Snorkeling Cruise to Molokini Crater & Turtle Town

S$244
Per adult
96% of travellers recommend
Snorkeling Cruise to Molokini Crater & Turtle Town
Guided Kayak Adventure on the Wailua River

Guided Secret Falls Tour with Snacks and Drinks

S$169
Per adult
98% of travellers recommend
Guided Secret Falls Tour with Snacks and Drinks
Waterfall & Rainforest Adventure

Waterfall & Rainforest Hiking Adventure

S$224
Per adult
98% of travellers recommend
Waterfall & Rainforest Hiking 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. 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.