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
Maluaka Beach featuring landscape views

Makena

A noteworthy feature of Makena is its stunning beaches. While you're in town, be sure to stop and check out Makena State Park Beach and Little Beach.

Find hotels in Makena

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 €665 per night from 24 Oct to 25 Oct
€665
24 Oct - 25 Oct
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
"Wonderful accommodations!"

Reviewed on 10 Oct 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 €766 per night from 9 Nov to 10 Nov
€766
9 Nov - 10 Nov
includes taxes & fees
9.6/10 Exceptional! (1,002 reviews)
"Wonderful!"

Reviewed on 6 Oct 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 €1,014 per night from 14 Oct to 15 Oct
€1,014
14 Oct - 15 Oct
includes taxes & fees
9.4/10 Exceptional! (1,007 reviews)
"This place was amazing, nicest place I’ve ever stayed. The room was big and clean. The staff were great….from the front desk staff to the room service women. Staff was also helpful when we asked questions I’m sure they’ve heard 1000 times. The restaurants were good, but pricey. We tried them all ..."

Reviewed on 9 Oct 2025

Fairmont Kea Lani Maui
See all 1,007 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 beach

Makena State Park Beach

Three distinct, undeveloped beaches and a dormant volcano crater form this scenic southern region of Maui.

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

Makena Golf Course

Play a round of golf in Kihei at Makena Golf Course, and enjoy other activities such as snorkelling. Amble around this romantic area's beautiful beaches and enjoy its seafood restaurants.

Makena Golf Course

Things to do

Lahaina Sunset Dinner Cruise

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

€119
per adult
80% of travellers recommend
From Ma'alaea Harbor: Sunset Dinner Cruise Aboard the Quicksilver
Molokini Island

Molokini and Turtle Town Snorkeling Adventure Aboard the Malolo

€136
per adult
88% of travellers recommend
Molokini and Turtle Town Snorkeling Adventure Aboard the Malolo
Encounter Hawaii's Marine Life

Maui Ocean Center All Day Admission Ticket

€47
per adult
90% of travellers recommend
Maui Ocean Center All Day Admission Ticket
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.