Wailea Holidays

Book a Hotel + Flight or Car together to unlock savings

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 18.604.116 ₫ per night from 28 Jan to 29 Jan
18.604.116 ₫
23.790.171 ₫ total
28 Jan - 29 Jan
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
rooms and pools were excellent

Reviewed on 10 Jan 2026

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 20.890.215 ₫ per night from 19 Jan to 20 Jan
20.890.215 ₫
26.514.816 ₫ total
19 Jan - 20 Jan
includes taxes & fees
9.6/10 Exceptional! (1,000 reviews)
Service was good

Reviewed on 8 Jan 2026

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 24.770.014 ₫ per night from 2 Feb to 3 Feb
24.770.014 ₫
30.964.781 ₫ total
2 Feb - 3 Feb
includes taxes & fees
9.4/10 Exceptional! (1,009 reviews)
Fantastic experience all around.

Reviewed on 7 Jan 2026

Fairmont Kea Lani Maui
See all 1,232 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 1null000null000 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

Wailea Beach featuring swimming, a beach and tropical scenes

Wailea Beach

Nothing says holiday like spending a lazy day at Wailea Beach, a popular beach in Kihei. Wander the seaside or discover the beautiful sunsets in this romantic area.

Wailea Beach
Makena Beach State Park featuring a beach

Makena State Park Beach

If a restful holiday is part of your travel plans, Makena State Park Beach might be the perfect place to visit during your trip to Kihei. Stroll along the seaside in this romantic area or seek out the snorkelling spots.

Makena State Park Beach
Polo Beach

Polo Beach

If a restful holiday is part of your travel plans, Polo Beach might be the perfect place to visit during your trip to Kihei. Wander the seaside or discover the beautiful sunsets in this relaxing area.

Polo Beach