Wailea Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €185 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Kahana Beach Vacation Club

Kahana Beach Vacation Club

3 out of 5
Price was €3,113, price is now €2,048 per person
€2,048
per person
9 May - 16 May
found 1 day ago
Return flight included
Dublin (DUB) to Kahului (OGG)
8.4/10 Very Good! (744 reviews)
Clean and quiet. Kitchen was well stocked with kitchen items. Easy check in process. We had an awesome ocean view.

Reviewed on 26 Feb 2026

Sands of Kahana

Sands of Kahana

3 out of 5
Save 100% on your flight
Price was €3,765, price is now €2,304 per person
€2,304
per person
9 May - 16 May
found 1 day ago
Return flight included
Dublin (DUB) to Kahului (OGG)
8.2/10 Very Good! (453 reviews)
The room was great!! Super spacious, comfortable, and affordable. The staff were nice as well.

Reviewed on 19 Feb 2026

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

4 out of 5
Price was €3,680, price is now €2,542 per person
€2,542
per person
9 May - 16 May
found 1 day ago
Return flight included
Dublin (DUB) to Kahului (OGG)
9.6/10 Exceptional! (292 reviews)
The staff was great. The location was perfect. Everything was in walking distance. The only issue was it said ocean view when it should have said partial ocean view. I was a little disappointed.

Reviewed on 19 Feb 2026

Kahana Villa

Kahana Villa

3 out of 5
Price was €3,422, price is now €2,364 per person
€2,364
per person
9 May - 16 May
found 1 day ago
Return flight included
Dublin (DUB) to Kahului (OGG)
8/10 Very Good! (351 reviews)
Staff was very helpful. Room was clean. Shows a lot of wear but was kept up.

Reviewed on 26 Feb 2026

OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Price was €3,030, price is now €2,126 per person
€2,126
per person
9 May - 16 May
found 1 day ago
Return direct flight included
Dublin (DUB) to Kahului (OGG)
9/10 Wonderful! (1,465 reviews)
Kind Staff, property, beach access, location, clean room,

Reviewed on 26 Feb 2026

Where to stay in Wailea

Find the best Wailea areas and neighborhoods for the activities you enjoy most. Learn more about Wailea
Aloha state of mind #lifeatexpedia

South Kihei

3 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 €719 per night from 11 Mar to 12 Mar
€719
11 Mar - 12 Mar
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
Everything was great especially the grounds absolutely stunning. The only knock i would give it is the outside of the overall hotel needs a bit of paint or some refreshment other than that the rooms were spacious clean and the grounds were gorgeous kids loved the pool and beach very much overall ...

Reviewed on 25 Feb 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 €955 per night from 21 Mar to 22 Mar
€955
21 Mar - 22 Mar
includes taxes & fees
9.6/10 Exceptional! (1,001 reviews)
Staff was spectacularly welcoming and courteous!

Reviewed on 26 Feb 2026

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 €836 per night from 8 Mar to 9 Mar
€836
8 Mar - 9 Mar
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
nice room and location. Love everything here - especially the early yoga/meditation class we took under the big tree.

Reviewed on 17 Feb 2026

Wailea Beach Resort - Marriott, Maui
See all 1,224 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 €2,048, 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

Pineapple creme brûlée! #foodporn #delicious

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 Beach State Park which includes a beach

Makena State Park Beach

3/5(1 review)

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

Makena State Park Beach

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

2-Hour Whale Watch(s)

2-Hour Whale Watch Tour from Ma'alaea Harbor

€42
per adult
90% of travellers recommend
2-Hour Whale Watch Tour from Ma'alaea Harbor
Lahaina Sunset Dinner Cruise

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

€118
per adult
82% of travellers recommend
From Ma'alaea Harbor: Sunset Dinner Cruise Aboard the Quicksilver
Molokini Island

Maui Snorkeling Adventure to Molokini and Turtle Town

€135
per adult
90% of travellers recommend
Maui Snorkeling Adventure to Molokini and Turtle Town
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.