Wailea Holidays & Package Deals

Q: 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 .

Your Wailea Holiday

Lose yourself in the magic of this picturesque neighbourhood with a Wailea holiday package. From its surfing and coastal beaches to its views, there's something here for every traveller. Not sure what to do and see during your trip to Wailea? Nearby attractions such as Wailea Beach, Kamaole Beach Park and Keawakapu Beach North are good places to start. Whatever your travel plans or budget, booking your dream Wailea holiday is quick and easy with Expedia.

Top Holiday Package Deals in Wailea

Price found within the past 48 hours. Click for updated prices.

Maui Beach Vacation Club

North Kihei

AU$2,025

per person

24 Aug - 31 Aug

found 1 day ago

Return flight included

Sydney (SYD) to Kahului (OGG)

8.4/10 Very Good! (883 reviews)

The kitchen is very well equipped. If your plan is to explore Hawaii and be able to cook like you do at home, this is a great place. Walmart and Safeway are perfect supermarkets for your shopping. There is no A/C, but believe me, you don’t need it. It’s a safe place and very well ventilated. The room temperature is perfect and it stays cool all night.

Reviewed on 16 June 2026

Maui Banyan Vacation Club

South Kihei

AU$2,033

per person

24 Aug - 31 Aug

found 1 day ago

Return flight included

Sydney (SYD) to Kahului (OGG)

8/10 Very Good! (371 reviews)

Staff was nice, I did find cockroaches in my room. When I told the staff they asked me what I wanted them to do about it.... other than that there is a nice full kitchen and an easy walk to the BEACH.

Reviewed on 14 June 2026

Grand Wailea Maui, A Waldorf Astoria Resort

Wailea

Save 100% on your flight

AU$4,923

per person

24 Aug - 31 Aug

found 1 day ago

Return flight included

Sydney (SYD) to Kahului (OGG)

8.8/10 Excellent! (1,014 reviews)

It’s got an amazing location. It felt like they are letting the hotel go down a bit though. The staff serving the pool area was paper thin. Cabana rentals that use to be $500 are now $1700/day. Our room had a broken ceiling light we had to have a repair man do for over a hour and even after that it stopped working again. The tongs and glasses in our room had built up food grime on them. Wait times at restaurants were long to nonexistent there, even though they had plenty of open tables. Just not the happy experience we use to have in years past going there.

Reviewed on 15 June 2026

Maui Coast Hotel

South Kihei

AU$2,748

per person

22 July - 29 July

found 11 hours ago

Return flight included

Sydney (SYD) to Kahului (OGG)

9.6/10 Exceptional! (2,624 reviews)

The rooms were large with plenty of room for storage. Microwave and refrigerator were very handy. It was close to stores so we could have food for breakfast or snacks to avoid eating out every meal. Cafe had good food and a nice setting. Both pools were comfortable and well maintained. Two spas were nice along with a shallow pool for children. We were a large family group and were able to bring in food and eat at the pool area. Pool bar had good drinks as well as dinner available. Free laundry service was also a great perk. In general, I would stay here again.

Reviewed on 17 June 2026

Our guide on where to stay in Wailea

Find the best Wailea areas and neighborhoods for the activities you enjoy most. Learn more about Wailea

A sunset over a beach with palm trees and a few people walking.

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.

Our pick of the best Wailea Hotel Deals

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

AU$1,452

12 July - 13 July

includes taxes & fees

8.8/10 Excellent! (1,019 reviews)

"It’s got an amazing location. It felt like they are letting the hotel go down a bit though. The staff serving the pool area was paper thin. Cabana rentals that use to be $500 are now $1700/day. Our room had a broken ceiling light we had to have a repair man do for over a hour and even after that ..."

Reviewed on 15 June 2026

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive Kihei HI

AU$1,679

8 July - 9 July

includes taxes & fees

9.6/10 Exceptional! (1,000 reviews)

"Absolutely beautiful! Staff were all friendly and attentive. We really appreciated the cleanliness, amenities, and high level of service."

Reviewed on 25 May 2026

Wailea Beach Resort - Marriott, Maui

3700 Wailea Alanui Dr Kihei HI

AU$1,311

5 July - 6 July

includes taxes & fees

9.2/10 Wonderful! (1,000 reviews)

"The hotel was very clean. The rooms were big as well."

Reviewed on 16 June 2026

See all 1,226 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 AU$2,025, 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.