Vacation to Wailea

Choose one or more items to build your trip:

Top Vacation Package Deals in Wailea

The Ritz-Carlton Maui, Kapalua
Aston Maui Kaanapali Villas
Grand Wailea Maui, A Waldorf Astoria Resort
Wailea Beach Resort - Marriott, Maui
Sheraton Maui Resort & Spa

Wailea Hotel Deals

Wailea Beach Resort - Marriott, Maui
Wailea Beach Resort - Marriott, Maui
4.5 out of 5
3700 Wailea Alanui Dr, Kihei, HI, 96753
The price is $705 per night from Aug 21 to Aug 22
4.5/5 Wonderful! (570 reviews)
"Great location, walkable distance to shopping for rainy days and oceanfront. Facilities are beautiful and lots of pool options for kids. There are only 2 restaurants. One is higher end and other is more of a cafe (but still pricey). Food was great at both restaurants but after being there for several ..."

Reviewed on Aug 6, 2022

Wailea Beach Resort - Marriott, Maui
Four Seasons Resort Maui at Wailea
Four Seasons Resort Maui at Wailea
5 out of 5
3900 Wailea Alanui Drive, Kihei, HI, 96753
The price is $1,395 per night from Aug 23 to Aug 24
4.8/5 Exceptional! (999 reviews)
"The hotel is situated on a beautiful spot on the beach It is truly luxurious the architecture and interior design wonderful The concierge helped us prior to our arrival with outside activities which were top notch The staff was wonderful The grounds fitness tennis great We ate in all the restaurants ..."

Reviewed on Aug 8, 2022

Four Seasons Resort Maui at Wailea
Fairmont Kea Lani Maui
Fairmont Kea Lani Maui
4.5 out of 5
4100 Wailea Alanui Dr, Kihei, HI, 96753
The price is $1,070 per night from Aug 23 to Aug 24
4.6/5 Exceptional! (996 reviews)
"Beautiful property with a courteous and friendly staff who was on point. Everyday I received a text asking how they could be of assistance. They were so willing to help and prompt in every way. Loved our stay here and would definitely return with the family someday soon."

Reviewed on May 2, 2022

Fairmont Kea Lani Maui
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 vacation package cost?
Starting from as little as $2,148, you can customize your Wailea vacation package. Simply combine flights, hotels and car rentals and we’ll reward you with discounts.
If I'm not able to travel, can I cancel my Wailea vacation package?
Yes, you can cancel your Wailea booking if your plans have been upended. Whether you’ll incur a penalty or not depends on your hotel, airline or car rental company. You may be able to cancel or change for free if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.
How do I get a cheap travel package to Wailea?
One of the easiest ways to save money (and time) is to combine your bookings with Expedia. Flights, hotels, tours and rental cars — we’ve got them all. Choose the combination that best matches you and save as much as $583*. And of course, we do understand that a travel package is never a one-size-fits-all. That’s why we offer more than 550 air carriers and 1,000,000 hotel options from all over the world, so you can craft your very own custom-built Wailea getaway.
When is the best time of year to visit Wailea?
You’ll have to consider your priorities to find the right answer. Typically, you’ll score the best deals in , while is when hotel rates generally rise. Wailea is at its busiest in . If you want a more laid-back escape, would be a better time to visit.
How far in advance should I book my Wailea vacation?
It can be difficult to know exactly when the best time is to book your trip to Wailea. But usually the earlier you book, the better the prices. In some cases, you can reserve your flights and hotels up to 12 months before your departure date. If you’re hoping for a last-minute getaway, no need to panic! There are great deals featured on Expedia every day.
What does an Expedia Wailea travel package include?
Packages include rental cars, hotels and flights, but you can combine any of them to create your perfect Wailea escape. You can also add on experiences and activities once you’ve made your booking. You’re in charge! When you combine your bookings with Expedia, you’ll enjoy discounts you won’t find elsewhere.
What should I know before booking a Wailea travel package?
A Expedia travel package can be customized for your circumstances and is a terrific way to make your money go further. What you include is totally up to you. Rental cars, hotels and flights — choose any combination that works with your plans.
Does Expedia offer Book Now, Pay Later Wailea vacation packages?
Thanks to the joint efforts of Expedia and online lender Affirm, you can split the cost of your vacation package over multiple payments. For financial flexibility, take advantage of our Book Now, Pay Later option and work out a payment plan to match your situation.
Can I choose my airline with a Wailea Expedia vacation package?
Expedia offers access to more than 550 partner airlines worldwide, so you definitely can. Simply choose your preferred carrier and craft your ideal Wailea getaway.
Can I travel to Wailea right now?
Expedia’s Covid-19 Travel Advisor is the place to find current information about travel restrictions and quarantine policies for Wailea. Be in the know before you go!

Popular places to visit

Things to do