Wailea Vacations

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Your Wailea Vacation

Lock in a vacation package to Wailea and get set to experience its surfing, coastal beaches and views. However you'd like to spend your break in this picturesque neighborhood, you'll find plenty of opportunities to mix relaxation and fun. Wondering what to see and do during your trip to Wailea? Nearby attractions such as Wailea Beach, Kamaole Beach Park and Keawakapu Beach North are good places to start. No matter your travel plans or the size of your budget, booking your dream Wailea vacation has never been easier with Expedia.

The Latest Wailea Vacation Packages

OUTRIGGER Kaanapali Beach Resort
Aston Mahana at Kaanapali
Aston Maui Hill
Aston Maui Kaanapali Villas
Aston Kaanapali Shores
Prices and availability subject to change. Additional terms may apply.

Wailea Hotel Deals

Wailea Beach Resort - Marriott, Maui
Wailea Beach Resort - Marriott, Maui
4.5 out of 5
3700 Wailea Alanui Dr, Kihei, HI
The price is $709 per night from Apr 3 to Apr 4
$709
$891 total
includes taxes & fees
Apr 3 - Apr 4
9/10 Wonderful! (776 reviews)
"Simply stunning. Highly recommend."

Reviewed on Mar 15, 2024

Wailea Beach Resort - Marriott, Maui
Andaz Maui at Wailea Resort - a concept by Hyatt
Andaz Maui at Wailea Resort - a concept by Hyatt
4.5 out of 5
3550 Wailea Alanui Dr, Kihei, HI
The price is $720 per night from Apr 8 to Apr 9
$720
$908 total
includes taxes & fees
Apr 8 - Apr 9
9.2/10 Wonderful! (998 reviews)
Wonderful stay.
"Wonderful place! Awesome! Beds! Breakfast Buffett is AMAZING!! After that foo was way overpriced for quality. But many restaurants around hotel to eat that were wonderful."

Reviewed on Mar 2, 2024

Andaz Maui at Wailea Resort - a concept by Hyatt
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 $995 per night from Apr 6 to Apr 7
$995
$1,174 total
includes taxes & fees
Apr 6 - Apr 7
9.6/10 Exceptional! (999 reviews)
"Best hotel stay EVER. Incredibly attentive and helpful service. Too many detailed amenities to mention. Easy to navigate. Large butvfelt cozy. Beautiful setting. As close to perfect as you csn get this side of heaven."

Reviewed on Feb 25, 2024

Four Seasons Resort Maui at 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.

Explore other types of vacation packages

Frequently asked questions

How much does a Wailea vacation package cost?
The most affordable Wailea package is $783, so your dream vacation can become a reality — without it costing a fortune. Combine flights, hotels, car rentals and more to custom build a package that matches your traveling style.
How do I get a cheap travel package to Wailea?
Crafting your own Wailea vacation 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 vacation 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 vacation?
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 organizing an upscale romantic escape or a budget family adventure, browse our vacation packages today.
If I'm not able to travel, can I cancel my Wailea vacation package?
Yes, you can. We realize life doesn’t always go to plan, so we’re here to help if you need to make changes to your Wailea vacation 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.

Discover the most popular places to visit in Wailea

Things to do

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.