Wailea Packages (Flight + Hotel)

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Where to stay in Wailea

Find the best Wailea areas and neighborhoods for the activities you enjoy most. Learn more about Wailea
Maluaka Beach showing landscape views

Makena

A noteworthy feature of Makena is its stunning beaches. While you're in town, be sure to stop and check out Makena State Park Beach and Little Beach.

Find hotels in Makena

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 ฿18,872 per night from 13 Nov to 14 Nov
฿18,872
฿24,384 total
13 Nov - 14 Nov
includes taxes & fees
8.8/10 Excellent! (1,012 reviews)
Great way to keep kids burning calories, and fun to relax as well. The fog generator in the cavern by the bar is amazing, but wish slides were all open and more unique fog was available.

Reviewed on 24 Oct 2025

Grand Wailea Maui, A Waldorf Astoria Resort
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

4.5 out of 5
3700 Wailea Alanui Dr, Kihei, HI
The price is ฿18,054 per night from 16 Nov to 17 Nov
฿18,054
฿23,496 total
16 Nov - 17 Nov
includes taxes & fees
9/10 Wonderful! (1,007 reviews)
we came for a family trip and it couldnt have gone better. staff was great pool were awesome. highly recommend and would come back!

Reviewed on 13 Oct 2025

Wailea Beach Resort - Marriott, Maui
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr, Kihei, HI
The price is ฿26,104 per night from 30 Oct to 31 Oct
฿26,104
฿32,722 total
30 Oct - 31 Oct
includes taxes & fees
9.4/10 Exceptional! (1,014 reviews)
Exceptional spa services.

Reviewed on 19 Oct 2025

Fairmont Kea Lani Maui
See all 1,180 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 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.

Things to do

Lahaina Sunset Dinner Cruise

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

฿4,575
per adult
80% of travellers recommend
From Ma'alaea Harbor: Sunset Dinner Cruise Aboard the Quicksilver
Calypso Sunset Dinner Cruise

Ma'alaea Sunset Dinner Cruise - Prime Rib, Island Fish, Chicken or Pasta

฿4,902
per adult
90% of travellers recommend
Ma'alaea Sunset Dinner Cruise - Prime Rib, Island Fish, Chicken or Pasta
Encounter Hawaii's Marine Life

Maui Ocean Center All Day Admission Ticket

฿1,812
per adult
90% of travellers recommend
Maui Ocean Center All Day Admission Ticket
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.