Wailea Vacations from $794

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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

Aston Mahana at Kaanapali

Aston Mahana at Kaanapali

3.5 out of 5
Save 100% on your flight
per person
Jun 3 - Jun 8
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
9/10 Wonderful! (1,433 reviews)
Amazing staff and location! Highly recommended!

Reviewed on Apr 18, 2024

Aston at the Maui Banyan

Aston at the Maui Banyan

3 out of 5
Save 100% on your flight
per person
Jul 10 - Jul 17
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
7.6/10 Good! (1,000 reviews)
I rented 3 condos for a group of10. Two were remodeled ours was not but clean looked nice view amazing but dated. One of the condos did not have an elevator. Difficult with luggage and small children. Had a nice clean pool. The grounds were beautiful. Staff was excellent. The location was amazing. 5 minute walk to a beautiful beach. Many restaurants and shops were very walkable, and I would definitely book these condos next time,

Reviewed on Mar 7, 2024

Aston Maui Hill

Aston Maui Hill

3 out of 5
Save 100% on your flight
per person
Jul 5 - Jul 9
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
9/10 Wonderful! (678 reviews)
I stayed in same place six years ago. It was very nice, so I went back again. It is not as clear as before, I am disappointed.

Reviewed on Apr 15, 2024

Aston Kaanapali Shores

Aston Kaanapali Shores

3.5 out of 5
Save 100% on your flight
per person
Jun 3 - Jun 8
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
8.6/10 Excellent! (2,956 reviews)
It took a while to check in. The property could use a bit of an update. We did enjoy our time overall.

Reviewed on Apr 16, 2024

Aston at Papakea Resort

Aston at Papakea Resort

3 out of 5
Save 100% on your flight
per person
Jul 5 - Jul 9
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
8.2/10 Very Good! (1,327 reviews)
Very responsive staff!

Reviewed on Jul 8, 2023

Prices and availability subject to change. Additional terms may apply.

Wailea Hotel Deals

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 $790 per night from May 3 to May 4
$790
$990 total
includes taxes & fees
May 3 - May 4
8.8/10 Excellent! (1,000 reviews)
"Potentially the most beautiful (semi all inclusive) resort in Maui. It was a treat and a delight to stay here. M"

Reviewed on Apr 6, 2024

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 $799 per night from Apr 20 to Apr 21
$799
$998 total
includes taxes & fees
Apr 20 - Apr 21
9/10 Wonderful! (791 reviews)
"We have stayed at other properties in Maui in the past and used to walk to Wailea Beach Resort for our daily Starbucks fix. We have always thought the property was just the right amount of "fancy" (big, grand spaces, open air design, very elegantly laid out property) but with a definite chill/older ..."

Reviewed on Apr 16, 2024

Wailea Beach Resort - Marriott, Maui
Fairmont Kea Lani Maui
Fairmont Kea Lani Maui
4.5 out of 5
4100 Wailea Alanui Dr, Kihei, HI
The price is $1,029 per night from May 6 to May 7
$1,029
$1,273 total
includes taxes & fees
May 6 - May 7
9.2/10 Wonderful! (997 reviews)
"Very clean. Pool and Beach were amazing. Best Hotel I have ever been to."

Reviewed on Apr 13, 2024

Fairmont Kea Lani Maui
See all 1,216 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Wailea vacation package cost?
The most affordable Wailea package is $794, 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

Image for Wailea Beach

Wailea Beach

4.5/5(1,614 reviews)

This stretch of powdery sand is part of an upscale resort community and is an ideal place to sunbathe, snorkel, and dive with Hawaiian green turtles and manta rays.

Wailea Beach
Image for Makena State Park Beach

Makena State Park Beach

4.5/5(438 reviews)

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

Makena State Park Beach
Image for Maluaka Beach

Maluaka Beach

4.5/5(101 reviews)

This is part of Maui’s so-called “Turtle Town,” a prime spot for sighting the inquisitive Hawaiian green turtles that are very common here.

Maluaka Beach

Things to do

Image for Luxury Molokini & Turtle Snorkel Sail with Breakfast, Lunch & Open Bar

Luxury Molokini & Turtle Snorkel Sail with Breakfast, Lunch & Open Bar

$289
Per adult
96% of travellers recommend
Luxury Molokini & Turtle Snorkel Sail with Breakfast, Lunch & Open Bar
Image for Family and Couple Beach Photos

Family and Couple Beach Photos

$99
Per adult
100% of travellers recommend
Family and Couple Beach Photos
Image for E-Scooter Snorkel With Photo and Video At Turtle Town

E-Scooter Snorkel With Photo and Video At Turtle Town

$118
Per adult
98% of travellers recommend
E-Scooter Snorkel With Photo and Video At Turtle Town
See all activities in Kihei

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