Wailea Vacations

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Price found within the past 48 hours. Click for updated prices.
  • Suite, 2 Bedrooms | Living area | TV
    Aug 12 - Aug 14

    Maui Beach Vacation Club + Flight

    North Kihei
    2 nights
    2.5 star property
    8.4/10 - Very Good (874 reviews)
    "The permanent resident couple that I was next to is a nightmare.The man is intimidating and the way he looked at me made me feel uneasy. The woman is rude and inconsiderate. Woke me up at 3:30am everyday making loud noises. I know everyone has complained about her and nothing has been done. It’s a shame because I would love to return."
    Reviewed May 25, 2026
    Roundtrip • Oahu (HNL) - Maui (OGG)
    HNL - OGG • Nonstop OGG - HNL • Nonstop
    ￥73,280
    ￥54,728
    per traveler
    found 1 day ago
    Maui Beach Vacation Club
  • Outdoor spa tub
    Aug 12 - Aug 14

    Hotel Wailea, Relais & Chateaux - Adults Only + Flight

    Wailea
    2 nights
    5.0 star property
    9.4/10 - Exceptional (1,001 reviews)
    Roundtrip • Oahu (HNL) - Maui (OGG)
    HNL - OGG • Nonstop OGG - HNL • Nonstop
    Save 100% on your flight
    ￥197,117
    ￥138,141
    per traveler
    found 1 day ago
    Hotel Wailea, Relais & Chateaux - Adults Only
  • Studio Suite, 1 Queen Bed | Terrace/patio
    Aug 12 - Aug 14

    Maui Banyan Vacation Club + Flight

    South Kihei
    2 nights
    3.0 star property
    8.0/10 - Very Good (371 reviews)
    "Room is clean with full kitchen, nice beaches just across the road"
    Reviewed May 28, 2026
    Roundtrip • Oahu (HNL) - Maui (OGG)
    HNL - OGG • Nonstop OGG - HNL • Nonstop
    ￥80,845
    ￥57,192
    per traveler
    found 1 day ago
    Maui Banyan Vacation Club
  • Exterior detail
    Aug 12 - Aug 14

    Fairmont Kea Lani Maui + Flight

    Wailea
    2 nights
    5.0 star property
    9.4/10 - Exceptional (1,003 reviews)
    "What a fantastic hotel! I travelled to Maui with my husband and two children aged 5 & 8. Upton arrival the valet helped with our bags, gave the children and us gorgeous necklaces and check-in was quick! I didn’t like that the room we received was such a stretch to walk to so came back and the really helpful manager, despite being almost at full capacity moved us to a higher room category with a beautiful partial ocean view. Whilst we were there there was rain on and off but the hotel made sure..."
    Reviewed May 11, 2026
    Roundtrip • Oahu (HNL) - Maui (OGG)
    HNL - OGG • Nonstop OGG - HNL • Nonstop
    Save 100% on your flight
    ￥258,562
    ￥188,201
    per traveler
    found 1 day ago
    Fairmont Kea Lani Maui
  • Outdoor pool
    Aug 12 - Aug 14

    Hampton Inn & Suites Maui North Shore + Flight

    Kahului
    2 nights
    3.0 star property
    9.2/10 - Wonderful (242 reviews)
    "Absolutely beautiful property and great location"
    Reviewed May 27, 2026
    Roundtrip • Oahu (HNL) - Maui (OGG)
    HNL - OGG • Nonstop OGG - HNL • Nonstop
    ￥106,367
    ￥80,544
    per traveler
    found 1 day ago
    Hampton Inn & Suites Maui North Shore

Where to stay in Wailea

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

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.

Find hotels in South Kihei

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 ￥148,057 per night from Jun 14 to Jun 15
￥148,057
￥186,109 total
Jun 14 - Jun 15
includes taxes & fees
8.8/10 Excellent! (1,009 reviews)
"Clean huge rooms with a great view, very friendly staff, lot of pool access, spa treatment was phenomenal."

Reviewed on May 26, 2026

Grand Wailea Maui, A Waldorf Astoria Resort
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
The price is ￥175,301 per night from Jun 28 to Jun 29
￥175,301
￥217,572 total
Jun 28 - Jun 29
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
"Very happy with our stay and with the staff. All were very friendly."

Reviewed on May 19, 2026

Fairmont Kea Lani Maui
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 ￥134,786 per night from Jun 2 to Jun 3
￥134,786
￥160,008 total
Jun 2 - Jun 3
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 May 25, 2026

Four Seasons Resort Maui at Wailea
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 vacation package cost?
The most affordable Wailea package is , 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

Wailea Beach

Wailea Beach

4.5/5(1,632 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
Makena State Park Beach

Makena State Park Beach

4.5/5(450 reviews)

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

Makena State Park Beach
Little Beach

Little Beach

4.5/5(14 reviews)

Why not spend a carefree afternoon at Little Beach during your travels in Kihei? Wander the seaside or discover the beautiful sunsets in this relaxing area.

Little Beach

Things to do

Maui Ocean Center All Day Admission Ticket

Maui Ocean Center All Day Admission Ticket

￥8,699
per adult
90% of travellers recommend
Maui Ocean Center All Day Admission Ticket
Maui: Molokini & Turtle Town Snorkel & Waterslide Adventure

Maui: Molokini & Turtle Town Snorkel & Waterslide Adventure

￥30,890
per adult
94% of travellers recommend
Maui: Molokini & Turtle Town Snorkel & Waterslide Adventure
Lahaina Sunset Dinner Cruise

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

￥21,927
per adult
84% of travellers recommend
From Ma'alaea Harbor: Sunset Dinner Cruise Aboard the Quicksilver
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.