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Top Holiday Package Deals in Wailea
Price found within the past 48 hours. Click for updated prices.
OUTRIGGER Kaanapali Beach Resort
Save 100% on your flight
per person
Dec. 16 - Dec. 23
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
8.8/10 Excellent! (1,001 reviews)
When first arrived, I noticed the staff very friendly, the placed stunning, very clean. The pool clean but no jacuzzi. The room is gorgeous and clean with stunning view. Walking distance to the beach.
Reviewed on Sep. 26, 2024
Aston Mahana at Kaanapali
Save 100% on your flight
per person
Dec. 16 - Dec. 23
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
9/10 Wonderful! (1,537 reviews)
Proximity to all local eateries and beach and grocery store is perfect! Very quiet. No frills other than a place with kitchen, washer/dryer, and fantastic ocean view. There was no housekeeping service during our stay which we did not mind. Water and elevator got shut off for a few hours but we worked around it. Pool and jacuzzi are perfect! Highly recommend this place.
Reviewed on Sep. 25, 2024
Aston Kaanapali Shores
Save 100% on your flight
per person
Dec. 16 - Dec. 23
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
8.6/10 Excellent! (3,243 reviews)
We have stayed here a few times before. The room we had was furnished with older and very uncomfortable furniture. The couch was a pull out that we did not use but was so hard to sit on. Not enough cooking pans and pots, and the pillows were hard and small. I remember this being much nicer 8 years ago. Great employees, the beach is right there.
Reviewed on Sep. 26, 2024
Wailea Hotel Deals
Four Seasons Resort Maui at Wailea
3900 Wailea Alanui Drive, Kihei, HI
The price is CA $1,067 per night from Oct. 15 to Oct. 16
CA $1,067
CA $1,259 total
includes taxes & fees
Oct 15 - Oct 16
9.6/10 Exceptional! (993 reviews)
"Best place to relax and have a great time"
Reviewed on Sep. 19, 2024
Grand Wailea Maui, A Waldorf Astoria Resort
3850 Wailea Alanui Drive, Kihei, HI
The price is CA $889 per night from Oct. 16 to Oct. 17
CA $889
CA $1,136 total
includes taxes & fees
Oct 16 - Oct 17
8.8/10 Excellent! (999 reviews)
"The price is high because very few properties can have such luxury. There are many great properties nearby but this is the penultimate with a tiki meets art deco neo classical architecture/styling. My only disappointment is that they no longer have a (walnut) lei upon arrival. I’d assume after the ..."
Reviewed on Sep. 23, 2024
Fairmont Kea Lani Maui
4100 Wailea Alanui Dr, Kihei, HI
The price is CA $1,006 per night from Oct. 26 to Oct. 27
CA $1,006
CA $1,265 total
includes taxes & fees
Oct 26 - Oct 27
9.2/10 Wonderful! (1,006 reviews)
"It wasn’t perfect! We reserved the suite for 3 person, for 4 nights, but they had everything in the suite for 2 people and we had to ask them every day to provide us extra towels, cups, etc."
Reviewed on Sep. 24, 2024
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
Discover the most popular places to visit in Wailea
Wailea Beach
4.5/5(295 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.
Makena State Park Beach
4.5/5(105 reviews)
Three distinct, undeveloped beaches and a dormant volcano crater form this scenic southern region of Maui.
Maluaka Beach
4/5(25 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.
Things to do
Makena Turtle Town Eco Adventure in Maui
CA $133
Per adult
80% of travellers recommend
Night Time Snorkel At Turtle Town With Lights And Stars
CA $175
Per adult
Brewery and Beach Cruise in a Vintage VW Bus
CA $270
Per adult
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Flights
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.