
Olowalu Vacation Packages
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Your Olowalu Vacation
Get ready to experience Olowalu on your own terms with a custom Olowalu vacation package! Discovering the best parts of this city is simpler with a base in a neighborhood such as Wailuku Heights, which is good for views, among other things. Ready to venture out and explore? West Maui Mountains, Launiupoko Beach Park and Puamana Beach Park are some of the best places to visit during a trip to Olowalu. Stop daydreaming and start doing. Browse the many options on Expedia today and finally put your Olowalu vacation plans into action!
Top Olowalu Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Grand Champions
Wailea
Price was CA $2,021, price is now CA $1,577 per person
CA $1,577
per person
Sep 8 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kahului (OGG)
9.2/10 Wonderful! (5 reviews)
Grand Champions exceeded every expectation. The property is beautifully maintained with lush tropical landscaping that instantly sets the tone for a relaxing Maui getaway. The unit was spotless, well-appointed, and had everything we needed — the kitchen was fully equipped, the beds were comfortable, and the lanai was the perfect spot for morning coffee.
The location in Wailea is unbeatable: quiet and private, yet minutes from world-class beaches, restaurants, and Shops at Wailea. The pools were pristine and never crowded, and the grounds feel more like a resort than a condo complex.
Check-in was seamless and communication with the host was prompt and professional throughout. We’d absolutely stay here again and recommend it to anyone looking for a comfortable, upscale base to explore South Maui. Mahalo!
Reviewed on Apr 20, 2026

Hotel Wailea, Relais & Chateaux - Adults Only
Wailea
Price was CA $5,987, price is now CA $4,352 per person
CA $4,352
per person
Aug 26 - Sep 2
found 21 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
9.4/10 Exceptional! (1,002 reviews)
If there isn’t a wedding going on watch the sunset from the front lawn area by the old ice cream truck. Better view than from the birdcage. More open and less blockage.
Great high end vibe.
Reviewed on Jun 22, 2026


Palms at Wailea Maui
Wailea
Price was CA $2,783, price is now CA $2,127 per person
CA $2,127
per person
Sep 8 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kahului (OGG)
8.4/10 Very good! (542 reviews)
Liked the grounds as they were nicely manicured. Disliked the dated furniture, carpet and leaking restroom.
Reviewed on Jun 17, 2026

Maui Banyan Vacation Club
South Kihei
Price was CA $3,026, price is now CA $2,326 per person
CA $2,326
per person
Jul 27 - Aug 3
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Kahului (OGG)
8/10 Very good! (372 reviews)
Staff was nice, I did find cockroaches in my room. When I told the staff they asked me what I wanted them to do about it.... other than that there is a nice full kitchen and an easy walk to the BEACH.
Reviewed on Jun 14, 2026
Olowalu Hotel Deals

Four Seasons Resort Maui at Wailea
3900 Wailea Alanui Drive Kihei HI
The price is CA $1,343 per night from Jul 8 to Jul 9
CA $1,343
CA $1,687 total
Jul 8 - Jul 9
includes taxes & fees

The Westin Maui Resort & Spa, Ka'anapali
2365 Kaanapali Pkwy Lahaina HI
Fully refundableReserve now, pay when you stay
The price is CA $1,022 per night from Jul 19 to Jul 20
CA $1,022
CA $1,295 total
Jul 19 - Jul 20
includes taxes & fees
9.2/10 Wonderful! (1,083 reviews)
"Amazing place with lots to do. Make sure to sign up for activities a day in advance, fills up quickly."
Reviewed on Jun 23, 2026

Grand Wailea Maui, A Waldorf Astoria Resort
3850 Wailea Alanui Drive Kihei HI
The price is CA $1,120 per night from Jul 8 to Jul 9
CA $1,120
CA $1,422 total
Jul 8 - Jul 9
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
"Overall a really nice stay at the Wailea. Our room got upgraded to a fantastic ocean view room in the Chapel wing. The pools were fantastic and so much fun with all the water slides. We would always arrive mid to late morning. The breakfast buffet was not as good as I had hoped. All the baked items ..."
Reviewed on Jun 22, 2026
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.
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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.







