Kaupakulua Vacation Packages
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Your Kaupakulua Vacation
Say farewell to the stress of planning and hello to a Kaupakulua vacation package. With the finer details organized before you leave, you can focus on discovering every inch of this city, starting with Haiku, which is great for views, walking and nature. Fill your schedule with tours of Hookipa Beach Park, Kuau Bay Beach and Maui Spa Retreat, some of the top attractions you really should see during a trip to Kaupakulua. Your dream Kaupakulua vacation is clicks away. Search accommodations, flights and more on Expedia for a trip that's tailored just for you.
Top Kaupakulua Vacation Deals
Price found within the past 48 hours. Click for updated prices.
OUTRIGGER Kaanapali Beach Resort
Price was CA $3,304, price is now CA $1,905 per person
CA $1,905
per person
Jun 4 - Jun 11
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
9.2/10 Wonderful! (1,669 reviews)
Wonderful cultural experience every cultural educator was amazing!!! Best part actually. DO NOT buy tours at the concierge or the breakfast vouchers. Breakfast at Maui Brewing not worth it (the servers were actually not happy to take them either) and using the $100 tour credit at concierge was still more expensive than just buying from the tour company right on the beach or online. Felt very ripped off by the hotel on that part. Plenty of places to get breakfast that are much better.
Reviewed on Mar 25, 2026
Kahana Beach Vacation Club
Price was CA $4,042, price is now CA $2,122 per person
CA $2,122
per person
May 16 - May 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Kahului (OGG)
8.6/10 Excellent! (814 reviews)
We were at the property for the biggest storm in 95 years and they did such a good job of keeping things safe for us and getting the hot tub and pool up and running as soon as possible when the storm settled down. We had a great time. Room was very clean, it was quiet, and we had a beautiful view of the ocean. Would definitely stay here again.
Reviewed on Mar 20, 2026
Hotel Wailea, Relais & Chateaux - Adults Only
Wailea
Price was CA $5,808, price is now CA $3,397 per person
CA $3,397
per person
Jun 16 - Jun 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Kahului (OGG)
9.4/10 Exceptional! (1,001 reviews)
Literally the best hotel experience I’ve had.
Reviewed on Mar 21, 2026
The Whaler Resort Kaanapali Beach
Price was CA $4,208, price is now CA $2,482 per person
CA $2,482
per person
May 8 - May 15
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
9.6/10 Exceptional! (367 reviews)
The resort was in the perfect location! We had a wonderful time walking up and down the beach and Whaler Village is literally right next to it less than five min walk. They had tons of shops and great food options!
Reviewed on Mar 27, 2026
Kaupakulua Hotel Deals
Four Seasons Resort Maui at Wailea
3900 Wailea Alanui Drive Kihei HI
The price is CA $1,101 per night from Apr 10 to Apr 11
CA $1,101
CA $1,307 total
Apr 10 - Apr 11
includes taxes & fees
9.6/10 Exceptional! (1,000 reviews)
Four Seasons is worth every penny, every time. They are excellent. This property and the service is unmatched in the area. I stayed all of last week and then came back. Staff is so excellent. Property is gorgeous. It's just perfect. A lot of things aren't worth the price these days, but I have to ...
Reviewed on Mar 19, 2026
Maui Seaside Hotel
100 W Kaahumanu Ave Kahului HI
Fully refundableReserve now, pay when you stay
The price is CA $345 per night from Mar 29 to Mar 30
CA $345
CA $451 total
Mar 29 - Mar 30
includes taxes & fees
8.8/10 Excellent! (1,317 reviews)
We arrived with one of us feeling ill and we were given early check-in with a room with a better view than we reserved. We loved our poolside room with ocean view from the lanai. It was a very clean motel room. The beach and ocean is a few steps away but it is right next to a working harbor.The pool ...
Reviewed on Mar 26, 2026
Fairmont Kea Lani Maui
4100 Wailea Alanui Dr Kihei HI
The price is CA $1,482 per night from Apr 26 to Apr 27
CA $1,482
CA $1,842 total
Apr 26 - Apr 27
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
Staff was incredibly welcoming and helpful. Bar/restaurant staff were amazing. Pools were clean and poolside servers were very friendly. Overall an amazing property with wonderful staff
Reviewed on Mar 16, 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.
What to do in Kaupakulua
Maui Beach Parks Self-Guided Driving Audio Tour
CA $18
per traveller
90% of travellers recommend
Waterfalls of West Maui and Molokai Helicopter tour
CA $574
per traveller
Maui: Road to Hana Adventure with Farm to Table Lunch
CA $355
per adult
92% of travellers recommend
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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.
