Kaupakulua Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Sands of Kahana
Price was CA $2,703, price is now CA $1,619 per person
CA $1,619
per person
May 24 - May 28
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Kahului (OGG)
8.2/10 Very Good! (500 reviews)
The staff was great! Easy check in. The grounds are gorgeous, the room was spacious and clean! Our hot water heater wasn’t working one night and we had a staff member up there to fix it within an hour. We loved that it was right by the beach and had captain jacks bar! We can’t wait to come back!
Reviewed on Mar 2, 2026
Hotel Wailea, Relais & Chateaux - Adults Only
Wailea
Price was CA $6,898, price is now CA $4,123 per person
CA $4,123
per person
May 24 - May 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Kahului (OGG)
9.4/10 Exceptional! (1,001 reviews)
Everything was exceptional!
Great property, quiet and peaceful
Reviewed on Jan 6, 2026
Hono Koa Vacation Club
Price was CA $4,099, price is now CA $2,461 per person
CA $2,461
per person
May 16 - May 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Kahului (OGG)
8.6/10 Excellent! (206 reviews)
The condo was clean, roomy and perfect. The location was great! I would recommend!
Reviewed on Jan 30, 2026
Hyatt Vacation Club at Ka'anapali Beach, Maui
Price was CA $6,151, price is now CA $3,919 per person
CA $3,919
per person
Apr 27 - May 4
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
9.2/10 Wonderful! (89 reviews)
Amazing resort. Welcoming staff. Lots of activities. Clean rooms and property. Comfortable beds. Stocked kitchen. Huge bathrooms with lots of counter space. The balcony was our favorite space - dining table and four chairs, two comfortable chairs with table and a lounge couch….but the view was the winner…ocean, island of Lanai, whale watching, mountains, plus gorgeous views of the pools and grounds. We loved the poolside bar and grill and had many meals poolside.
Reviewed on Mar 3, 2026
Kaupakulua Hotel Deals
Grand Wailea Maui, A Waldorf Astoria Resort
3850 Wailea Alanui Drive Kihei HI
The price is CA $1,247 per night from Apr 3 to Apr 4
CA $1,247
CA $1,568 total
Apr 3 - Apr 4
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
Enjoyed everything about this property. Great service and amenities!
Reviewed on Mar 5, 2026
Four Seasons Resort Maui at Wailea
3900 Wailea Alanui Drive Kihei HI
The price is CA $1,642 per night from Mar 9 to Mar 10
CA $1,642
CA $2,038 total
Mar 9 - Mar 10
includes taxes & fees
9.6/10 Exceptional! (1,007 reviews)
Staff
Reviewed on Feb 28, 2026
Maui Seaside Hotel
100 W Kaahumanu Ave Kahului HI
Fully refundableReserve now, pay when you stay
The price is CA $297 per night from Mar 9 to Mar 10
CA $297
CA $393 total
Mar 9 - Mar 10
includes taxes & fees
8.8/10 Excellent! (1,308 reviews)
We stayed in a renovated room. The property was very clean, updated, convenient to the airport, quiet and had super comfortable beds. The staff was super friendly. We only stayed one night because our longer term property was ready the next day. The area is a bit busier than some of the resort spots ...
Reviewed on Mar 6, 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 Zipline Eco Adventure: 8 Lines through the Jungle
CA $225
per adult
100% of travellers recommend
Waterfalls of West Maui and Molokai Helicopter tour
CA $574
per traveller
Maui Beach Parks Self-Guided Driving Audio Tour
CA $21
per traveller
90% of travellers recommend
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
