Kaupakulua Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, 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.
Lumeria Maui Educational Retreat Center

Lumeria Maui Educational Retreat Center

Save 100% on your flight
CA $2,343
per person
Nov 27 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Kelowna (YLW) to Kahului (OGG)
8.6/10 Excellent! (229 reviews)
Maui Banyan Vacation Club

Maui Banyan Vacation Club

South Kihei
Save 100% on your flight
CA $2,655
per person
Dec 19 - Dec 26
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
8/10 Very good! (395 reviews)
Good. Well equipped, microwave and kitchen. Standing shower. Clise to kamaole beaches

Reviewed on Oct 12, 2026

Hotel Wailea Maui

Hotel Wailea Maui

Wailea
CA $5,424
per person
Dec 22 - Dec 28
found 23 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
9.4/10 Exceptional! (1,002 reviews)
Maui Beach Vacation Club

Maui Beach Vacation Club

North Kihei
Save 100% on your flight
CA $2,597
per person
Dec 3 - Dec 10
found 7 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
8.4/10 Very good! (961 reviews)
Maui Banyan - Maui Condo & Home

Maui Banyan - Maui Condo & Home

South Kihei
Save 100% on your flight
CA $3,227
per person
Dec 30 - Jan 6
found 14 hours ago
Roundtrip flight included
Vancouver (YVR) to Kahului (OGG)
7.8/10 Good! (63 reviews)

Ready to book your vacation to Kaupakulua?

Choose your dates

Kaupakulua Hotel Deals

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI
CA $1,078
CA $1,372 total
Oct 30 - Oct 31
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
"Having stayed at the Grand Wailea three times now, it's disappointing to see how much the overall experience has changed. The rooms remain comfortable, and the staff continue to be exceptionally friendly and helpful. Unfortunately, the quality of the amenities, services, and overall experience has ..."

Reviewed on Oct 13, 2026

Grand Wailea Maui, A Waldorf Astoria Resort
Maui Coast Hotel

Maui Coast Hotel

2259 S Kihei Rd Kihei HI
Fully refundableReserve now, pay when you stay
CA $241
CA $352 total
Oct 19 - Oct 20
includes taxes & fees
9.6/10 Exceptional! (2,702 reviews)
"Staff is very friendly and professional. Rooms in the new Kai building are wonderful! I love having Miso Phat Sushi and Kihei Cafe right there!!!! Salt water pool is divine."

Reviewed on Oct 15, 2026

Maui Coast Hotel
Maui Seaside Hotel

Maui Seaside Hotel

100 W Kaahumanu Ave Kahului HI
Fully refundableReserve now, pay when you stay
CA $239
CA $326 total
Nov 12 - Nov 13
includes taxes & fees
Maui Seaside Hotel
See all 6,112 properties in Kaupakulua
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 Tour

Maui Beach Parks Self-Guided Driving Audio Tour

CA $21
per traveller
90% of travellers recommend
Maui Beach Parks Self-Guided Driving Audio Tour
Maui Pineapple Farm Tour

Maui Pineapple Farm Tour

CA $125
per adult
92% of travellers recommend
Maui Pineapple Farm Tour
Road To Hana Self-Guided Driving Audio Tour Bundle

Best of Maui: Self-Guided Driving Audio Tour Bundle

CA $35
per traveller
100% of travellers recommend
Best of Maui: Self-Guided Driving Audio Tour Bundle
See all activities in Kaupakulua

Frequently asked questions

How much does a Kaupakulua vacation package cost?
You'll find cheap prices from CA $2,343 on Expedia for your Kaupakulua break. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Kaupakulua costs.
What are the cheapest months to go to Kaupakulua?
You can usually find lower rates and better availability in January, February and April. Browse our cheap Kaupakulua vacation packages and you could land some excellent off-season deals.
How many days is enough for Kaupakulua?
The ideal length for your Kaupakulua vacation depends on what you'd like to do. Generally, a handful of days to a week will give you plenty of time to check out all the main attractions and discover some hidden gems along the way.
How to find the best Kaupakulua package deals?
Landing a cheap Kaupakulua package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget, apply a few filters and browse what's available. You can personalize your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Kaupakulua package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Kaupakulua vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll generally snag a better deal than booking each component individually. And you'll still have the flexibility to create a tailored Kaupakulua vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Kaupakulua?
If you're considering an impromptu Kaupakulua adventure, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score awesome deals on your hotels and flights by booking ahead.
How to plan a trip to Kaupakulua?
  1. Pick your travel dates: What you want to do in Kaupakulua and your preferred season will help you decide when to get away.
  2. Set a budget: Consider costs like transportation, flights and meals when calculating how much to save for your trip to Kaupakulua. Then, select a property that suits your budget, whether that's an economical option or a high-end getaway.
  3. Decide how long to go for: Now that you're more familiar with Kaupakulua, you can figure out the right length of your vacation. Pull together a rough itinerary and allocate enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalized Kaupakulua vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.