Kaupakulua Vacations from $1,782

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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.

The Latest Kaupakulua vacation packages

Price found within the past 48 hours. Click for updated prices.
Palms at Wailea Maui

Palms at Wailea Maui

3.5 out of 5
Wailea
Price was $2,854, price is now $1,782 per person
$1,782
per person
Jun 15 - Jun 22
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
8.4/10 Very Good! (530 reviews)
Excellent renovated space. Could be better stocked like the other rental companies, but overall a great stay and unit well located in the complex.

Reviewed on Apr 14, 2026

Hyatt Vacation Club at Ka'anapali Beach, Maui

Hyatt Vacation Club at Ka'anapali Beach, Maui

3.5 out of 5
Price was $2,924, price is now $1,865 per person
$1,865
per person
Jun 19 - Jun 24
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
9.2/10 Wonderful! (96 reviews)
We had a beach view balcony and the room was very clean. We stayed a week and the great staff cleaned daily. Every one was very friendly and helpful. The parking is valet and your car is always ready when you need it.

Reviewed on Apr 12, 2026

The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua

5 out of 5
Save 100% on your flight
Price was $2,674, price is now $1,784 per person
$1,784
per person
May 16 - May 21
found 16 hours ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
9.2/10 Wonderful! (1,002 reviews)
Felt more like a Marriott than a Ritz. Hotel is okay, pool heater was out for the week, room was somewhat worn, AC was noisy. Not the same level of Ritz or Four Season's for the cost that I expect. Not a bad experience but not worth the cost compared to other 5 stars. I would not stay there again.

Reviewed on Apr 15, 2026

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
Wailea
Save 100% on your flight
Price was $5,407, price is now $3,704 per person
$3,704
per person
Jun 2 - Jun 9
found 15 hours ago
Roundtrip non-stop flight included
Burbank (BUR) to Kahului (OGG)
9.4/10 Exceptional! (1,000 reviews)
Beautiful hotel, very unique experience. Everyone was very nice and helpful. We enjoyed our stay

Reviewed on Apr 8, 2026

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
Wailea
Save 100% on your flight
Price was $5,739, price is now $3,999 per person
$3,999
per person
Jun 15 - Jun 22
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)
8.8/10 Excellent! (1,001 reviews)
Perfect location for day drinking

Reviewed on Apr 14, 2026

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Discover the most popular places to visit in Kaupakulua

Twin Falls

Commune with nature and explore the great outdoors at Twin Falls during your travels in Haiku. While you're in the area, stroll along the beautiful beaches.

Twin Falls

Haiku Park

Explore the great outdoors at Haiku Park, a lovely green space in Pauwela. Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.

Haiku Park

Haleakala Bike Company

You can take time to visit Haleakala Bike Company during your travels to Pauwela. Wander the beautiful beaches and seaside in the area.

Haleakala Bike Company

What to do in Kaupakulua

Kahului: Self-Driving Audio Tour of Road to Hana

Road to Hana Maui Tour: Self-Guided Audio Drive

$15
per traveler
82% of travellers recommend
Road to Hana Maui Tour: Self-Guided Audio Drive
Orchid Airport Lei Greeting

Orchid Airport Lei Greeting (Maui, Kahului Airport, OGG)

$47
per adult
100% of travellers recommend
Orchid Airport Lei Greeting (Maui, Kahului Airport, OGG)
Maui: Road to Hana Adventure with Farm to Table Lunch

Maui: Road to Hana Adventure with Farm to Table Lunch

$259
per adult
92% of travellers recommend
Maui: Road to Hana Adventure with Farm to Table Lunch
See all activities in Kaupakulua

Kaupakulua Hotel Deals

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive Kihei HI
$716 nightly
The price is $850 total per night from May 6 to May 7
$850 total
May 6 - May 7
Total with taxes and fees
8.8/10 Excellent! (1,012 reviews)
Perfect location for day drinking

Reviewed on Apr 14, 2026

Grand Wailea Maui, A Waldorf Astoria Resort
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
3900 Wailea Alanui Drive Kihei HI
$765 nightly
The price is $908 total per night from Apr 30 to May 1
$908 total
Apr 30 - May 1
Total with taxes and fees
9.6/10 Exceptional! (1,001 reviews)
Wonderful Hotel Great restaurants staffed by true professionals

Reviewed on Apr 14, 2026

Four Seasons Resort Maui at Wailea
Maui Coast Hotel

Maui Coast Hotel

3.5 out of 5
2259 S Kihei Rd Kihei HI
Fully refundableReserve now, pay when you stay
$272 nightly
The price is $323 total per night from May 5 to May 6
$323 total
May 5 - May 6
Total with taxes and fees
9.6/10 Exceptional! (2,572 reviews)
Only was there for a night stay. However the amenities they have and conveniences of location are perfect. Will be staying again.

Reviewed on Apr 15, 2026

Maui Coast Hotel
See all 6,133 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.

Find the Best Kaupakulua Vacation Packages

Kaupakulua Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Kahului Airport (OGG)
Max Temp Winter
75ºF
Max Temp Summer
80ºF
Top Sights
Twin Falls and Haiku Park

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Frequently asked questions

How much does a Kaupakulua vacation package cost?
Offering great value package deals from $1,782 on Expedia, you'll be thrilled with how little a vacation to Kaupakulua costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Kaupakulua?
You're likely to find lower rates and greater availability in September, October and December. Explore our cheap Kaupakulua vacation packages and you could land some great off-season discounts.
How many days is enough for Kaupakulua?
The ideal duration for your Kaupakulua vacation depends on what you'd like to do. Typically, a handful of days to a week will give you time to visit all the main sights and discover some hidden spots along the way.
How to find the best Kaupakulua package deals?
Use Expedia's handy filters to find some tempting Kaupakulua package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Kaupakulua package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Kaupakulua vacation as a package?
You can enjoy significant savings on your next Kaupakulua retreat by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to see the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Kaupakulua?
Secure amazing discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Kaupakulua getaway.
Does Expedia offer Book Now, Pay Later Kaupakulua vacation packages?
Jet off on your perfect trip to Kaupakulua with Expedia's Book Now, Pay Later vacations. No need to scrimp and save or wait until your next payday — we've joined forces with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans allow you to spread the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's easy to budget for your trip and snap up bargains while they last.

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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.