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.
Kihei Kai Nani

Kihei Kai Nani

3.5 out of 5
South Kihei
Price was CA $1,935, price is now CA $1,331 per person
CA $1,331
per person
Sep 14 - Sep 20
found 16 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kahului (OGG)
10/10 Exceptional! (1 review)
Great communication with owner. The bedroom has a queen bed and there is a queen size sofa bed. Air conditioner unit in the living room only. The plenty of dish and cook wear. Washer and dryer in unit. Beach is literally across the street and 2 others on both sides. Kamaole I beach has best water clarity for snorkeling. Building 10 is super quiet.

Reviewed on May 16, 2026

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
Wailea
Price was CA $6,874, price is now CA $4,522 per person
CA $4,522
per person
Sep 27 - Oct 3
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Kahului (OGG)
9.4/10 Exceptional! (1,000 reviews)
The property was beautiful and well maintained. Lush garden spaces. Pool area and loungers being available along with poolside service was great. Room was large and felt very private. Overall quiet property and relaxing stay. Beach picnic excursion was great as well!

Reviewed on Jul 8, 2026

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
Wailea
Price was CA $5,725, price is now CA $4,059 per person
CA $4,059
per person
Sep 3 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
8.8/10 Excellent! (1,004 reviews)
Overall, the Grand Wailea is a great hotel, however, as a guest you feel like you’re just a cog in the machine. We had a great time, but never felt that over the top service / experience that you would expect for a hotel with the reputation that it has / costs as much as it does

Reviewed on Jul 14, 2026

Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
North Kihei
Price was CA $3,807, price is now CA $2,746 per person
CA $2,746
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Kahului (OGG)
8.4/10 Very good! (903 reviews)
There was no AC in rooms however the ceiling fans provided cool air flow and the weather was windy so breeze flowed well through open windows- staff were friendly and the condo had every supplies that was needed- great place for vacation!

Reviewed on Jul 15, 2026

Wailea Grand Champions - Maui Condo & Home

Wailea Grand Champions - Maui Condo & Home

3 out of 5
Wailea
Price was CA $3,030, price is now CA $2,186 per person
CA $2,186
per person
Sep 14 - Sep 20
found 16 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kahului (OGG)
7.8/10 Good! (20 reviews)

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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
The price is CA $1,246 per night from Aug 14 to Aug 15
CA $1,246
CA $1,571 total
Aug 14 - Aug 15
includes taxes & fees
8.8/10 Excellent! (1,016 reviews)
"Overall, the Grand Wailea is a great hotel, however, as a guest you feel like you’re just a cog in the machine. We had a great time, but never felt that over the top service / experience that you would expect for a hotel with the reputation that it has / costs as much as it does"

Reviewed on Jul 14, 2026

Grand Wailea Maui, A Waldorf Astoria Resort
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
The price is CA $1,419 per night from Aug 8 to Aug 9
CA $1,419
CA $1,768 total
Aug 8 - Aug 9
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
"It would have been nice to have another restaurant available for lunch. The only ones open were Sushi (my family doesn't eat sushi) and the Ama (which was packed). Ko only served at the bar. It was a bit frustrating."

Reviewed on Jul 13, 2026

Fairmont Kea Lani Maui
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
3900 Wailea Alanui Drive Kihei HI
The price is CA $2,102 per night from Jul 20 to Jul 21
CA $2,102
CA $2,587 total
Jul 20 - Jul 21
includes taxes & fees
9.6/10 Exceptional! (1,000 reviews)
"Excellent staff and service!"

Reviewed on Jul 8, 2026

Four Seasons Resort Maui at Wailea
See all 6,019 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.
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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 $127
per adult
92% of travellers recommend
Maui Pineapple Farm Tour
Kahului Airport Custom Lei Greeting - Choose Your Lei

Kahului Airport Custom Lei Greeting - Choose Your Lei (OGG)

CA $88
per child
94% of travellers recommend
Kahului Airport Custom Lei Greeting - Choose Your Lei (OGG)
See all activities in Kaupakulua

Frequently asked questions

How much does a Kaupakulua vacation package cost?
You'll find cheap prices from CA $1,331 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.

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.