Kaupakulua Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Kaupakulua

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 21.564.329 ₫ per night from 21 Jul to 22 Jul
21.564.329 ₫
27.305.594 ₫ total
21 Jul - 22 Jul
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
"Very beautiful grounds and friendly staff. It was very crowded. Small pool and lots of people. All restaurants were booked, with the exception of quick service poolside bar & grill."

Reviewed on 6 Jul 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 27.322.583 ₫ per night from 6 Aug to 7 Aug
27.322.583 ₫
33.996.175 ₫ total
6 Aug - 7 Aug
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
"Breathtaking place!"

Reviewed on 2 Jul 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 30.110.065 ₫ per night from 20 Jul to 21 Jul
30.110.065 ₫
37.461.191 ₫ total
20 Jul - 21 Jul
includes taxes & fees
9.6/10 Exceptional! (1,003 reviews)
"My kids loved the kids club great stuff"

Reviewed on 3 Jul 2026

Four Seasons Resort Maui at Wailea
See all 6,017 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.

Frequently asked questions

How much does a Kaupakulua holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday to Kaupakulua costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Kaupakulua?
January, February and April are the best times to search for cheap Kaupakulua holiday packages. Opting to travel in less busy months means you can typically find lower prices on hotels and flights.
How many days is enough for Kaupakulua?
The ideal length of your Kaupakulua holiday depends on what you'd like to do and see. Typically, a few days to a week will give you plenty of time to go to all the major attractions and explore some hidden treasures 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 holiday package as early as possible.
Is it cheaper to book a Kaupakulua holiday as a package?
You can enjoy significant savings on your next Kaupakulua retreat by booking a customised holiday 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 holiday 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.
How to plan a trip to Kaupakulua?

  1. Choose your dates: What you plan to do in Kaupakulua and your favourite season can help you decide when to go.
  2. Calculate your budget: Ensure you have enough money to pay for everything from food and transportation to airfares and activities. Your accommodation will likely be the largest expense during your trip to Kaupakulua.
  3. Determine how many days away: Start by making a list of all the attractions you'd like to experience in Kaupakulua. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your airfare and accommodation: After you've nailed down your trip dates and duration, book the ideal Kaupakulua holiday package for you.

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