Kaupakulua Vacations

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    Save up to SARĀ 5,400 when you book a flight and hotel together*

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Find the Best Kaupakulua Vacation Packages

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 SARĀ 3,240 per night from Aug 9 to Aug 10
SARĀ 3,240
SARĀ 4,089 total
9 Aug - 10 Aug
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 youā€™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 14 July 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 SARĀ 3,789 per night from Aug 8 to Aug 9
SARĀ 3,789
SARĀ 4,721 total
8 Aug - 9 Aug
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 13 July 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 SARĀ 5,614 per night from Aug 6 to Aug 7
SARĀ 5,614
SARĀ 6,910 total
6 Aug - 7 Aug
includes taxes & fees
9.6/10 Exceptional! (1,000 reviews)
"Excellent staff and service!"

Reviewed on 8 July 2026

Four Seasons Resort Maui at Wailea
See all 6,015 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 vacation package cost?
You'll find cheap prices 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 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.