Olowalu Vacations

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

    Save up to ₩1,660,000 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

Find the Best Olowalu Vacation Packages

Olowalu Hotel Deals

Aston Kaanapali Shores

Aston Kaanapali Shores

3.5 out of 5
3445 Lower Honoapiilani Hwy Lahaina HI
Fully refundableReserve now, pay when you stay
The price is ₩366,566 per night from Aug 9 to Aug 10
₩366,566
₩477,878 total
Aug 9 - Aug 10
includes taxes & fees
8.8/10 Excellent! (4,218 reviews)
"Great amenities. Courteous staff. Good value."

Reviewed on Aug 2, 2026

Aston Kaanapali Shores
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 ₩1,052,791 per night from Sep 1 to Sep 2
₩1,052,791
₩1,343,174 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"The property was great, awesome pools , beautiful beach ."

Reviewed on Jul 31, 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
The price is ₩1,187,456 per night from Aug 26 to Aug 27
₩1,187,456
₩1,503,627 total
Aug 26 - Aug 27
includes taxes & fees
9.6/10 Exceptional! (1,000 reviews)
"Our stay was amazing. The staff and service were absolutely off the charts. The newly opened spa was the nicest I have ever been in. The food at the adult pool and service by the bar staff was impeccable. The main thing that stuck out to me was the genuine kindness and pride that the staff puts into ..."

Reviewed on Jul 22, 2026

Four Seasons Resort Maui at Wailea
See all 13,126 properties in Olowalu
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 an Olowalu vacation package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation to Olowalu costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Olowalu?
If you're hoping to snag a cheap Olowalu vacation package, consider planning a trip in January, February and September. You'll typically find better prices on flights and accommodations during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Olowalu?
Usually, a handful of days is enough to go to the top attractions during your Olowalu vacation. But if you prefer to have some time to relax or take day tours, think about extending your itinerary.
How to find the best Olowalu package deals?
Start your search for an Olowalu package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Olowalu package deal right away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Olowalu adventure underway.
Is it cheaper to book an Olowalu vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component separately. And you'll still have the freedom to create a personalized Olowalu vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Olowalu?
Land incredible discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Olowalu escape.
How to plan a trip to Olowalu?

  1. Pick the best time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to go to Olowalu.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and dining out to activities and flights. Your accommodations will probably be the biggest expense during your trip to Olowalu.
  3. Decide how long to go for: Now that you know more about Olowalu, you can figure out the ideal length of your vacation. Create a draft plan and give yourself enough time for all the things you want to do.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to choose an Olowalu vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.