Olowalu Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

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Top hotels in Olowalu

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 ฿26,874 per night from 31 Jul to 1 Aug
฿26,874
฿34,055 total
31 Jul - 1 Aug
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"The seating at the pool is a huge problem. They do not have enough seats and will remove your items if you do not go back to your seat once every hour. One employee actually admitted to throwing our items away, instead of holding them as they’re supposed too. This is hard considering there are many ..."

Reviewed on 4 Jul 2026

Grand Wailea Maui, A Waldorf Astoria Resort
The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

4.5 out of 5
2365 Kaanapali Pkwy Lahaina HI
Fully refundableReserve now, pay when you stay
The price is ฿15,891 per night from 20 Jul to 21 Jul
฿15,891
฿20,782 total
20 Jul - 21 Jul
includes taxes & fees
9.2/10 Wonderful! (1,101 reviews)
"Entire stay was excellent!"

Reviewed on 4 Jul 2026

The Westin Maui Resort & Spa, Ka'anapali
Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
2780 Kekaa Dr Lahaina HI
Fully refundableReserve now, pay when you stay
The price is ฿7,465 per night from 13 Jul to 14 Jul
฿7,465
฿10,622 total
13 Jul - 14 Jul
includes taxes & fees
8.6/10 Excellent! (1,767 reviews)
"S"

Reviewed on 4 Jul 2026

Royal Lahaina Resort & Bungalows
See all 13,080 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.

What to do in Olowalu

Lahaina Sunset Dinner Cruise

From Ma'alaea Harbor: Sunset Dinner Cruise Aboard the Quicksilver

฿4,598
per adult
84% of travellers recommend
From Ma'alaea Harbor: Sunset Dinner Cruise Aboard the Quicksilver
Myths of Maui Luau at the Royal Lahaina Resort

Myths of Maui Luau at the Royal Lahaina Resort

฿5,566
per adult
86% of travellers recommend
Myths of Maui Luau at the Royal Lahaina Resort
Sail Maui 'Alihilani Sunset Sail

Akialoa Sunset Sail with Open Bar & Delicious Appetizers from Ma'alaea

฿3,418
per adult
96% of travellers recommend
Akialoa Sunset Sail with Open Bar & Delicious Appetizers from Ma'alaea
See all activities in Olowalu

Frequently asked questions

How much does an Olowalu holiday package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a holiday 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 holiday package, consider planning a trip in January, February and September. You'll typically find better prices on flights and accommodation 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 holiday. 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 holiday as a package?
Expedia holiday 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 personalised Olowalu holiday by choosing your preferred type of stay, airline and car class.
When to book a holiday 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, favourite 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 accommodation 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 holiday. 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 holiday package that brings all your bookings together.

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.