Olowalu Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Olowalu Holiday
Our pick of the best Olowalu Hotel Deals
Grand Wailea Maui, A Waldorf Astoria Resort
3850 Wailea Alanui Drive Kihei HI
NZ$1,802
12 Oct - 13 Oct
includes taxes & fees
8.8/10 Excellent! (1,011 reviews)
"Everything was just FANTASTIC. Please don't laugh. The only thing that we can think of that for you guys to do something about, and only if you are allowed to do something about it, is too many black bees at the smoking hut areas."
Reviewed on 27 Sept 2026
Maui Coast Hotel
2259 S Kihei Rd Kihei HI
Fully refundableReserve now, pay when you stay
NZ$493
29 Sept - 30 Sept
includes taxes & fees
9.6/10 Exceptional! (2,695 reviews)
"Free shuttle within 3 miles was amazing"
Reviewed on 28 Sept 2026
Royal Lahaina Resort & Bungalows
2780 Kekaa Dr Lahaina HI
Fully refundableReserve now, pay when you stay
NZ$1,085
26 Oct - 27 Oct
includes taxes & fees
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
Myths of Maui Luau at the Royal Lahaina Resort
NZ$296
per adult
86% of travellers recommend
Akialoa Sunset Sail with Open Bar & Delicious Appetizers from Ma'alaea
NZ$182
per adult
96% of travellers recommend
Original Sunset Cocktail Cruise with Appetizers & Open Bar from Ka'anapali
NZ$240
per adult
90% of travellers recommend
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?
- 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.
- 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.
- 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.
- 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
