Olowalu Holidays

Photo by Chris Fiegel

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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 S$1,326 per night from 31 Jul to 1 Aug
S$1,326
31 Jul - 1 Aug
includes taxes & fees
8.8/10 Excellent! (1,014 reviews)
"Amazing location in the very friendly stuff"

Reviewed on 12 Jul, 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 S$2,146 per night from 28 Jul to 29 Jul
S$2,146
28 Jul - 29 Jul
includes taxes & fees
9.6/10 Exceptional! (1,005 reviews)
"Excellent staff and service!"

Reviewed on 8 Jul, 2026

Four Seasons Resort Maui at Wailea
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 S$428 per night from 22 Jul to 23 Jul
S$428
22 Jul - 23 Jul
includes taxes & fees
8.8/10 Excellent! (4,175 reviews)
"Did not expect or was notified of Beach contamination sign which ruined the mood."

Reviewed on 11 Jul, 2026

Aston Kaanapali Shores
See all 13,103 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

Underwater Submarine Adventure

Maui Underwater Submarine Adventure

S$207
per adult
94% of travellers recommend
Maui Underwater Submarine Adventure
Lahaina Sunset Dinner Cruise

Sunset Dinner Cruise aboard Quicksilver: Prime Rib, Fish, Chicken or Pasta

S$172
per adult
84% of travellers recommend
Sunset Dinner Cruise aboard Quicksilver: Prime Rib, Fish, Chicken or Pasta
Maui: Molokini & Turtle Town Snorkel & Waterslide Adventure

Maui: Molokini & Turtle Town Snorkel & Waterslide Adventure

S$266
per adult
94% of travellers recommend
Maui: Molokini & Turtle Town Snorkel & Waterslide Adventure
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.