Olowalu Vacations

Book a Hotel + Flight together to unlock savings

Photo by Chris Fiegel

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 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

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 2,747 per night from Aug 20 to Aug 21
SARĀ 2,747
SARĀ 3,504 total
20 Aug - 21 Aug
includes taxes & fees
Grand Wailea Maui, A Waldorf Astoria Resort
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 SARĀ 929 per night from Aug 17 to Aug 18
SARĀ 929
SARĀ 1,303 total
17 Aug - 18 Aug
includes taxes & fees
8.6/10 Excellent! (1,768 reviews)
"Clean property, spa was great, walkable to everything"

Reviewed on 21 July 2026

Royal Lahaina Resort & Bungalows
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 SARĀ 1,630 per night from Aug 16 to Aug 17
SARĀ 1,630
SARĀ 2,152 total
16 Aug - 17 Aug
includes taxes & fees
9.2/10 Wonderful! (1,135 reviews)
"The room was clean with an ocean view as requested. We had access to the Lanai Lounge which was amazing! The staff was friendly and always willing to help and answer any questions we had. It had restaurants on site and was next to a mall. Location was ideal!"

Reviewed on 20 July 2026

The Westin Maui Resort & Spa, Ka'anapali
See all 13,082 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?
You can pick up a vacation package to this top destination on Expedia. But how much your vacation to Olowalu costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Olowalu?
If you're looking to book a cheap Olowalu vacation package, consider traveling in January, February and September. You'll generally find lower prices on hotels and flights during these months ā€” ideal for budget-conscious travelers.
How to find the best Olowalu package deals?
Use Expedia's filter tool to help you find some great Olowalu package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Olowalu package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book an Olowalu vacation as a package?
You can enjoy significant savings on your Olowalu escape by booking a tailored vacation package. Check the "Package" heading, then select your travel dates and destination to browse the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Olowalu?
Enjoy amazing discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Olowalu trip.
How to plan a trip to Olowalu?

  1. Choose when to get away: Check your diary and pack your bags. Your preferred time of year and the activities on offer will also help you decide when to escape to Olowalu.
  2. Set your budget: Consider expenses such as transportation, flights and meals when working out how much to put aside for your trip to Olowalu. Then, select a property that matches your budget, whether that's an economical option or a more luxurious getaway.
  3. Decide how many days away: Start by making a list of all the activities and attractions you'd like to experience in Olowalu. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a personalized Olowalu vacation package.