An underwater scene with a diver and a turtle.
Photo by Chris Fiegel
Open Photo by Chris Fiegel

Olowalu Vacations from $1,084

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The Latest Olowalu Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Sep 28 - Oct 3

    Aston Maui Hill + Flight

    South Kihei
    5 nights
    3.0 star property
    9.0/10 - Wonderful (946 reviews)
    "Super clean, super nice stuff. Looks every second in that place"
    Reviewed July 20, 2026
    Roundtrip Burbank (BUR) - Maui (OGG)
    BUR - OGG1 stop OGG - BUR1 stop
    Save 100% on your flight
    $1,630
    $1,084
    per traveler
    found 1 day ago
    Aston Maui Hill
  • Sep 28 - Oct 3

    Hotel Wailea, Relais & Chateaux - Adults Only + Flight

    Wailea
    5 nights
    5.0 star property
    9.4/10 - Exceptional (1,000 reviews)
    "The property was beautiful and well maintained. Lush garden spaces. Pool area and loungers being available along with poolside service was great. Room was large and felt very private. Overall quiet property and relaxing stay. Beach picnic excursion was great as well!"
    Reviewed July 8, 2026
    Roundtrip Burbank (BUR) - Maui (OGG)
    BUR - OGG1 stop OGG - BUR1 stop
    Save 100% on your flight
    $3,615
    $1,908
    per traveler
    found 1 day ago
    Hotel Wailea, Relais & Chateaux - Adults Only
  • Sep 28 - Oct 3

    Maui Beach Vacation Club + Flight

    North Kihei
    5 nights
    2.5 star property
    8.4/10 - Very Good (915 reviews)
    "There was no AC in rooms however the ceiling fans provided cool air flow and the weather was windy so breeze flowed well through open windows- staff were friendly and the condo had every supplies that was needed- great place for vacation!"
    Reviewed July 15, 2026
    Roundtrip Burbank (BUR) - Maui (OGG)
    BUR - OGG1 stop OGG - BUR1 stop
    Save 100% on your flight
    $1,787
    $1,122
    per traveler
    found 1 day ago
    Maui Beach Vacation Club
  • Sep 28 - Oct 3

    Mana Kai Maui- Official Onsite Rental + Flight

    South Kihei
    5 nights
    3.5 star property
    9.0/10 - Wonderful (1,004 reviews)
    "The stay was perfectly located in a great area. We loved the snorkeling right off the beach. We could walk to many places we enjoyed."
    Reviewed July 18, 2026
    Roundtrip Burbank (BUR) - Maui (OGG)
    BUR - OGG1 stop OGG - BUR1 stop
    Save 100% on your flight
    $2,225
    $1,448
    per traveler
    found 1 day ago
    Mana Kai Maui- Official Onsite Rental
  • Sep 28 - Oct 3

    Palms at Wailea Maui + Flight

    Wailea
    5 nights
    3.5 star property
    8.4/10 - Very Good (545 reviews)
    "The condo was close to the main area in Kihei. Quick drive to local restaurants, shops, and the market . Property was clean and quiet. The kitchen was fully stocked with pots and pans so we were able to cook meals at the condo. The condo also had beach chairs and toys available to use when you went to the beaches. Beautiful lanai to hang out. The pool area was great for a chill day. Great for families with young kids. Overall exceeded our expectations."
    Reviewed July 16, 2026
    Roundtrip Burbank (BUR) - Maui (OGG)
    BUR - OGG1 stop OGG - BUR1 stop
    Save 100% on your flight
    $2,099
    $1,465
    per traveler
    found 1 day ago
    Palms at Wailea Maui

What to do in Olowalu

Olowalu Hotel Deals

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 from $1,084 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'd like to book a cheap Olowalu vacation package, consider visiting in October, November and December. You'll usually find lower rates on accommodations and flights during these months — perfect for travelers wishing to save money.

How many days is enough for Olowalu?

The ideal length of your Olowalu vacation depends on what you'd like to do. Generally, a handful of days to a week will give you enough time to tick off all the major sights and explore some hidden spots along the way.

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. Choose your dates: The things you plan to do in Olowalu and your preferred season can help you decide when to get away.
  2. Calculate your budget: Make sure you have enough money to pay for everything from food and transportation to airfares and activities. Your accommodations will likely be the largest expense during your trip to Olowalu.
  3. Use Expedia's trip planning tool to discover Olowalu: Research every aspect of your trip to Olowalu with this handy planner. Invite friends or family to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Decide your trip length: Think about how much time you'd like to spend exploring Olowalu. Plan your days so you can get to all the activities and attractions you're interested in without rushing.
  5. Combine your accommodations and airfare: Once you've settled on your travel dates and duration, lock in the perfect Olowalu vacation package for you.
  6. Book activities and experiences in advance: Whether it's entrance to a big attraction or a day trip, you won't have to worry about missing out on the highlights of Olowalu. Find all the fun things to do in Olowalu with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Olowalu vacation packages?

Your Olowalu getaway is meant to be a relaxing escape from your busy life, not a reason for money worries. So to allow you more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.