A coastal landscape with a prominent green hill and a rocky shoreline.
Photo by Ed Mayfield
Open Photo by Ed Mayfield

Kahakuloa Vacations from $800

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The Latest Kahakuloa Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Sep 18 - Sep 23

    Kihei Kai Nani + Flight

    South Kihei
    5 nights
    3.5 star property
    10/10 - Exceptional (1 review)
    "Great communication with owner. The bedroom has a queen bed and there is a queen size sofa bed. Air conditioner unit in the living room only. The plenty of dish and cook wear. Washer and dryer in unit. Beach is literally across the street and 2 others on both sides. Kamaole I beach has best water clarity for snorkeling. Building 10 is super quiet. "
    Reviewed May 16, 2026
    Roundtrip Los Angeles (LAX) - Maui (OGG)
    LAX - OGGNonstop OGG - LAX1 stop
    $1,128
    $800
    per traveler
    found 1 day ago
    Kihei Kai Nani
  • 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
    $3,691
    $2,038
    per traveler
    found 1 day ago
    Hotel Wailea, Relais & Chateaux - Adults Only
  • Sep 28 - Oct 2

    Maui Beach Vacation Club + Flight

    North Kihei
    4 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 - BUR2 stops
    Save 100% on your flight
    $1,473
    $1,004
    per traveler
    found 1 day ago
    Maui Beach Vacation Club
  • 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
  • Sep 28 - Oct 2

    Aston Maui Hill + Flight

    South Kihei
    4 nights
    3.0 star property
    9.0/10 - Wonderful (944 reviews)
    "If you are looking for a family room, this one is perfect! We did not use the pool because it’s too far from us. We are up the hill."
    Reviewed July 14, 2026
    Roundtrip Burbank (BUR) - Maui (OGG)
    BUR - OGG1 stop OGG - BUR2 stops
    Save 100% on your flight
    $1,400
    $995
    per traveler
    found 1 day ago
    Aston Maui Hill

What to do in Kahakuloa

Kahakuloa 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 a Kahakuloa vacation package cost?

You can snap up a vacation package to this top destination from $800 on Expedia. However, how much your vacation to Kahakuloa costs will depend on the length of stay, hotel choice and season.

What are the cheapest months to go to Kahakuloa?

If you'd like to book a cheap Kahakuloa vacation package, consider planning a trip in October, November and December. You'll generally find better prices on airfares and hotels during these months — perfect for budget-conscious travelers.

How many days is enough for Kahakuloa?

Typically, a handful of days is enough to see the major attractions during your Kahakuloa vacation. But if you want to have some time to relax or take day trips, consider extending your itinerary.

How to find the best Kahakuloa package deals?

Landing a cheap Kahakuloa package deal is a cinch with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can fine-tune your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to view the most economical Kahakuloa package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are often lower.

Is it cheaper to book a Kahakuloa vacation as a package?

You can enjoy significant savings on your Kahakuloa getaway by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to browse some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.

When to book a vacation package to Kahakuloa?

If you've got your Kahakuloa travel dates finalized, book as early as you can to score some terrific deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are ideal for impromptu escapes.

How to plan a trip to Kahakuloa?

  1. Choose the right time to travel: Your schedule, favorite season and the type of weather you enjoy can all influence your decision on when to travel to Kahakuloa.
  2. Figure out your budget: Ensure you have enough money to cover everything from dining out and transportation to activities and airfares. Your hotel will probably be the biggest expense during your trip to Kahakuloa.
  3. Organize your Kahakuloa escape with our trip planning tool: Look for and book stays and activities all in one place. You can also collaborate with your group to plan an unforgettable trip to Kahakuloa together.
  4. Determine how many days away: Start by compiling a list of the attractions you want to get to in Kahakuloa. Then, estimate how long you'll need for each, including any travel time.
  5. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a customized Kahakuloa vacation package.
  6. Book any activities or day trips: Now to the fun part — locking in everything you want to do and see. Check out some of the top things to do in Kahakuloa in Kahakuloa and book your tickets early to save time (and maybe some cash too!).

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

If you're anything like us, you love jet-setting around the world but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Kahakuloa break over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you see them.