Kaanapali Hillside Vacations

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Find the Best Kaanapali Hillside Vacation Packages

Kaanapali Hillside Hotel Deals

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 ₩366,325 per night from Aug 10 to Aug 11
₩366,325
₩505,223 total
Aug 10 - Aug 11
includes taxes & fees
8.2/10 Very Good! (1,366 reviews)
"The hotel was great and the breakfast package was worth it. Our room seemed alittle dated but was still very nice. Best smelling soap and shampoo ever"

Reviewed on Jul 12, 2025

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 ₩742,289 per night from Aug 10 to Aug 11
₩742,289
₩955,218 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (864 reviews)
"Great location! We enjoyed our stay so much my kids really loved Valley Alley nice break away from the sun. All the staff were so friendly 10/10"

Reviewed on Jul 11, 2025

The Westin Maui Resort & Spa, Ka'anapali
OUTRIGGER Kaanapali Beach Resort
OUTRIGGER Kaanapali Beach Resort
3.5 out of 5
2525 Kaanapali Parkway, Lahaina, HI
Fully refundableReserve now, pay when you stay
The price is ₩403,642 per night from Aug 11 to Aug 12
₩403,642
₩549,244 total
Aug 11 - Aug 12
includes taxes & fees
9/10 Wonderful! (1,188 reviews)
"Great hotel, great atmosphere. You can walk to restaurants and shops. Perfect location. Gorgeous beach. Would go back again. The only drawback is once you get there they give you no chairs or loungers for the beach! They rent loungers for 25 dollars a day which is crazy. We had to buy 2 chairs from ..."

Reviewed on Jul 13, 2025

OUTRIGGER Kaanapali Beach Resort
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 Kaanapali Hillside vacation package cost?
You'll find cheap prices on Expedia for your Kaanapali Hillside break. However, a range of factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Kaanapali Hillside costs.
What are the cheapest months to go to Kaanapali Hillside?
The off-season is the best time to visit Kaanapali Hillside if you're hoping to keep costs down. Another tip for getting cheap Kaanapali Hillside vacation packages? Try to avoid public holidays and any major events.
How many days is enough for Kaanapali Hillside?
Typically, a handful of days is enough to explore the top sights during your Kaanapali Hillside vacation. But if you prefer to have more time to unwind or go on day trips, think about extending your itinerary.
How to find the best Kaanapali Hillside package deals?
Start your search for a Kaanapali Hillside package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Kaanapali Hillside package deal right away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Kaanapali Hillside escape underway.
Is it cheaper to book a Kaanapali Hillside vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and stays separately. Better still, you can tailor your Kaanapali Hillside getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Kaanapali Hillside?
If you're planning an impromptu Kaanapali Hillside vacation, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land awesome deals on your hotels and flights by booking ahead.
How to plan a trip to Kaanapali Hillside?

  1. Pick your travel dates: The things you plan to do in Kaanapali Hillside and your favorite season can help you decide when to get away.
  2. Set your budget: Factor in costs like food, flights and transportation when calculating how much to set aside for your trip to Kaanapali Hillside. Then, select a hotel that matches your budget, whether that's a wallet-friendly stay or a swankier retreat.
  3. Set the duration of your trip: Start by making a list of all the attractions you'd like to get to in Kaanapali Hillside. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your accommodations and airfare: After you've settled on your trip dates and duration, book the perfect Kaanapali Hillside vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.