Kaanapali Hillside Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to AED 148 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Find the Best Kaanapali Hillside Vacation Packages

Kaanapali Hillside Hotel Deals

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 AED 2,307 per night from Jun 9 to Jun 10
AED 2,307
AED 2,901 total
includes taxes & fees
9 Jun - 10 Jun
9/10 Wonderful! (817 reviews)
"Amazing resort , friendly staff and stunning views."

Reviewed on 2 June 2025

The Westin Maui Resort & Spa, Ka'anapali
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 AED 771 per night from Jun 30 to Jul 1
AED 771
AED 1,105 total
includes taxes & fees
30 Jun - 1 Jul
8.2/10 Very Good! (1,326 reviews)
"Loved the ocean beach the water was fantastic, the room was a little musty enjoyed the restaurant and bar. People who worked there were so very helpful and nice 👍"

Reviewed on 1 June 2025

Royal Lahaina Resort & Bungalows
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 AED 1,296 per night from Jun 30 to Jul 1
AED 1,296
AED 1,724 total
includes taxes & fees
30 Jun - 1 Jul
9/10 Wonderful! (1,099 reviews)
"This hotel is located walkable to Whalers Village and the Black Rock beach. The hotel is a bit dated but they are renovating rooms. The pool needs renovations and the loungers need to be replaced. Con: There is no fitness room or partners with gyms. There are many cards to keep track of…need one ..."

Reviewed on 2 June 2025

OUTRIGGER Kaanapali Beach Resort
See all 8,294 properties in Kaanapali Hillside
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 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.