Kaanapali Hillside Vacation Packages

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Your Kaanapali Hillside Vacation

Lock in a Kaanapali Hillside vacation package and get ready to experience all this lively city has to offer. Consider staying in the neighborhood of Napili, which is great for walking, coastal beaches and hiking. A trip to Kaanapali Hillside is a terrific opportunity to do some sightseeing. Check out popular attractions like Kaanapali Beach, Kapalua Golf Club Plantation Course and D.T. Fleming Beach Park. Whoever you're taking a break with and whether your budget is big or small, your dream Kaanapali Hillside vacation is only clicks away with Expedia.

Top Kaanapali Hillside vacation deals

Price found within the past 48 hours. Click for updated prices.
  • A swimming pool with a hot tub, surrounded by palm trees and lounge chairs.
    Dec 11 - Dec 13

    Castle at Maui Banyan + Flight

    South Kihei
    2 nights
    3.5 star property
    7.8/10 - Good (309 reviews)
    "All good but our cheap jazz got the small room with two beds and it was small room for sure"
    Reviewed November 6, 2026
    Roundtrip • Vancouver (YVR) - Maui (OGG)
    YXX - OGG • 1 stop OGG - YXX • 1 stop
    CA $2,551
    CA $1,111
    per traveller
    found 1 day ago
    Castle at Maui Banyan
  • A hotel room with a large bed, a television, a desk with a chair, a window with a view of palm trees, and a ceiling fan.
    Dec 24 - Dec 29

    Maui Banyan Vacation Club + Flight

    South Kihei
    5 nights
    3.0 star property
    8.0/10 - Very good (405 reviews)
    Roundtrip • Edmonton (YEG) - Maui (OGG)
    YEG - OGG • Nonstop OGG - YEG • 1 stop
    CA $3,752
    CA $2,491
    per traveller
    found 1 day ago
    Maui Banyan Vacation Club
  • A bar area with a view of palm trees and the ocean at sunset.
    Dec 24 - Dec 29

    Hotel Wailea Maui + Flight

    Wailea
    5 nights
    5.0 star property
    9.4/10 - Exceptional (1,003 reviews)
    Roundtrip • Edmonton (YEG) - Maui (OGG)
    YEG - OGG • Nonstop OGG - YEG • 1 stop
    CA $11,552
    CA $7,719
    per traveller
    found 1 day ago
    Hotel Wailea Maui
  • A staircase with a view of a garden, palm trees, and a bridge.
    Jan 22 - Jan 25

    Fairmont Kea Lani Maui + Flight

    Wailea
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,004 reviews)
    "2nd time staying here. I know that this place may be pricey, but everything about this place makes it worth it. From the moment we drove up to the time we left, The entire staff makes you feel the Maui love. The amenities are terrific. No charge for umbrellas or lounge chairs at the beach. Every night they offer turndown service for your room. You walk in the hallways and every one on the staff is greeting you with an “Aloha”! My wife and I have been coming to Maui for 9 years and the Fairmont..."
    Reviewed November 7, 2026
    Roundtrip • Edmonton (YEG) - Maui (OGG)
    YEG - OGG • 1 stop OGG - YEG • 1 stop
    CA $4,083
    CA $2,793
    per traveller
    found 1 hour ago
    Fairmont Kea Lani Maui
  • An outdoor dining area with a table set for two, surrounded by lush tropical plants and a wooden fence.
    Jan 20 - Jan 25

    Grand Champions + Flight

    Wailea
    5 nights
    2.5 star property
    9.2/10 - Wonderful (9 reviews)
    "Nothing"
    Reviewed September 30, 2026
    Roundtrip • Toronto (YYZ) - Maui (OGG)
    YYZ - HNL • 2 stops HNL - YYZ • 1 stop
    CA $3,736
    CA $2,559
    per traveller
    found 15 hours ago
    Grand Champions

Kaanapali Hillside Hotel Deals

View from room

Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
2.7 km from Kaanapali Hillside
8.8 out of 10, Excellent, (4,435 reviews)
"It’s such a nice hotel for a good price and we’re definitely coming back regularly."
The price is CA $260
CA $351 total
includes taxes & fees
Nov 27 - Nov 28
Aston Kaanapali Shores
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.
See all properties in Kaanapali Hillside

Frequently Asked Questions

How much does a Kaanapali Hillside vacation package cost?

You'll find cheap prices from CA $1,111 on Expedia for your Kaanapali Hillside getaway. However, factors like the length of stay, hotel choice and season will determine how much your vacation to Kaanapali Hillside costs.

What are the cheapest months to go to Kaanapali Hillside?

To score cheap Kaanapali Hillside vacation packages, plan your getaway outside of peak times like public holidays and major events. You'll generally find lower prices and better availability for hotels and flights.

How many days is enough for Kaanapali Hillside?

When planning your Kaanapali Hillside vacation, a few days will be enough to explore all the highlights. Be sure to visit Whalers Village — it's one of the major sights in this destination. If you're after more adventure, think about basing yourself here and setting off on some day tours from Kaanapali Hillside.

How to find the best Kaanapali Hillside package deals?

Landing a cheap Kaanapali Hillside package deal is a breeze with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most affordable Kaanapali Hillside package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.

Is it cheaper to book a Kaanapali Hillside vacation as a package?

An Expedia vacation package could save you hundreds of dollars when compared to booking accommodations and flights separately. Better still, you can personalize your Kaanapali Hillside getaway to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.

How to plan a trip to Kaanapali Hillside?

  1. Choose your travel dates: The things you want to do in Kaanapali Hillside and your favourite season can help you decide when to travel.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and dining out to airfares and activities. Your hotel will likely be the largest expense during your trip to Kaanapali Hillside.
  3. Decide how long to go for: Now that you know more about Kaanapali Hillside, you can figure out the right length of your break. Pull together a rough itinerary and give yourself enough time for all the things you want to do.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to pick a Kaanapali Hillside vacation package that brings all your bookings together.

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