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.
Hotel Wailea, Relais & Chateaux - Adults Only
Wailea
CA $3,505
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Kahului (OGG)
9.4/10 Exceptional! (1,000 reviews)
Everything was excellent, form the location to the incredible food!
Reviewed on Sep 22, 2026
Ready to book your vacation to Kaanapali Hillside?
Kaanapali Hillside Hotel Deals
Royal Lahaina Resort & Bungalows
2780 Kekaa Dr Lahaina HI
CA $701
CA $907 total
Sep 27 - Sep 28
includes taxes & fees
8.6/10 Excellent! (1,863 reviews)
"Great location. Could use a jacuzzi!"
Reviewed on Sep 23, 2026
The Westin Maui Resort & Spa, Ka'anapali
2365 Kaanapali Pkwy Lahaina HI
Fully refundableReserve now, pay when you stay
CA $946
CA $1,204 total
Oct 12 - Oct 13
includes taxes & fees
9.2/10 Wonderful! (1,261 reviews)
"Very comfortable facility with a well trained professional staff. It is a "must visit" location."
Reviewed on Sep 21, 2026
Aston Kaanapali Shores
3445 Lower Honoapiilani Hwy Lahaina HI
Fully refundableReserve now, pay when you stay
CA $313
CA $413 total
Sep 26 - Sep 27
includes taxes & fees
8.8/10 Excellent! (4,326 reviews)
"Ants in the bathroom"
Reviewed on Sep 22, 2026
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 from CA $1,570 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?
- Choose your travel dates: The things you want to do in Kaanapali Hillside and your favourite season can help you decide when to travel.
- 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.
- 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.
- 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.
