Kaanapali Hillside Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Maui Beach Vacation Club
North Kihei
CA $830
per person
Sep 7 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Kahului (OGG)
8.4/10 Very good! (922 reviews)
Must admit when we arrived and found there was no AC was a little worried, but the orientation of the unit meant the breezes blowing through made it just lovely. The beach was literally just over the road and super calm. Pool was great, location great for Kīhei Lahaina and the airport. Really enjoyed our stay
Reviewed on Aug 8, 2026
Hotel Wailea, Relais & Chateaux - Adults Only
Wailea
CA $4,453
per person
Oct 17 - Oct 24
found 1 day ago
Roundtrip flight included
Edmonton (YEA) to Kahului (OGG)
9.4/10 Exceptional! (1,003 reviews)
This is a super nice adult only hotel. Nice and quiet. Staff is wonderful. On point. Hotel car service is excellent with luxury cars available. The room is nice. Large and spacious. My only critique is that the restaurant has a limited menu. But selection is great. Highly recommend.
Reviewed on Jul 25, 2026
Maui Banyan Vacation Club
South Kihei
CA $1,196
per person
Nov 1 - Nov 5
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Kahului (OGG)
8/10 Very good! (382 reviews)
Excellent property, check-in/out was easy (they let me check in early), great location, parking extremely easy every day.
Only thing to plan for that is different from some other rentals: don’t expect anything to already be in the kitchen as far as foo/spices/condiments or things like that. Some places will at least have salt & pepper non-perishable essentials like that, maybe umbrellas or chairs, this place did not so do just be prepared to bring everything you plan to need (bathroom has the basics though: shampoo/conditioner, soap, towels etc.).
Great stay, very satisfied and would more than happily repeat.
Reviewed on Aug 3, 2026
Wailea Beach Villas
Wailea
CA $2,898
per person
Sep 7 - Sep 10
found 14 hours ago
Roundtrip non-stop flight included
Edmonton (YEA) to Kahului (OGG)
9.8/10 Exceptional! (197 reviews)
Luxury condo right on Wailea beach with restaurants and shops nearby. I loved the beach view adult only pool, and that it was crowded.
Reviewed on Jul 31, 2026
Ready to book your vacation to Kaanapali Hillside?
Kaanapali Hillside Hotel Deals
Aston Kaanapali Shores
3445 Lower Honoapiilani Hwy Lahaina HI
Fully refundableReserve now, pay when you stay
CA $325
CA $427 total
Aug 14 - Aug 15
includes taxes & fees
8.8/10 Excellent! (4,243 reviews)
"Room was outdated and dirty. Second to last day a cockroach fell down from the cabinet. We traveled with a big group and they seemed to have cleaner room. It’s sits on a great location for shopping and eatery but the beach is next to the runoff. For being our first time in Maui we definitely learned ..."
Reviewed on Aug 8, 2026
Royal Lahaina Resort & Bungalows
2780 Kekaa Dr Lahaina HI
Fully refundableReserve now, pay when you stay
CA $332
CA $469 total
Sep 1 - Sep 2
includes taxes & fees
8.6/10 Excellent! (1,791 reviews)
"The property is beautiful with Banyan trees, plumeria trees, and many other flowers and greenery. The staff were kind and helpful. The bungalow we stayed in was newly renovated and very comfortable. The beach was perfect for swimming. When I visited there were no waves, the water was crystal clear ..."
Reviewed on Aug 7, 2026
The Westin Maui Resort & Spa, Ka'anapali
2365 Kaanapali Pkwy Lahaina HI
Fully refundableReserve now, pay when you stay
CA $559
CA $744 total
Aug 21 - Aug 22
includes taxes & fees
9.2/10 Wonderful! (1,172 reviews)
"Nice facilities and amenities. Beware that the room credits are only for overpriced food and drink (from limited choices)."
Reviewed on Aug 8, 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 $830 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.
