Kaanapali Hillside Vacations from $822
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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.
The Latest Kaanapali Hillside vacation packages
Price found within the past 48 hours. Click for updated prices.
Maui Banyan Vacation Club
South Kihei
Save 100% on your flight
Price was $2,234, price is now $1,298 per person
$1,298
per person
Dec 30 - Jan 5
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
8/10 Very Good! (399 reviews)
Room had a weird smell and cockroaches. Found was in my bed in the middle of the night. It is an island
Reviewed on Oct 26, 2026
Hotel Wailea Maui
Wailea
Price was $7,610, price is now $5,017 per person
$5,017
per person
Dec 30 - Jan 5
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
9.4/10 Exceptional! (1,002 reviews)
Hotel Wailea was paradise! The grounds and the room were beautiful and clean. The customer service was EXCELLENT!!!! My husband and I didn’t want to leave. If you are looking for an adult only relaxing experience, I HIGHLY recommend Hotel Wailea. You will not be disappointed!
Reviewed on Oct 19, 2026
The Residences at Kamaole Sands Resort
South Kihei
Price was $2,733, price is now $1,986 per person
$1,986
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
10/10 Exceptional! (5 reviews)
Bonus was there were beach chairs, towels and an umbrella. We only used two chairs as our family were busy snorkeling or boarding away while 1-2 sat out and rested. Clean, right down from beach park 3...stocked pantry got some add-ons and pots and pans enough to allow us making most of our meals. Great times and great communication from host. Thanks! Lucas
Reviewed on Aug 30, 2026
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View all tripsKaanapali Hillside Hotel Deals
Aston Kaanapali Shores
3445 Lower Honoapiilani Hwy Lahaina HI
Fully refundableReserve now, pay when you stay
$242 nightly
The price is $287 total per night from Nov 9 to Nov 10
$287 total
Nov 9 - Nov 10
Total with taxes and fees
8.8/10 Excellent! (4,412 reviews)
"The room didn’t look renovated but it was clean and traditional. The resort itself offered a lot of amenities and was gorgeous. Everyone was really nice and welcoming. They do make you pay for parking which is annoying but it was like 12$/a day.The resort was beautiful and i really enjoyed the pools. ..."
Reviewed on Oct 27, 2026
Royal Lahaina Resort & Bungalows
2780 Kekaa Dr Lahaina HI
Fully refundableReserve now, pay when you stay
$243 nightly
The price is $288 total per night from Nov 2 to Nov 3
$288 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (1,948 reviews)
"Nice place, one day cleaning staff only brought clean towels but didn’t actually clean the room but that was the only issue"
Reviewed on Oct 27, 2026
The Westin Maui Resort & Spa, Ka'anapali
2365 Kaanapali Pkwy Lahaina HI
Fully refundableReserve now, pay when you stay
$642 nightly
The price is $762 total per night from Nov 1 to Nov 2
$762 total
Nov 1 - Nov 2
Total with taxes and fees
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.
Find the Best Kaanapali Hillside Vacation Packages
Kaanapali Hillside Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Kahului Airport (OGG) |
Top Sights | Kaanapali Beach, Black Rock and Kahekili Beach |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
