Kaanapali Hillside Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Kaanapali Hillside

4 outdoor pools, open 8:00 AM to 10:00 PM, cabanas (surcharge)
OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
Lahaina
8.8 out of 10, Excellent, (2878)
"Wonderful stay! "
United States
Quiauna
The price is NT$8,972
NT$27,225 total
includes taxes & fees
Dec 11 - Dec 12
OUTRIGGER Honua Kai Resort & Spa
Exterior
Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa

5.0 star property
Lahaina
The price is NT$9,372
NT$12,713 total
includes taxes & fees
Dec 8 - Dec 9
Royal Lahaina Bungalows & Spa
Aerial view
Kuleana Club - 504

Kuleana Club - 504

3.0 star property
Lahaina
The price is NT$15,682
NT$25,106 total
includes taxes & fees
Jan 2 - 2026/1/3
Kuleana Club - 504
Beach nearby, white sand, beach towels
Napili Village Hotel

Napili Village Hotel

3.0 star property
Lahaina
9.0 out of 10, Wonderful, (136)
"Exactly what we were looking for! Close walking distance to beach and dining!"
United States
Tessa
The price is NT$7,147
NT$8,431 total
includes taxes & fees
Dec 8 - Dec 9
Napili Village Hotel
2 outdoor pools, cabanas (surcharge), pool umbrellas
The Westin Nanea Ocean Villas, Ka'anapali

The Westin Nanea Ocean Villas, Ka'anapali

4.0 star property
Lahaina
9.4 out of 10, Exceptional, (472)
"Spacious rooms and fun pools"
United States
Vanessa
The price is NT$17,469
NT$20,607 total
includes taxes & fees
Dec 21 - Dec 22
The Westin Nanea Ocean Villas, Ka'anapali
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Kaanapali Hillside Hotel Reviews

Sheraton Maui Resort & Spa

Sheraton Maui Resort & Spa

10/10 Excellent
"Great "
Manjula A 6-night trip
Posted 1 day ago
Sheraton Maui Resort & Spa

Find out more about Kaanapali Hillside

Search for holiday rentals in Kaanapali Hillside on Expedia! You can easily find your home rentals, villas, holiday apartments in Kaanapali Hillside using one of the methods below:

  • View our selection of featured holiday rentals in Kaanapali Hillside
  • Use the map to find apartments and other holiday homes in the Kaanapali Hillside neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Kaanapali Hillside while they last

Look no further and take a look at our great range of rental properties in Kaanapali Hillside!

Frequently asked questions

Can I find a vacation rental in Kaanapali Hillside?

Yes, we have vacation rentals near well known sights in Kaanapali Hillside, or you can select a more secluded option if you want a relaxing place to stay.

What’s there to see and do in Kaanapali Hillside?

Explore the area and family-friendly sights such as Hawaii Nature Center of Iao Valley, or get out into nature at a spot like Kaanapali Beach. Kaanapali Kai Course at Kaanapali Golf Resort and Kaanapali Golf Courses are a couple of places you'll find in the larger area.

What’s a vacation rental in Kaanapali Hillside like?

A vacation rental is a private property you can book for a long or short time in Kaanapali Hillside. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a small group gathering.