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Our top choices for Kaanapali Hillside holiday rentals

OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.0 star property
Lahaina
8.8 out of 10, Excellent, (2881)
"Wonderful stay! "
United States
Quiauna
The price is ฿9,293
฿25,489 total
includes taxes & fees
18 Dec - 19 Dec
OUTRIGGER Honua Kai Resort & Spa

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (316)
"great time, great resort, helpful staff"
Canada
Prableen
The price is ฿10,514
฿24,008 total
includes taxes & fees
15 Jan - 16 Jan 2026
The Whaler Resort Kaanapali Beach

Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.6 out of 10, Excellent, (3921)
"Best hotel I stayed at "
United States
Nohely
The price is ฿10,042
฿12,774 total
includes taxes & fees
17 Dec - 18 Dec
Aston Kaanapali Shores

Maui Beach Vacation Club

Maui Beach Vacation Club
2.5 star property
North Kihei
8.2 out of 10, Very good, (820)
"The rooms were clean and spacious and had all the basics that we needed. We found the beds and furniture comfortable. The staff was very friendly and the location was very convenient for our needs. That being said, the no AC situation proved to be problematic for a number of reasons all of which boil down to noise. The courtyard serves as a funnel for all the noise from the neighbors whether or not they are trying to be noisy. We would hear lots "
United States
Sabrina
Maui Beach Vacation Club

Kahana Beach Vacation Club

Kahana Beach Vacation Club
3.0 star property
Lahaina
8.6 out of 10, Excellent, (753)
"Excellent Resort from all areas "
United States
Kausik
Kahana Beach Vacation Club

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (1712)
"Excellent stay. "
United States
casey william
The price is ฿11,616
฿13,703 total
includes taxes & fees
21 Dec - 22 Dec
Napili Shores Maui by OUTRIGGER

Sands of Kahana

Sands of Kahana
3.0 star property
Lahaina
8.2 out of 10, Very good, (458)
"Size for the price was great"
United States
Ben
Sands of Kahana

Kahana Falls Maui by VRI Americas

Kahana Falls Maui by VRI Americas
3.5 star property
Lahaina
8.2 out of 10, Very good, (976)
"The Entire staff of Kahana Falls Resort was very welcoming and very attentive to our needs. "
United States
Greg
Kahana Falls Maui by VRI Americas

Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Lahaina
8.8 out of 10, Excellent, (2516)
"We enjoyed the property "
United States
Therese
The price is ฿11,144
฿15,930 total
includes taxes & fees
17 Dec - 18 Dec
Aston Maui Kaanapali Villas

Kahana Villa

Kahana Villa
3.0 star property
Lahaina
8.0 out of 10, Very good, (352)
" Great stay!!! Easy and quiet place next to beach.Feels like home"
United States
Jose
Kahana Villa

Royal Kahana Maui by OUTRIGGER

Royal Kahana Maui by OUTRIGGER
3.0 star property
Lahaina
8.0 out of 10, Very good, (1400)
"Room was beautiful and had an amazing view"
United States
Becky
Royal Kahana Maui by OUTRIGGER

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 ฿19,618
฿23,289 total
includes taxes & fees
12 Jan - 13 Jan 2026
The Westin Nanea Ocean Villas, Ka'anapali

Kapalua Villas Maui

Kapalua Villas Maui
4.0 star property
Lahaina
8.8 out of 10, Excellent, (959)
"Gorgeous property, the staff, beach, hiking close by, restaurants in area all were great. Room was spotless and we were able to check in early."
United States
Arturo
Kapalua Villas Maui

The Westin Ka'anapali Ocean Resort Villas

The Westin Ka'anapali Ocean Resort Villas
4.0 star property
Lahaina
8.6 out of 10, Excellent, (1126)
"Perfect stay"
United States
hao
The price is ฿14,102
฿16,635 total
includes taxes & fees
23 Dec - 24 Dec
The Westin Ka'anapali Ocean Resort Villas

Kaanapali Alii

Kaanapali Alii
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (958)
"Views were fantastic, as were beach and pool access, hotel was very clean."
Canada
Ryan
Kaanapali Alii

Aston at Papakea Resort

Aston at Papakea Resort
3.0 star property
Lahaina
8.2 out of 10, Very good, (1396)
"Everything was great very good stay "
Canada
Paul
Aston at Papakea Resort

The Gardens at West Maui

The Gardens at West Maui
3.0 star property
Lahaina
8.4 out of 10, Very good, (521)
"We stayed here for 4 days easy check in and check out process "
United States
Relda
The Gardens at West Maui

Kaanapali Maui at the Eldorado by OUTRIGGER

Kaanapali Maui at the Eldorado by OUTRIGGER
3.0 star property
Lahaina
8.6 out of 10, Excellent, (872)
"Courteous staff, close to the beach, to the Ka’anapali golf courses, to whalers village, and the pool. "
United States
Rosa
Kaanapali Maui at the Eldorado by OUTRIGGER

Castle Napili Surf Beach Resort

Castle Napili Surf Beach Resort
3.5 star property
Lahaina
9.8 out of 10, Exceptional, (155)
"Loved the location and beach "
United States
Brenda Vanessa
Castle Napili Surf Beach Resort

Aston Mahana at Kaanapali

Aston Mahana at Kaanapali
3.5 star property
Kaanapali
9.0 out of 10, Wonderful, (1718)
"Gorgeous views, spacious suite, very friendly staff, amazing stay had a wonderful family vacation, can't wait to go back."
Canada
Lidia E
Aston Mahana at Kaanapali
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.
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Top Kaanapali Hillside Hotel Reviews

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:

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Frequently asked questions

Can I find a holiday rental in Kaanapali Hillside?

Yes, there are holiday rentals close to the most popular sights in Kaanapali Hillside, or you can select a more secluded option if you're looking for a relaxing 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 wider area.

What’s a holiday rental in Kaanapali Hillside like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kaanapali Hillside. Holiday rentals feature amenities like WiFi and washers and dryers so you'll feel right at home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for family gatherings.