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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Kaanapali Hillside holiday rentals

A tropical garden with a waterfall, lush greenery, and a gazebo.

1. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,354 reviews)
"Great Stay"
United States
Roopa Rani
The price is ฿8,027
฿10,525 total
includes taxes & fees
10 Oct - 11 Oct
Aston Kaanapali Shores
A swimming pool with a curved design, surrounded by palm trees and lounge chairs, with a building in the background.

2. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Kannapali Beach Area
8.8 out of 10, Excellent, (2,641 reviews)
"The property was a fantastic place to stay. The beach that is in front of the property is excellent for swimming and snorkeling."
United States
Marie
The price is ฿7,400
฿11,772 total
includes taxes & fees
1 Nov - 2 Nov
Aston Maui Kaanapali Villas
A view of a beach with palm trees and a sailboat on the water.

3. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.6 out of 10, Exceptional, (483 reviews)
"Great place"
United States
Alessio
The price is ฿8,235
฿22,038 total
includes taxes & fees
7 Oct - 8 Oct
The Whaler Resort Kaanapali Beach
A beach with clear blue water, palm trees, and a resort in the background.

4. Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (241 reviews)
"thank you for the best stay! perfect location, stunning beach with walking distance to beach, cafe, and rentals. room had everything we needed, recommend upgrading to ocean view it was a treat!"
United States
ASHLEY
The price is ฿6,599
฿7,833 total
includes taxes & fees
1 Nov - 2 Nov
Napili Village Hotel
A beach with clear turquoise water, sandy shore, palm trees, and a resort building in the background.

5. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,889 reviews)
"Love this place!"
United States
Diana
The price is ฿7,024
฿8,338 total
includes taxes & fees
1 Nov - 2 Nov
Napili Shores Maui by OUTRIGGER
A resort pool with red umbrellas, palm trees, and a view of the ocean.

6. OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (3,060 reviews)
"We had a great stay at the"
United States
Aprille A
The price is ฿12,655
฿32,900 total
includes taxes & fees
26 Oct - 27 Oct
OUTRIGGER Honua Kai Resort & Spa
A beach view with lounge chairs and a clear sky.

7. Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (656 reviews)
"Nice and clean stay! "
United States
Beverly
The price is ฿9,436
฿11,202 total
includes taxes & fees
5 Oct - 6 Oct
Napili Sunset on the Beach
A resort with a pool, palm trees, a waterfall, and a view of the ocean.

8. The Westin Ka'anapali Ocean Resort Villas

The Westin Ka'anapali Ocean Resort Villas
4.0 star property
Kannapali Beach Area
8.6 out of 10, Excellent, (1,167 reviews)
"The facilities were exactly as described. Our ocean front room and the hotel amenities were wonderful."
Canada
James
The price is ฿16,612
฿19,720 total
includes taxes & fees
11 Oct - 12 Oct
The Westin Ka'anapali Ocean Resort Villas
Lobby

9. Aston at The Whaler on Kaanapali Beach

Aston at The Whaler on Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.2 out of 10, Wonderful, (1,564 reviews)
"Great location, very nice condo, pool, and beach access."
United States
Stewart
The price is ฿11,786
฿20,923 total
includes taxes & fees
25 Oct - 26 Oct
Aston at The Whaler on Kaanapali Beach
A spacious living room with a large window overlooking the ocean, furnished with wicker chairs, a sofa, and a glass coffee table.

10. Aston Mahana at Kaanapali

Aston Mahana at Kaanapali
3.5 star property
Kaanapali
9.0 out of 10, Wonderful, (1,833 reviews)
"Clean nice resort,with beautiful views and reasonable pricing!"
United States
Amit
The price is ฿8,296
฿10,844 total
includes taxes & fees
7 Oct - 8 Oct
Aston Mahana at Kaanapali
A balcony with a table set for dining, overlooking a pool and palm trees, with a view of the ocean and mountains in the distance.

11. Honua Kai Konea Resort by KBM

Honua Kai Konea Resort by KBM
4.5 star property
Kaanapali
9.4 out of 10, Exceptional, (102 reviews)
"Great staff, easy check in."
United States
Jane
The price is ฿14,461
฿33,620 total
includes taxes & fees
14 Oct - 15 Oct
Honua Kai Konea Resort by KBM
A resort with a pool, palm trees, and a view of the ocean.

12. 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, (533 reviews)
"It was beautiful hotel and we love to walk to the beach."
United States
Maria
The price is ฿18,766
฿22,278 total
includes taxes & fees
19 Oct - 20 Oct
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.
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Top Kaanapali Hillside Hotel Reviews

Aston Kaanapali Shores

Aston Kaanapali Shores

10/10 Excellent
"Very old outdated"
Don 1-night trip
Posted 1 hour ago
Aston Kaanapali Shores

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. Whalers Village and Kahekili Beach 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.