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Kaanapali Hillside Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Kaanapali Hillside vacation rentals

A swimming pool with a curved design, surrounded by palm trees and lounge chairs, with a building in the background.

1. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Kannapali Beach Area
8.8 out of 10, Excellent, (2,646 reviews)
"Great place will stay again!"
United States
Joseph
The price is P13,603
P21,735 total
includes taxes & fees
Nov 6 - Nov 7
Aston Maui Kaanapali Villas
A tropical garden with a waterfall, lush greenery, and a gazebo.

2. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,376 reviews)
"Great Stay"
United States
Roopa Rani
The price is P14,510
P19,088 total
includes taxes & fees
Oct 28 - Oct 29
Aston Kaanapali Shores
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, (497 reviews)
"We loved everything and the location was perfect!!"
United States
Lenore
The price is P15,401
P41,213 total
includes taxes & fees
Oct 18 - Oct 19
The Whaler Resort Kaanapali Beach
A resort with a pool, palm trees, and a view of the ocean.

4. 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, (534 reviews)
"It was beautiful hotel and we love to walk to the beach."
United States
Maria
The price is P35,095
P41,662 total
includes taxes & fees
Oct 30 - Oct 31
The Westin Nanea Ocean Villas, Ka'anapali
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, (1,901 reviews)
"Great trip!"
United States
Jennifer
The price is P14,067
P16,700 total
includes taxes & fees
Oct 27 - Oct 28
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, (3,066 reviews)
"Such a lovely stay. The hotel is in a great location, everyone was very kind. I would definitely stay here again!"
United States
Andrea
The price is P17,819
P50,115 total
includes taxes & fees
Nov 13 - Nov 14
OUTRIGGER Honua Kai Resort & Spa
A beach with clear blue water, palm trees, and a resort in the background.

7. Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (247 reviews)
"We loved how quiet and relaxing the property was. The employees and atmosphere were amazing."
United States
Joshua
The price is P11,527
P13,684 total
includes taxes & fees
Nov 8 - Nov 9
Napili Village Hotel
A beach view with lounge chairs and a clear sky.

8. 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 P18,823
P22,345 total
includes taxes & fees
Nov 3 - Nov 4
Napili Sunset on the Beach
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.

9. Honua Kai Konea Resort by KBM

Honua Kai Konea Resort by KBM
4.5 star property
Kaanapali
9.4 out of 10, Exceptional, (103 reviews)
The price is P22,341
P57,291 total
includes taxes & fees
Oct 16 - Oct 17
Honua Kai Konea Resort by KBM
Lobby

10. 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, (1,566 reviews)
"Great location, very nice condo, pool, and beach access."
United States
Stewart
The price is P22,041
P39,129 total
includes taxes & fees
Oct 25 - Oct 26
Aston at The Whaler on Kaanapali Beach
A resort with a pool, palm trees, a waterfall, and a view of the ocean.

11. 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, (1,168 reviews)
"The facilities were exactly as described. Our ocean front room and the hotel amenities were wonderful."
Canada
James
The price is P31,066
P36,879 total
includes taxes & fees
Oct 20 - Oct 21
The Westin Ka'anapali Ocean Resort Villas
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

Maui Seaside Hotel

Maui Seaside Hotel

10/10 Excellent
"For me, a hotel stay feels promising from the moment I open the door and catch the fresh, clean scent of the bed linens—it’s a clear sign of a great stay."
Marivic 2-night trip
Posted 4 hours ago
Maui Seaside Hotel

Find out more about Kaanapali Hillside

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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. Whalers Village and Kahekili Beach 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.