Kaanapali Hillside Vacation Rentals

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Our top choices for Kaanapali Hillside vacation rentals

Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (3,950 reviews)
"Good resort"
United States
Sumit
The price is P17,573
P22,622 total
includes taxes & fees
Jan 19 - Jan 20
Aston Kaanapali Shores

Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Lahaina
8.8 out of 10, Excellent, (2,537 reviews)
"Nice clean room, nice staff and very quiet. "
United States
Marjie
The price is P21,662
P30,998 total
includes taxes & fees
Jan 21 - Jan 22
Aston Maui Kaanapali Villas

OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.0 star property
Lahaina
8.8 out of 10, Excellent, (2,901 reviews)
"Wonderful stay! "
United States
Quiauna
The price is P28,500
P65,516 total
includes taxes & fees
Jan 23 - Jan 24
OUTRIGGER Honua Kai Resort & Spa

Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (647 reviews)
"Location was excellent"
United States
Polly
The price is P16,687
P19,809 total
includes taxes & fees
Jan 19 - Jan 20
Napili Sunset on the Beach

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, (482 reviews)
"Wonderful place to stay. "
United States
Sharon Lynn
The price is P37,065
P44,000 total
includes taxes & fees
Feb 1 - Feb 2
The Westin Nanea Ocean Villas, Ka'anapali

Kuleana Club - 509

Kuleana Club - 509
3.0 star property
Lahaina
The price is P10,979
P25,363 total
includes taxes & fees
Jan 22 - Jan 23
Kuleana Club - 509

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (151 reviews)
"Exactly what we were looking for! Close walking distance to beach and dining!"
United States
Tessa
The price is P12,510
P14,851 total
includes taxes & fees
Jan 21 - Jan 22
Napili Village Hotel

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (339 reviews)
"Great location and great views of beach"
United States
VenkataRamadas
The price is P29,126
P56,260 total
includes taxes & fees
Feb 16 - Feb 17
The Whaler Resort Kaanapali Beach

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (1,737 reviews)
"Beautiful and quiet piece of paradise. "
United States
Amy
The price is P21,357
P25,354 total
includes taxes & fees
Jan 30 - Jan 31
Napili Shores Maui by OUTRIGGER
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

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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 are some of the best vacation home rentals in Kaanapali Hillside?

Kapalua Golf Villas by KBM Resorts: Visitors like this Kaanapali Hillside vacation home rental. It is located on the beach and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, an oven, and a microwave. Kick off your shoes and enjoy yourself with a terrace and a garden.

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 Kaanapali Kai Course at Kaanapali Golf Resort 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.