Kaanapali Hillside Holiday Rentals

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Kaanapali Hillside

AEI at Kaanapali Shores

4.0 star property
8.8 out of 10, Excellent, (350)
"Great location , amazing views to the sunset , great staff , cute small bar at the second pool with stunning view to the sunset. Perfect beach access."
AEI at Kaanapali Shores

The Whaler Resort Kaanapali Beach

4.0 star property
9.4 out of 10, Exceptional, (190)
"What i liked is everything was very close and easy access plus shopping, eating beach very Enjoyable trip "
The price is NZ$1,151
includes taxes & fees
31 July - 1 Aug
The Whaler Resort Kaanapali Beach

Aston Maui Kaanapali Villas

3.0 star property
8.8 out of 10, Excellent, (2420)
"Awesome stay, would definitely stay again "
The price is NZ$524
includes taxes & fees
2 July - 3 July
Aston Maui Kaanapali Villas

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3614)
"Great place. "
The price is NZ$397
includes taxes & fees
17 July - 18 July
Aston Kaanapali Shores

#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool

2.0 star property
10.0 out of 10, Exceptional, (9)
"We had an amazing vacation with our kids and grandkids. We have already booked again for next year"
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool

Napili Shores Maui by OUTRIGGER

3.0 star property
8.8 out of 10, Excellent, (1620)
"Lovely, older quiet place to stay."
The price is NZ$641
includes taxes & fees
2 July - 3 July
Napili Shores Maui by OUTRIGGER

Maui Beach Vacation Club

2.5 star property
8.2 out of 10, Very good, (759)
"Great place to stay!!"
Maui Beach Vacation Club

The Westin Nanea Ocean Villas, Ka'anapali

4.0 star property
9.2 out of 10, Wonderful, (459)
"Very welcoming and friendly, room was absolutely amazing. Resort was beautiful and clean. Staff was also a delight, I had forgotten my sweater and they emailed me within days to let me know I had forgotten it and that they could ship it out to me. Definitely recommend! :)"
The price is NZ$1,283
includes taxes & fees
18 July - 19 July
The Westin Nanea Ocean Villas, Ka'anapali

AEI at The Mahana Kaanapali Resort

4.0 star property
8.8 out of 10, Excellent, (257)
"The property is situated nicely between high-end resorts. A lengthy boardwalk is available for miles."
AEI at The Mahana Kaanapali Resort

The Westin Ka'anapali Ocean Resort Villas

4.0 star property
8.6 out of 10, Excellent, (1110)
"The resort was beautiful. The hospitality in all seas was top notch. "
The price is NZ$1,159
includes taxes & fees
8 July - 9 July
The Westin Ka'anapali Ocean Resort Villas

Napili Village Hotel

3.0 star property
9.0 out of 10, Wonderful, (104)
"Ok, good location, close to beach"
The price is NZ$428
includes taxes & fees
15 July - 16 July
Napili Village Hotel

Honua Kai Konea Resort by KBM

4.0 star property
9.6 out of 10, Exceptional, (50)
"Property is amazing, very close to the beach. Everything is clean and convenient to everywhere."
The price is NZ$1,828
includes taxes & fees
10 July - 11 July
Honua Kai Konea Resort by KBM

Kahana Beach Vacation Club

3.0 star property
8.4 out of 10, Very good, (683)
"Love that it’s only a step away from the beach."
Kahana Beach Vacation Club

Kaanapali Alii

4.0 star property
9.4 out of 10, Exceptional, (910)
"The property was beautiful, staff was nice, and the resort is family friendly."
Kaanapali Alii

Castle Napili Surf Beach Resort

3.5 star property
10.0 out of 10, Exceptional, (125)
"Everything is close to walk to and it’s nice it’s not a giant resort"
Castle Napili Surf Beach Resort

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2790)
"Nice property, super helpful staff"
The price is NZ$1,390
includes taxes & fees
30 July - 31 July
OUTRIGGER Honua Kai Resort & Spa

Aston Mahana at Kaanapali

3.5 star property
9.0 out of 10, Wonderful, (1631)
"Spectacular view!!!! Loved it!"
Aston Mahana at Kaanapali

AEI at Papakea Resort Maui

3.5 star property
8.6 out of 10, Excellent, (84)
"Best view ever! Loved to be as close to the water as possible and 40 feet is great. The carpet needs replacing and the unit is old. But I was fine with that. Was out walking and snorkeling most of the time. "
AEI at Papakea Resort Maui

Sugar Beach Resort

3.0 star property
8.6 out of 10, Excellent, (1070)
"Loved the fully stocked kitchen and amenities available. It was a delightful stay! We would stay here again."
Sugar Beach Resort

Marriott's Maui Ocean Club - Lahaina & Napili Towers

4.0 star property
8.8 out of 10, Excellent, (187)
"Clean rooms, coffee available, nice bar, 3 terrific pool areas and exquisitely manicured grounds."
The price is NZ$1,159
includes taxes & fees
14 July - 15 July
Marriott's Maui Ocean Club - Lahaina & Napili Towers
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.
Save an average of 15% on thousands of hotels when you're signed in

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 are some of the best holiday rentals that Kaanapali Hillside has to offer?

#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool: This holiday home rental outside of Kaanapali Hillside is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 11 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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 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.