Kaanapali Hillside Holiday Rentals

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Holiday Rentals in Kaanapali Hillside

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
Lahaina
8.8 out of 10, Excellent, (2875)
"Wonderful stay! "
United States
Quiauna
The price is NZ$1,513
includes taxes & fees
11 Dec - 12 Dec
OUTRIGGER Honua Kai Resort & Spa

The Whaler Resort Kaanapali Beach

4.0 star property
Lahaina
9.6 out of 10, Exceptional, (310)
"great time, great resort, helpful staff"
Canada
Prableen
The price is NZ$1,331
includes taxes & fees
4 Jan - 5 Jan 2026
The Whaler Resort Kaanapali Beach

Kahana Beach Vacation Club

3.0 star property
Lahaina
8.4 out of 10, Very good, (749)
"Excellent Resort from all areas "
United States
Kausik
Kahana Beach Vacation Club

Aston Kaanapali Shores

3.5 star property
Lahaina
8.6 out of 10, Excellent, (3900)
"Was a great place to stay"
United States
Christine
The price is NZ$776
includes taxes & fees
6 Dec - 7 Dec
Aston Kaanapali Shores

Napili Shores Maui by OUTRIGGER

3.0 star property
Lahaina
9.0 out of 10, Wonderful, (1707)
"Excellent stay. "
United States
casey william
The price is NZ$674
includes taxes & fees
6 Dec - 7 Dec
Napili Shores Maui by OUTRIGGER

Maui Beach Vacation Club

2.5 star property
North Kihei
8.2 out of 10, Very good, (817)
"A excelent service in the office. Nice and clean room y all the hotel. I recommend this hotel."
United States
Blanca I
Maui Beach Vacation Club

Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014

Lahaina
10.0 out of 10, Exceptional, (271)
"It was perfect! When we come back we will definitely use this condo again!"
United States
Jeffrey J.
The price is NZ$1,630
includes taxes & fees
15 Dec - 16 Dec
Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014

Aston Maui Kaanapali Villas

3.0 star property
Lahaina
8.8 out of 10, Excellent, (2510)
"Great place! Very clean, friendly staff, beautiful grounds, lots to do with in walking distance. The best part that we enjoyed was the beach it was outstanding! highly recommend."
Canada
Natalia
The price is NZ$803
includes taxes & fees
1 Jan - 2 Jan 2026
Aston Maui Kaanapali Villas

Kahana Falls Maui by VRI Americas

3.5 star property
Lahaina
8.0 out of 10, Very good, (970)
"All of the above and good access to the beach ⛱️"
United States
Joshua
Kahana Falls Maui by VRI Americas

Sands of Kahana

3.0 star property
Lahaina
8.2 out of 10, Very good, (457)
"Size for the price was great"
United States
Ben
Sands of Kahana

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 NZ$1,145
includes taxes & fees
18 Dec - 19 Dec
The Westin Nanea Ocean Villas, Ka'anapali

The Westin Ka'anapali Ocean Resort Villas

4.0 star property
Lahaina
8.6 out of 10, Excellent, (1124)
"Clean room, amazing staff and great location and beach access "
United States
Amanda
The price is NZ$915
includes taxes & fees
12 Dec - 13 Dec
The Westin Ka'anapali Ocean Resort Villas

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

Royal Kahana Maui by OUTRIGGER

3.0 star property
Lahaina
8.0 out of 10, Very good, (1399)
"Room was beautiful and had an amazing view"
United States
Becky
Royal Kahana Maui by OUTRIGGER

The Gardens at West Maui

3.0 star property
Lahaina
8.4 out of 10, Very good, (518)
"We stayed here for 4 days easy check in and check out process "
United States
Relda
The Gardens at West Maui

Kaanapali Alii

4.0 star property
Lahaina
9.6 out of 10, Exceptional, (954)
"Views were fantastic, as were beach and pool access, hotel was very clean."
Canada
Ryan
Kaanapali Alii

Kapalua Villas Maui

4.0 star property
Lahaina
8.8 out of 10, Excellent, (958)
"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

Royal Lahaina Bungalows & Spa

5.0 star property
Lahaina
The price is NZ$650
includes taxes & fees
18 Dec - 19 Dec
Royal Lahaina Bungalows & Spa

Castle Napili Surf Beach Resort

3.5 star property
Lahaina
9.8 out of 10, Exceptional, (152)
"Loved the location and beach "
United States
Brenda Vanessa
Castle Napili Surf Beach Resort

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
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

Everything you need to know about Kaanapali Hillside holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Kaanapali Hillside holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kaanapali Hillside holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Kaanapali Hillside holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kaanapali Hillside. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kaanapali Hillside holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kaanapali Hillside holiday rentals we have selected for you start as low as NZ$650 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Kaanapali Hillside rentals

At Expedia, we put the best Kaanapali Hillside holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Kaanapali Hillside rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kaanapali Hillside holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kaanapali Hillside. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!: This holiday home rental outside of Kaanapali Hillside is located on the beach, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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. 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.