Kaanapali Hillside holiday homes

We found 5,357 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Kaanapali Hillside to find one that's perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for spending time at your holiday home, which might include cable TV and a washer and dryer. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Kaanapali Hillside

Showing deals for:8 Aug - 15 Aug

Image gallery for Last minute discounts available, please ask.

Outdoor dining
9.8 out of 10 rating
Exceptional
(105 reviews)

Last minute discounts available, please ask.

Kahana, HI

8% off
Price is NZ$42,409
NZ$6,058 per night
includes taxes & fees
Last minute discounts available, please ask.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Find the perfect holiday rental for your Kaanapali Hillside getaway

Learn about the unique charm of Kaanapali Hillside with a stay in a holiday home rental. This city has something for everyone. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in Kaanapali Hillside

Do you want to find top things to see and do in the city? Venture out of your cosy holiday rental and check out everything that makes Kaanapali Hillside a fun spot to go on holiday. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Kaanapali Kai Course at Kaanapali Golf Resort (1 mi / 1.6 km)
  • Kaanapali Golf Courses (1 mi / 1.6 km)
  • Kapalua Golf Resort Bay Course (5 mi / 8.1 km)
  • Kapalua Resort (5.1 mi / 8.1 km)
  • Kapalua Golf Club Plantation Course (6.1 mi / 9.8 km)
  • The Dunes at Maui Lani (13.7 mi / 22.1 km)

Exploring the natural features in Kaanapali Hillside

Whether you're an active traveller or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Kaanapali Hillside. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Kaanapali Beach (1.3 mi / 2.1 km)
  • Black Rock (1.1 mi / 1.8 km)
  • Honokowai Beach Park (1.9 mi / 3 km)
  • Kahana Beach (3 mi / 4.8 km)
  • Napili Bay Beach (4.7 mi / 7.6 km)
  • Napili Bay (4.8 mi / 7.7 km)

Transport options to and around Kaanapali Hillside

The nearest airport is in Kapalua, HI (JHM-West Maui), located 2.4 mi (3.9 km) from the city centre. If you're unable to find a flight that fits your schedule, you could also fly into Kahului, HI (OGG), which is 15.8 mi (25.5 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Kaanapali Hillside?
The most in-demand types of holiday homes in Kaanapali Hillside are condos. Ready for more choices? Bookabach has plenty of options to match the needs of our guests, so you’ll see properties in all shapes and sizes, and for all budgets. The ideal fit is ready and waiting for you — get hold of yours today.
How much does it cost to rent a holiday home in Kaanapali Hillside?
Property type, length of stay and time of year are some factors that can influence the price of a holiday home. Simply add your travel dates to find the ultimate escape. From comfy cottages to sprawling luxury villas, all Bookabach holiday homes provide amazing value.
How much does it cost to rent a beach house in Kaanapali Hillside?
Prices for beach houses in Kaanapali Hillside differ depending on the size and style of the property and time of year you’re travelling. All you have to do is enter your travel dates into Bookabach and the number of guests to see your home options and prices. From there you can use our filters to narrow your search results by amenities, nearby activities, ratings and more.
Are there pet-friendly holiday homes in Kaanapali Hillside?
Good news! Yes. You can pick from three holiday homes that allow pets in Kaanapali Hillside. Many of our pet-friendly holiday homes even have an outdoor space for your furry pal to have fun in, special dog beds, complimentary treats and proximity to parks or green space. Apply the “Pets allowed” filter to find your pawfect pad on Bookabach.
Can I rent a house with a pool in Kaanapali Hillside?
Grab your swimsuit and swim ring, because there are three houses with a private pool in Kaanapali Hillside. Unwind at one of these popular holiday homes and every day will be a pool day. Simply enter your travel dates into Bookabach, then use the “pool” filter to find the perfect place to make a splash!
What are popular home amenities in Kaanapali Hillside?
When it comes to home amenities that guests look for in Kaanapali Hillside, a swimming pool, a barbecue grill and nearby museums are the most popular. With Bookabach holiday homes, you’ll discover options to fit your style and taste, whether you’re going away with family, friends or even pets.
Are there holiday homes in Kaanapali Hillside that welcome kids?
With three family-friendly holiday properties to select from in Kaanapali Hillside, now is a fantastic time to introduce your kids to the joys of travel. Check our “Properties good for families” filter to browse stays that feature conveniences perfect for travelling families, like multiple bedrooms, patios, entertainment units and bunk beds.
What are the top attractions for families in Kaanapali Hillside?
There’s a ton of wonderful things to see and do with the family in Kaanapali Hillside, including:

  • Kaanapali Beach
  • Black Rock
  • Napili Bay Beach

Are there one-bedroom holiday homes in Kaanapali Hillside?
Yes, there are two one-bedroom properties in Kaanapali Hillside to select from. A one-bedroom holiday home is a great option if it’s only two of you or if you’re travelling solo. Toss in more space, convenience and privacy than a standard hotel, and you’ll be sure to have a memorable trip.
How can I find holiday homes with air conditioning in Kaanapali Hillside?
Pick from three holiday homes with air conditioning in Kaanapali Hillside giving you that cool, cool breeze and extra element of comfort. Enter your chosen travel dates and then use our filters to search for stays with air conditioning.
How old do you have to be to rent a holiday home in Kaanapali Hillside?
The minimum age is normally 16, 18 or 21. It can differ from one property to another on Bookabach, so look at the rules of your chosen Kaanapali Hillside holiday home before booking your trip.
How long can I rent a holiday home in Kaanapali Hillside for?
It’s down to the Kaanapali Hillside property. To view a list of options offering extended stays, just enter your dates and number of people into the Bookabach search page. You can look forward to having the whole place to yourself, along with amenities such as a full kitchen, air conditioning and outdoor spaces to run around in. Be on the lookout for long-term stays that offer discounted weekly or monthly prices.

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