Kaanapali Hillside Vacation Rentals

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Vacation Rentals in Kaanapali Hillside

Aston Maui Kaanapali Villas

3.0 star property
8.8 out of 10, Excellent, (2455)
"Great family resort! Huge room that was perfect for our family of 5. 2 bedrooms and a huge kitchen/living room made for the perfect staycation on Island. "
The price is CA $193
CA $350 total
includes taxes & fees
Sep 22 - Sep 23
Aston Maui Kaanapali Villas

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3726)
"Great area and great place to stay"
The price is CA $246
CA $331 total
includes taxes & fees
Sep 23 - Sep 24
Aston Kaanapali Shores

The Whaler Resort Kaanapali Beach

4.0 star property
9.6 out of 10, Exceptional, (229)
"Great property and views"
The price is CA $309
CA $892 total
includes taxes & fees
Sep 11 - Sep 12
The Whaler Resort Kaanapali Beach

Kahana Falls Maui by VRI Americas

3.5 star property
8.0 out of 10, Very good, (924)
"Great place! The staff was very nice and the property was very cute! Loved the waterfall pool "
Kahana Falls Maui by VRI Americas

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

10.0 out of 10, Exceptional, (264)
"We loved our stay! The views are breathtaking, we felt like we were on our own little private beach, and the condo had everything we needed for a wonderful vacation. We saw turtles everyday and loved sitting on the lanai/patio and looking at the ocean. "
The price is CA $435
CA $969 total
includes taxes & fees
Sep 17 - Sep 18
Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014

Napili Shores Maui by OUTRIGGER

3.0 star property
9.0 out of 10, Wonderful, (1661)
"The location was great to restaurants and the beach."
The price is CA $313
CA $369 total
includes taxes & fees
Sep 24 - Sep 25
Napili Shores Maui by OUTRIGGER

Aston at The Whaler on Kaanapali Beach

4.0 star property
9.2 out of 10, Wonderful, (1487)
"Clean with a beach view nice gym and pool "
Aston at The Whaler on Kaanapali Beach

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2831)
"Very clean and convenient, great location and great beaches"
The price is CA $485
CA $1,305 total
includes taxes & fees
Sep 16 - Sep 17
OUTRIGGER Honua Kai Resort & Spa

Maui Beach Vacation Club

2.5 star property
8.2 out of 10, Very good, (797)
"Just a great stay! "
Maui Beach Vacation Club

Aston at Papakea Resort

3.0 star property
8.2 out of 10, Very good, (1382)
"Everything was excellent "
Aston at Papakea Resort

Aston Mahana at Kaanapali

3.5 star property
9.0 out of 10, Wonderful, (1645)
"My 3rd time staying here at Mahana and would come back again and again :)"
Aston Mahana at Kaanapali

The Westin Ka'anapali Ocean Resort Villas

4.0 star property
8.6 out of 10, Excellent, (1114)
"We had a wonderful stay at the Westin KOR! It was so comfortable especially the beds! The pools were so fun and our kids had a blast. We loved the beach, the boardwalk and the parking too it was so easy to get to our villa. There was a tsunami warning while we were there which took up one day of vacation, we didnt get a text to evacuate"
The price is CA $619
CA $730 total
includes taxes & fees
Sep 17 - Sep 18
The Westin Ka'anapali Ocean Resort Villas

Kapalua Villas Maui

4.0 star property
8.8 out of 10, Excellent, (952)
"The view of the ocean was great and I was happy just to be there. It was old and a little poorly built, windows or doors were hard to open, etc. Some renovated parts were comfortable. The dryer was broken, which was inconvenient, but housekeeping provided new towels daily and offered to do laundry for free. Cooking utensils were very well stocked"
The price is CA $318
CA $1,107 total
includes taxes & fees
Oct 11 - Oct 12
Kapalua Villas Maui

The Westin Nanea Ocean Villas, Ka'anapali

4.0 star property
9.2 out of 10, Wonderful, (468)
"Very nice place to stay"
The price is CA $663
CA $783 total
includes taxes & fees
Sep 24 - Sep 25
The Westin Nanea Ocean Villas, Ka'anapali

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

2.0 star property
10.0 out of 10, Exceptional, (11)
"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

Kahana Beach Vacation Club

3.0 star property
8.4 out of 10, Very good, (713)
"Really nice and accommodating staff!! We loved our little cozy suite! The ocean view was beautiful!!"
Kahana Beach Vacation Club

Maui Sunset

3.5 star property
8.8 out of 10, Excellent, (469)
"Good place to spend your vacation "
Maui Sunset

AEI at Kaanapali Shores

4.0 star property
8.8 out of 10, Excellent, (440)
"Great location and good beachfront!"
AEI at Kaanapali Shores

Marriott's Maui Ocean Club - Lahaina & Napili Towers

4.0 star property
8.8 out of 10, Excellent, (191)
"It was a great place to spend a vacation for the whole family. "
The price is CA $619
CA $730 total
includes taxes & fees
Sep 24 - Sep 25
Marriott's Maui Ocean Club - Lahaina & Napili Towers

AEI at The Mahana Kaanapali Resort

4.0 star property
8.8 out of 10, Excellent, (276)
"Great location and facilities "
AEI at The Mahana Kaanapali Resort
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

Find out more about Kaanapali Hillside

Everything you need to know about Kaanapali Hillside vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Kaanapali Hillside vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Kaanapali Hillside vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kaanapali Hillside vacation rentals we have selected for you start as low as CA $193 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 vacation 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 vacation.

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 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?

#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool: Visitors like this Kaanapali Hillside vacation home rental. It is located on the beach and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

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 Whalers Village 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.