Kaanapali Hillside Vacation Rentals

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Vacation Rentals in Kaanapali Hillside

Our top choices for Kaanapali Hillside vacation rentals

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3695)
"Great area and great place to stay"
$185 nightly
The price is $218
Sep 2 - Sep 3
Total with taxes and fees
Aston Kaanapali Shores

Aston Maui Kaanapali Villas

3.0 star property
8.8 out of 10, Excellent, (2449)
"Great place! Room was a good size, very clean spacious, full kitchen, nice staff. We enjoyed our stay! "
$215 nightly
The price is $254
Sep 10 - Sep 11
Total with taxes and fees
Aston Maui Kaanapali Villas

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

10.0 out of 10, Exceptional, (263)
"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. "
$603 nightly
The price is $702
Sep 1 - Sep 2
Total with taxes and fees
Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014

The Whaler Resort Kaanapali Beach

4.0 star property
9.6 out of 10, Exceptional, (224)
"Perfect location right on the beach. Shopping and restaurants next door."
$555 nightly
The price is $654
Sep 2 - Sep 3
Total with taxes and fees
The Whaler Resort Kaanapali Beach

Napili Shores Maui by OUTRIGGER

3.0 star property
9.0 out of 10, Wonderful, (1654)
"Check-in was easy, the staff were very friendly and helpful. The room was clean and comfortable. Great place to stay."
$329 nightly
The price is $388
Sep 1 - Sep 2
Total with taxes and fees
Napili Shores Maui by OUTRIGGER

Aston at The Whaler on Kaanapali Beach

4.0 star property
9.2 out of 10, Wonderful, (1483)
"It was a nice place to stay"
Aston at The Whaler on Kaanapali Beach

Kahana Falls Maui by VRI Americas

3.5 star property
8.0 out of 10, Very Good, (915)
"Great Aloha spirit and a great location and pool."
Kahana Falls Maui by VRI Americas

Maui Beach Vacation Club

2.5 star property
8.2 out of 10, Very Good, (792)
"Just a great stay! "
Maui Beach Vacation Club

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2829)
"Really liked the resort"
$792 nightly
The price is $860
Sep 30 - Oct 1
Total with taxes and fees
OUTRIGGER Honua Kai Resort & Spa

Aston Mahana at Kaanapali

3.5 star property
9.0 out of 10, Wonderful, (1643)
"Beautiful location "
Aston Mahana at Kaanapali

Aston at Papakea Resort

3.0 star property
8.2 out of 10, Very Good, (1382)
"A208 was terrific. We loved the view and the sound of ocean and accessibility to the beach. Would love to see a few more hooks in place to hang towels and some written information about sites and where to go etc. - like a welcome notebook "
Aston at Papakea Resort

#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

The Westin Ka'anapali Ocean Resort Villas

4.0 star property
8.6 out of 10, Excellent, (1113)
"The resort was beautiful. The hospitality in all seas was top notch. "
$447 nightly
The price is $527
Sep 7 - Sep 8
Total with taxes and fees
The Westin Ka'anapali Ocean Resort Villas

AEI at Kaanapali Shores

4.0 star property
8.8 out of 10, Excellent, (434)
"Great location and good beachfront!"
AEI at Kaanapali Shores

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"
$680 nightly
The price is $802
Oct 1 - Oct 2
Total with taxes and fees
Kapalua Villas Maui

The Westin Nanea Ocean Villas, Ka'anapali

4.0 star property
9.2 out of 10, Wonderful, (466)
"Very nice place to stay"
$479 nightly
The price is $565
Sep 16 - Sep 17
Total with taxes and fees
The Westin Nanea Ocean Villas, Ka'anapali

Kahana Beach Vacation Club

3.0 star property
8.4 out of 10, Very Good, (708)
"Great place to stay "
Kahana Beach Vacation Club

Maui Sunset

3.5 star property
8.8 out of 10, Excellent, (468)
"Good place to spend your vacation "
Maui Sunset

AEI at The Mahana Kaanapali Resort

4.0 star property
8.8 out of 10, Excellent, (272)
"Great location and facilities "
AEI at The Mahana Kaanapali Resort

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. "
$447 nightly
The price is $527
Sep 14 - Sep 15
Total with taxes and fees
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.
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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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Kaanapali Hillside in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $218 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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?

Spectacular Sunset and Ocean Views with Pool & Hotbub near Kaanapali Beach: Visitors like this Kaanapali Hillside vacation home rental. It is located in the city center and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 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 garden, a selection of games, and a hot tub 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.