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. "
$210 nightly
The price is $248
Sep 11 - Sep 12
Total with taxes and fees
Aston Maui Kaanapali Villas

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3724)
"Great area and great place to stay"
$212 nightly
The price is $250
Sep 23 - Sep 24
Total with taxes and fees
Aston Kaanapali Shores

The Whaler Resort Kaanapali Beach

4.0 star property
9.6 out of 10, Exceptional, (229)
"Great property and views"
$555 nightly
The price is $654
Sep 10 - Sep 11
Total with taxes and fees
The Whaler Resort Kaanapali Beach

Kahana Falls Maui by VRI Americas

3.5 star property
8.0 out of 10, Very Good, (923)
"Great hotel. We will come again."
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. "
$603 nightly
The price is $702
Sep 17 - Sep 18
Total with taxes and fees
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, (1658)
"The location was great to restaurants and the beach."
$299 nightly
The price is $353
Sep 10 - Sep 11
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, (1485)
"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)
"Really liked the resort"
$873 nightly
The price is $943
Sep 16 - Sep 17
Total with taxes and fees
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)
"Excellent property. "
Aston at Papakea Resort

Aston Mahana at Kaanapali

3.5 star property
9.0 out of 10, Wonderful, (1645)
"Excellent location"
Aston Mahana at Kaanapali

The Westin Ka'anapali Ocean Resort Villas

4.0 star property
8.6 out of 10, Excellent, (1114)
$447 nightly
The price is $527
Sep 16 - Sep 17
Total with taxes and fees
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"
$680 nightly
The price is $802
Oct 9 - Oct 10
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, (468)
"Very nice place to stay"
$479 nightly
The price is $565
Sep 23 - Sep 24
Total with taxes and fees
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)
"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 Kaanapali Shores

4.0 star property
8.8 out of 10, Excellent, (440)
"I recommend this place."
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. "
$447 nightly
The price is $527
Sep 23 - Sep 24
Total with taxes and fees
Marriott's Maui Ocean Club - Lahaina & Napili Towers

AEI at The Mahana Kaanapali Resort

4.0 star property
8.8 out of 10, Excellent, (275)
"Great location and facilities "
AEI at The Mahana Kaanapali Resort
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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 $248 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?

#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.