Kaanapali Hillside Holiday Rentals

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Our top choices for Kaanapali Hillside holiday rentals

Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,051 reviews)
"Beautiful location and friendly helpful staff. Nice clean rooms and resort. "
Canada
Megan Ruth
The price is NZ$705
includes taxes & fees
18 Apr - 19 Apr
Aston Kaanapali Shores

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (176 reviews)
"Great location "
United States
John Roger
The price is NZ$393
includes taxes & fees
22 Apr - 23 Apr
Napili Village Hotel

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,783 reviews)
"Ocean view, comfortable room, nice bar on property, well located"
United States
Rosanne Marie
The price is NZ$539
includes taxes & fees
14 Apr - 15 Apr
Napili Shores Maui by OUTRIGGER

Unit 24 Waena Inn - Maui Private Suite

Unit 24 Waena Inn - Maui Private Suite
Wailuku
9.6 out of 10, Exceptional, (17 reviews)
"Excellent location, assigned parking"
United States
Virinchi Roy S.
The price is NZ$565
includes taxes & fees
9 Apr - 10 Apr
Unit 24 Waena Inn - Maui Private Suite

Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (654 reviews)
"Clean room amd friendly staff."
United States
Chris
The price is NZ$576
includes taxes & fees
11 Apr - 12 Apr
Napili Sunset on the Beach

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (378 reviews)
"Beautiful views, wonderful staff, clean & spacious room! Would love to stay again someday. "
United States
Sophia
The price is NZ$1,379
includes taxes & fees
12 Apr - 13 Apr
The Whaler Resort Kaanapali Beach

Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Lahaina
8.8 out of 10, Excellent, (2,557 reviews)
"Best Maui location"
United States
Chris
The price is NZ$799
includes taxes & fees
11 Apr - 12 Apr
Aston Maui Kaanapali Villas

Bright, Beautiful, Remodeled Island Sands 505 Condo

Bright, Beautiful, Remodeled Island Sands 505 Condo
Wailuku
9.4 out of 10, Exceptional, (57 reviews)
"Stay was great, condo was well equipped, great location and beautiful view."
United States
Tara C.
The price is NZ$1,564
includes taxes & fees
12 Apr - 13 Apr
Bright, Beautiful, Remodeled Island Sands 505 Condo

Romantic Beachfront Getaway

Romantic Beachfront Getaway
Maalaea Bay
9.6 out of 10, Exceptional, (43 reviews)
"Excellent location. "
United States
Thomas
The price is NZ$812
includes taxes & fees
9 Apr - 10 Apr
Romantic Beachfront Getaway

OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC

OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC
Wailuku
9.6 out of 10, Exceptional, (167 reviews)
"Great location on the island, nice accommodations. "
United States
Chris P.
The price is NZ$591
includes taxes & fees
11 Apr - 12 Apr
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC

Unit 23 Waena Inn - Maui Private Suite

Unit 23 Waena Inn - Maui Private Suite
Wailuku
10.0 out of 10, Exceptional, (10 reviews)
"Fairly central location. Helpful and due to the length of our stay, offered for us to use washer/dryer, snorkels, beach towels. "
United States
Suzan F.
The price is NZ$568
includes taxes & fees
9 Apr - 10 Apr
Unit 23 Waena Inn - Maui Private Suite

Oceanside condo, full kitchen, ocean view. Fully renovated 2023

Oceanside condo, full kitchen, ocean view. Fully renovated 2023
Central Kihei
9.4 out of 10, Exceptional, (67 reviews)
"The room was perfect! "
United States
Gillian
The price is NZ$610
includes taxes & fees
9 Apr - 10 Apr
Oceanside condo, full kitchen, ocean view. Fully renovated 2023

OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (2,945 reviews)
"Nice staff/clean rooms. Overall very nice"
Canada
Anastassiya
The price is NZ$1,381
includes taxes & fees
22 Apr - 23 Apr
OUTRIGGER Honua Kai Resort & Spa

This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!

This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!
North Kihei
10.0 out of 10, Exceptional, (39 reviews)
"we really enjoyed our stay here. It is clean and maintained well and close to the beach."
United States
stuti s.
The price is NZ$797
includes taxes & fees
10 Apr - 11 Apr
This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!

Sugar Beach Resort Oceanview 1 bed/1 bath

Sugar Beach Resort Oceanview 1 bed/1 bath
North Kihei
9.6 out of 10, Exceptional, (117 reviews)
"Condo is fully stocked and decorated beautifully! "
United States
erin t.
The price is NZ$766
includes taxes & fees
13 Apr - 14 Apr
Sugar Beach Resort Oceanview 1 bed/1 bath

Oceanfront condo with pool & balcony - walk to dining, activities, and more

Oceanfront condo with pool & balcony - walk to dining, activities, and more
Wailuku
9.4 out of 10, Exceptional, (132 reviews)
"Beautiful view!!"
United States
Gene E.
The price is NZ$1,172
includes taxes & fees
25 Apr - 26 Apr
Oceanfront condo with pool & balcony - walk to dining, activities, and more

Ocean View 2-bedroom condo with pool and AC in wonderful Kihei

Ocean View 2-bedroom condo with pool and AC in wonderful Kihei
North Kihei
9.8 out of 10, Exceptional, (26 reviews)
"Nice place"
Canada
PC SHOP
The price is NZ$821
includes taxes & fees
14 Apr - 15 Apr
Ocean View 2-bedroom condo with pool and AC in wonderful Kihei

Direct Beachfront Newly Remodeled!

Direct Beachfront Newly Remodeled!
North Kihei
9.2 out of 10, Wonderful, (28 reviews)
"Very nice right on the beach "
United States
MATILDA
The price is NZ$709
includes taxes & fees
30 Apr - 1 May
Direct Beachfront Newly Remodeled!

SUMMER SPECIAL!!! OWNER HOST DIRECT OCEAN FRONT Longest Sandy Beach on Maui

SUMMER SPECIAL!!! OWNER HOST DIRECT OCEAN FRONT Longest Sandy Beach on Maui
North Kihei
10.0 out of 10, Exceptional, (145 reviews)
"Our host was so responsive, kind and helpful! "
United States
Laura C.
The price is NZ$1,013
includes taxes & fees
16 Apr - 17 Apr
SUMMER SPECIAL!!! OWNER HOST DIRECT OCEAN FRONT Longest Sandy Beach on Maui

The Westin Ka'anapali Ocean Resort Villas

The Westin Ka'anapali Ocean Resort Villas
4.0 star property
Lahaina
8.6 out of 10, Excellent, (1,133 reviews)
"Staff friendly, great room and cleanliness. Amenties were excellent. "
United States
WILLIAM
The price is NZ$932
includes taxes & fees
16 Apr - 17 Apr
The Westin Ka'anapali Ocean Resort Villas
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$539 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?

The #1 Luxury OCEAN FRONT Mansion! Sleeps 32: 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 11 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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. Whalers Village and Kaanapali Kai Course at Kaanapali Golf Resort 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.