Holiday Rentals in Kaanapali Hillside

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Our top choices for Kaanapali Hillside holiday rentals

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,793 reviews)
"Super clean room with fantastic view of the sea. Short walk to Napili beach. Great breakfast at the Gazebo restaurant "
United States
Mark
The price is €239
includes taxes & fees
16 May - 17 May
Napili Shores Maui by OUTRIGGER

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (397 reviews)
"Great staff, clean room, felt at home"
Canada
Matthew
The price is €618
includes taxes & fees
13 May - 14 May
The Whaler Resort Kaanapali Beach

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (182 reviews)
"The property is beautiful and located just steps away from the beach."
United States
Patricia
The price is €256
includes taxes & fees
11 May - 12 May
Napili Village Hotel

Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,091 reviews)
"Nice and safe place to stay"
United States
Kristen
The price is €290
includes taxes & fees
12 May - 13 May
Aston Kaanapali Shores

Unit 25 Waena Inn - Maui Private Suite

Unit 25 Waena Inn - Maui Private Suite
Wailuku
9.8 out of 10, Exceptional, (15 reviews)
"Great place "
United States
Noah S.
The price is €288
includes taxes & fees
11 May - 12 May
Unit 25 Waena Inn - Maui Private Suite

Bright, Beautiful, Remodeled Island Sands 505 Condo

Bright, Beautiful, Remodeled Island Sands 505 Condo
Wailuku
9.4 out of 10, Exceptional, (57 reviews)
"The property was very clean and well maintained! We enjoyed our stay. "
United States
Cindy B.
The price is €748
includes taxes & fees
7 Jun - 8 Jun
Bright, Beautiful, Remodeled Island Sands 505 Condo

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 €283
includes taxes & fees
11 May - 12 May
Napili Sunset on the Beach

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 €547
includes taxes & fees
12 May - 13 May
Oceanfront condo with pool & balcony - walk to dining, activities, and more

Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Lahaina
8.8 out of 10, Excellent, (2,564 reviews)
"Great location for beach lovers and family vacation. "
United States
meryem
The price is €407
includes taxes & fees
10 Jun - 11 Jun
Aston Maui Kaanapali Villas

Rustic retreat with panoramic views at Pu'u O Hoku Ranch

Rustic retreat with panoramic views at Pu'u O Hoku Ranch
Kaunakakai
10.0 out of 10, Exceptional, (95 reviews)
"Very kind and gracious staff at the Ranch. We had the weekend all to ourselves in the cottage. Enjoyed gourmet Chef pre-made meals, hiked every trail and loved the solitude. Highly recommend!"
United States
Gail D.
The price is €684
includes taxes & fees
11 May - 12 May
Rustic retreat with panoramic views at Pu'u O Hoku Ranch

Romantic Beachfront Getaway

Romantic Beachfront Getaway
Maalaea Bay
9.6 out of 10, Exceptional, (43 reviews)
"Excellent location. "
United States
Thomas
The price is €407
includes taxes & fees
18 May - 19 May
Romantic Beachfront Getaway

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, (1,137 reviews)
"Never a bad stay here!! "
United States
Michele
The price is €458
includes taxes & fees
17 May - 18 May
The Westin Ka'anapali Ocean Resort Villas

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, (27 reviews)
"Nice place"
Canada
PC SHOP
The price is €400
includes taxes & fees
12 May - 13 May
Ocean View 2-bedroom condo with pool and AC in wonderful Kihei

Top Floor Beachfront Condo with Ocean view

Top Floor Beachfront Condo with Ocean view
North Kihei
9.8 out of 10, Exceptional, (53 reviews)
"Kristal was a very welcoming host. Place was exactly what we were looking for. Great location, convenient stores nearby. The local beach was peaceful and relaxing. Had an amazing trip."
Canada
Vicki R.
The price is €439
includes taxes & fees
21 May - 22 May
Top Floor Beachfront Condo with Ocean view

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, (147 reviews)
"Our host was helpful and answered our questions in a timely manner. The amenities were great and the beach was not crowded."
United States
Thomas F.
The price is €507
includes taxes & fees
11 May - 12 May
SUMMER SPECIAL!!! OWNER HOST DIRECT OCEAN FRONT Longest Sandy Beach on Maui

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 €410
includes taxes & fees
1 Jun - 2 Jun
Sugar Beach Resort Oceanview 1 bed/1 bath

Panoramic Maui Sunset Ocean Views

Panoramic Maui Sunset Ocean Views
Central Kihei
9.2 out of 10, Wonderful, (54 reviews)
"The view was spectacular."
United States
Brett S.
The price is €746
includes taxes & fees
15 May - 16 May
Panoramic Maui Sunset Ocean Views

Unit 23 Waena Inn - Maui Private Suite

Unit 23 Waena Inn - Maui Private Suite
Wailuku
10.0 out of 10, Exceptional, (11 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 €271
includes taxes & fees
11 May - 12 May
Unit 23 Waena Inn - Maui Private Suite

Steps to the Beach, Affordable w/Free Parking

Steps to the Beach, Affordable w/Free Parking
North Kihei
9.6 out of 10, Exceptional, (170 reviews)
"Clean, across the street from beach and whale center. Great location to get to other places on the island. "
Canada
wayneiversonphotosk
The price is €386
includes taxes & fees
14 May - 15 May
Steps to the Beach, Affordable w/Free Parking

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, (169 reviews)
"Great location on the island, nice accommodations. "
United States
Chris P.
The price is €356
includes taxes & fees
25 May - 26 May
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC
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, apart-hotels, 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 €239 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?

Kapalua Golf Villas Resort by KBM: 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. Kitchen amenities include a fridge, an oven and a microwave. Kick off your shoes and enjoy yourself with a terrace and a garden.

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 Kahekili Beach 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.