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Our top choices for Kaanapali Hillside holiday rentals

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 £280
includes taxes & fees
29 Apr - 30 Apr
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC

Sugar Beach 102 Gorgeous Remodeled Home Beachfront Condo Home

Sugar Beach 102 Gorgeous Remodeled Home Beachfront Condo Home
North Kihei
9.4 out of 10, Exceptional, (44 reviews)
"The pool and hot tub are great and very easy to access. The views are stunning. And the grounds are kept incredibly clean and groomed. "
United States
Guy C.
The price is £410
includes taxes & fees
3 May - 4 May
Sugar Beach 102 Gorgeous Remodeled Home Beachfront Condo Home

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 £318
includes taxes & fees
28 Apr - 29 Apr
Sugar Beach Resort Oceanview 1 bed/1 bath

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, (69 reviews)
"The room was perfect! "
United States
Gillian
The price is £260
includes taxes & fees
28 Apr - 29 Apr
Oceanside condo, full kitchen, ocean view. Fully renovated 2023

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 £238
includes taxes & fees
1 May - 2 May
Unit 25 Waena Inn - Maui Private Suite

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 £250
includes taxes & fees
28 Apr - 29 Apr
Unit 23 Waena Inn - Maui Private Suite

Romantic Beachfront Getaway

Romantic Beachfront Getaway
Maalaea Bay
9.6 out of 10, Exceptional, (43 reviews)
"Excellent location. "
United States
Thomas
The price is £355
includes taxes & fees
28 Apr - 29 Apr
Romantic Beachfront Getaway

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 £678
includes taxes & fees
2 May - 3 May
Bright, Beautiful, Remodeled Island Sands 505 Condo

New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.

New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.
North Kihei
9.6 out of 10, Exceptional, (16 reviews)
"Perfect ocean views for morning coffee. Close to all the restaurants and good beaches "
United States
Michael A.
The price is £324
includes taxes & fees
28 Apr - 29 Apr
New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.

Top Floor Beachfront Condo with Ocean view

Top Floor Beachfront Condo with Ocean view
North Kihei
9.8 out of 10, Exceptional, (52 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 £387
includes taxes & fees
1 May - 2 May
Top Floor Beachfront Condo with Ocean view

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
North Kihei
9.6 out of 10, Exceptional, (299 reviews)
"Great unit for my needs and owner was very helpful and responsive when needed. Idea location for most Kihei activities "
United States
James B.
The price is £290
includes taxes & fees
28 Apr - 29 Apr
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
North Kihei
10.0 out of 10, Exceptional, (273 reviews)
"Perfectly situated on Maui island to easily visit everything and come back to condo to sleep."
Canada
Jean-Philippe R.
The price is £290
includes taxes & fees
2 May - 3 May
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

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 £498
includes taxes & fees
16 May - 17 May
Oceanfront condo with pool & balcony - walk to dining, activities, and more

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, (40 reviews)
"Had lots of great and useful amenities "
United States
Rochelle P.
The price is £360
includes taxes & fees
4 May - 5 May
This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” 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, (145 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 £440
includes taxes & fees
10 May - 11 May
SUMMER SPECIAL!!! OWNER HOST DIRECT OCEAN FRONT Longest Sandy Beach on Maui

Direct Beachfront with Spectacular Oceanviews!

Direct Beachfront with Spectacular Oceanviews!
Wailuke
9.8 out of 10, Exceptional, (51 reviews)
"Awesome little spot. Exactly what me and my wife were looking for. Highly recommend it! Had everything we needed and was close to all the spots we wanted to check out."
United States
Garrett F.
The price is £236
includes taxes & fees
11 May - 12 May
Direct Beachfront with Spectacular Oceanviews!

Steps to the Beach, Affordable w/Free Parking

Steps to the Beach, Affordable w/Free Parking
North Kihei
9.6 out of 10, Exceptional, (169 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 £326
includes taxes & fees
5 May - 6 May
Steps to the Beach, Affordable w/Free Parking

MARCH DEALS- Beachfront Condo With Amazing Oceanfront Views.

MARCH DEALS- Beachfront Condo With Amazing Oceanfront Views.
North Kihei
9.6 out of 10, Exceptional, (40 reviews)
"Unit was awesome, great decor. Very well stocked with everything you need. Great location. This unit was much nicer than others we stayed at on this property. "
United States
daryl m.
MARCH DEALS- Beachfront Condo With Amazing Oceanfront Views.

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 £356
includes taxes & fees
3 May - 4 May
Ocean View 2-bedroom condo with pool and AC in wonderful Kihei

Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!

Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!
North Kihei
9.8 out of 10, Exceptional, (206 reviews)
"Gorgeous condo right on the beach! Zero complaints! Thank you for sharing your home."
United States
Susan C.
Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!
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 £290 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 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.