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Our top choices for Kaanapali Hillside holiday rentals

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (187 reviews)
"Amazing location, great garden/ pool view. Comfortable and clean room, close to beach and snorkeling. Would definitely stay there again."
United States
Patrick James
The price is £180
includes taxes & fees
17 Jun - 18 Jun
Napili Village Hotel

Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly

Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly
North Kihei
9.0 out of 10, Wonderful, (9 reviews)
"Great stay, clean place. Close walk to the beach. The pool and hot tub were great and well taken care of"
United States
Danniella
The price is £266
includes taxes & fees
21 Jun - 22 Jun
Kihei · Pool / Hot Tub / Beach access / AC / Baby friendly

Warm Winter Getaway w/ a View - BEACHFRONT PROPERTY A13 at Kihei Sands

Warm Winter Getaway w/ a View - BEACHFRONT PROPERTY A13 at Kihei Sands
North Kihei
9.8 out of 10, Exceptional, (72 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: It was an amazing stay and a great place! I will be back!"
United States
Lauree M.
The price is £452
includes taxes & fees
15 Jun - 16 Jun
Warm Winter Getaway w/ a View - BEACHFRONT PROPERTY A13 at Kihei Sands

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
9.8 out of 10, Exceptional, (278 reviews)
"Absolutely perfect stay! Kevin was very kind and very communicative. I highly recommend staying here when visiting Kīhei."
United States
Sylvia
The price is £296
includes taxes & fees
15 Jun - 16 Jun
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

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, (171 reviews)
"Great location on the island, nice accommodations. "
United States
Chris P.
The price is £303
includes taxes & fees
22 Jun - 23 Jun
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC

Steps to the Beach, Affordable w/Free Parking

Steps to the Beach, Affordable w/Free Parking
North Kihei
9.6 out of 10, Exceptional, (171 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
15 Jun - 16 Jun
Steps to the Beach, Affordable w/Free Parking

Simply Amazing Oceanfront Condo! Milowai 310

Simply Amazing Oceanfront Condo! Milowai 310
Wailuku
10.0 out of 10, Exceptional, (21 reviews)
"Very good location and amenities. "
United States
Jiaxing B.
The price is £398
includes taxes & fees
15 Jun - 16 Jun
Simply Amazing Oceanfront Condo! Milowai 310

Bright, Beautiful, Remodeled Island Sands 505 Condo

Bright, Beautiful, Remodeled Island Sands 505 Condo
Wailuku
9.4 out of 10, Exceptional, (58 reviews)
"The property was very clean and well maintained! We enjoyed our stay. "
United States
Cindy B.
The price is £633
includes taxes & fees
15 Jun - 16 Jun
Bright, Beautiful, Remodeled Island Sands 505 Condo

Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View

Tracy’s Tropical Treasure #4 "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 £387
includes taxes & fees
4 Jul - 5 Jul
Tracy’s Tropical Treasure #4 "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, (118 reviews)
"Great location, great property and great condo. "
Canada
DIANNE V.
The price is £343
includes taxes & fees
15 Jun - 16 Jun
Sugar Beach Resort Oceanview 1 bed/1 bath

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
9.8 out of 10, Exceptional, (302 reviews)
"Exceptional host, comfy beds and pillows, great location!"
United States
Brenda C.
The price is £296
includes taxes & fees
6 Jul - 7 Jul
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

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, (75 reviews)
"We loved our stay! Great location"
United States
Madison
The price is £256
includes taxes & fees
15 Jun - 16 Jun
Oceanside condo, full kitchen, ocean view. Fully renovated 2023

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 £489
includes taxes & fees
17 Jun - 18 Jun
Oceanfront condo with pool & balcony - walk to dining, activities, and more

Direct Beachfront Newly Remodeled!

Direct Beachfront Newly Remodeled!
North Kihei
9.2 out of 10, Wonderful, (31 reviews)
"Very clean and comfortable. Loved the grassy area with lounge chairs to watch the sunset. Appreciated the cooler for day use to keep drinks cold. "
United States
Joleen B.
The price is £273
includes taxes & fees
15 Jun - 16 Jun
Direct Beachfront Newly Remodeled!

Romantic Beachfront Getaway

Romantic Beachfront Getaway
Maalaea Bay
9.6 out of 10, Exceptional, (43 reviews)
"Excellent location. "
United States
Thomas
The price is £359
includes taxes & fees
15 Jun - 16 Jun
Romantic Beachfront Getaway

🤙 June-July-August SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE

🤙 June-July-August SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE
North Kihei
10.0 out of 10, Exceptional, (141 reviews)
"This is the perfect getaway spot. Great direct view of the ocean and beach. "
United States
Mike H.
The price is £452
includes taxes & fees
24 Jun - 25 Jun
🤙 June-July-August SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE

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 £327
includes taxes & fees
18 Jun - 19 Jun
New Central AC! Oceanfront Steps from the Beach, with Pool, Jacuzzi, & BBQ.

Updated Napili Shores Studio King Bed A/C Walk to Napili Bay

Updated Napili Shores Studio King Bed A/C Walk to Napili Bay
Lahaina
9.8 out of 10, Exceptional, (149 reviews)
"Good communication, great location, comfortable bed and convenient layout "
United States
Aliyah K.
The price is £284
includes taxes & fees
19 Jun - 20 Jun
Updated Napili Shores Studio King Bed A/C Walk to Napili Bay

Ocean View Studio Steps to Beach - Pool, Spa & Pickleball - Free parking & Wi-Fi

Ocean View Studio Steps to Beach - Pool, Spa & Pickleball - Free parking & Wi-Fi
North Kihei
9.0 out of 10, Wonderful, (100 reviews)
"The accommodation was just as described and shown in the photos! The only issue we had were hundreds of little gnats but we were told it was because of the recent rainfall! "
United States
Cindy
The price is £300
includes taxes & fees
15 Jun - 16 Jun
Ocean View Studio Steps to Beach - Pool, Spa & Pickleball - Free parking & Wi-Fi

Kuleana Club - 511

Kuleana Club - 511
3.5 star property
Lahaina
10.0 out of 10, Exceptional, (1 review)
"Room was very clean and well equipped. Nice pool and helpful staff in premise. "
United States
Baron
Kuleana Club - 511
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 £180 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.