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Kaanapali Hillside Holiday Rentals

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Our top choices for Kaanapali Hillside holiday rentals

1. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Kannapali Beach Area
8.8 out of 10, Excellent, (2,646 reviews)
"Great place will stay again!"
United States
Joseph
The price is AU$498
includes taxes & fees
6 Nov - 7 Nov
Aston Maui Kaanapali Villas

2. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,376 reviews)
"Great Stay"
United States
Roopa Rani
The price is AU$436
includes taxes & fees
28 Oct - 29 Oct
Aston Kaanapali Shores

3. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.6 out of 10, Exceptional, (497 reviews)
"We loved everything and the location was perfect!!"
United States
Lenore
The price is AU$944
includes taxes & fees
18 Oct - 19 Oct
The Whaler Resort Kaanapali Beach

4. The Westin Nanea Ocean Villas, Ka'anapali

The Westin Nanea Ocean Villas, Ka'anapali
4.0 star property
Lahaina
9.4 out of 10, Exceptional, (534 reviews)
"It was beautiful hotel and we love to walk to the beach."
United States
Maria
The price is AU$954
includes taxes & fees
30 Oct - 31 Oct
The Westin Nanea Ocean Villas, Ka'anapali

5. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,901 reviews)
"Great trip!"
United States
Jennifer
The price is AU$383
includes taxes & fees
27 Oct - 28 Oct
Napili Shores Maui by OUTRIGGER

6. OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (3,066 reviews)
"Such a lovely stay. The hotel is in a great location, everyone was very kind. I would definitely stay here again!"
United States
Andrea
The price is AU$1,148
includes taxes & fees
13 Nov - 14 Nov
OUTRIGGER Honua Kai Resort & Spa

7. Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (247 reviews)
"We loved how quiet and relaxing the property was. The employees and atmosphere were amazing."
United States
Joshua
The price is AU$284
includes taxes & fees
2 Nov - 3 Nov
Napili Village Hotel

8. Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (656 reviews)
"Nice and clean stay! "
United States
Beverly
The price is AU$512
includes taxes & fees
3 Nov - 4 Nov
Napili Sunset on the Beach

9. Honua Kai Konea Resort by KBM

Honua Kai Konea Resort by KBM
4.5 star property
Kaanapali
9.4 out of 10, Exceptional, (103 reviews)
"Great staff, easy check in."
United States
Jane
The price is AU$1,307
includes taxes & fees
14 Oct - 15 Oct
Honua Kai Konea Resort by KBM

10. Remodeled Ocean View Studio at The Whaler 518-Kaanapali Beach-Walk to Dining

Remodeled Ocean View Studio at The Whaler 518-Kaanapali Beach-Walk to Dining
Kannapali Beach Area
9.6 out of 10, Exceptional, (80 reviews)
"Good view, good location!"
United States
Nate M.
The price is AU$1,272
includes taxes & fees
14 Oct - 15 Oct
Remodeled Ocean View Studio at The Whaler 518-Kaanapali Beach-Walk to Dining

11. Summertime Special Prices!! Book Now!

Summertime Special Prices!! Book Now!
Kannapali Beach Area
10.0 out of 10, Exceptional, (175 reviews)
"Great communication from host. Condo was perfect with all the amenities one could need. Nice location convenient for walking, shopping, dining….Very quiet perfect for relaxing."
United States
Karen K.
The price is AU$844
includes taxes & fees
14 Oct - 15 Oct
Summertime Special Prices!! Book Now!

12. Aston at The Whaler on Kaanapali Beach

Aston at The Whaler on Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.2 out of 10, Wonderful, (1,566 reviews)
"Great location, very nice condo, pool, and beach access."
United States
Stewart
The price is AU$896
includes taxes & fees
25 Oct - 26 Oct
Aston at The Whaler on Kaanapali Beach

13. Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!

Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!
Kannapali Beach Area
10.0 out of 10, Exceptional, (205 reviews)
"This condo was perfect for my family of 4! It was the perfect location. We have been to this resort the last 5 years and this is by far the best place. The owners are easy to get a hold off and graciously let us extend our trip 1 day due to a delay. Thank you for allowing us to stay in your lovely place. We hope to return next year!"
United States
Lori T.
The price is AU$841
includes taxes & fees
17 Oct - 18 Oct
Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!

14. The Westin Ka'anapali Ocean Resort Villas

The Westin Ka'anapali Ocean Resort Villas
4.0 star property
Kannapali Beach Area
8.6 out of 10, Excellent, (1,168 reviews)
"The facilities were exactly as described. Our ocean front room and the hotel amenities were wonderful."
Canada
James
The price is AU$845
includes taxes & fees
20 Oct - 21 Oct
The Westin Ka'anapali Ocean Resort Villas

15. Direct Ocean Front~Kaanapali Beach~West Maui Paradise Welcomes You!

Direct Ocean Front~Kaanapali Beach~West Maui Paradise Welcomes You!
Lahaina
9.8 out of 10, Exceptional, (179 reviews)
"We truly enjoyed our stay in Maui. The room was perfect, and just as advertised. Seeing the sea turtles from the balcony and the amazing sunsets were some of our favorite parts of the trip. You literally cannot get any closer to the water, which was great at night, listening to the waves crash. Looking forward to our next trip!"
United States
Anthony P.
The price is AU$797
includes taxes & fees
29 Oct - 30 Oct
Direct Ocean Front~Kaanapali Beach~West Maui Paradise Welcomes You!

16. Hawaiiana Suite for 3, Private Beach Club, walk Kaanapali Beach, Gym

Hawaiiana Suite for 3, Private Beach Club, walk Kaanapali Beach, Gym
Kannapali Beach Area
9.0 out of 10, Wonderful, (45 reviews)
"Air conditioning was great. Room was very clean and easy check in process. We only stayed 2 nights here but it would have worked perfectly for extended stays as well! "
United States
Stephanie S.
The price is AU$686
includes taxes & fees
28 Oct - 29 Oct
Hawaiiana Suite for 3, Private Beach Club, walk Kaanapali Beach, Gym

17. Beachfront clubhouse, new furnishings, 1st floor, bonus 2 bathroom

Beachfront clubhouse, new furnishings, 1st floor, bonus 2 bathroom
Kannapali Beach Area
9.8 out of 10, Exceptional, (18 reviews)
"Loved the location and amenities. Golf cart rides to the cabana and best beach were a major plus for us. Only wish there was a restaurant on the premises. Will return again!"
United States
Peggy V.
Beachfront clubhouse, new furnishings, 1st floor, bonus 2 bathroom

18. Beautiful Oceanfront Condo at Pikake 20 Feet From the Water A/C Amazing Views

Beautiful Oceanfront Condo at Pikake 20 Feet From the Water A/C Amazing Views
Lahaina
10.0 out of 10, Exceptional, (322 reviews)
"We loved our stay. Beautiful patio view & very walkable to many restaurants, bakeries & coffee spots. "
United States
Richard H.
Beautiful Oceanfront Condo at Pikake 20 Feet From the Water A/C Amazing Views

19. 1 bedroom at Honua Kai Mountain view remodeled April 2023 King Bed, Central AC

1 bedroom at Honua Kai Mountain view remodeled April 2023 King Bed, Central AC
Lahaina
10.0 out of 10, Exceptional, (102 reviews)
"Amazing stay!"
United States
Andrea P.
1 bedroom at Honua Kai Mountain view remodeled April 2023 King Bed, Central AC

20. Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC

Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC
Lahaina
8.6 out of 10, Excellent, (111 reviews)
"Everything was great !"
United States
Michael
The price is AU$1,085
includes taxes & fees
14 Oct - 15 Oct
Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, 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, 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 favourite 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 depend 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 AU$284 per night. Entering your travel dates in the search wizard might find you 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?

Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!: 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 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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.