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Our top choices for Kaanapali Hillside holiday rentals

1. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,421 reviews)
"Great stay at a great price"
United States
Dina
The price is £212
includes taxes & fees
3 Dec - 4 Dec
Aston Kaanapali Shores

2. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Kannapali Beach Area
8.8 out of 10, Excellent, (2,659 reviews)
"Amazing and relaxing resort"
United States
Mariano
The price is £254
includes taxes & fees
3 Dec - 4 Dec
Aston Maui Kaanapali Villas

3. Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
4.0 star property
Kannapali Beach Area
8.4 out of 10, Very good, (260 reviews)
"Great property very close to everything"
United States
Carroll M
The price is £297
includes taxes & fees
30 Nov - 1 Dec
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

4. OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (3,085 reviews)
"Nice and clean resort, staff was very friendly and accommodating"
United States
Trung
The price is £568
includes taxes & fees
2 Dec - 3 Dec
OUTRIGGER Honua Kai Resort & Spa

5. 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, (1,170 reviews)
"The facilities were exactly as described. Our ocean front room and the hotel amenities were wonderful."
Canada
James
The price is £304
includes taxes & fees
20 Nov - 21 Nov
The Westin Ka'anapali Ocean Resort Villas

6. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.6 out of 10, Exceptional, (515 reviews)
"Amazing stay!"
United States
zachary
The price is £480
includes taxes & fees
1 Dec - 2 Dec
The Whaler Resort Kaanapali Beach

7. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,910 reviews)
"Very nice location and grounds. Throughly enjoyed our stay!"
United States
Steve
The price is £217
includes taxes & fees
16 Nov - 17 Nov
Napili Shores Maui by OUTRIGGER

8. Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (257 reviews)
"amazing location"
United States
Adrian
The price is £149
includes taxes & fees
4 Nov - 5 Nov
Napili Village Hotel

9. 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 £199
includes taxes & fees
15 Nov - 16 Nov
Napili Sunset on the Beach

10. The Whaler 518 – Remodeled Ocean View Studio on Kāʻanapali Beach

The Whaler 518 – Remodeled Ocean View Studio on Kāʻanapali Beach
Kannapali Beach Area
9.6 out of 10, Exceptional, (82 reviews)
"Good view, good location!"
United States
Nate M.
The price is £701
includes taxes & fees
21 Nov - 22 Nov
The Whaler 518 – Remodeled Ocean View Studio on Kāʻanapali Beach

11. Honua Kai Konea Resort by KBM

Honua Kai Konea Resort by KBM
4.5 star property
Kaanapali
9.4 out of 10, Exceptional, (105 reviews)
"Great staff, easy check in."
United States
Jane
The price is £643
includes taxes & fees
5 Nov - 6 Nov
Honua Kai Konea Resort by KBM

12. 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, (206 reviews)
"Loved this place. Perfect! Grounds and room very clean and well equipped kitchen with even Tupperware. Great lay out with plenty of space. Lovely lanai and walking distance to the beach or golf cart ride. Covered building cabana with outdoor shower and bathrooms with use of beach chairs. Close to shops and pickleball."
United States
Robert C.
The price is £480
includes taxes & fees
4 Nov - 5 Nov
Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!

13. Marriott's Maui Ocean Club - Lahaina & Napili Towers

Marriott's Maui Ocean Club - Lahaina & Napili Towers
4.0 star property
Kannapali Beach Area
8.8 out of 10, Excellent, (234 reviews)
"Best resort for kids"
United States
Mai Ka
The price is £328
includes taxes & fees
4 Dec - 5 Dec
Marriott's Maui Ocean Club - Lahaina & Napili Towers

14. Summertime Special Prices!! Book Now!

Summertime Special Prices!! Book Now!
Kannapali Beach Area
10.0 out of 10, Exceptional, (177 reviews)
"Great location. Place had all the facilities for a wonderful stay and close to the golf courses."
United States
Brent T.
The price is £449
includes taxes & fees
12 Nov - 13 Nov
Summertime Special Prices!! Book Now!

15. 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, (543 reviews)
"great family stay"
United States
Justin
The price is £355
includes taxes & fees
2 Dec - 3 Dec
The Westin Nanea Ocean Villas, Ka'anapali

16. 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)
"Condo had a great view of turtles playing in the water right off the beach. Snorkeling in front of the condo was pretty good but better just north of the property."
United States
joseph s.
The price is £347
includes taxes & fees
5 Nov - 6 Nov
Direct Ocean Front~Kaanapali Beach~West Maui Paradise Welcomes You!

17. 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 £586
includes taxes & fees
11 Nov - 12 Nov
Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC

18. 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.
The price is £509
includes taxes & fees
7 Nov - 8 Nov
Beachfront clubhouse, new furnishings, 1st floor, bonus 2 bathroom

19. Pikake - West Maui Beachfront Condo! 20 Feet from the Ocean!

Pikake - West Maui Beachfront Condo! 20 Feet from the Ocean!
Lahaina
9.8 out of 10, Exceptional, (185 reviews)
"The location is what makes this place nice. It has its own little private beach which was great for our kids."
United States
Greg A.
The price is £405
includes taxes & fees
4 Nov - 5 Nov
Pikake - West Maui Beachfront Condo! 20 Feet from the Ocean!

20. Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!

Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!
Lahaina
9.8 out of 10, Exceptional, (279 reviews)
"We had a great time in Maui! We were there to rest and relax and celebrate our anniversary."
United States
Traci B.
The price is £397
includes taxes & fees
4 Nov - 5 Nov
Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!
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 £149 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?

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.