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Kaanapali Hillside Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Kaanapali Hillside vacation rentals

A swimming pool with a curved design, surrounded by palm trees and lounge chairs, with a building in the background.

1. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Kannapali Beach Area
8.8 out of 10, Excellent, (2,644 reviews)
"Great place will stay again!"
United States
Joseph
The price is ￥34,225
￥54,684 total
includes taxes & fees
Nov 6 - Nov 7
Aston Maui Kaanapali Villas
A tropical garden with a waterfall, lush greenery, and a gazebo.

2. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,368 reviews)
"Great Stay"
United States
Roopa Rani
The price is ￥37,770
￥49,522 total
includes taxes & fees
Oct 15 - Oct 16
Aston Kaanapali Shores
A view of a beach with palm trees and a sailboat on the water.

3. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.6 out of 10, Exceptional, (489 reviews)
"Great place"
United States
Alessio
The price is ￥38,748
￥103,692 total
includes taxes & fees
Oct 18 - Oct 19
The Whaler Resort Kaanapali Beach
A beach with clear turquoise water, sandy shore, palm trees, and a resort building in the background.

4. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,896 reviews)
"Great property"
United States
Shawn
The price is ￥35,415
￥42,042 total
includes taxes & fees
Nov 1 - Nov 2
Napili Shores Maui by OUTRIGGER
A resort pool with red umbrellas, palm trees, and a view of the ocean.

5. OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (3,065 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 ￥56,213
￥150,846 total
includes taxes & fees
Nov 8 - Nov 9
OUTRIGGER Honua Kai Resort & Spa
A resort with a pool, palm trees, and a view of the ocean.

6. 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, (533 reviews)
"It was beautiful hotel and we love to walk to the beach."
United States
Maria
The price is ￥88,298
￥104,820 total
includes taxes & fees
Oct 23 - Oct 24
The Westin Nanea Ocean Villas, Ka'anapali
A beach with clear blue water, palm trees, and a resort in the background.

7. Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (243 reviews)
"Loved the free parking and on-site laundry!"
United States
Thomas
The price is ￥25,152
￥29,858 total
includes taxes & fees
Nov 1 - Nov 2
Napili Village Hotel
A beach view with lounge chairs and a clear sky.

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 ￥47,357
￥56,218 total
includes taxes & fees
Nov 4 - Nov 5
Napili Sunset on the Beach
A beach view with palm trees, a clear sky, and a distant mountain.

9. 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)
"Nice room. You can’t go wrong at the whaler. The shower leaked a little. Overall good experience"
United States
Alaba G.
The price is ￥33,001
￥144,196 total
includes taxes & fees
Oct 14 - Oct 15
Remodeled Ocean View Studio at The Whaler 518-Kaanapali Beach-Walk to Dining
A round table with two chairs on a balcony overlooking a clear blue sea and a distant mountain.

10. 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 ￥25,438
￥73,253 total
includes taxes & fees
Oct 11 - Oct 12
Direct Ocean Front~Kaanapali Beach~West Maui Paradise Welcomes You!
A balcony with a table set for dining, overlooking a pool and palm trees, with a view of the ocean and mountains in the distance.

11. Honua Kai Konea Resort by KBM

Honua Kai Konea Resort by KBM
4.5 star property
Kaanapali
9.4 out of 10, Exceptional, (102 reviews)
"Great staff, easy check in."
United States
Jane
The price is ￥56,735
￥144,815 total
includes taxes & fees
Oct 14 - Oct 15
Honua Kai Konea Resort by KBM
Lobby

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 ￥55,454
￥98,446 total
includes taxes & fees
Oct 25 - Oct 26
Aston at The Whaler on Kaanapali Beach
A swimming pool with lounge chairs and palm trees in the background.

13. 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 ￥27,001
￥95,285 total
includes taxes & fees
Oct 29 - Oct 30
Summertime Special Prices!! Book Now!
A modern kitchen with a central island, stainless steel appliances, and a view to a patio area.

14. 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 ￥27,001
￥95,285 total
includes taxes & fees
Oct 22 - Oct 23
Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!
A tropical garden with a waterfall, a gazebo, and lush vegetation.

15. 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 ￥14,211
￥118,014 total
includes taxes & fees
Oct 11 - Oct 12
Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC
A resort with a pool, palm trees, a waterfall, and a view of the ocean.

16. 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, (1,167 reviews)
"The facilities were exactly as described. Our ocean front room and the hotel amenities were wonderful."
Canada
James
The price is ￥78,161
￥92,786 total
includes taxes & fees
Oct 15 - Oct 16
The Westin Ka'anapali Ocean Resort Villas
A dining area with a view of the ocean, two chairs, a table with plates and glasses, and a sofa.

17. 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, (321 reviews)
"We loved our stay. Beautiful patio view & very walkable to many restaurants, bakeries & coffee spots. "
United States
Richard H.
The price is ￥39,317
￥88,405 total
includes taxes & fees
Oct 30 - Oct 31
Beautiful Oceanfront Condo at Pikake 20 Feet From the Water A/C Amazing Views
A beachside seating area with metal chairs and tables, overlooking a clear blue ocean.

18. Kāʻanapali Ocean View Condo with Beachfront Cabana for Guests

Kāʻanapali Ocean View Condo with Beachfront Cabana for Guests
Kannapali Beach Area
10.0 out of 10, Exceptional, (171 reviews)
"Very peaceful and relaxing stay! "
United States
jason s.
The price is ￥33,949
￥82,475 total
includes taxes & fees
Nov 3 - Nov 4
Kāʻanapali Ocean View Condo with Beachfront Cabana for Guests
A patio with two barbecue grills, a pathway, and a view of the sea and mountains.

19. Kuleana Club - 511

Kuleana Club - 511
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (2 reviews)
"Room was very clean and well equipped. Nice pool and helpful staff in premise. "
United States
Baron
The price is ￥24,632
￥62,045 total
includes taxes & fees
Oct 22 - Oct 23
Kuleana Club - 511
A balcony with a round table, two chairs, and a view of the ocean with sailboats.

20. Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014

Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014
Lahaina
10.0 out of 10, Exceptional, (293 reviews)
"We enjoyed our stay here very much. The location is amazing and easy to find. The condo was very clean and had a wonderful beach vibe. Check in was super simple and the entire staff was super nice and helpful. The owner was very easy to get in touch with and very helpful. We would definitely return here again someday."
United States
KristyAnn C.
The price is ￥62,371
￥128,342 total
includes taxes & fees
Oct 11 - Oct 12
Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014
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

Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

10/10 Excellent
"We had a wonderful stay at Royal Lahaina! The staff was extremely friendly, welcoming, and always smiling, making us feel the Hawaiian atmosphere from the moment we arrived. The hotel was clean, beautifully renovated, and offered amazing ocean views. We loved the peaceful atmosphere and the location, which was perfect for relaxing while still being close to nearby attractions. The trolley service to Whalers Village was a great bonus and made getting around very convenient. The Myths of Maui luau was another highlight of our stay. We really enjoyed the show and the authentic Hawaiian atmosphere. The resort had a special charm that made our experience feel truly Hawaiian. Overall, we had a fantastic stay and would happily return. The welcoming staff and warm Hawaiian hospitality made our visit to Maui even more memorable!"
Anna 4-night trip
Posted 1 hour ago
Royal Lahaina Resort & Bungalows

Find out more about Kaanapali Hillside

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Frequently asked questions

Can I find a vacation rental in Kaanapali Hillside?

Yes, we have vacation rentals near well known sights in Kaanapali Hillside, or you can select a more secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Kaanapali Hillside?

Legendary Estate 50 Steps to Maui’s Best Beach! New! 5 Bedroom, Pool With Slide!: Visitors like this Kaanapali Hillside vacation home rental. It is located on the beach and has an outdoor pool, a balcony, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 larger area.

What’s a vacation rental in Kaanapali Hillside like?

A vacation rental is a private property you can book for a long or short time in Kaanapali Hillside. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a small group gathering.