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Holiday Rentals in Kaanapali Hillside

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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, (4,347 reviews)
"Great Stay"
United States
Roopa Rani
The price is €277
includes taxes & fees
10 Oct - 11 Oct
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, (2,640 reviews)
"The property was a fantastic place to stay. The beach that is in front of the property is excellent for swimming and snorkeling."
United States
Marie
The price is €312
includes taxes & fees
1 Nov - 2 Nov
Aston Maui Kaanapali Villas

3. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.6 out of 10, Exceptional, (482 reviews)
"Great place"
United States
Alessio
The price is €584
includes taxes & fees
7 Oct - 8 Oct
The Whaler Resort Kaanapali Beach

4. Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (240 reviews)
"thank you for the best stay! perfect location, stunning beach with walking distance to beach, cafe, and rentals. room had everything we needed, recommend upgrading to ocean view it was a treat!"
United States
ASHLEY
The price is €191
includes taxes & fees
1 Nov - 2 Nov
Napili Village Hotel

5. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,888 reviews)
"Love this place!"
United States
Diana
The price is €274
includes taxes & fees
6 Oct - 7 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, (3,059 reviews)
"We had a great stay at the"
United States
Aprille A
The price is €872
includes taxes & fees
26 Oct - 27 Oct
OUTRIGGER Honua Kai Resort & Spa

7. 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 €295
includes taxes & fees
6 Oct - 7 Oct
Napili Sunset on the Beach

8. 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 €519
includes taxes & fees
13 Oct - 14 Oct
The Westin Ka'anapali Ocean Resort Villas

9. Summertime Special Prices!! Book Now!

Summertime Special Prices!! Book Now!
Kannapali Beach Area
10.0 out of 10, Exceptional, (173 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 €532
includes taxes & fees
14 Oct - 15 Oct
Summertime Special Prices!! Book Now!

10. 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)
"We loved our room!! The shower and bed were our highlights for sure. Definitely recommend staying here!!"
United States
Emily A.
The price is €521
includes taxes & fees
3 Oct - 4 Oct
Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!

11. 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, (1,564 reviews)
"Great location, very nice condo, pool, and beach access."
United States
Stewart
The price is €554
includes taxes & fees
25 Oct - 26 Oct
Aston at The Whaler on Kaanapali Beach

12. Aston Mahana at Kaanapali

Aston Mahana at Kaanapali
3.5 star property
Kaanapali
9.0 out of 10, Wonderful, (1,833 reviews)
"Clean nice resort,with beautiful views and reasonable pricing!"
United States
Amit
The price is €287
includes taxes & fees
7 Oct - 8 Oct
Aston Mahana at Kaanapali

13. 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 €440
includes taxes & fees
28 Oct - 29 Oct
Hawaiiana Suite for 3, Private Beach Club, walk Kaanapali Beach, Gym

14. 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 €817
includes taxes & fees
14 Oct - 15 Oct
Honua Kai Konea Resort by KBM

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, (178 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.
Direct Ocean Front~Kaanapali Beach~West Maui Paradise Welcomes You!

16. 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 €823
includes taxes & fees
10 Oct - 11 Oct
Remodeled Ocean View Studio at The Whaler 518-Kaanapali Beach-Walk to Dining

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, (109 reviews)
"Everything was great !"
United States
Michael
The price is €676
includes taxes & fees
5 Oct - 6 Oct
Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC

18. 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 €590
includes taxes & fees
19 Oct - 20 Oct
The Westin Nanea Ocean Villas, Ka'anapali

19. Direct Oceanfront ground floor - Kuleana 706

Direct Oceanfront ground floor - Kuleana 706
Lahaina
9.6 out of 10, Exceptional, (135 reviews)
"Wonderful property, great support team from Epic Realty. everything was wonderful. We stayed at Kuleana Resort 4 times, and we've recommended it to several of our friend, and we will stay there again if we have a chance."
United States
Margarita R.
The price is €762
includes taxes & fees
3 Oct - 4 Oct
Direct Oceanfront ground floor - Kuleana 706

20. Top Floor, Corner Unit, Pool View, Kaanapali Beach

Top Floor, Corner Unit, Pool View, Kaanapali Beach
Kannapali Beach Area
9.4 out of 10, Exceptional, (63 reviews)
"Everything about stay was wonderfulCentrally located , easy to get to from airportStudio room perfect for our needs. Close to pool and rides to beach made it easy Thank you for a great stay "
United States
Terri B.
Top Floor, Corner Unit, Pool View, Kaanapali Beach
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 €191 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.