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Our top choices for Kaanapali Hillside holiday rentals

1. Aston at The Whaler on Kaanapali Beach

Aston at The Whaler on Kaanapali Beach
4.0 star property
Lahaina
9.2 out of 10, Wonderful, (1,552 reviews)
"Lovely place with full amenities and walk out patio in the lawn. Would definitely book again!"
United States
Heidi
The price is £457
includes taxes & fees
6 Aug - 7 Aug
Aston at The Whaler on Kaanapali Beach

2. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (443 reviews)
"Beach view was excellent. Property is close to shopping and restaurants."
United States
Susan
The price is £471
includes taxes & fees
9 Aug - 10 Aug
The Whaler Resort Kaanapali Beach

3. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Lahaina
8.8 out of 10, Excellent, (2,603 reviews)
"Great location and friendly staff"
Canada
Daniel
The price is £271
includes taxes & fees
16 Aug - 17 Aug
Aston Maui Kaanapali Villas

4. Studio Kaanapali Beach, Sleeps 3, Beach Cabana, Jacuzzi, Gr Floor Convenience

Studio Kaanapali Beach, Sleeps 3, Beach Cabana, Jacuzzi, Gr Floor Convenience
Kaanapali
10.0 out of 10, Exceptional, (38 reviews)
"Overall, everything was a great experience. Very clean room close to shopping close to the beach close to restaurants. Had a wonderful experience."
United States
Edward
The price is £345
includes taxes & fees
4 Aug - 5 Aug
Studio Kaanapali Beach, Sleeps 3, Beach Cabana, Jacuzzi, Gr Floor Convenience

5. Beautiful Ocean and Outer Island Views! See Whales in season!

Beautiful Ocean and Outer Island Views! See Whales in season!
Lahaina
9.4 out of 10, Exceptional, (90 reviews)
"Overall a 4/5 experience! I would stay here again without a doubt. Simple check-in process, attentive host, great ocean views, and a well equipped condo. The only drawback I can think of was in regards to some of the aging furnishings. "
United States
Timo S.
The price is £295
includes taxes & fees
3 Aug - 4 Aug
Beautiful Ocean and Outer Island Views! See Whales in season!

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

Top Floor, Corner Unit, Pool View, Kaanapali Beach
Kaanapali
9.4 out of 10, Exceptional, (61 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.
The price is £336
includes taxes & fees
26 Aug - 27 Aug
Top Floor, Corner Unit, Pool View, Kaanapali Beach

7. Renovated Studio Ka’anapali Shores | Pools, AC, Beach Access

Renovated Studio Ka’anapali Shores | Pools, AC, Beach Access
lahaina
9.6 out of 10, Exceptional, (20 reviews)
The price is £571
includes taxes & fees
3 Aug - 4 Aug
Renovated Studio Ka’anapali Shores | Pools, AC, Beach Access

8. 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, (107 reviews)
"Lovely room in a great location. Check in and check out were super easy, great amenities"
United States
Michaela F.
The price is £567
includes taxes & fees
4 Aug - 5 Aug
Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC

9. OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (3,013 reviews)
"Great place to stay especially if it’s your first time!"
United States
Jessica
The price is £625
includes taxes & fees
1 Sept - 2 Sept
OUTRIGGER Honua Kai Resort & Spa

10. Oceanview Corner/Studio Condo at Kaanapali Shores Resort - Unit 742

Oceanview Corner/Studio Condo at Kaanapali Shores Resort - Unit 742
Lahaina
8.8 out of 10, Excellent, (113 reviews)
"Great location Clean Room Great property"
United States
Robert T.
The price is £573
includes taxes & fees
13 Aug - 14 Aug
Oceanview Corner/Studio Condo at Kaanapali Shores Resort - Unit 742

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

Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!
Lahaina
10.0 out of 10, Exceptional, (202 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 £457
includes taxes & fees
3 Aug - 4 Aug
Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!

12. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,218 reviews)
"Great location, good value for the money."
United States
ANGELO
The price is £246
includes taxes & fees
9 Aug - 10 Aug
Aston Kaanapali Shores

13. Kāʻanapali Ocean View Condo with Beachfront Cabana for Guests

Kāʻanapali Ocean View Condo with Beachfront Cabana for Guests
Lahaina
10.0 out of 10, Exceptional, (169 reviews)
"Very peaceful and relaxing stay! "
United States
jason s.
The price is £380
includes taxes & fees
22 Aug - 23 Aug
Kāʻanapali Ocean View Condo with Beachfront Cabana for Guests

14. Summertime Special Prices!! Book Now!

Summertime Special Prices!! Book Now!
Lahaina
10.0 out of 10, Exceptional, (169 reviews)
"Very nicely decorated, clean, spacious, close to beach"
United States
Sandra L.
The price is £451
includes taxes & fees
14 Aug - 15 Aug
Summertime Special Prices!! Book Now!

15. Ocean View, Kaanapali Golf Course front, Beach Cabana

Ocean View, Kaanapali Golf Course front, Beach Cabana
Kaanapali
9.8 out of 10, Exceptional, (54 reviews)
"Great location. The condo was immaculate and they thought of everything you might need. I would definitely recommend and stay there again."
United States
Patti A.
The price is £360
includes taxes & fees
28 Aug - 29 Aug
Ocean View, Kaanapali Golf Course front, Beach Cabana

16. Kuleana Club - 504

Kuleana Club - 504
3.5 star property
Lahaina
8.0 out of 10, Very good, (1 review)
The price is £286
includes taxes & fees
13 Aug - 14 Aug
Kuleana Club - 504

17. Direct Oceanfront ground floor - Kuleana 706

Direct Oceanfront ground floor - Kuleana 706
Lahaina
9.6 out of 10, Exceptional, (132 reviews)
"We had a pretty good stay. Condo is older but served its purpose. Beautiful view and really close to waters edge!"
United States
Susan N.
The price is £644
includes taxes & fees
4 Aug - 5 Aug
Direct Oceanfront ground floor - Kuleana 706

18. Oceanview Corner Suite at Honua Kai – Sunshine & Serenity

Oceanview Corner Suite at Honua Kai – Sunshine & Serenity
Lahaina
9.2 out of 10, Wonderful, (123 reviews)
"Clean and well appointed property! The amenities at the resort were also wonderful. Will be back!"
United States
Kristen M.
The price is £632
includes taxes & fees
20 Aug - 21 Aug
Oceanview Corner Suite at Honua Kai – Sunshine & Serenity

19. 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, (274 reviews)
"Amazing trip!"
United States
Eric L.
The price is £361
includes taxes & fees
14 Aug - 15 Aug
Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!

20. Absolutely Beachfront -- Hale Mahina Beach Resort -- B206

Absolutely Beachfront -- Hale Mahina Beach Resort -- B206
Napili-Honokowai
9.4 out of 10, Exceptional, (75 reviews)
"Yes, everything was great."
United States
TIMOTHY M.
The price is £339
includes taxes & fees
5 Aug - 6 Aug
Absolutely Beachfront -- Hale Mahina Beach Resort -- B206
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 £218 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 Napili Bay are other popular places to visit in the 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.