Default HTG hotel image

Kaanapali Hillside Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Kaanapali Hillside holiday rentals

1. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Lahaina
8.8 out of 10, Excellent, (2,619 reviews)
"Great place"
United States
Luis MANUEL
The price is NZ$611
includes taxes & fees
1 Sept - 2 Sept
Aston Maui Kaanapali Villas

2. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,272 reviews)
"Great location!"
United States
Shad
The price is NZ$465
includes taxes & fees
24 Aug - 25 Aug
Aston Kaanapali Shores

3. The Westin Ka'anapali Ocean Resort Villas

The Westin Ka'anapali Ocean Resort Villas
4.0 star property
Lahaina
8.6 out of 10, Excellent, (1,149 reviews)
"Great for families. Safe, clean, and beautiful."
Canada
Jennifer
The price is NZ$983
includes taxes & fees
28 Aug - 29 Aug
The Westin Ka'anapali Ocean Resort Villas

4. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (452 reviews)
"We love The Whaler!"
United States
Jacob
The price is NZ$1,063
includes taxes & fees
23 Aug - 24 Aug
The Whaler Resort Kaanapali Beach

5. OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (3,027 reviews)
"We found this resort clean, family friendly,"
United States
Amanda
The price is NZ$1,565
includes taxes & fees
24 Aug - 25 Aug
OUTRIGGER Honua Kai Resort & Spa

6. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,859 reviews)
"Wonderful Beach and right next door to kapalua!"
United States
joe
The price is NZ$503
includes taxes & fees
23 Aug - 24 Aug
Napili Shores Maui by OUTRIGGER

7. Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (220 reviews)
"Great stay, thank you"
United States
Elizabeth
The price is NZ$595
includes taxes & fees
2 Sept - 3 Sept
Napili Village Hotel

8. Honua Kai Hokulani Resort by KBM

Honua Kai Hokulani Resort by KBM
4.0 star property
Kaanapali
8.6 out of 10, Excellent, (31 reviews)
"Beautiful property with wonderful staff."
United States
Lance
The price is NZ$2,156
includes taxes & fees
19 Sept - 20 Sept
Honua Kai Hokulani Resort by KBM

9. Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (657 reviews)
"Clean room amd friendly staff."
United States
Chris
The price is NZ$558
includes taxes & fees
23 Aug - 24 Aug
Napili Sunset on the Beach

10. Studio Kaanapali Beach, Beach Cabana, Jacuzzi, Gr Floor Convenience

Studio Kaanapali Beach, 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
Studio Kaanapali Beach, Beach Cabana, Jacuzzi, Gr Floor Convenience

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, (203 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 NZ$1,010
includes taxes & fees
23 Aug - 24 Aug
Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!

12. 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, (1,555 reviews)
"Lovely place with full amenities and walk out patio in the lawn. Would definitely book again!"
United States
Heidi
The price is NZ$705
includes taxes & fees
30 Aug - 31 Aug
Aston at The Whaler on Kaanapali Beach

13. 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, (523 reviews)
"Clean, comfortable property with lots of amenities on the water! Helpful concierge to book excursions. I would stay again!"
United States
Kathryn
The price is NZ$1,230
includes taxes & fees
4 Sept - 5 Sept
The Westin Nanea Ocean Villas, Ka'anapali

14. Summertime Special Prices!! Book Now!

Summertime Special Prices!! Book Now!
Lahaina
10.0 out of 10, Exceptional, (171 reviews)
"Our stay at this condo in Maui was perfect! It met all of our needs and had everything we were looking for. The beach was just a short walk away, which made it super convenient and relaxing. The hosts were amazing and always available if we needed anything during our stay. We would absolutely stay here again and highly recommend it to anyone visiting Maui!"
United States
Misty B.
The price is NZ$969
includes taxes & fees
9 Sept - 10 Sept
Summertime Special Prices!! Book Now!

15. FANTASTIC OCEAN VIEW, LUSH GARDENS, QUIET REMODELED END UNIT, 2 KING BEDS, A/C

FANTASTIC OCEAN VIEW, LUSH GARDENS, QUIET REMODELED END UNIT, 2 KING BEDS, A/C
Lahaina
9.8 out of 10, Exceptional, (181 reviews)
"Property was clean, well supplied and convenient location for all our activities on Maui. Communication was excellent with the owners when we had any questions. Would definitely stay here again!! Even got to see a rainbow while sitting on our Lani."
United States
Marisa M.
The price is NZ$1,805
includes taxes & fees
24 Aug - 25 Aug
FANTASTIC OCEAN VIEW, LUSH GARDENS, QUIET REMODELED END UNIT, 2 KING BEDS, A/C

16. 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)
"Fantastic room. Always clean and well stocked.Host is wonderful to work with.Our favorite place to visit."
United States
Wayne W.
The price is NZ$829
includes taxes & fees
9 Sept - 10 Sept
Kāʻanapali Ocean View Condo with Beachfront Cabana for Guests

17. 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 NZ$815
includes taxes & fees
28 Aug - 29 Aug
Ocean View, Kaanapali Golf Course front, Beach Cabana

18. 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 NZ$750
includes taxes & fees
26 Aug - 27 Aug
Top Floor, Corner Unit, Pool View, Kaanapali Beach

19. Great value Sleeps 3, Private Beach Club, walk Kaanapali Beach, Gym

Great value Sleeps 3, Private Beach Club, walk Kaanapali Beach, Gym
Kaanapali
9.0 out of 10, Wonderful, (44 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 NZ$747
includes taxes & fees
14 Sept - 15 Sept
Great value Sleeps 3, Private Beach Club, walk Kaanapali Beach, Gym

20. 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
Lahaina
9.6 out of 10, Exceptional, (79 reviews)
"Great view very clean great bed "
United States
Tiffany
The price is NZ$1,545
includes taxes & fees
30 Aug - 31 Aug
Remodeled Ocean View Studio at The Whaler 518-Kaanapali Beach-Walk to Dining
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.
Save an average of 15% on thousands of hotels when you're signed in

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 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 NZ$465 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 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.