Default HTG hotel image

Holiday Rentals in Kaanapali Hillside

  • 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. 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 €508
includes taxes & fees
31 Aug - 1 Sept
The Westin Ka'anapali Ocean Resort Villas

2. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Lahaina
8.8 out of 10, Excellent, (2,617 reviews)
"Great place"
United States
Luis MANUEL
The price is €315
includes taxes & fees
1 Sept - 2 Sept
Aston Maui Kaanapali Villas

3. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,263 reviews)
"Great location, clean rooms and great service!"
Mexico
Monique Nicole
The price is €247
includes taxes & fees
21 Aug - 22 Aug
Aston Kaanapali Shores

4. OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (3,022 reviews)
"We found this resort clean, family friendly,"
United States
Amanda
The price is €812
includes taxes & fees
18 Sept - 19 Sept
OUTRIGGER Honua Kai Resort & Spa

5. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (450 reviews)
"We love The Whaler!"
United States
Jacob
The price is €549
includes taxes & fees
19 Aug - 20 Aug
The Whaler Resort Kaanapali Beach

6. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,856 reviews)
"Wonderful Beach and right next door to kapalua!"
United States
joe
The price is €313
includes taxes & fees
1 Sept - 2 Sept
Napili Shores Maui by OUTRIGGER

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

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
4.0 star property
Lahaina
8.4 out of 10, Very good, (253 reviews)
"Was beautiful, pool was the best out of all the resorts on Ka’anapali"
United States
Donald
The price is €524
includes taxes & fees
1 Sept - 2 Sept
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

8. Honua Kai Hokulani Resort by KBM

Honua Kai Hokulani Resort by KBM
4.0 star property
Kaanapali
8.8 out of 10, Excellent, (30 reviews)
"Beautiful property with wonderful staff."
United States
Lance
The price is €1,148
includes taxes & fees
27 Aug - 28 Aug
Honua Kai Hokulani Resort by KBM

9. Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (219 reviews)
"Great stay, thank you"
United States
Elizabeth
The price is €341
includes taxes & fees
15 Sept - 16 Sept
Napili Village Hotel

10. 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 €288
includes taxes & fees
19 Aug - 20 Aug
Napili Sunset on the Beach

11. 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, (522 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 €635
includes taxes & fees
1 Sept - 2 Sept
The Westin Nanea Ocean Villas, Ka'anapali

12. 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 €934
includes taxes & fees
20 Aug - 21 Aug
FANTASTIC OCEAN VIEW, LUSH GARDENS, QUIET REMODELED END UNIT, 2 KING BEDS, A/C

13. 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 €516
includes taxes & fees
31 Aug - 1 Sept
Aston at The Whaler on Kaanapali Beach

14. 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 €444
includes taxes & fees
29 Aug - 30 Aug
Kāʻanapali Ocean View Condo with Beachfront Cabana for Guests

15. Luxurious Ground Floor, Perfect Family Spot, Private Lanai, 1 Min to Pool/Beach

Luxurious Ground Floor, Perfect Family Spot, Private Lanai, 1 Min to Pool/Beach
Lahaina
10.0 out of 10, Exceptional, (186 reviews)
"This condo was absolutely perfect for our trip. Great for kids, easy to access, fabulous resort, and excellent communication with the host- above and beyond!"
United States
Kelsey T.
Luxurious Ground Floor, Perfect Family Spot, Private Lanai, 1 Min to Pool/Beach

16. 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 €526
includes taxes & fees
19 Aug - 20 Aug
Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!

17. Summertime Special Prices!! Book Now!

Summertime Special Prices!! Book Now!
Lahaina
10.0 out of 10, Exceptional, (170 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 €529
includes taxes & fees
16 Sept - 17 Sept
Summertime Special Prices!! Book Now!

18. 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 €431
includes taxes & fees
28 Aug - 29 Aug
Ocean View, Kaanapali Golf Course front, Beach Cabana

19. 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 €815
includes taxes & fees
15 Sept - 16 Sept
Remodeled Ocean View Studio at The Whaler 518-Kaanapali Beach-Walk to Dining

20. Oceanfront Property - 60 feet from the ocean. Beautiful views, free WiFi

Oceanfront Property - 60 feet from the ocean. Beautiful views, free WiFi
Lahaina
10.0 out of 10, Exceptional, (124 reviews)
"We loved our stay in Papakea Resort."
United States
Maryia B.
The price is €762
includes taxes & fees
22 Aug - 23 Aug
Oceanfront Property - 60 feet from the ocean. Beautiful views, free WiFi
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, 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 €247 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.