Default HTG hotel image

Kaanapali Hillside Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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
Lahaina
8.8 out of 10, Excellent, (2,619 reviews)
"Great place"
United States
Luis MANUEL
The price is ￥36,966
￥58,034 total
includes taxes & fees
Sep 1 - Sep 2
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, (4,278 reviews)
"Great location!"
United States
Shad
The price is ￥33,268
￥44,211 total
includes taxes & fees
Aug 25 - Aug 26
Aston Kaanapali Shores
A resort with a pool, palm trees, a waterfall, and a view of the ocean.

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 ￥78,680
￥93,401 total
includes taxes & fees
Aug 30 - Aug 31
The Westin Ka'anapali Ocean Resort Villas
A view of a beach with palm trees and a sailboat on the water.

4. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (454 reviews)
"We love The Whaler!"
United States
Jacob
The price is ￥36,145
￥100,984 total
includes taxes & fees
Aug 25 - Aug 26
The Whaler Resort Kaanapali Beach
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, (3,027 reviews)
"We found this resort clean, family friendly,"
United States
Amanda
The price is ￥55,259
￥138,952 total
includes taxes & fees
Aug 26 - Aug 27
OUTRIGGER Honua Kai Resort & Spa
A beach with clear turquoise water, sandy shore, palm trees, and a resort building in the background.

6. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,860 reviews)
"Wonderful Beach and right next door to kapalua!"
United States
joe
The price is ￥39,784
￥47,227 total
includes taxes & fees
Aug 25 - Aug 26
Napili Shores Maui by OUTRIGGER
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, (220 reviews)
"Great stay, thank you"
United States
Elizabeth
The price is ￥47,643
￥56,558 total
includes taxes & fees
Sep 2 - Sep 3
Napili Village Hotel
A resort with a swimming pool, palm trees, and a view of the ocean.

8. Honua Kai Hokulani Resort by KBM

Honua Kai Hokulani Resort by KBM
4.0 star property
Kaanapali
8.8 out of 10, Excellent, (32 reviews)
"Beautiful property with wonderful staff."
United States
Lance
The price is ￥84,688
￥204,884 total
includes taxes & fees
Sep 19 - Sep 20
Honua Kai Hokulani Resort by KBM
A beach view with lounge chairs and a clear sky.

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 ￥44,692
￥53,056 total
includes taxes & fees
Aug 25 - Aug 26
Napili Sunset on the Beach
A beach with waves at sunset.

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
The price is ￥23,843
￥74,176 total
includes taxes & fees
Aug 30 - Aug 31
Studio Kaanapali Beach, Beach Cabana, Jacuzzi, Gr Floor Convenience
A modern kitchen with a central island, stainless steel appliances, and a view to a patio area.

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 ￥27,896
￥96,270 total
includes taxes & fees
Aug 25 - Aug 26
Modern Renovated Kaanapali Studio! We have the Best Reviews for a Reason!!
A spacious living room with a large window overlooking the ocean, a comfortable sofa set, a coffee table, and a flat-screen TV mounted on the wall.

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 ￥28,738
￥66,947 total
includes taxes & fees
Aug 31 - Sep 1
Aston at The Whaler on Kaanapali Beach
A resort with a pool, palm trees, and a view of the ocean.

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 ￥98,422
￥116,838 total
includes taxes & fees
Sep 6 - Sep 7
The Westin Nanea Ocean Villas, Ka'anapali
A swimming pool with lounge chairs and palm trees in the background.

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 ￥27,180
￥95,918 total
includes taxes & fees
Sep 9 - Sep 10
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 ￥42,773
￥172,543 total
includes taxes & fees
Aug 25 - Aug 26
FANTASTIC OCEAN VIEW, LUSH GARDENS, QUIET REMODELED END UNIT, 2 KING BEDS, A/C
A beachside seating area with metal chairs and tables, overlooking a clear blue ocean.

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 ￥30,995
￥79,747 total
includes taxes & fees
Sep 9 - Sep 10
Kāʻanapali Ocean View Condo with Beachfront Cabana for Guests
An aerial view of a beachside resort with a long building featuring multiple shaded areas and a pool.

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 ￥26,863
￥77,595 total
includes taxes & fees
Aug 28 - Aug 29
Ocean View, Kaanapali Golf Course front, Beach Cabana
A beach with clear blue water and a sandy shore.

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 ￥23,843
￥74,176 total
includes taxes & fees
Aug 26 - Aug 27
Top Floor, Corner Unit, Pool View, Kaanapali Beach
A beach with a wooden deck and lounge chairs.

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 ￥23,843
￥74,176 total
includes taxes & fees
Sep 14 - Sep 15
Great value Sleeps 3, Private Beach Club, walk Kaanapali Beach, Gym
A beach view with palm trees, a clear sky, and a distant mountain.

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 ￥37,353
￥152,825 total
includes taxes & fees
Aug 30 - Aug 31
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Kaanapali Hillside Hotel Reviews

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

10/10 Excellent
"Clean room, friendly staff, great location and views!"
Luis A 5-night trip
Posted 5 hours ago
The Whaler Resort Kaanapali Beach

Find out more about Kaanapali Hillside

Search for holiday rentals in Kaanapali Hillside on Expedia! You can easily find your home rentals, villas, holiday apartments in Kaanapali Hillside using one of the methods below:

  • View our selection of featured holiday rentals in Kaanapali Hillside
  • Use the map to find apartments and other holiday homes in the Kaanapali Hillside neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Kaanapali Hillside while they last

Look no further and take a look at our great range of rental properties in Kaanapali Hillside!

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?

Kapalua Golf Villas Resort by KBM: You might want to consider this vacation rental near Kaanapali Hillside, which 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. 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 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.