Search Holiday Rentals in Kaanapali Hillside

Start date: Check-in selected.
To Date
End date: Check-out

    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

Tonight
21 Oct - 22 Oct
Tomorrow
22 Oct - 23 Oct
This weekend
24 Oct - 26 Oct
Next weekend
31 Oct - 2 Nov

Top Holiday Rentals in Kaanapali Hillside

Exterior
Aston Kaanapali Shores
Aston Kaanapali Shores
3.5 star property
8.6 out of 10, Excellent, (3806)
"Awesome stay we loved it"
United States
Cody
The price is ฿7,792
฿10,152 total
includes taxes & fees
26 Oct - 27 Oct
Aston Kaanapali Shores
Exterior
Aston Maui Kaanapali Villas
Aston Maui Kaanapali Villas
3.0 star property
8.8 out of 10, Excellent, (2475)
"Beautiful quiet property on the beach with dining options and shopping a short walk or shuttle ride away"
United States
Gilda
The price is ฿7,396
฿11,605 total
includes taxes & fees
4 Nov - 5 Nov
Aston Maui Kaanapali Villas
4 outdoor pools, open 8:00 AM to 10:00 PM, pool cabanas (surcharge)
OUTRIGGER Honua Kai Resort & Spa
OUTRIGGER Honua Kai Resort & Spa
4.0 star property
8.8 out of 10, Excellent, (2854)
"Resort was beautiful and family friendly. Definitely will stay here again with the rest of the family"
United States
Alisha
The price is ฿8,996
฿25,691 total
includes taxes & fees
22 Nov - 23 Nov
OUTRIGGER Honua Kai Resort & Spa
Beach nearby, white sand, beach towels
Napili Village Hotel
Napili Village Hotel
3.0 star property
9.0 out of 10, Wonderful, (119)
"Great place "
United States
Destiny
The price is ฿4,843
฿5,713 total
includes taxes & fees
26 Oct - 27 Oct
Napili Village Hotel
2 outdoor pools, pool cabanas (surcharge), pool umbrellas
The Westin Ka'anapali Ocean Resort Villas
The Westin Ka'anapali Ocean Resort Villas
4.0 star property
8.6 out of 10, Excellent, (1118)
"Great location, lots of amenitie"
United States
Johanna
The price is ฿14,561
฿17,176 total
includes taxes & fees
29 Oct - 30 Oct
The Westin Ka'anapali Ocean Resort Villas
Sun deck
Napili Sunset on the Beach
Napili Sunset on the Beach
2.5 star property
9.2 out of 10, Wonderful, (647)
"Nice on beach location. Smaller resort with friendly staff. Kitchenettes well appointed and shared grill worked well. Excellent snorkeling directly off resort."
United States
Raphael
The price is ฿9,159
฿10,804 total
includes taxes & fees
26 Oct - 27 Oct
Napili Sunset on the Beach
Exterior
The Whaler Resort Kaanapali Beach
The Whaler Resort Kaanapali Beach
4.0 star property
9.6 out of 10, Exceptional, (272)
"Beautiful place, highly recommend!"
United States
Eric
The price is ฿9,917
฿23,638 total
includes taxes & fees
21 Nov - 22 Nov
The Whaler Resort Kaanapali Beach
3 outdoor pools, pool cabanas (surcharge), pool loungers
Marriott's Maui Ocean Club - Lahaina & Napili Towers
Marriott's Maui Ocean Club - Lahaina & Napili Towers
4.0 star property
8.8 out of 10, Excellent, (193)
"It was a great place to spend a vacation for the whole family. "
United States
Melanie
The price is ฿14,561
฿17,176 total
includes taxes & fees
4 Nov - 5 Nov
Marriott's Maui Ocean Club - Lahaina & Napili Towers
Beach/ocean view
Paki Maui 103
Paki Maui 103
2.0 star property
The price is ฿32,542
฿48,160 total
includes taxes & fees
23 Oct - 24 Oct
Paki Maui 103
Condo, 1 Bedroom | Beach/ocean view
Kuleana 208 - 1Br Condo
Kuleana 208 - 1Br Condo
3.0 star property
8.0 out of 10, Very good, (1)
The price is ฿5,013
฿33,834 total
includes taxes & fees
23 Oct - 24 Oct
Kuleana 208 - 1Br Condo
Exterior
Royal Lahaina Bungalows & Spa
Royal Lahaina Bungalows & Spa
5.0 star property
The price is ฿9,164
฿12,554 total
includes taxes & fees
16 Nov - 17 Nov
Royal Lahaina Bungalows & Spa
Aerial view
Kuleana Club - 307
Kuleana Club - 307
3.0 star property
The price is ฿4,749
฿12,327 total
includes taxes & fees
29 Oct - 30 Oct
Kuleana Club - 307
Villa, 1 Bedroom, Oceanfront (Bay 36B3 Gold ,1Bath) | 1 bedroom, in-room safe, individually decorated, individually furnished
Kapalua Villas Maui
Kapalua Villas Maui
4.0 star property
8.8 out of 10, Excellent, (955)
"Gorgeous property, the staff, beach, hiking close by, restaurants in area all were great. Room was spotless and we were able to check in early."
United States
Arturo
The price is ฿7,274
฿25,854 total
includes taxes & fees
22 Nov - 23 Nov
Kapalua Villas Maui
Exterior
Kuleana Club - 210
Kuleana Club - 210
4.0 star property
8.0 out of 10, Very good, (1)
"We had an incredible stay at this beautiful property. The home was spacious and well-appointed, offering plenty of room for everyone to relax comfortably. Located in a gated community, we felt secure and appreciated the added sense of privacy and exclusivity. One of the absolute highlights was the private beach access—just a short walk away and never crowded. It felt like our own slice of paradise where we could unwind and enjoy the ocean without the usual tourist hustle. The landscaping and...
United States
Suresh
The price is ฿5,212
฿21,519 total
includes taxes & fees
6 Nov - 7 Nov
Kuleana Club - 210
2 outdoor pools, pool cabanas (surcharge), pool umbrellas
The Westin Nanea Ocean Villas, Ka'anapali
The Westin Nanea Ocean Villas, Ka'anapali
4.0 star property
9.2 out of 10, Wonderful, (469)
"Very nice place to stay"
United States
Thomas
The price is ฿15,610
฿18,414 total
includes taxes & fees
4 Nov - 5 Nov
The Westin Nanea Ocean Villas, Ka'anapali
Aerial view
Kuleana Club - 513
Kuleana Club - 513
3.0 star property
The price is ฿5,336
฿13,019 total
includes taxes & fees
13 Nov - 14 Nov
Kuleana Club - 513
Aerial view
Kuleana Club - 701
Kuleana Club - 701
3.0 star property
Kuleana Club - 701
3 outdoor pools, pool cabanas (surcharge), pool loungers
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
4.0 star property
8.4 out of 10, Very good, (235)
"Beautiful, clean and the stagg was great! "
United States
Joshua
The price is ฿15,343
฿18,099 total
includes taxes & fees
4 Nov - 5 Nov
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Aerial view
Kuleana Club - 510
Kuleana Club - 510
3.0 star property
The price is ฿6,098
฿13,918 total
includes taxes & fees
13 Nov - 14 Nov
Kuleana Club - 510
Studio | Property grounds
Whaler 518 Oceanview Studio Condo Condo by RedAwning
Whaler 518 Oceanview Studio Condo Condo by RedAwning
3.5 star property
The price is ฿9,025
฿30,878 total
includes taxes & fees
12 Nov - 13 Nov
Whaler 518 Oceanview Studio Condo Condo by RedAwning
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

Hilton Vacation Club Ka'anapali Beach Maui

Hilton Vacation Club Ka'anapali Beach Maui

10/10 Excellent
"Clean room, polite and friendly staff, grounds well maintained "
Allison 6-night trip
Posted 2 days ago
Hilton Vacation Club Ka'anapali Beach Maui

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 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’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. Kaanapali Kai Course at Kaanapali Golf Resort and Kaanapali Golf Courses 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.