Photo by Mike Gauthier

Search Holiday Rentals in Kahakuloa

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

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Kahakuloa holiday rentals

Garden
Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
9.0 out of 10, Wonderful, (12)
"Loved having the hot tub to come home to!!"
United States
Pedro
The price is ฿4,747
฿8,714 total
includes taxes & fees
5 Jan - 6 Jan 2026
Yonegan Maui Getaways - Haiku
Aerial view
Kuleana Club - 306

Kuleana Club - 306

Kuleana Club - 306
3.0 star property
Lahaina
The price is ฿7,055
฿21,222 total
includes taxes & fees
8 Jan - 9 Jan 2026
Kuleana Club - 306
4 outdoor pools, open 8:00 AM to 10:00 PM, pool cabanas (surcharge)
OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.0 star property
Lahaina
8.8 out of 10, Excellent, (2886)
"Wonderful stay! "
United States
Quiauna
The price is ฿12,666
฿31,607 total
includes taxes & fees
15 Jan - 16 Jan 2026
OUTRIGGER Honua Kai Resort & Spa
Beach nearby, white sand, beach towels
Napili Village Hotel

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (145)
"Exactly what we were looking for! Close walking distance to beach and dining!"
United States
Tessa
The price is ฿7,046
฿8,365 total
includes taxes & fees
22 Jan - 23 Jan 2026
Napili Village Hotel
Exterior
The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (327)
"great time, great resort, helpful staff"
Canada
Prableen
The price is ฿10,373
฿23,686 total
includes taxes & fees
23 Jan - 24 Jan 2026
The Whaler Resort Kaanapali Beach
Exterior
Aston Kaanapali Shores

Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (3928)
"Loved the 2 pools and 2 hot tub, staff is great…thank you!"
United States
Candida
The price is ฿9,923
฿12,622 total
includes taxes & fees
31 Dec - 1 Jan 2026
Aston Kaanapali Shores
Exterior
Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Lahaina
8.8 out of 10, Excellent, (2520)
"We enjoyed the property "
United States
Therese
The price is ฿9,798
฿14,383 total
includes taxes & fees
1 Jan - 2 Jan 2026
Aston Maui Kaanapali Villas
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 Kahakuloa Hotel Reviews

Aston Kaanapali Shores

Aston Kaanapali Shores

10/10 Excellent
"Loved the 2 pools and 2 hot tub, staff is great…thank you!"
Candida 1-night trip
Posted 3 days ago
Aston Kaanapali Shores

Find out more about Kahakuloa

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

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

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

Frequently asked questions

Can I find a holiday rental in Kahakuloa?

Yes, there are holiday rentals close to the most popular sights in Kahakuloa, or you can select a more secluded option if you're looking for a relaxing stay. Kahakuloa is known for its beaches and restaurants. Make sure you have time to check out the sporting events while you're in the area.

What are some of the best holiday rentals that Kahakuloa has to offer?

Yonegan Maui Getaways - Haiku : This holiday home rental outside of Kahakuloa is located near the beach, and has 1 hot tub, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a microwave, kitchenware and a coffee maker.

What’s there to see and do in Kahakuloa?

Explore the area and family-friendly sights such as Hawaii Nature Center of Iao Valley, or get out into nature at a spot like Kahakuloa Beach. In the wider area, you’ll find Kaanapali Beach and Kapalua Golf Club Plantation Course.

What’s a holiday rental in Kahakuloa like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Kahakuloa. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from shared hotel lifts and busy front desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for a family getaway.