Photo by Lisa A Schmidt

Kalaupapa Holiday Rentals

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
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Kalaupapa

Napili Shores Maui by OUTRIGGER

3.0 star property
Lahaina
9.0 out of 10, Wonderful, (1707)
"Excellent stay. "
United States
casey william
The price is NZ$674
includes taxes & fees
7 Dec - 8 Dec
Napili Shores Maui by OUTRIGGER

Aston Kaanapali Shores

3.5 star property
Lahaina
8.6 out of 10, Excellent, (3900)
"Was a great place to stay"
United States
Christine
The price is NZ$774
includes taxes & fees
8 Dec - 9 Dec
Aston Kaanapali Shores

Aston Mahana at Kaanapali

3.5 star property
Kaanapali
9.0 out of 10, Wonderful, (1711)
"Gorgeous views, spacious suite, very friendly staff, amazing stay had a wonderful family vacation, can't wait to go back."
Canada
Lidia E
The price is NZ$807
includes taxes & fees
11 Dec - 12 Dec
Aston Mahana at Kaanapali

Napili Sunset on the Beach

2.5 star property
Lahaina
9.2 out of 10, Wonderful, (647)
"Location was excellent"
United States
Polly
The price is NZ$574
includes taxes & fees
19 Dec - 20 Dec
Napili Sunset on the Beach

Napili Village Hotel

3.0 star property
Lahaina
9.0 out of 10, Wonderful, (136)
"Exactly what we were looking for! Close walking distance to beach and dining!"
United States
Tessa
The price is NZ$426
includes taxes & fees
7 Dec - 8 Dec
Napili Village Hotel

Timeshare Oceanview Studio in Maui

3.0 star property
Lahaina
9.2 out of 10, Wonderful, (5)
"Room was perfect, staff extremely friendly and views were amazing!"
United States
Elizabeth
Timeshare Oceanview Studio in Maui

Paki Maui 103

2.0 star property
Lahaina
The price is NZ$2,560
includes taxes & fees
19 Dec - 20 Dec
Paki Maui 103

Napili Shores D229 Studio Bedroom Condo by RedAwning

3.5 star property
Lahaina
8.0 out of 10, Very good, (1)
Napili Shores D229 Studio Bedroom Condo by RedAwning

Kuleana Club - 509

3.0 star property
Lahaina
The price is NZ$974
includes taxes & fees
22 Dec - 23 Dec
Kuleana Club - 509

Kaanapali Shores #159 2 Bedroom Condo by RedAwning

3.5 star property
Lahaina
The price is NZ$2,416
includes taxes & fees
15 Dec - 16 Dec
Kaanapali Shores #159 2 Bedroom Condo by RedAwning

Hale Mahina B304

2.0 star property
Lahaina
The price is NZ$1,989
includes taxes & fees
19 Dec - 20 Dec
Hale Mahina B304

Kuleana Club - 502

3.0 star property
Lahaina
The price is NZ$746
includes taxes & fees
12 Dec - 13 Dec
Kuleana Club - 502

Kahana Reef 210

2.0 star property
Lahaina
The price is NZ$2,209
includes taxes & fees
19 Dec - 20 Dec
Kahana Reef 210

Ka'anapali Shores 160

3.5 star property
Lahaina
The price is NZ$2,509
includes taxes & fees
19 Dec - 20 Dec
Ka'anapali Shores 160

Kuleana Club - 504

3.0 star property
Lahaina
The price is NZ$1,397
includes taxes & fees
2 Jan - 3 Jan 2026
Kuleana Club - 504

Kahana Reef 222

2.0 star property
Lahaina
The price is NZ$2,209
includes taxes & fees
19 Dec - 20 Dec
Kahana Reef 222

Kahana Reef 320

2.0 star property
Lahaina
The price is NZ$2,209
includes taxes & fees
19 Dec - 20 Dec
Kahana Reef 320

Maui Kai 804 Oceanfront 1 Bd/1ba 1 Bedroom Condo by RedAwning

3.5 star property
Lahaina
Maui Kai 804 Oceanfront 1 Bd/1ba 1 Bedroom Condo by RedAwning

Kuleana 310

2.5 star property
Lahaina
The price is NZ$2,336
includes taxes & fees
19 Dec - 20 Dec
Kuleana 310

Valley Isle 1108b 2 Bedroom Condo by RedAwning

3.5 star property
Lahaina
10.0 out of 10, Exceptional, (1)
"The view to the ocean from our room was everything we wanted , beautiful property and would definitely book for next trip. Thank you 😊 "
United States
Sonia Isabel
Valley Isle 1108b 2 Bedroom 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Kalaupapa Hotel Reviews

Find out more about Kalaupapa

Everything you need to know about Kalaupapa 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 Kalaupapa 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 Kalaupapa holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Kalaupapa holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kalaupapa. 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 Kalaupapa 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 Kalaupapa holiday rentals we have selected for you start as low as NZ$426 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Kalaupapa rentals

At Expedia, we put the best Kalaupapa 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 Kalaupapa 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 Kalaupapa 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 Kalaupapa. 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 Kalaupapa?

Yes, there are holiday rentals close to the most popular sights in Kalaupapa, or you can select a more secluded option if you're looking for a relaxing stay. Kalaupapa is known for its local tours and seaside. Make sure you have time to check out the churches and parks during your trip.

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

Kapalua Golf Villas by KBM Resorts: This holiday home rental outside Kalaupapa 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 can I see and do in Kalaupapa?

Kalaupapa National Historical Park and Moloka'i Beaches are a couple of lovely local spots to get outside and enjoy nature. St. Philomena Church and Molokaʻi Museum & Cultural Center are a couple of places you'll find in the wider area.

What are holiday rentals like in Kalaupapa?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Kalaupapa. Holiday rentals feature extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can provide a sense of security away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for family trips or small group gatherings.