Photo by Lisa A Schmidt

Search Holiday Rentals in Kalaupapa

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

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Top Holiday Rentals in Kalaupapa

Aston Kaanapali Shores
Exterior

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3764)
"Great stay"
The price is 8.431.668 ₫
10.725.143 ₫ total
includes taxes & fees
28 Oct - 29 Oct
Aston Kaanapali Shores
Kahana Falls Maui by VRI Americas
Studio Suite | Living area | 45-inch TV with cable channels, DVD player

Kahana Falls Maui by VRI Americas

3.5 star property
8.0 out of 10, Very good, (931)
"rooms were nice , clean, staff was friendly "
Kahana Falls Maui by VRI Americas
Napili Shores Maui by OUTRIGGER
On the beach

Napili Shores Maui by OUTRIGGER

3.0 star property
9.0 out of 10, Wonderful, (1668)
"The location was great to restaurants and the beach."
The price is 7.108.276 ₫
8.385.064 ₫ total
includes taxes & fees
25 Oct - 26 Oct
Napili Shores Maui by OUTRIGGER
Aston Mahana at Kaanapali
Outdoor pool

Aston Mahana at Kaanapali

3.5 star property
9.0 out of 10, Wonderful, (1665)
"Friendly staff, amazing rooms and beautiful views"
Aston Mahana at Kaanapali
Aston at Papakea Resort
Surfing/boogie boarding

Aston at Papakea Resort

3.0 star property
8.2 out of 10, Very good, (1384)
"Everything was excellent "
Aston at Papakea Resort
AEI at Kaanapali Shores
Exterior

AEI at Kaanapali Shores

4.0 star property
8.8 out of 10, Excellent, (472)
"Great vibes and amenities."
AEI at Kaanapali Shores
Kapalua Villas Maui
Villa, 1 Bedroom, Oceanfront (Bay 36B3 Gold ,1Bath) | 1 bedroom, in-room safe, individually decorated, individually furnished

Kapalua Villas Maui

4.0 star property
8.8 out of 10, Excellent, (954)
"Everything about this property was amazing. We loved the stag and the facilities. The pools were amazing and easy beach access allowed you to be in the water in 5 minutes. There was a grocery store right across the street making it very easy to grab anything you may need. We did try the food trucks one time (average plate was $25 which got you food court quality and portion size at any mall.)"
The price is 5.898.470 ₫
20.964.660 ₫ total
includes taxes & fees
31 Oct - 1 Nov
Kapalua Villas Maui
Kahana Beach Vacation Club
Standard Room, 1 Bedroom | Living area | 55-inch flat-screen TV with cable channels

Kahana Beach Vacation Club

3.0 star property
8.4 out of 10, Very good, (723)
"Great place to stay "
Kahana Beach Vacation Club
The Gardens at West Maui
Suite, 1 Bedroom | Iron/ironing board, free WiFi

The Gardens at West Maui

3.0 star property
8.6 out of 10, Excellent, (501)
"Great for family! "
The Gardens at West Maui
Castle Napili Surf Beach Resort
On the beach, white sand

Castle Napili Surf Beach Resort

3.5 star property
9.8 out of 10, Exceptional, (139)
"Beautiful place, great for vacation with kids "
Castle Napili Surf Beach Resort
Napili Village Hotel
Beach nearby, white sand, beach towels

Napili Village Hotel

3.0 star property
8.8 out of 10, Excellent, (115)
"Great place "
The price is 4.560.295 ₫
5.379.416 ₫ total
includes taxes & fees
3 Oct - 4 Oct
Napili Village Hotel
AEI at The Mahana Kaanapali Resort
Outdoor pool, pool umbrellas, pool loungers

AEI at The Mahana Kaanapali Resort

4.0 star property
8.8 out of 10, Excellent, (282)
"Highly recommended, will be back someday"
AEI at The Mahana Kaanapali Resort
Royal Kahana Maui by OUTRIGGER
Condo, 2 Bedrooms, 2 Bathrooms, Oceanfront (Unit 1110) | Living area | 65-inch Smart TV with cable channels

Royal Kahana Maui by OUTRIGGER

3.0 star property
8.0 out of 10, Very good, (1388)
"Our condo was absolutely stunning, and just as pictured. Staff was amazing. Will definitely come back. "
The price is 13.451.839 ₫
27.490.657 ₫ total
includes taxes & fees
31 Oct - 1 Nov
Royal Kahana Maui by OUTRIGGER
Sands of Kahana
Outdoor pool

Sands of Kahana

3.0 star property
8.2 out of 10, Very good, (447)
"Great pool and beautiful beach "
Sands of Kahana
Castle at Moloka'i Shores
Property grounds

Castle at Moloka'i Shores

3.0 star property
7.2 out of 10, Good, (168)
"No AC - was HOT Staff very friendly "
Castle at Moloka'i Shores
Kahana Villa
Tennis court

Kahana Villa

3.0 star property
8.0 out of 10, Very good, (348)
" Great stay!!! Easy and quiet place next to beach.Feels like home"
Kahana Villa
Maui Kai
Basic Room, 1 Bedroom (Corner, Specific Unit May Vary) | Balcony view

Maui Kai

3.0 star property
9.2 out of 10, Wonderful, (425)
"It is quite and kind of tucked away from the other places the Views from our balcony was awesome. We had Mountains in the front and the ocean in the back. I would definitely stay there again."
Maui Kai
Napili Sunset on the Beach
Sun deck

Napili Sunset on the Beach

2.5 star property
9.2 out of 10, Wonderful, (647)
"Rooms are very dated, although clean. "
The price is 7.427.106 ₫
8.761.328 ₫ total
includes taxes & fees
3 Oct - 4 Oct
Napili Sunset on the Beach
AEI at Papakea Resort Maui
Sports facility

AEI at Papakea Resort Maui

3.5 star property
8.6 out of 10, Excellent, (91)
"It was a nice quiet place with great ocean views."
AEI at Papakea Resort Maui
Napili Point by KBM
Condo, Balcony, Ocean View (NAP-C37) | View from room

Napili Point by KBM

4.0 star property
9.6 out of 10, Exceptional, (13)
"The location was great for us. Peaceful and close enough to Napili Bay and the coastal trail. A lot of places on Napili Bay have AC issues but our condo was perfect the entire trip!"
Napili Point by KBM
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 Kalaupapa Hotel Reviews

Kahana Beach Vacation Club

Kahana Beach Vacation Club

10/10 Excellent
"Partial beach view. Friendly staff. Very clean room. Perfect and cozy studio. Loved having the mini kitchen with full size refrigerator. "
Glenda 2-night trip
Posted 1 day ago
Kahana Beach Vacation Club

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 can I see and do in Kalaupapa?

Explore the area and family-friendly sights such as Coffees of Hawaii Plantation Store, or get out into nature at a spot like Kalaupapa National Historical Park. 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.