A coastal landscape with a prominent green hill and a smaller rock formation in the sea.

Kalaupapa Vacation Rentals

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Our top choices for Kalaupapa vacation rentals

1. Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
8.8 out of 10, Excellent, (263 reviews)
"amazing location"
United States
Adrian
The price is CA $328
CA $389 total
includes taxes & fees
Dec 8 - Dec 9
Napili Village Hotel

2. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,918 reviews)
"Very nice location and grounds. Throughly enjoyed our stay!"
United States
Steve
The price is CA $346
CA $409 total
includes taxes & fees
Nov 17 - Nov 18
Napili Shores Maui by OUTRIGGER

3. Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (656 reviews)
"Nice and clean stay! "
United States
Beverly
The price is CA $348
CA $413 total
includes taxes & fees
Dec 12 - Dec 13
Napili Sunset on the Beach

4. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,443 reviews)
"Beautiful resort."
United States
Shawn
The price is CA $259
CA $349 total
includes taxes & fees
Nov 16 - Nov 17
Aston Kaanapali Shores

5. 100 Ridge Rd

100 Ridge Rd
2.5 star property
Lahaina
The price is CA $554
CA $1,136 total
includes taxes & fees
Nov 16 - Nov 17
100 Ridge Rd

6. Kapalua Ridge Villas Resort by KBM

Kapalua Ridge Villas Resort by KBM
4.5 star property
Lahaina
9.4 out of 10, Exceptional, (19 reviews)
"Todo excelente!"
Mexico
Lizbeth
The price is CA $438
CA $1,220 total
includes taxes & fees
Dec 5 - Dec 6
Kapalua Ridge Villas Resort by KBM

7. Royal Kahana 309 1 Bedroom Condo 1 Condo by RedAwning

Royal Kahana 309 1 Bedroom Condo 1 Condo by RedAwning
3.5 star property
Lahaina
The price is CA $299
CA $1,691 total
includes taxes & fees
Nov 16 - Nov 17
Royal Kahana 309 1 Bedroom Condo 1 Condo by RedAwning

8. Kuleana Club - 502

Kuleana Club - 502
3.5 star property
Lahaina
The price is CA $227
CA $566 total
includes taxes & fees
Nov 20 - Nov 21
Kuleana Club - 502

9. Hololani

Hololani
3.0 star property
Lahaina
9.6 out of 10, Exceptional, (5 reviews)
"Great room all around. Incredible view, super clean, and all the amenities one could need (except A/C, but at least they provide plenty of fans and there are large sliding doors to allow cooler outside air inside). Really a great place and great value. Highly recommend!"
United States
Jason
The price is CA $1,167
CA $1,979 total
includes taxes & fees
Nov 18 - Nov 19
Hololani

10. Hale Mahina B304

Hale Mahina B304
3.0 star property
Lahaina
The price is CA $1,426
CA $1,692 total
includes taxes & fees
Nov 16 - Nov 17
Hale Mahina B304

11. Kuleana Club - 404

Kuleana Club - 404
2.5 star property
Lahaina
The price is CA $241
CA $831 total
includes taxes & fees
Nov 19 - Nov 20
Kuleana Club - 404

12. Oceanfront Whale Watching Sunsets Island Views on Big Lanai

Oceanfront Whale Watching Sunsets Island Views on Big Lanai
2.0 star property
Lahaina
The price is CA $1,377
CA $2,298 total
includes taxes & fees
Dec 3 - Dec 4
Oceanfront Whale Watching Sunsets Island Views on Big Lanai

13. Kuleana Club - 316

Kuleana Club - 316
3.5 star property
Lahaina
10.0 out of 10, Exceptional, (3 reviews)
"Excellent place! Great views of the beach and the sunset."
United States
Howie
Kuleana Club - 316

14. Kapalua Bay Villas Resort by KBM

Kapalua Bay Villas Resort by KBM
5.0 star property
Kapalua
10.0 out of 10, Exceptional, (1 review)
"Service was impeccable, they took care of our every need promptly and gracefully. Beautiful setting."
United States
Mariana
The price is CA $771
CA $1,615 total
includes taxes & fees
Dec 5 - Dec 6
Kapalua Bay Villas Resort by KBM

15. Napili Shores D229 Studio Bedroom Condo by RedAwning

Napili Shores D229 Studio Bedroom Condo by RedAwning
3.5 star property
Lahaina
8.0 out of 10, Very good, (1 review)
The price is CA $410
CA $1,756 total
includes taxes & fees
Nov 16 - Nov 17
Napili Shores D229 Studio Bedroom Condo by RedAwning

16. Papakea Resort by KBM

Papakea Resort by KBM
4.0 star property
Lahaina
10.0 out of 10, Exceptional, (5 reviews)
"Very nice property we enjoyed everything about it"
United States
Lorena
The price is CA $582
CA $1,223 total
includes taxes & fees
Dec 5 - Dec 6
Papakea Resort by KBM

17. Napili Shores A203 Of Studio Condo by RedAwning

Napili Shores A203 Of Studio Condo by RedAwning
3.0 star property
Lahaina
The price is CA $466
CA $1,823 total
includes taxes & fees
Nov 16 - Nov 17
Napili Shores A203 Of Studio Condo by RedAwning

18. Napili Point Resort by KBM

Napili Point Resort by KBM
4.0 star property
Napili-Honokowai
9.0 out of 10, Wonderful, (24 reviews)
"Everything was perfect couldn’t have asked for anything more. The view was amazing. Would highly recommend staying here. Definitely 5 stars!!"
United States
Nicholas
The price is CA $503
CA $1,297 total
includes taxes & fees
Dec 7 - Dec 8
Napili Point Resort by KBM

19. Napili Shores A202 Of Studio 1 Bedroom Condo by RedAwning

Napili Shores A202 Of Studio 1 Bedroom Condo by RedAwning
3.0 star property
Lahaina
The price is CA $530
CA $1,899 total
includes taxes & fees
Nov 23 - Nov 24
Napili Shores A202 Of Studio 1 Bedroom Condo by RedAwning

20. Condo, Ocean View, 1-bedroom

Condo, Ocean View, 1-bedroom
4.0 star property
Napili-Honokowai
The price is CA $785
CA $1,599 total
includes taxes & fees
Nov 30 - Dec 1
Condo, Ocean View, 1-bedroom
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.
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Top Kalaupapa Hotel Reviews

Find out more about Kalaupapa

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Kalaupapa. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Kalaupapa?

Yes, you can find vacation rentals near top sights in Kalaupapa, or you can choose a more remote option if you're looking for relaxation. 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 vacation home rentals in Kalaupapa?

Kapalua Golf Villas Resort by KBM: This vacation home rental outside Kalaupapa 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 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 larger area.

What are vacation rentals like in Kalaupapa?

Vacation rentals are privately owned properties you can book for a couple days or more in Kalaupapa. Vacation rentals provide amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for small groups.