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

Kalaupapa Holiday Rentals

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Our top choices for Kalaupapa holiday rentals

1. sweet escape - Moloka'i living

sweet escape - Moloka'i living
Kaunakakai
9.6 out of 10, Exceptional, (27 reviews)
"The condo was very clean and private"
United States
Frank
The price is NZ$658
includes taxes & fees
2 Oct - 3 Oct
sweet escape - Moloka'i living

2. COCONUT COVE CONDO–Molokai Shores 303

COCONUT COVE CONDO–Molokai Shores 303
Kaunakakai
9.0 out of 10, Wonderful, (27 reviews)
"The condo kitchen is well equipped, and the place is well located and comfortable. The host is very helpful. I would definitely want to rent from them again. "
United States
Mary C.
The price is NZ$646
includes taxes & fees
5 Oct - 6 Oct
COCONUT COVE CONDO–Molokai Shores 303

3. 2BR Ocean View w/Lanai and Kitchen - Molokai Shores 217

2BR Ocean View w/Lanai and Kitchen - Molokai Shores 217
Kaunakakai
8.6 out of 10, Excellent, (13 reviews)
"Place was quite comfortable and great layout. We stayed at Hotel Molokai prior trip and would highly reccomend this place over Hotel Molokai. "
United States
Ryan
The price is NZ$1,231
includes taxes & fees
6 Oct - 7 Oct
2BR Ocean View w/Lanai and Kitchen - Molokai Shores 217

4. Modern Oceanfront W/Lanai and WiFi–Molokai Shores

Modern Oceanfront W/Lanai and WiFi–Molokai Shores
KAUNAKAKAI
9.0 out of 10, Wonderful, (34 reviews)
"nice place to stay"
United States
Kevin
The price is NZ$1,038
includes taxes & fees
3 Oct - 4 Oct
Modern Oceanfront W/Lanai and WiFi–Molokai Shores

5. September Sale! Molokai Island Retreat

September Sale! Molokai Island Retreat
Kaunakakai
10.0 out of 10, Exceptional, (20 reviews)
"Great place"
United States
PATRICK C.
The price is NZ$539
includes taxes & fees
13 Oct - 14 Oct
September Sale! Molokai Island Retreat

6. Efficiency

Efficiency
Maunaloa
8.8 out of 10, Excellent, (11 reviews)
Efficiency

7. Ocean Front-Unobstructed Views- Beautiful Upgraded Condo

Ocean Front-Unobstructed Views- Beautiful Upgraded Condo
Maunaloa
9.8 out of 10, Exceptional, (87 reviews)
The price is NZ$612
includes taxes & fees
8 Oct - 9 Oct
Ocean Front-Unobstructed Views- Beautiful Upgraded Condo

8. Rustic retreat with panoramic views at Pu'u O Hoku Ranch

Rustic retreat with panoramic views at Pu'u O Hoku Ranch
Kaunakakai
10.0 out of 10, Exceptional, (96 reviews)
"The Sunrise Cottage, and indeed the entire Pu'u o Hoku Ranch is a hidden gem. We may be biased since we held our wedding celebration here back in 2016, but to return ten years later and find it even more lovely was a delight. Molokai isn't for everyone, but to those drawn to it a wonderful adventure awaits. We'll return as often as they'll have us. Mahalo to all those who made our stay so wonderful."
United States
Scott J.
The price is NZ$1,378
includes taxes & fees
2 Oct - 3 Oct
Rustic retreat with panoramic views at Pu'u O Hoku Ranch

9. Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (240 reviews)
"thank you for the best stay! perfect location, stunning beach with walking distance to beach, cafe, and rentals. room had everything we needed, recommend upgrading to ocean view it was a treat!"
United States
ASHLEY
The price is NZ$366
includes taxes & fees
2 Oct - 3 Oct
Napili Village Hotel

10. Gorgeous Napili Shores G258 Newly remodeled Studio Condo

Gorgeous Napili Shores G258 Newly remodeled Studio Condo
lahaina
10.0 out of 10, Exceptional, (18 reviews)
"Beautiful unit with thoughtful amenities- especially the beach gear. Great view from the balcony. Comfy bed amd linens."
United States
Elaine E.
The price is NZ$1,375
includes taxes & fees
27 Oct - 28 Oct
Gorgeous Napili Shores G258 Newly remodeled Studio Condo

11. Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!

Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!
Lahaina
9.8 out of 10, Exceptional, (277 reviews)
"Amazing trip!"
United States
Eric L.
The price is NZ$876
includes taxes & fees
5 Oct - 6 Oct
Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!

12. 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 NZ$1,495
includes taxes & fees
2 Oct - 3 Oct
Kapalua Bay Villas Resort by KBM

13. Fabulous Oceanfront Retreat at Kuleana 622 3rd Floor Condo A/C

Fabulous Oceanfront Retreat at Kuleana 622 3rd Floor Condo A/C
Lahaina
9.6 out of 10, Exceptional, (45 reviews)
"Good location. Close to beaches, restaurants and other fun activities "
United States
Nancy F.
The price is NZ$1,396
includes taxes & fees
9 Oct - 10 Oct
Fabulous Oceanfront Retreat at Kuleana 622 3rd Floor Condo A/C

14. The Napili Bay, Steps to Sand, Studio, King bed, Remodeled in June of 2023

The Napili Bay, Steps to Sand, Studio, King bed, Remodeled in June of 2023
Lahaina
10.0 out of 10, Exceptional, (41 reviews)
"The host is always very accommodating and nice. The condo is very nice. We love staying there. "
United States
John D.
The Napili Bay, Steps to Sand, Studio, King bed, Remodeled in June of 2023

15. OCEAN VIEW 2 Bdrm condo with Secluded Beach - Kahana Sunset C7

OCEAN VIEW 2 Bdrm condo with Secluded Beach - Kahana Sunset C7
Lahaina
9.8 out of 10, Exceptional, (58 reviews)
"The location and friendliness "
United States
Patricia R.
The price is NZ$1,767
includes taxes & fees
2 Oct - 3 Oct
OCEAN VIEW 2 Bdrm condo with Secluded Beach - Kahana Sunset C7

16. Ultra Modern/Coastal-Remodel, Oceanview, AC - Napili Shores G154

Ultra Modern/Coastal-Remodel, Oceanview, AC - Napili Shores G154
Lahaina
9.8 out of 10, Exceptional, (19 reviews)
"Great updated room. Very comfortable bed. Kitchen was well set up. We really enjoyed staying here. We will return."
United States
Stephen T.
The price is NZ$1,375
includes taxes & fees
23 Oct - 24 Oct
Ultra Modern/Coastal-Remodel, Oceanview, AC - Napili Shores G154

17. Top Floor! Direct Ocean View! Vaulted Ceilings! Winter Spec! #218

Top Floor! Direct Ocean View! Vaulted Ceilings! Winter Spec! #218
Lahaina
9.6 out of 10, Exceptional, (115 reviews)
"Great location to everything and timely easy communication ."
United States
Vicki P.
The price is NZ$841
includes taxes & fees
6 Oct - 7 Oct
Top Floor! Direct Ocean View! Vaulted Ceilings! Winter Spec! #218

18. Updated Studio, AC, steps to beach

Updated Studio, AC, steps to beach
Lahaina
9.8 out of 10, Exceptional, (162 reviews)
"Wonderful place to stay. Our host Evelyn very kindly allowed us to extend our stay with 0 issues after the recent Kona storm. We had a great time and experience - fully recommend. "
United States
MeMe C.
Updated Studio, AC, steps to beach

19. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,888 reviews)
"Love this place!"
United States
Diana
The price is NZ$551
includes taxes & fees
2 Oct - 3 Oct
Napili Shores Maui by OUTRIGGER

20. Luxury Oceanfront Studio at Napili Shores, Renovated|Direct Ocean Views | AC

Luxury Oceanfront Studio at Napili Shores, Renovated|Direct Ocean Views | AC
Lahaina
9.8 out of 10, Exceptional, (74 reviews)
"The room was just as shown on the pictures with a wonderful ocean view from the second story. We loved that it was not part of one of the huge resorts and location was ideal. We will definitely hope to be back there soon! Perfect for a couple. "
United States
Brent K.
The price is NZ$1,568
includes taxes & fees
6 Oct - 7 Oct
Luxury Oceanfront Studio at Napili Shores, Renovated|Direct Ocean Views | AC
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Kalaupapa holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Kalaupapa. 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 Kalaupapa. 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 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.Ā 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday 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 Kalaupapa short-term rentals, that won’t be hard to do.

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 Resort by KBM: 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.