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

Kalaupapa Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Kalaupapa vacation rentals

A sunset view with palm trees and a pool area.

1. sweet escape - Moloka'i living

sweet escape - Moloka'i living
Kaunakakai
9.4 out of 10, Exceptional, (28 reviews)
"The condo was very clean and private"
United States
Frank
The price is ļæ„23,634
ļæ„64,913 total
includes taxes & fees
Nov 3 - Nov 4
sweet escape - Moloka'i living
A well-maintained lawn with palm trees and outdoor seating areas, overlooking a body of water.

2. COCONUT COVE CONDOā€“Molokai Shores 303

COCONUT COVE CONDOā€“Molokai Shores 303
Kaunakakai
9.0 out of 10, Wonderful, (28 reviews)
"Great place. Easy to rent and enjoy"
United States
Chris R.
The price is ļæ„23,634
ļæ„56,003 total
includes taxes & fees
Nov 5 - Nov 6
COCONUT COVE CONDOā€“Molokai Shores 303
A resort with multiple buildings, a swimming pool, and a view of the ocean.

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 ļæ„32,930
ļæ„105,707 total
includes taxes & fees
Nov 3 - Nov 4
2BR Ocean View w/Lanai and Kitchen - Molokai Shores 217
A tropical view with a table set with a fruit plate, a dragon fruit, and a mug.

4. Molokai Island Retreat Wavecrest-Ocean Views

Molokai Island Retreat Wavecrest-Ocean Views
Kaunakakai
10.0 out of 10, Exceptional, (20 reviews)
"It was a beautiful stay !!!!Ocean View, clean room, on point communication with our host, Loved our staycation "
United States
Esther-Jean O.
The price is ļæ„16,378
ļæ„45,627 total
includes taxes & fees
Nov 3 - Nov 4
Molokai Island Retreat Wavecrest-Ocean Views
A building with a pool, surrounded by tropical vegetation and palm trees, overlooking a clear blue ocean.

5. Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (257 reviews)
"I had a good time in my stay"
United States
Dawa
The price is ļæ„26,402
ļæ„31,341 total
includes taxes & fees
Nov 3 - Nov 4
Napili Village Hotel
A cozy living room with a sofa, chairs, and a dining area.

6. 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 is well laid out with beautiful views. Well stocked with the basics and kitchen wares. Your privacy is respected also. I highly recommend the ranch tour when you first get there to get you oriented to this beautiful 14000 acre ranch. My wife and I hiked over 40 miles of the trails in 5 days and did not complete them all. Beautiful special place with spectacular views everywhere. The host is very informative, pleasant, excellent communication, and take care of your needs."
United States
Carl C.
The price is ļæ„66,963
ļæ„119,914 total
includes taxes & fees
Nov 16 - Nov 17
Rustic retreat with panoramic views at Pu'u O Hoku Ranch
A beach with clear turquoise water, sandy shore, palm trees, and a resort building in the background.

7. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,909 reviews)
"Very nice location and grounds. Throughly enjoyed our stay!"
United States
Steve
The price is ļæ„38,824
ļæ„46,090 total
includes taxes & fees
Nov 16 - Nov 17
Napili Shores Maui by OUTRIGGER
A beach view with lounge chairs and a clear sky.

8. 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 ļæ„35,440
ļæ„42,072 total
includes taxes & fees
Nov 15 - Nov 16
Napili Sunset on the Beach
View from room

9. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,421 reviews)
"Great stay at a great price"
United States
Dina
The price is ļæ„33,468
ļæ„44,407 total
includes taxes & fees
Dec 3 - Dec 4
Aston Kaanapali Shores
A tropical resort setting with a pool, palm trees, and a dining area with a table set for two.

10. 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 ļæ„64,685
ļæ„150,485 total
includes taxes & fees
Nov 3 - Nov 4
Papakea Resort by KBM
A resort with multiple buildings, a swimming pool, and a rocky shoreline with clear blue water.

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

Ultra Modern/Coastal-Remodel, Oceanview, AC - Napili Shores G154
Lahaina
10.0 out of 10, Exceptional, (21 reviews)
"We had a wonderful time at the property."
United States
Tracy H.
The price is ļæ„31,197
ļæ„141,549 total
includes taxes & fees
Nov 18 - Nov 19
Ultra Modern/Coastal-Remodel, Oceanview, AC - Napili Shores G154
A balcony with a table set for two, overlooking a beach with palm trees and a view of the ocean.

12. Luxury Oceanfront Studio at Napili Shores A203 View of Lanai and Molokai

Luxury Oceanfront Studio at Napili Shores A203 View of Lanai and Molokai
Lahaina
9.8 out of 10, Exceptional, (58 reviews)
"Lovely place hope to stay here again"
United States
Margaret H.
The price is ļæ„28,518
ļæ„137,863 total
includes taxes & fees
Nov 13 - Nov 14
Luxury Oceanfront Studio at Napili Shores A203 View of Lanai and Molokai
A balcony with a view of the ocean, a table set with food and drinks, and a vase with flowers.

13. 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)
"Fantastic stay! The place was perfect - perfectly located and perfectly appointed. The check in and check out processes were effortless. Weā€™re already looking forward to our next stay at this marvelous property!"
United States
Mike D.
The price is ļæ„32,300
ļæ„143,425 total
includes taxes & fees
Nov 12 - Nov 13
Luxury Oceanfront Studio at Napili Shores, Renovated|Direct Ocean Views | AC
A table set with a bottle of champagne, two glasses, a decorative plant, and a woven basket, overlooking a scenic view of the sea and mountains.

14. Breathtaking Oceanfront Studio Napili Shores A106

Breathtaking Oceanfront Studio Napili Shores A106
Lahaina
9.4 out of 10, Exceptional, (88 reviews)
"Awesome stay and experience. Room was perfect and the views were Devine."
United States
Gary K.
The price is ļæ„30,409
ļæ„140,397 total
includes taxes & fees
Nov 9 - Nov 10
Breathtaking Oceanfront Studio Napili Shores A106
A balcony with a table set for breakfast, overlooking a golf course and ocean.

15. Gorgeous Napili Shores G258 Newly remodeled Studio Condo

Gorgeous Napili Shores G258 Newly remodeled Studio Condo
lahaina
10.0 out of 10, Exceptional, (20 reviews)
"Great property and great room. Will definitely stay here again"
United States
Zackary J.
The price is ļæ„33,403
ļæ„144,642 total
includes taxes & fees
Nov 30 - Dec 1
Gorgeous Napili Shores G258 Newly remodeled Studio Condo
A bedroom with a large bed, a ceiling fan, a view of the ocean, and a balcony with a chair and table.

16. Kapalua Bay 30G1 Oceanfront Luxury & Breathtaking Views 1BR/2BA

Kapalua Bay 30G1 Oceanfront Luxury & Breathtaking Views 1BR/2BA
Lahaina
9.6 out of 10, Exceptional, (55 reviews)
"Directions, access info spot on. Beautiful views from upstairs and downstairs. "
United States
Joseph A.
The price is ļæ„38,760
ļæ„158,591 total
includes taxes & fees
Nov 7 - Nov 8
Kapalua Bay 30G1 Oceanfront Luxury & Breathtaking Views 1BR/2BA
A tropical garden with a pond, palm trees, and a building with balconies.

17. Studio w Pool Steps to Sandy Beach-Napili Shores D127

Studio w Pool Steps to Sandy Beach-Napili Shores D127
Lahaina
9.2 out of 10, Wonderful, (59 reviews)
"We love this property! Weā€™ve stayed here many times. I really appreciated that we were able to check in early because the property was ready."
United States
Jeanne D.
The price is ļæ„20,242
ļæ„77,723 total
includes taxes & fees
Nov 3 - Nov 4
Studio w Pool Steps to Sandy Beach-Napili Shores D127
A balcony with wicker chairs and a table set for two, overlooking a sunset over the ocean.

18. Romantic Oceanfront: Relax 25' from the Waves! 230+ Great Reviews!

Romantic Oceanfront: Relax 25' from the Waves! 230+ Great Reviews!
Lahaina
9.8 out of 10, Exceptional, (241 reviews)
"This is a very cozy little unit right on the waterā€™s edge. It is cleverly organized and seems larger as a result. The decor is thoughtful, and we especially loved the bronze sculpture on the lanai! We ate dinner on the lanai at sunset every day and it was lovely. There is no elevator in the building, so pack accordingly or bring a strong friend. That aside, this is a nice little place to relax and enjoy the ocean."
United States
William C.
Romantic Oceanfront: Relax 25' from the Waves! 230+ Great Reviews!
A coastal hotel with a balcony overlooking the sea, a stone pathway, and a grassy area.

19. Luxury Ocean View Condo - Kahana Sunset D4 - A/C & 5G WiFi - Pool

Luxury Ocean View Condo - Kahana Sunset D4 - A/C & 5G WiFi - Pool
Lahaina
10.0 out of 10, Exceptional, (107 reviews)
"Very nice, easy to communicate with manager. Great location! The condo was stocked better than any other rental we have rented in the past! That alone made our stay way more enjoyable!!"
United States
Ryan N.
The price is ļæ„36,176
ļæ„127,531 total
includes taxes & fees
Nov 4 - Nov 5
Luxury Ocean View Condo - Kahana Sunset D4 - A/C & 5G WiFi - Pool
A table with two drinks and a flower on a balcony overlooking the ocean.

20. Kapalua Ridge Villas Resort by KBM

Kapalua Ridge Villas Resort by KBM
4.5 star property
Lahaina
9.6 out of 10, Exceptional, (18 reviews)
"Todo excelente!"
Mexico
Lizbeth
The price is ļæ„63,810
ļæ„138,035 total
includes taxes & fees
Nov 20 - Nov 21
Kapalua Ridge Villas Resort 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.
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Top Kalaupapa Hotel Reviews

Aston Kaanapali Shores

Aston Kaanapali Shores

8/10 Good
"Pool, hot tub, and beach access were outstanding. The room/suite was adequately furnished but lacked style."
Martin 7-night trip
Posted 5 hours ago
Aston Kaanapali Shores

Find out more about Kalaupapa

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

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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 MolokaŹ»i 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.