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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Kalaupapa vacation rentals

On the beach, beach towels

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
$309 nightly
The price is $363
Sep 21 - Sep 22
Total with taxes and fees
sweet escape - Moloka'i living
Property grounds

2. COCONUT COVE CONDO–Molokai Shores 303

COCONUT COVE CONDO–Molokai Shores 303
Kaunakakai
9.0 out of 10, Wonderful, (26 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.
$304 nightly
The price is $358
Sep 22 - Sep 23
Total with taxes and fees
COCONUT COVE CONDO–Molokai Shores 303
Exterior

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
$595 nightly
The price is $697
Sep 27 - Sep 28
Total with taxes and fees
2BR Ocean View w/Lanai and Kitchen - Molokai Shores 217
Property grounds

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
$479 nightly
The price is $563
Sep 21 - Sep 22
Total with taxes and fees
Modern Oceanfront W/Lanai and WiFi–Molokai Shores
Outdoor dining

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.
$258 nightly
The price is $302
Sep 21 - Sep 22
Total with taxes and fees
September Sale! Molokai Island Retreat
Sun loungers, beach towels

6. Efficiency

Efficiency
Maunaloa
8.8 out of 10, Excellent, (11 reviews)
"I enjoyed my stay in the condo- it was small yet had everything I needed and the best thing it offered the best view of the sunset on the island!"
United States
Sabina B.
$228 nightly
The price is $267
Sep 20 - Sep 21
Total with taxes and fees
Efficiency
Pool

7. Ocean Front-Unobstructed Views- Beautiful Upgraded Condo

Ocean Front-Unobstructed Views- Beautiful Upgraded Condo
Maunaloa
9.8 out of 10, Exceptional, (86 reviews)
"Great location. Newly remodeled. Was clean and great condition."
United States
Tristan
$292 nightly
The price is $341
Sep 22 - Sep 23
Total with taxes and fees
Ocean Front-Unobstructed Views- Beautiful Upgraded Condo
Beach nearby

8. Ke Nani Kai Unit 156- More Molokai

Ke Nani Kai Unit 156- More Molokai
Maunaloa
9.0 out of 10, Wonderful, (65 reviews)
"We had a blast. Better than the pictures. "
United States
Lisa W.
$350 nightly
The price is $410
Sep 22 - Sep 23
Total with taxes and fees
Ke Nani Kai Unit 156- More Molokai
Books

9. 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.
$714 nightly
The price is $798
Sep 20 - Sep 21
Total with taxes and fees
Rustic retreat with panoramic views at Pu'u O Hoku Ranch
Beach nearby, white sand, beach towels

10. Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (230 reviews)
"Great place! It’s quite and 30 seconds to the beach."
United States
Alysson E
$202 nightly
The price is $240
Oct 16 - Oct 17
Total with taxes and fees
Napili Village Hotel
Property grounds

11. Gorgeous Napili Shores G258 Newly remodeled Studio Condo

Gorgeous Napili Shores G258 Newly remodeled Studio Condo
lahaina
10.0 out of 10, Exceptional, (16 reviews)
"Beautiful unit with thoughtful amenities- especially the beach gear. Great view from the balcony. Comfy bed amd linens."
United States
Elaine E.
$709 nightly
The price is $800
Sep 23 - Sep 24
Total with taxes and fees
Gorgeous Napili Shores G258 Newly remodeled Studio Condo
Property grounds

12. 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, (276 reviews)
"Amazing trip!"
United States
Eric L.
$428 nightly
The price is $500
Sep 27 - Sep 28
Total with taxes and fees
Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!
On the beach

13. 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.
$709 nightly
The price is $800
Sep 22 - Sep 23
Total with taxes and fees
Ultra Modern/Coastal-Remodel, Oceanview, AC - Napili Shores G154
Terrace/patio

14. Top Floor Gem! Direct Ocean Views! Near Kaanapali #215

Top Floor Gem! Direct Ocean Views! Near Kaanapali #215
Lahaina
9.6 out of 10, Exceptional, (99 reviews)
"Highly recommend! My girlfriend and I had a great stay here. Excellent location in Honokōwai, easy walking to great eats and things to do. "
United States
Jeremy F.
$434 nightly
The price is $459
Sep 20 - Sep 21
Total with taxes and fees
Top Floor Gem! Direct Ocean Views! Near Kaanapali #215
On the beach

15. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,880 reviews)
"Love this place!"
United States
Diana
$228 nightly
The price is $270
Sep 23 - Sep 24
Total with taxes and fees
Napili Shores Maui by OUTRIGGER
Outdoor dining

16. Spacious Studio/Spectacular Ocean View/Pool/Gym

Spacious Studio/Spectacular Ocean View/Pool/Gym
Lahaina
9.8 out of 10, Exceptional, (55 reviews)
"Beautiful view, convenient location, great host communication"
United States
Sandra B.
$321 nightly
The price is $376
Sep 29 - Sep 30
Total with taxes and fees
Spacious Studio/Spectacular Ocean View/Pool/Gym
On the beach

17. 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, (57 reviews)
"The location and friendliness "
United States
Patricia R.
$913 nightly
The price is $1,037
Sep 20 - Sep 21
Total with taxes and fees
OCEAN VIEW 2 Bdrm condo with Secluded Beach - Kahana Sunset C7
Outdoor dining

18. Oceanfront Kapalua Bay Villa 23G1 Gated Coastal Elegance

Oceanfront Kapalua Bay Villa 23G1 Gated Coastal Elegance
Lahaina
9.6 out of 10, Exceptional, (75 reviews)
"We had an amazing time here. We stayed for half a month & it was a fantastic time. They were so fast to respond to anything we needed or asked. A week into our stay the washer broke down. They had maintenance out within a day & a new washer just within a couple of days. They also got us extra towels in the meantime until we could do a load of towels! They were great about communicating overall. It was a great spot to stay, right by one of the pools, & by the ocean. We loved our stay!"
United States
Alana
$898 nightly
The price is $1,019
Sep 26 - Sep 27
Total with taxes and fees
Oceanfront Kapalua Bay Villa 23G1 Gated Coastal Elegance
Garden

19. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,318 reviews)
"We loved the grounds and people. Definitely will be booking to stay there, again."
United States
Scot
$248 nightly
The price is $295
Sep 20 - Sep 21
Total with taxes and fees
Aston Kaanapali Shores
Outdoor dining

20. Beautiful Ocean and Outer Island Views! See Whales in season!

Beautiful Ocean and Outer Island Views! See Whales in season!
Lahaina
9.4 out of 10, Exceptional, (92 reviews)
"The room was clean, the view from the balcony was awesome, and the overall experience was great. I'd recommend the place."
United States
Jasdeep Singh
$355 nightly
The price is $373
Oct 6 - Oct 7
Total with taxes and fees
Beautiful Ocean and Outer Island Views! See Whales in season!
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

Napili Kai Beach Resort

Napili Kai Beach Resort

10/10 Excellent
"Great! Great! Great! 1 week stay at Napili Kai , we have a great time. Definitely recommend to families with small children, Napili bay is the best beach for small children. We booked a family studio and it had everything we needed, we really enjoyed the fully equipped kitchen."
walter 4-night trip
Posted 13 hours ago
Napili Kai Beach Resort

Find out more about Kalaupapa

Everything you need to know about Kalaupapa vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Kalaupapa vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kalaupapa vacation 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 low season months. For more hustle and bustle, you may prefer to visit Kalaupapa in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $240 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Kalaupapa rentals

At Expedia, we put the best Kalaupapa vacation 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 vacation.

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.

Explore a world of travel with Expedia

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.