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

Kalaupapa Holiday Rentals

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Kalaupapa holiday rentals

On the beach, beach towels

sweet escape - Moloka'i living

sweet escape - Moloka'i living
Kaunakakai
9.6 out of 10, Exceptional, (25 reviews)
"The condo was very clean and private"
United States
Frank
The price is HK$902
HK$3,003 total
includes taxes & fees
16 Aug - 17 Aug
sweet escape - Moloka'i living
Exterior

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

2BR Ocean View w/Lanai and Kitchen - Molokai Shores 217
Kaunakakai
9.0 out of 10, Wonderful, (12 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 HK$1,874
HK$5,785 total
includes taxes & fees
26 Jul - 27 Jul
2BR Ocean View w/Lanai and Kitchen - Molokai Shores 217
Property grounds

Modern Oceanfront W/Lanai and WiFiā€“Molokai Shores

Modern Oceanfront W/Lanai and WiFiā€“Molokai Shores
KAUNAKAKAI
9.0 out of 10, Wonderful, (34 reviews)
"The place was lovely, comfortable, and convenient. The amenities were great, the view stellar, and the administrative staff friendly. "
United States
Lisa Ann L.
The price is HK$1,600
HK$4,913 total
includes taxes & fees
2 Aug - 3 Aug
Modern Oceanfront W/Lanai and WiFiā€“Molokai Shores
Property grounds

COCONUT COVE CONDOā€“Molokai Shores 303

COCONUT COVE CONDOā€“Molokai Shores 303
Kaunakakai
9.0 out of 10, Wonderful, (24 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 HK$1,176
HK$2,902 total
includes taxes & fees
1 Aug - 2 Aug
COCONUT COVE CONDOā€“Molokai Shores 303
Garden

Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,193 reviews)
"We were very happy with our stay."
United States
Joni
The price is HK$1,709
HK$2,261 total
includes taxes & fees
17 Aug - 18 Aug
Aston Kaanapali Shores
Outdoor dining

Molokai Island Retreat Wavecrest- Ocean Views

Molokai Island Retreat Wavecrest- Ocean Views
Kaunakakai
10.0 out of 10, Exceptional, (18 reviews)
"Great place"
United States
PATRICK C.
The price is HK$971
HK$2,571 total
includes taxes & fees
4 Aug - 5 Aug
Molokai Island Retreat Wavecrest- Ocean Views
Pool

Ocean Front-Unobstructed Views- Beautiful Upgraded Condo

Ocean Front-Unobstructed Views- Beautiful Upgraded Condo
Maunaloa
9.8 out of 10, Exceptional, (85 reviews)
"Great location. Newly remodeled. Was clean and great condition."
United States
Tristan
The price is HK$882
HK$2,545 total
includes taxes & fees
26 Jul - 27 Jul
Ocean Front-Unobstructed Views- Beautiful Upgraded Condo
On the beach

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,834 reviews)
"Perfect place to relax has everything you need you can stay in and cook for yourself or you can go to the restaurant plenty of options up the street perfect place to be in paradise"
United States
monica gene
The price is HK$1,635
HK$1,941 total
includes taxes & fees
11 Aug - 12 Aug
Napili Shores Maui by OUTRIGGER
Books

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, (95 reviews)
The price is HK$3,332
HK$6,254 total
includes taxes & fees
17 Aug - 18 Aug
Rustic retreat with panoramic views at Pu'u O Hoku Ranch
Beach nearby, white sand, beach towels

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (203 reviews)
The price is HK$2,506
HK$2,975 total
includes taxes & fees
14 Aug - 15 Aug
Napili Village Hotel
Beach/ocean view

Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (657 reviews)
"Clean room amd friendly staff."
United States
Chris
The price is HK$2,204
HK$2,617 total
includes taxes & fees
26 Jul - 27 Jul
Napili Sunset on the Beach
Sun-loungers, beach towels

Efficiency

Efficiency
Maunaloa
9.4 out of 10, Exceptional, (9 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.
The price is HK$314
HK$2,296 total
includes taxes & fees
1 Aug - 2 Aug
Efficiency
Pool

Aston Kaanapali Shores | Oceanfront Resort Amenities

Aston Kaanapali Shores | Oceanfront Resort Amenities
Kaanapali
The price is HK$1,952
HK$2,597 total
includes taxes & fees
19 Aug - 20 Aug
Aston Kaanapali Shores | Oceanfront Resort Amenities
Interior

Ocean Front Napili Point C20 Amazing View A/C Freshly Remodeled for 2025!

Ocean Front Napili Point C20 Amazing View A/C Freshly Remodeled for 2025!
Napili, Lahaina
9.0 out of 10, Wonderful, (99 reviews)
"We had a wonderful stay at Napili Point. A well stocked kitchen, amazing views, and great updated bathrooms! We loved sitting on the lanai watching the whales and turtles and amazing sunsets!!"
United States
Nicole M.
The price is HK$2,580
HK$5,997 total
includes taxes & fees
22 Jul - 23 Jul
Ocean Front Napili Point C20 Amazing View A/C Freshly Remodeled for 2025!
Outdoor pool, a heated pool

Oceanfront Sea Turtle Paradise Newly Remodeled 7.5M Maui Gem Near Kaanapali

Oceanfront Sea Turtle Paradise Newly Remodeled 7.5M Maui Gem Near Kaanapali
Lahaina
10.0 out of 10, Exceptional, (123 reviews)
"We had a great stay! My kids really loved having the big grass to play in and the turtles on the beach to watch! It was so dreamy sitting outside watching the waves. "
United States
Camille B.
The price is HK$2,274
HK$6,061 total
includes taxes & fees
24 Jul - 25 Jul
Oceanfront Sea Turtle Paradise Newly Remodeled 7.5M Maui Gem Near Kaanapali
Outdoor dining

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, (59 reviews)
"The view from this room and lanai is the best ever. The condo is beautifully appointed and clean."
United States
Carol P.
The price is HK$1,733
HK$7,311 total
includes taxes & fees
26 Jul - 27 Jul
Luxury Oceanfront Studio at Napili Shores A203 View of Lanai and Molokai
Exterior

Location, Location, Location. You can't get closer to the ocean for this price

Location, Location, Location. You can't get closer to the ocean for this price
Lahaina
9.2 out of 10, Wonderful, (182 reviews)
"Wow! Great location. You really can't get closer to the ocean. It's clean and comfortable in a pretty quiet spot. "
United States
John S.
The price is HK$3,521
HK$9,895 total
includes taxes & fees
24 Jul - 25 Jul
Location, Location, Location. You can't get closer to the ocean for this price
On the beach, beach towels

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, (106 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 HK$2,252
HK$7,211 total
includes taxes & fees
3 Aug - 4 Aug
Luxury Ocean View Condo - Kahana Sunset D4 - A/C & 5G WiFi - Pool
Exterior

Updated Studio, AC, steps to beach

Updated Studio, AC, steps to beach
Lahaina
9.8 out of 10, Exceptional, (154 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.
The price is HK$1,235
HK$3,191 total
includes taxes & fees
24 Jul - 25 Jul
Updated Studio, AC, steps to beach
Outdoor pool

BEAUTIFUL OCEANFRONT MODERN West Maui Condo with Sunset Views!

BEAUTIFUL OCEANFRONT MODERN West Maui Condo with Sunset Views!
Lahaina
9.8 out of 10, Exceptional, (86 reviews)
"This place was very clean and we loved the location! "
United States
Tammy K.
The price is HK$1,658
HK$5,285 total
includes taxes & fees
1 Aug - 2 Aug
BEAUTIFUL OCEANFRONT MODERN West Maui Condo with Sunset Views!
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

Kapalua Villas Maui

Kapalua Villas Maui

10/10 Excellent
"Spacious villa ,gorgeous views ,host was great gave me all the information I needed and then some in a timely manner."
Edgar Homero 5-night trip
Posted 19 hours ago
Kapalua Villas Maui

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:

  • View our selection of featured holiday rentals in Kalaupapa
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  • Enter your travel dates to view the best deals on holiday rentals in Kalaupapa while they last

Look no further and take a look at our great range of rental properties in Kalaupapa!

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 of 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 MolokaŹ»i 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.