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

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 CA $162
CA $548 total
includes taxes & fees
Aug 13 - Aug 14
sweet escape - Moloka'i living

COCONUT COVE CONDO–Molokai Shores 303

COCONUT COVE CONDO–Molokai Shores 303
Kaunakakai
8.6 out of 10, Excellent, (25 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 CA $212
CA $526 total
includes taxes & fees
Aug 1 - Aug 2
COCONUT COVE CONDO–Molokai Shores 303

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 CA $337
CA $1,054 total
includes taxes & fees
Aug 16 - Aug 17
2BR Ocean View w/Lanai and Kitchen - Molokai Shores 217

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)
"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 CA $242
CA $825 total
includes taxes & fees
Aug 23 - Aug 24
Modern Oceanfront W/Lanai and WiFi–Molokai Shores

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 CA $56
CA $418 total
includes taxes & fees
Aug 3 - Aug 4
Efficiency

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
The price is CA $159
CA $456 total
includes taxes & fees
Aug 5 - Aug 6
Ocean Front-Unobstructed Views- Beautiful Upgraded Condo

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 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 CA $599
CA $1,125 total
includes taxes & fees
Aug 11 - Aug 12
Rustic retreat with panoramic views at Pu'u O Hoku Ranch

Garden View Second Floor Studio at Napili Shores – Steps to Napili Bay D229

Garden View Second Floor Studio at Napili Shores – Steps to Napili Bay D229
Lahaina
9.8 out of 10, Exceptional, (31 reviews)
"We didn’t know it was American spring break so it was kids screaming at the pool from 9am to 9 pm for the first week then some yahoos moved in next door for the second week and we got to listen to them loud talking, arguing and having sex…no so pleasant. "
Canada
Jason S.
The price is CA $166
CA $1,123 total
includes taxes & fees
Aug 2 - Aug 3
Garden View Second Floor Studio at Napili Shores – Steps to Napili Bay D229

Incredible OCEANFRONT condo with a view of Molokai! Royal Kahana 309

Incredible OCEANFRONT condo with a view of Molokai! Royal Kahana 309
Lahaina
8.8 out of 10, Excellent, (45 reviews)
"Five star view! Decent air conditioning. Clean but dated. This was within my budget, but the property would benefit with a new sofa and flooring. Spacious and sufficient. Loved visiting Maui. "
United States
Lorie C.
The price is CA $126
CA $1,070 total
includes taxes & fees
Jul 30 - Jul 31
Incredible OCEANFRONT condo with a view of Molokai! Royal Kahana 309

Aston Kaanapali Shores | Oceanfront Resort Amenities

Aston Kaanapali Shores | Oceanfront Resort Amenities
Kaanapali
The price is CA $351
CA $469 total
includes taxes & fees
Aug 2 - Aug 3
Aston Kaanapali Shores | Oceanfront Resort Amenities

Gorgeous Napili Shores G258 Newly remodeled Studio Condo

Gorgeous Napili Shores G258 Newly remodeled Studio Condo
lahaina
10.0 out of 10, Exceptional, (12 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 CA $197
CA $1,150 total
includes taxes & fees
Aug 14 - Aug 15
Gorgeous Napili Shores G258 Newly remodeled Studio Condo

OCEANFRONT 1 Bdrm Condo next to the water! Air conditioned - Kaleialoha 209

OCEANFRONT 1 Bdrm Condo next to the water! Air conditioned - Kaleialoha 209
Lahaina
9.2 out of 10, Wonderful, (38 reviews)
"Good location, amazing views!"
United States
Amanda S.
The price is CA $134
CA $1,082 total
includes taxes & fees
Jul 30 - Jul 31
OCEANFRONT 1 Bdrm Condo next to the water! Air conditioned - Kaleialoha 209

Royal Kahana 217 | Ocean View Studio Between Kaʻanapali & Kapalua

Royal Kahana 217 | Ocean View Studio Between Kaʻanapali & Kapalua
Lahaina
9.4 out of 10, Exceptional, (23 reviews)
"The view was fantastic for sunset."
United States
Lauren M.
The price is CA $167
CA $795 total
includes taxes & fees
Aug 6 - Aug 7
Royal Kahana 217 | Ocean View Studio Between Kaʻanapali & Kapalua

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, (274 reviews)
"Amazing trip!"
United States
Eric L.
The price is CA $184
CA $668 total
includes taxes & fees
Aug 2 - Aug 3
Aloha Hale Ocean View Maui Condo In Ocean Front/Beach Resort Swim with Turtles!

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, (18 reviews)
"great condo, nicely updated with everything you need for a wonderful stay !!"
United States
tom p.
The price is CA $173
CA $1,117 total
includes taxes & fees
Jul 30 - Jul 31
Ultra Modern/Coastal-Remodel, Oceanview, AC - Napili Shores G154

OCEANVIEW, 1 bed/1 bath condo at the exclusive gated Kapalua Bay Villa 32G4!

OCEANVIEW, 1 bed/1 bath condo at the exclusive gated Kapalua Bay Villa 32G4!
Lahaina
9.8 out of 10, Exceptional, (57 reviews)
"Beautiful condo in a beautiful location! We will definitely stay here again. "
United States
Amy L.
The price is CA $293
CA $1,361 total
includes taxes & fees
Aug 4 - Aug 5
OCEANVIEW, 1 bed/1 bath condo at the exclusive gated Kapalua Bay Villa 32G4!

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)
"Outstanding view!!!"
United States
Bob E.
The price is CA $190
CA $1,160 total
includes taxes & fees
Jul 30 - Jul 31
Fabulous Oceanfront Retreat at Kuleana 622 3rd Floor Condo A/C

Oceanfront Kapalua Bay Villa 23G1 Gated Coastal Elegance

Oceanfront Kapalua Bay Villa 23G1 Gated Coastal Elegance
Lahaina
9.6 out of 10, Exceptional, (74 reviews)
"Lovely stay at a beautiful property "
United States
Steve G.
The price is CA $288
CA $1,354 total
includes taxes & fees
Aug 12 - Aug 13
Oceanfront Kapalua Bay Villa 23G1 Gated Coastal Elegance

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, (90 reviews)
"Overall a 4/5 experience! I would stay here again without a doubt. Simple check-in process, attentive host, great ocean views, and a well equipped condo. The only drawback I can think of was in regards to some of the aging furnishings. "
United States
Timo S.
The price is CA $140
CA $560 total
includes taxes & fees
Jul 30 - Jul 31
Beautiful Ocean and Outer Island Views! See Whales in season!

Kuleana Club - 509

Kuleana Club - 509
3.5 star property
Lahaina
The price is CA $178
CA $504 total
includes taxes & fees
Jul 30 - Jul 31
Kuleana Club - 509
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 of 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.