Kalaupapa Vacation Rentals

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Our top choices for Kalaupapa vacation rentals

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (183 reviews)
"The property is beautiful and located just steps away from the beach."
United States
Patricia
The price is CA $277
CA $329 total
includes taxes & fees
May 22 - May 23
Napili Village Hotel

Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,098 reviews)
"Pools were great had available seating and kids loved the waterfall and hot tub."
United States
Doreen
The price is CA $436
CA $559 total
includes taxes & fees
May 20 - May 21
Aston Kaanapali Shores

Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (654 reviews)
"Clean room amd friendly staff."
United States
Chris
The price is CA $387
CA $459 total
includes taxes & fees
May 18 - May 19
Napili Sunset on the Beach

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,794 reviews)
"Everything was perfect! Will come back again"
United States
Alla
The price is CA $308
CA $365 total
includes taxes & fees
May 31 - Jun 1
Napili Shores Maui by OUTRIGGER

Kuleana Club - 715

Kuleana Club - 715
3.5 star property
Lahaina
The price is CA $448
CA $817 total
includes taxes & fees
Jun 13 - Jun 14
Kuleana Club - 715

Kuleana Club - 701

Kuleana Club - 701
3.5 star property
Lahaina
The price is CA $272
CA $609 total
includes taxes & fees
May 28 - May 29
Kuleana Club - 701

Sands Of Kahana 282 2 Bedroom Condo by RedAwning

Sands Of Kahana 282 2 Bedroom Condo by RedAwning
4.5 star property
Lahaina
The price is CA $743
CA $2,898 total
includes taxes & fees
May 18 - May 19
Sands Of Kahana 282 2 Bedroom Condo by RedAwning

Kuleana Club - 712

Kuleana Club - 712
3.5 star property
Lahaina
The price is CA $328
CA $675 total
includes taxes & fees
May 22 - May 23
Kuleana Club - 712

Hale Mahina B304

Hale Mahina B304
3.0 star property
Lahaina
The price is CA $1,328
CA $1,577 total
includes taxes & fees
May 22 - May 23
Hale Mahina B304

Sands of Kahana Resort by KBM

Sands of Kahana Resort by KBM
4.0 star property
Lahaina
The price is CA $4,989
CA $7,363 total
includes taxes & fees
May 17 - May 18
Sands of Kahana Resort by KBM

Kuleana Club - 315

Kuleana Club - 315
3.5 star property
Lahaina
The price is CA $283
CA $621 total
includes taxes & fees
May 29 - May 30
Kuleana Club - 315

Oceanfront Maui Condo

Oceanfront Maui Condo
2.0 star property
Lainaina
The price is CA $250
CA $770 total
includes taxes & fees
May 17 - May 18
Oceanfront Maui Condo

Kuleana Club - 707

Kuleana Club - 707
3.0 star property
Lahaina
The price is CA $295
CA $636 total
includes taxes & fees
May 28 - May 29
Kuleana Club - 707

Papakea H107 1 bedroom, 1 bath OceanView 1 Condo by RedAwning

Papakea H107 1 bedroom, 1 bath OceanView 1 Condo by RedAwning
3.5 star property
Lahaina
The price is CA $334
CA $1,906 total
includes taxes & fees
May 17 - May 18
Papakea H107 1 bedroom, 1 bath OceanView 1 Condo by RedAwning

Kaanapali Shores #159 2 Bedroom Condo by RedAwning

Kaanapali Shores #159 2 Bedroom Condo by RedAwning
3.5 star property
Lahaina
The price is CA $416
CA $1,512 total
includes taxes & fees
May 22 - May 23
Kaanapali Shores #159 2 Bedroom Condo by RedAwning

Maui Kai 908 Oceanfront 1 Bedroom 1 Condo by RedAwning

Maui Kai 908 Oceanfront 1 Bedroom 1 Condo by RedAwning
3.5 star property
Lahaina
The price is CA $445
CA $2,104 total
includes taxes & fees
Jun 2 - Jun 3
Maui Kai 908 Oceanfront 1 Bedroom 1 Condo by RedAwning

Napili Point C-12 - 2Br Condo

Napili Point C-12 - 2Br Condo
3.5 star property
Lahaina
The price is CA $650
CA $2,568 total
includes taxes & fees
May 29 - May 30
Napili Point C-12 - 2Br Condo

Kahana Sunset C7 2 Bedroom Condo by RedAwning

Kahana Sunset C7 2 Bedroom Condo by RedAwning
4.0 star property
Lahaina
The price is CA $779
CA $2,804 total
includes taxes & fees
May 22 - May 23
Kahana Sunset C7 2 Bedroom Condo by RedAwning

Valley Isle 1108b 2 Bedroom Condo by RedAwning

Valley Isle 1108b 2 Bedroom Condo by RedAwning
3.5 star property
Lahaina
10.0 out of 10, Exceptional, (1 review)
"The view to the ocean from our room was everything we wanted , beautiful property and would definitely book for next trip. Thank you 😊 "
United States
Sonia Isabel
The price is CA $644
CA $2,557 total
includes taxes & fees
May 22 - May 23
Valley Isle 1108b 2 Bedroom Condo by RedAwning

Valley Isle Resort by KBM

Valley Isle Resort by KBM
4.0 star property
Lahaina
9.0 out of 10, Wonderful, (4 reviews)
"Just an outstanding experience all the way through. We’ve stayed in other locations on Maui and I have to say this is our favorite. We plan to return again in the future."
United States
Gary Todd
The price is CA $1,769
CA $3,003 total
includes taxes & fees
May 21 - May 22
Valley Isle 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

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.