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Kalaupapa Vacation Rentals

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Our top choices for Kalaupapa vacation rentals

Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (3929)
"Loved the 2 pools and 2 hot tub, staff is great…thank you!"
United States
Candida
$339 nightly
The price is $403
Jan 17 - Jan 18, 2026
Total with taxes and fees
Aston Kaanapali Shores

COCONUT COVE CONDO–Molokai Shores 303

COCONUT COVE CONDO–Molokai Shores 303
Kaunakakai
8.8 out of 10, Excellent, (21)
"Clean spacious condo with great amenities."
United States
Matthew A.
$316 nightly
The price is $370
Jan 3 - Jan 4, 2026
Total with taxes and fees
COCONUT COVE CONDO–Molokai Shores 303

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (147)
"Exactly what we were looking for! Close walking distance to beach and dining!"
United States
Tessa
$338 nightly
The price is $401
Jan 19 - Jan 20, 2026
Total with taxes and fees
Napili Village Hotel

Maui Beachfront Paradise with AC, Beach gears, Snorkel, Surf, Pool & BBQ

Maui Beachfront Paradise with AC, Beach gears, Snorkel, Surf, Pool & BBQ
2.5 star property
Lahaina
10.0 out of 10, Exceptional, (1)
"This condo has amazing views and everything you need for a great stay. We saw a lot of whales from the balcony. They supply you with several items for your stay, i.e. tp, tissues, towels, dish soap, a few laundry soap pods. Also beach items as well, but we didn’t use those. All we had to buy for our stay was just what we wanted grocery wise. The property manager communicated very well and ensures your stay is great. We had a wonderful time and would rent this condo again! "
United States
Sara W.
$507 nightly
The price is $594
Jan 19 - Jan 20, 2026
Total with taxes and fees
Maui Beachfront Paradise with AC, Beach gears, Snorkel, Surf, Pool & BBQ

Kuleana Club - 306

Kuleana Club - 306
3.0 star property
Lahaina
$625 nightly
The price is $742
Jan 8 - Jan 9, 2026
Total with taxes and fees
Kuleana Club - 306

Molokai Island Retreat - Amazing Ocean Views!

Molokai Island Retreat - Amazing Ocean Views!
Kaunakakai
10.0 out of 10, Exceptional, (14)
"Great place"
United States
PATRICK C.
$301 nightly
The price is $352
Jan 2 - Jan 3, 2026
Total with taxes and fees
Molokai Island Retreat - Amazing Ocean Views!

Oceanview Corner/Studio Condo at Kaanapali Shores Resort - Unit 742

Oceanview Corner/Studio Condo at Kaanapali Shores Resort - Unit 742
Lahaina
8.8 out of 10, Excellent, (106)
"The property management company was excellent and very responsive. "
Canada
Rajesh
$713 nightly
The price is $805
Jan 5 - Jan 6, 2026
Total with taxes and fees
Oceanview Corner/Studio Condo at Kaanapali Shores Resort - Unit 742

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (1721)
"We really enjoyed the location for our 2nd stay at Napili Shores. "
United States
Mikael Christopher
$399 nightly
The price is $474
Jan 4 - Jan 5, 2026
Total with taxes and fees
Napili Shores Maui by OUTRIGGER

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
10.0 out of 10, Exceptional, (28)
"This place was great, just what we needed for my wife and I trip. You won’t regret booking this place."
United States
Sean N.
$782 nightly
The price is $886
Dec 29 - Dec 30
Total with taxes and fees
Garden View Second Floor Studio at Napili Shores – Steps to Napili Bay D229

Kahana Sunset C7 2 Bedroom Condo by RedAwning

Kahana Sunset C7 2 Bedroom Condo by RedAwning
4.0 star property
Lahaina
$1,165 nightly
The price is $1,383
Jan 8 - Jan 9, 2026
Total with taxes and fees
Kahana Sunset C7 2 Bedroom Condo by RedAwning

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, (12)
"Had a wonderful stay! Super clean & everything we needed was included. The pictures and description are completely accurate in showing your accommodations which is so refreshing!"
United States
Anonymous traveler
$792 nightly
The price is $897
Jan 5 - Jan 6, 2026
Total with taxes and fees
Ultra Modern/Coastal-Remodel, Oceanview, AC - Napili Shores G154

1-bedroom condo in Maunaloa, just 10 minutes from the beach

1-bedroom condo in Maunaloa, just 10 minutes from the beach
Maunaloa
10.0 out of 10, Exceptional, (1)
"Clean, relaxing, and enjoyable area in molokai. We will be booking here most often. "
United States
Kehaulani A.
$270 nightly
The price is $314
Dec 29 - Dec 30
Total with taxes and fees
1-bedroom condo in Maunaloa, just 10 minutes from the beach

Carefree In Paradise. Just steps to the beach!

Carefree In Paradise. Just steps to the beach!
Lahaina
9.6 out of 10, Exceptional, (143)
"This property was fantastic. Very clean and you just can’t beat the location - beautiful sandy beach on one side and a bay to snorkel in on the other. It was wonderful to have such a well appointed studio to come home to after adventuring around the island. "
United States
Kimberly C.
$372 nightly
The price is $435
Jan 27 - Jan 28, 2026
Total with taxes and fees
Carefree In Paradise. Just steps to the beach!

Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (647)
"Location was excellent"
United States
Polly
$281 nightly
The price is $334
Jan 1 - Jan 2, 2026
Total with taxes and fees
Napili Sunset on the Beach

Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC

Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC
Lahaina
8.6 out of 10, Excellent, (101)
"Over all a great spot. Lication"
Canada
shelly k.
$715 nightly
The price is $807
Jan 9 - Jan 10, 2026
Total with taxes and fees
Charming Studio at Oceanfront Ka’anapali Shores | Pools, Beach Access, AC

Efficiency

Efficiency
Maunaloa
9.6 out of 10, Exceptional, (7)
"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.
$248 nightly
The price is $313
Jan 1 - Jan 2, 2026
Total with taxes and fees
Efficiency

Great Deal! 1BR Condo at Oceanfront Kaanapali Shores | Pools, AC, Beach

Great Deal! 1BR Condo at Oceanfront Kaanapali Shores | Pools, AC, Beach
Lahaina
7.8 out of 10, Good, (85)
"Easy check in and great accommodations."
United States
Danh K.
$720 nightly
The price is $814
Jan 19 - Jan 20, 2026
Total with taxes and fees
Great Deal! 1BR Condo at Oceanfront Kaanapali Shores | Pools, AC, Beach

Tranquility on West Moloka'i

Tranquility on West Moloka'i
Maunaloa
9.8 out of 10, Exceptional, (10)
"great!"
United States
Kezia A.
$271 nightly
The price is $317
Jan 2 - Jan 3, 2026
Total with taxes and fees
Tranquility on West Moloka'i

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, (89)
"This property is so clean, well maintained and quiet. This unit offers very good views. The unit is well stuffed with amenities. Only drawback: It is not on the beach but if thats not a big deal, it is outstanding ! "
United States
Prabaha
$426 nightly
The price is $457
Jan 7 - Jan 8, 2026
Total with taxes and fees
Beautiful Ocean and Outer Island Views! See Whales in season!

Kuleana 613 1 Bdrm 1 Bedroom Condo by RedAwning

Kuleana 613 1 Bdrm 1 Bedroom Condo by RedAwning
4.0 star property
Lahaina
9.0 out of 10, Wonderful, (2)
" The apartment was prepared with all the necessary amenities. It was spotless, smelled great, had plenty of soaps, towels, and beach necessities, and air conditioning was even left on, so the apartment was quite comfortable upon our arrival. RedAwning is an excellent company with a superb customer relations attitude."
United States
Mariana
$823 nightly
The price is $976
Jan 10 - Jan 11, 2026
Total with taxes and fees
Kuleana 613 1 Bdrm 1 Bedroom Condo by RedAwning
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

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 $401 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.

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 by KBM Resorts: 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.