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, (3,988 reviews)
"Our room was great and the staff were always so friendly. Perfect place to stay for a good value. "
United States
Emily
The price is CA $518
CA $656 total
includes taxes & fees
Feb 21 - Feb 22
Aston Kaanapali Shores

Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (650 reviews)
"Great Hotel! Super clean! Has everything you need for perfect vacation!"
United States
Sergii
The price is CA $385
CA $456 total
includes taxes & fees
Feb 10 - Feb 11
Napili Sunset on the Beach

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (163 reviews)
"Amazing place to stay, loved it. "
United States
Jacqueline
The price is CA $332
CA $394 total
includes taxes & fees
Mar 3 - Mar 4
Napili Village Hotel

Kuleana Club - 504

Kuleana Club - 504
3.0 star property
Lahaina
The price is CA $474
CA $847 total
includes taxes & fees
Feb 20 - Feb 21
Kuleana Club - 504

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,750 reviews)
"Beautiful location, nice, clean rooms, friendly staff, and eating facilities on site!"
Canada
Larry Henry
The price is CA $475
CA $564 total
includes taxes & fees
Feb 10 - Feb 11
Napili Shores Maui by OUTRIGGER

Efficiency

Efficiency
Maunaloa
9.6 out of 10, Exceptional, (7 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 $52
CA $399 total
includes taxes & fees
Feb 10 - Feb 11
Efficiency

Kuleana Club - 316

Kuleana Club - 316
3.0 star property
Lahaina
The price is CA $488
CA $864 total
includes taxes & fees
Feb 13 - Feb 14
Kuleana Club - 316

Kuleana Club - 513

Kuleana Club - 513
3.0 star property
Lahaina
10.0 out of 10, Exceptional, (1 review)
"Clean room, easy check in process, great property with great pool and little beach area to see turtles. We were on the third floor and had to carry all our suitcases up the flights of stairs but being able to see the whales off the Lanai every morning was worth it "
Australia
Andrea
The price is CA $438
CA $805 total
includes taxes & fees
Feb 20 - Feb 21
Kuleana Club - 513

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 $572
CA $2,312 total
includes taxes & fees
Mar 1 - Mar 2
Kahana Sunset C7 2 Bedroom Condo by RedAwning

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 review)
"Clean, relaxing, and enjoyable area in molokai. We will be booking here most often. "
United States
Kehaulani A.
The price is CA $150
CA $456 total
includes taxes & fees
Mar 9 - Mar 10
1-bedroom condo in Maunaloa, just 10 minutes from the beach

COCONUT COVE CONDO–Molokai Shores 303

COCONUT COVE CONDO–Molokai Shores 303
Kaunakakai
8.8 out of 10, Excellent, (21 reviews)
"Clean spacious condo with great amenities."
United States
Matthew A.
The price is CA $205
CA $510 total
includes taxes & fees
Feb 21 - Feb 22
COCONUT COVE CONDO–Molokai Shores 303

Napili Point by KBM

Napili Point by KBM
4.0 star property
Napili-Honokowai
9.4 out of 10, Exceptional, (16 reviews)
"Nice location "
United States
Ryan
The price is CA $1,302
CA $2,360 total
includes taxes & fees
Mar 11 - Mar 12
Napili Point by KBM

Owner-Managed One Bedroom Condo

Owner-Managed One Bedroom Condo
2.5 star property
Lahaina
The price is CA $520
CA $726 total
includes taxes & fees
Feb 11 - Feb 12
Owner-Managed One Bedroom Condo

Tri Zone AC - You're invited! Come inside, the house is yours!

Tri Zone AC - You're invited! Come inside, the house is yours!
Lahaina
9.6 out of 10, Exceptional, (130 reviews)
"Cheryl’s place was awesome! Close proximity to shops and sandy beaches. Condo was clean and the property management team onsite was attentive to our needs. Would highly recommend this place for a family of 4."
United States
Erik W.
The price is CA $422
CA $958 total
includes taxes & fees
Feb 22 - Feb 23
Tri Zone AC - You're invited! Come inside, the house is yours!

Kaanapali Shores 734 North Facing Ocean View

Kaanapali Shores 734 North Facing Ocean View
Lahaina
9.0 out of 10, Wonderful, (16 reviews)
"The place was advertised and delivered the same. It was easy to book, easy to get info on and up to date on many things. I would stay again. The sheets smelt so clean for the entire trip."
Canada
Marion K.
The price is CA $185
CA $653 total
includes taxes & fees
Feb 10 - Feb 11
Kaanapali Shores 734 North Facing Ocean View

Ke Nani Kai Unit 156- More Molokai

Ke Nani Kai Unit 156- More Molokai
Maunaloa
9.2 out of 10, Wonderful, (56 reviews)
"A great place to stay and the best value you can get at Ke Nani Kai!"
Germany
Karlheinz S.
The price is CA $205
CA $592 total
includes taxes & fees
Mar 4 - Mar 5
Ke Nani Kai Unit 156- More Molokai

Oceanfront Lahaina | Front-Row Ocean Living, Adventure Out, Relax In

Oceanfront Lahaina | Front-Row Ocean Living, Adventure Out, Relax In
Lahaina
10.0 out of 10, Exceptional, (35 reviews)
"Annie's Surf Shack was everything we wanted for our trip to Maui. It's right on the water so the views of Molokai and Lanai were amazing (we saw rainbows over Molokai and turtles almost every day). Beautiful sunsets. quiet. A cute little bakery stand across the street and a local pub with good food just a couple of blocks away. It is close to Kaanapali and all the best snorkeling beaches. Comfy bed and good pillows."
United States
Tom R.
The price is CA $286
CA $827 total
includes taxes & fees
Mar 9 - Mar 10
Oceanfront Lahaina | Front-Row Ocean Living, Adventure Out, Relax In

3BD WALK TO THE BEACH | Luxury Remodel | HUGE DECK

3BD WALK TO THE BEACH | Luxury Remodel | HUGE DECK
Lahaina
10.0 out of 10, Exceptional, (61 reviews)
"Directly across the street from the bay for good snorkeling spot. Eat at the Gazebo for an unforgettable breakfast of macadamia nut and banana pancakes. Open air dining right on the beach."
United States
Rebecca B.
The price is CA $409
CA $1,185 total
includes taxes & fees
Feb 10 - Feb 11
3BD WALK TO THE BEACH | Luxury Remodel | HUGE DECK

Maui Kai 804 Oceanfront 1 Bd/1ba 1 Bedroom Condo by RedAwning

Maui Kai 804 Oceanfront 1 Bd/1ba 1 Bedroom Condo by RedAwning
3.5 star property
Lahaina
10.0 out of 10, Exceptional, (1 review)
"room was amazing best view with ocean front right out of your window turtles and whales right outside your window as well what a place def recommend just one thing needed for the ladies is more mirrors and a iron lol. "
United States
Louis Philip
The price is CA $627
CA $2,512 total
includes taxes & fees
Feb 22 - Feb 23
Maui Kai 804 Oceanfront 1 Bd/1ba 1 Bedroom Condo by RedAwning

🌊 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
9.8 out of 10, Exceptional, (118 reviews)
"It was wonderful. Beautiful ocean view. The kids used the snorkel gear and checked out the turtles. We really enjoyed it."
United States
Todd C.
The price is CA $430
CA $1,113 total
includes taxes & fees
Feb 10 - Feb 11
🌊 Oceanfront Sea Turtle Paradise Newly Remodeled $7.5M Maui Gem Near Kaanapali
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 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.