Photo by Lisa A Schmidt

Search Holiday Rentals in Kalaupapa

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Top Holiday Rentals in Kalaupapa

On the beach, white sand
Castle Napili Surf Beach Resort
3.5 star property
10.0 out of 10, Exceptional, (9)
"The bathroom and kitchen were generously stacked with everything we needed. The grounds were lovely and the unit very clean and comfortable. We had use of beach chairs and plenty of towels for the pool or beautiful beach. I highly recommend Castle Nāpili Surf Beach resort."
Castle Napili Surf Beach Resort
Outdoor pool
The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach!
10.0 out of 10, Exceptional, (72)
"We decided to leave a review after our 4th annual stay at this beautiful home. We are constantly blown away by the quality, the rare location right off Napili Bay and the 5 star management. This home can host large groups of every age also! What a treat to return each year and see the property get better and better. If you want the trip of your dreams, be sure to look here first. The furniture looks brand new every time we come"
The #1 Vacation Rental on Maui!! Steps to Maui's Best Beach!
Pool
TOP FLOOR - STUNNING OCEAN VIEWS - RENOVATED UNIT - KAANAPALI WELCOMES YOU!!!
10.0 out of 10, Exceptional, (104)
"This property is exactly what was described. Lisa is amazing to communicate with. We’ve been to the resort multiple times, but this condo was by far the best. "
The price is £495
per night
10 Jun - 11 Jun
TOP FLOOR - STUNNING OCEAN VIEWS - RENOVATED UNIT - KAANAPALI WELCOMES YOU!!!
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Private kitchen | Fridge, microwave, oven, stovetop
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
9.8 out of 10, Exceptional, (47)
"First, the property: it is more amazing than the listing/pictures can possibly project. Our family visit included 7 adult couples - each of them enjoyed a private master suite of type and quality one would expect of a top-tier luxury hotel. The suites are spread across three floors, all of which are above a bottom floor with laundry, swimming pool, outdoor bar-b-q set-up, and more-than-adequate space for lounging or (as we did) having a formal meal outdoors in a beautiful tropical setting. The...
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
Property grounds
AMAZING VALUE&DECOR- 5 STAR! Great location-Large lanai with ocean views!
9.8 out of 10, Exceptional, (120)
"Very enjoyable"
AMAZING VALUE&DECOR- 5 STAR! Great location-Large lanai with ocean views!
Property grounds
Romantic Maui: Your Home 25' from the Ocean ~ Relax with the Sun, Wind and Waves
9.8 out of 10, Exceptional, (199)
"Great condo for two. Fantastic view from the lanai. Convenient to local restaurants and activities."
Romantic Maui: Your Home 25' from the Ocean ~ Relax with the Sun, Wind and Waves
Sun-loungers, beach towels
KA 402 $109 Specials thru May Spacious West Maui Studio Steps to Ocean w AC Pool
9.6 out of 10, Exceptional, (41)
"Nice property in convenient location. Highly recommend."
KA 402 $109 Specials thru May Spacious West Maui Studio Steps to Ocean w AC Pool
Property grounds
My Perfect Stays: Jun 11-25 was $289 now $179
9.4 out of 10, Exceptional, (35)
"Aloha and Mahalo!! We loved the condo!! We Can’t wait to go back! Everything we needed was provided. First of all, the view we had, was Amazing!!! We are missing our breakfast at the patio every morning, seeing the sea turtles and for the first time whales! The sound of the Ocean , the Beautiful sunsets , our walks by the beach every day. Thank you so much for letting us stay at your place. From Duarte Family"
My Perfect Stays: Jun 11-25 was $289 now $179
Sun deck
Napili Sunset on the Beach
2.5 star property
9.2 out of 10, Wonderful, (555)
"We have stayed at Napili Sunset before, it has been a great experience both times. Really enjoyed our time, and highly recommend. "
The price is £212
per night
17 May - 18 May
Napili Sunset on the Beach
Outdoor pool
Aston Mahana at Kaanapali
3.5 star property
9.0 out of 10, Wonderful, (1469)
"Very nice and very well taking care of "
The price is £593
per night
4 Jun - 5 Jun
Aston Mahana at Kaanapali
Basic Room, 1 Bedroom (Corner, Specific Unit May Vary) | Balcony view
Maui Kai
3.0 star property
9.0 out of 10, Wonderful, (391)
"Love love love this property. They have thought of everything. Why did I even need to pack anything?Room was excellent. Right on the beach. Staff was always friendly and willing to go out of their way to help. Check in after hours was a breeze. Cool pool area we never used. Parking was always available no matter when we got back and free. Nice convenient area. Food truck courtyard looked interesting but never could find the entrance will definitely stay here again"
Maui Kai
Premier Studio Suite, 1 King Bed with Sofa bed, Partial Ocean View, Garden Area (Unit 1002) | View from room
Royal Kahana Resort by rkmaui
3.5 star property
9.0 out of 10, Wonderful, (166)
"Amazing beach right next to it with a chill atmosphere definitely will be back!"
Royal Kahana Resort by rkmaui
On the beach
Napili Shores Maui by OUTRIGGER
3.0 star property
8.8 out of 10, Excellent, (1467)
"Absolutely wonderful! It’s not a fancy resort, but beautiful garden areas, we had a wonderful view from our room, and it is clean and quiet. Awesome beach access, great for swimming. Property is kid-friendly and I would absolutely come here again! "
Napili Shores Maui by OUTRIGGER
Outdoor pool, pool umbrellas, pool loungers
AEI at The Mahana Kaanapali Resort
4.0 star property
8.8 out of 10, Excellent, (206)
"Honeymooners first time in Maui, we loved this hotel. In the touristy North-west section of Maui but right on the beach (beautiful sunsets), facility amenities were exactly what we were hoping for. Clean site and rooms, spacious room with full kitchen and living room and a washer/dryer in-unit. Concierge service was excellent at helping us book the tours/events we wanted despite short notice. Could have benefitted from more information about the facility at check-in, did not realize we had...
AEI at The Mahana Kaanapali Resort
Pool
OCEANFRONT condo with incredible view of Molokai! Royal Kahana 309
8.8 out of 10, Excellent, (18)
"We loved our stay and wished we could have stayed longer. Beautiful views of the ocean from the patio and bedroom. We even spotted some whales while sitting outside on the patio. Condo is part of a beautiful building and in close proximity to beaches. Condo is well decorated, comfy, and clean. Highly recommend staying here for your vacation!"
OCEANFRONT condo with incredible view of Molokai! Royal Kahana 309
Hypo-allergenic bedding, in-room safe, blackout curtains
Aston Kaanapali Shores
3.5 star property
8.6 out of 10, Excellent, (2998)
"Amazing views and right on the beach and pools were never packed "
The price is £268
per night
30 May - 31 May
Aston Kaanapali Shores
Villa, 2 Bedrooms, Oceanfront (Bay 19G2 Gold 2.5 Bath) | View from room
Kapalua Villas Maui
4.0 star property
8.6 out of 10, Excellent, (891)
"The views and location are amazing! "
Kapalua Villas Maui
View from property
Hono Koa Vacation Club
3.0 star property
8.6 out of 10, Excellent, (138)
"The Condo is Very Beautiful and well equipped. We feel at Home ."
Hono Koa Vacation Club
Exterior
AEI at Kaanapali Shores
4.0 star property
8.6 out of 10, Excellent, (277)
"It was a refreshing holiday with our family. The proximity to the beach and pool was convenient. Waking up each morning to the sight of the ocean was ‘heavenly’."
AEI at Kaanapali Shores
Condo, 2 Bedrooms, Kitchen, Ocean View | View from room
AEI at Papakea Resort Maui
3.5 star property
8.6 out of 10, Excellent, (68)
"This was an ideal place to go and enjoy the peace and serenity surrounding you while there. People were awesome and always there to help. Ocean views were amazing and so tranquil at the same time. I look forward to a return visit in the future. Aloha baby!"
AEI at Papakea Resort Maui
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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.

Other types of properties in Kalaupapa you may be interested in

3 outdoor pools, pool cabanas (surcharge), pool loungers
The Ritz-Carlton Maui, Kapalua
5.0 star property
9.2 out of 10, Wonderful, (1001)
"Amazing facility, great staff, always attentive and great for families!"
The price is £981
per night
27 May - 28 May
The Ritz-Carlton Maui, Kapalua
Outdoor pool
Aston Mahana at Kaanapali
3.5 star property
9.0 out of 10, Wonderful, (1469)
"Very nice and very well taking care of "
The price is £593
per night
4 Jun - 5 Jun
Aston Mahana at Kaanapali
Outdoor pool
Hilton Vacation Club Ka'anapali Beach Maui
4.0 star property
8.8 out of 10, Excellent, (1007)
"Nice and safe "
The price is £231
per night
24 May - 25 May
Hilton Vacation Club Ka'anapali Beach Maui
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.

Everything you need to know about Kalaupapa holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Kalaupapa holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Kalaupapa holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Kalaupapa holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Kalaupapa holiday rentals we have selected for you start as low as £212 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Kalaupapa rentals

At Expedia, we put the best Kalaupapa holiday 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 holiday.

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 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 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 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.

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