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Kalaupapa Holiday Rentals

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Holiday Rentals in Kalaupapa

Aston Kaanapali Shores
3.5 star property
8.6 out of 10, Excellent, (3025)
"Quiet! Safe! Grocery nearby!"
The price is NZ$575
includes taxes & fees
12 Jun - 13 Jun
Aston Kaanapali Shores
Kahana Beach Vacation Club
3.0 star property
8.4 out of 10, Very good, (546)
"My daughter and I had an amazing time here celebrating her master's degree. We booked a 1 BR and are so glad we did. The condo was HUGE. The bedroom was x-large, as well as the living are. Both with a large TV in each. We also had two full bathrooms (one with a tub and the other with a full size shower). The kitchen had everything you'd need to cook meals. We were pleasantly surprised with all the cooking tools and gadgets. Being recently renovated, everything was brand new. The only thing...
Kahana Beach Vacation Club
Aston Mahana at Kaanapali
3.5 star property
9.0 out of 10, Wonderful, (1481)
"All good"
The price is NZ$1,057
includes taxes & fees
4 Jun - 5 Jun
Aston Mahana at Kaanapali
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The Gardens at West Maui
3.0 star property
8.4 out of 10, Very good, (380)
"It’s a great place to stay, quiet, lots of parking. "
The Gardens at West Maui
Aston at Papakea Resort
3.0 star property
8.2 out of 10, Very good, (1331)
"nice "
Aston at Papakea Resort
Napili Shores Maui by OUTRIGGER
3.0 star property
8.8 out of 10, Excellent, (1474)
"Great natural setting"
Napili Shores Maui by OUTRIGGER
Sands of Kahana
3.0 star property
8.2 out of 10, Very good, (378)
"Very close to beach and clean. Kitchen had everything I needed. Safeway grocery store is about 10 minutes drive. Location is a bit remote to travel and see the other half of the island."
Sands of Kahana
Castle Napili Surf Beach Resort
3.5 star property
10.0 out of 10, Exceptional, (11)
"The location is far out from other sites on Maui so we spent more time driving than we would have liked, yet the condo was perfect, and Napili bay is wonderful."
Castle Napili Surf Beach Resort
AEI at Kaanapali Shores
4.0 star property
8.6 out of 10, Excellent, (279)
"The process at checkin was a little confusing whether to use bell man or not."
AEI at Kaanapali Shores
Kahana Falls Maui by VRI Americas
3.5 star property
8.0 out of 10, Very good, (782)
"Nice quiet place to stay. Even solo travelers. Not too many kids "
Kahana Falls Maui by VRI Americas
AEI at The Mahana Kaanapali Resort
4.0 star property
8.8 out of 10, Excellent, (209)
"Beautiful view!!! Excellent!"
AEI at The Mahana Kaanapali Resort
Hono Koa Vacation Club
3.0 star property
8.6 out of 10, Excellent, (146)
"We LOVED Hono Koa! So much so we didn’t want to leave. We are a family of five and two bedroom and two bathrooms were perfect for our family. We loved having a kitchen and bbqs and we cooked at the condo most nights making the trip much more affordable. We loved the pool and the grass area where we watched the sunset every night! We loved our neighbors and had an AMAZING TRIP! "
Hono Koa Vacation Club
Napili Sunset on the Beach
2.5 star property
9.2 out of 10, Wonderful, (559)
"Our ocean front 1 bedroom with loft was absolutely perfect. We booked this room for the last few days of our trip.We stood the first 5 days at a “fancy resort”,needless to say this was totally worth the price and location. We will be back in December and definitely be booking Napili Sunset for the majority of our stay. Just as short walk out to the water. "
The price is NZ$438
includes taxes & fees
4 Jun - 5 Jun
Napili Sunset on the Beach
Kapalua Villas Maui
4.0 star property
8.6 out of 10, Excellent, (895)
"The views and location are amazing! "
Kapalua Villas Maui
Kahana Villa
3.0 star property
8.0 out of 10, Very good, (295)
"Our unit is ocean facing and spacious. The unit needs some upgrades but is worth the money. After hour checking is smooth."
Kahana Villa
Royal Kahana Maui by OUTRIGGER
3.0 star property
8.0 out of 10, Very good, (1277)
"Royal Kahana is showing it's age despite the construction going on which made lots of noise during the day. Our unit was nicely renovated. The sliding glass door was noisy at night due to the high winds. Staff and security were very friendly. Parking was easy to find. We would come back."
Royal Kahana Maui by OUTRIGGER
Maui Kai
3.0 star property
9.0 out of 10, Wonderful, (393)
"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
AEI at Papakea Resort Maui
3.5 star property
8.6 out of 10, Excellent, (70)
"Very clean and located in great spot lots of food and shops within walking distance. For me personally I prefer the size of the resort it’s not overly crowded."
AEI at Papakea Resort Maui
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
9.8 out of 10, Exceptional, (48)
"I came with my group of around 30 and we had such a lovely time! Everyone had a comfortable place to sleep and we all enjoyed the closeness to the beach. Also, the host were very communicative and helpful throughout our stay. Highly recommend this place to anyone who wants to stay in Maui!"
The #1 Luxury OCEAN FRONT Mansion! Sleeps 32
Royal Kahana Resort by rkmaui
3.5 star property
9.0 out of 10, Wonderful, (168)
"Pay for parking i didnt like! Nothing to do in area"
Royal Kahana Resort by rkmaui
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See all available properties in Kalaupapa
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

Aston Kaanapali Shores
3.5 star property
8.6 out of 10, Excellent, (3025)
"Quiet! Safe! Grocery nearby!"
The price is NZ$575
includes taxes & fees
12 Jun - 13 Jun
Aston Kaanapali Shores
Hilton Vacation Club Ka'anapali Beach Maui
4.0 star property
8.8 out of 10, Excellent, (1014)
"Lovely room with ocean view "
The price is NZ$531
includes taxes & fees
2 Jul - 3 Jul
Hilton Vacation Club Ka'anapali Beach Maui
Kahana Beach Vacation Club
3.0 star property
8.4 out of 10, Very good, (546)
"My daughter and I had an amazing time here celebrating her master's degree. We booked a 1 BR and are so glad we did. The condo was HUGE. The bedroom was x-large, as well as the living are. Both with a large TV in each. We also had two full bathrooms (one with a tub and the other with a full size shower). The kitchen had everything you'd need to cook meals. We were pleasantly surprised with all the cooking tools and gadgets. Being recently renovated, everything was brand new. The only thing...
Kahana Beach Vacation Club
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Kalaupapa holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Kalaupapa. 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 Kalaupapa. 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 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 holiday 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 Kalaupapa short-term rentals, that won’t be hard to do.

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 are some of the best holiday rentals that Kalaupapa has to offer?

The #1 Luxury OCEAN FRONT Mansion! Sleeps 32: This holiday home rental outside of Kalaupapa is located on the beach, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 11 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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.

Recent reviews of Kalaupapa properties
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