Visiting the island of Moloka'i from O'ahu on a six-passenger propeller plane and landing right in the old leper colony of Kalaupapa was one of the coolest experiences to-date. These gorgeous #beaches lie just beneath some of the tallest sea cliffs in the world. The only way to get to Kalaupapa is on a private tour, either by small plane, donkeys or hiking.

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Compare 102 Vacation Homes in Kalaupapa with updated reviews, rates, and availability.

"We had a fantastic time! Everything was even better than we expected. We only wish we’d had a little more sunshine"

"We loved our stay in this villa! We will be back for years to come! "

AED 4,974 total

includes taxes & fees

5 May - 6 May

"My family was super excited about the place and location of the Condo but when we arrived at the property the dishwasher and ice machine in the fridge did not work and when we contacted Vacasa they said it was an owner issue. The plates and mugs and silverware were not clean from the outset so we hand washed every item before using it. We then hand washed after every meal. ( There were 6 of us so a ridiculous amount of vacation time was spent at the sink!) The condo is in an amazing location but...

"This home is absolutely beautiful and accommodated our family of 25 well! It’s a block from the beach and has a great pool for kids of all ages! We loved our stay! "

"We loved our four days at this home. It was beautiful and so close to a lovely beach. Just wish we could have stayed longer!!"

"Great location, clean, and accommodating! They had tons of beach accessories for the whole family. Would stay here again!"

"We loved our stay at the Kahana Beach House. It was a perfect size for our group of eight family and friends. We were all in Maui for our first time, and the location was great for exploring West Maui, snorkeling, and scuba. The sunsets at Kahana Point were priceless. Morning runs up to the Kapalua Coastal Trail were great to start the day. Loved this place a lot, and would definitely stay here again when on Maui."

"The Fleetwood Villa is a perfect choice for a family vacation. It is able to accommodate 6-10 people with ease. Everyone is comfortable and yet still have some privacy. This home has the best stocked kitchen we've ever seen at any rental. We are "foodies" and we lacked nothing when it came to dishes, pans, or even spices! We even found Birthday decorations for our Daughter in law's Birthday while we were there! The hosts responded quickly to any questions we had.The ONLY downside was while there...

"Quiet and family friendly! "

"Cute, clean and well stocked for a great stay. The rental was very comfortable and in a great location."

AED 5,334 total

includes taxes & fees

29 Apr - 30 Apr

"Perfect 10-day stay with 3 generations celebrating our matriarch’s 90th birthday! Exquisite, clean property with the most perfect location.Myra, the property manager, met us on arrival and was so welcoming. It was a trip we will always remember and would love to repeat!"

"11of us stayed at this lovely place. We enjoyed every bit of it. Plenty of room for everyone to be together - or to find a quiet spot to chill. Lots of kitchen supplies to make dinner for everyone and we could all eat together at the patio table outside. After a couple lessons, we mastered the fine art of serving at ping pong. LOVED the pool! It was professionally cleaned at least twice during our 8 day stay. Property manager Myra was super responsive and helpful. Excellent beaches, easy...

"We usually stay at a property that is right on the beach and has direct access to the sand. So my husband specifically was quite apprehensive about this townhouse, and he could not have been more wrong. This property was just absolutely wonderful and had everything you could ask for.- The walk to the beach is only three to four minutes and it's super easy to make with kids. The beach is the best accessible swimmable beach we have ever been to in Hawaii, and we have been to quite a few.- The...

"Great property, lots of space and large lanai, well equipped, close to several beautiful beaches. Very quiet and relaxing. Bit of a drive to any amenities. "

"Overall terrific. I didn’t give 5 stars because the property was a bit janky (one slider was broken, the kitchen screen door barely could move so we left it open all day), TV remotes didn’t work (buttons to change channels would toggle)….but really - very minor gripes when considering how easy everything was and communication with the property management. We were happy to stay here and truly enjoyed our time! It was comfy and clean! (No dead cockroaches!!) "

"We enjoyed this great condo. Only complaint? Weird random steps everywhere that you will stub your feet on in the night. The porch was amazing. "

"We loved this home. It was beautiful and had everything one needs in a holiday home. Our family of six did not feel crowded at all. It is within walking distance to a good beach and within 10 minutes to Fleming or Slaughterhouse beaches. There is also the Whaler's Village with shops, good dining and beaches about 15 minutes driving away. The host was very responsive. My only suggestion is that the VRBO place coordinates for the property in the directions. GPS took us to the property next door....

"The screened in wrap around lanai was wonderful as was the open air concept living room. This condo complex has well established gardens, and is located a short walk from some of the beautiful beaches on the west end of Molokai. "

"We loved the condo - it's a 2 minute walk to Napili Beach and has a private and lovely back deck for grilling and hanging out."

"Great condo with a great view. Perfect spot for a getaway without the kids. Unit was in great condition and it’s clear the owners take good care of it and ensure it’s up to date. Views from the lanai were perfect for whale watching. Complex grounds and landscaping are beautiful and create a great Hawaiian feel. We enjoyed our stay in this unit and would definitely come back."

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Other property types in Kalaupapa

2 outdoor pools, pool umbrellas, sun loungers

"This property is perfect for families - they do need to upgrade the suites with more accommodating flooring than carpet that’s been there for many years. Pools are fabulous - the bigger pool could be a little warmer given the breezes you get there. We loved the pool by the beach more for that reason - perfect temperature. People were kind, it was great to walk around and down to other hotels. Walked back and forth to Duke’s easily! "

AED 1,176 total

includes taxes & fees

30 Apr - 1 May

Condo, Multiple Beds (Sands of Kahana 354) | Interior

"Great value resort. Beach is right in front of you, only gripe would be parking was a bit crowded. Most nights had to find parking at the sister resort up the street. "