Discover a selection of 58 vacation rentals in Kalaupapa that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $75 per night, and houses and condos are popular options for a stay in Kalaupapa. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Kalaupapa
Destination guide

Kalaupapa – a gateway to the "Friendly Isle"

Perched on Hawaii's most isolated island, Kalaupapa is a laidback community surrounded by the kind of beauty that only Mother Nature could conjure up. It's wild, rugged and off the beaten track. In fact, the island claims that, by law, no building is allowed to be built taller than a palm tree. While Kauai is known for stunning scenery and Maui champions postcard-perfect beaches, Molokaʻi markets itself as the "Friendly Isle". Spend a few days exploring this slice of paradise and you'll soon understand why.

Things to do

Discover Kalaupapa National Historical Park

Kalaupapa vacation rentals put you at the doorstep of one of the most interesting reserves in the Hawaiian Islands. While it was once used as a colony for lepers, today Kalaupapa National Historical Park offers a glimpse at Hawaii's untamed wilderness. It's set on the impossibly beautiful Kalaupapa Peninsula, a remote stretch of Molokaʻi, fringed by gleaming sandy beaches and soaring sea cliffs. Visitor numbers are limited, which means you'll need to arrange tours. You can also head up to Kalaupapa Lookout. The sky-high vantage point is perched on the edge of a 1600-foot-high cliff and commands sweeping views over the Kalaupapa Peninsula and the dormant Kauhako Crater.


Get face to face with Hawaiian humpbacks in Kalaupapa

If Kalaupapa vacation rentals feel a little isolated, why not stay in Kaunakakai, Molokaʻi's biggest town? Every Saturday morning it hosts a colorful farmers market, where you can pick up everything from tropical fruit and organic veg to freshly strung lei garlands and local handicrafts. It's a great excuse to stock up and whip up your own island-inspired feasts. Kaunakakai is also a fantastic base for organizing Molokaʻi daytrips. You can make a splash with ocean kayaking and stand-up paddle boarding, get face to face with humpbacks on a whale-watching tour or soar over the island on a scenic flight.


Year-round sun in Kalaupapa

Thanks to its tropical climate, daily highs rarely drop below the 70s. This means Kalaupapa vacation rentals are ideal for year-round travel. Spring, summer and fall are great times to visit, with sunny days and breezy evenings. Most of the rain falls during the winter, though there's every chance of sunshine and it's always warm enough to swim. Winter is also prime whale-watching season, with 1000s of humpbacks migrating along the Molokaʻi coast.

Natural features

Be awed by Kalaupapa Peninsula sea cliffs

Locals boast that Molokaʻi is the most "authentic" island in the Hawaiian archipelago. Not only is it rich in native culture, but it also harbors a wonderland of remote rainforests, kaleidoscopic barrier reefs and sheer oceanside cliffs. In fact, the Kalaupapa Peninsula is so dramatic that it boasts some of the tallest sea cliffs on the planet, soaring over 2000 feet above the Pacific Ocean. It's worth noting that there's no road access to Kalaupapa vacation rentals, which means the only way in is by air, mule or foot.

How many vacation rentals are available around Kalaupapa?

Our 2021 property listings offer a large selection of 58 vacation rentals around Kalaupapa. From 2 house rentals to 56 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.