Vacation rentals in Kalaupapa

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Top-rated vacation rentals in Kalaupapa

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Guest favorite

Condo in Maunaloa

4.93 out of 5 average rating, 103 reviews

Beach Condo on Molokai

Unit is located within an attractive condominium complex on the island’s northwest shore called Paniolo Hale, which translates “Cowboy House” in Hawaiian. The units all have wrap-around, screened-in porches or lanais. When the French doors on the living room are open, the living space expands to include this semi-enclosed area effectively blurring the boundaries between interior and exterior space. It’s a great place to eat meals, read, overlook the ocean, or even sleep as a cool breeze blows and waves break gently in the distance. Unit is a 5-minute walk to Kepuhi Beach (which it overlooks) and a 10-minute walk to Makehorse Beach. Although the condominium complex dates back to 1980, the bathroom and kitchen have recently been renovated. Unit amenities include: Washer & dryer, Stainless steel electric stove with range, Stainless steel refrigerator with filtered water and icemaker, Microwave, New dishes and glasses, Hand-sewn quilts decorating the walls.

Feb 24 – Mar 3

G$40,139 GYD per night

Guest favorite

Guesthouse in Kula

4.98 out of 5 average rating, 165 reviews

Upcountry Alpaca, Llama, and Rabbit working farm

Experience Maui's first working fiber farm, home to Alpacas, Llamas, and Angora rabbits. Sitting at 3300 ft above sea level, Cottontail Farm enjoys perfect weather days and crisp, cool nights. The cooler temperatures are perfect for our wool producing animals that graze just outside your cottage in the back yard. Our alpacas and llamas are quiet observers but also provide plenty of entertainment of their own. Our group of Angora rabbits can be seen out the window hopping around their enclosures.

Nov 29 – Dec 6

G$56,575 GYD per night

Guest favorite

Apartment in Maunaloa

4.95 out of 5 average rating, 97 reviews

Peace of Paradise at Kepuhi Beach Resort #2224

(TA#086363955201) Oceanfront condo w/views of amazing sunsets, beautiful grounds and occasional whale sightings right from our 2nd floor lanai. Updated with custom art, fresh linens, full size futon, gel topper for the king size bed, fully equipped kitchen and vanity areas. Two ceiling fans and trade winds will keep you cool and comfortable. Washer/dryer, stereo, flat screen TV, free Wi-Fi all add to your comfort. Spend idyllic days lounging at the beach/pool or off on an island adventure!

Sep 23 – 30

G$21,873 GYD per night

Superhost

Condo in Kaunakakai

5.0 out of 5 average rating, 3 reviews

Molokai Shores Beachfront Beauty

The "Friendly Isle" of Molokai is a hidden gem and a nature-lover's paradise. This condo is located alongside Hawaii’s only barrier reef, and it offers a serene escape. Settle into a Polynesian-style of living and experience the birthplace of the Hula. Explore outdoor adventures from lush hiking trails to majestic waterfalls. At sunset, meet new friends, BBQ, "talk story" and listen to Hawaiian music. It feels like being on a cruise, with a stop on a forgotten island, where time stood still.

May 28 – Jun 4

G$24,193 GYD per night

Guest favorite

Condo in Wailuku. Maui

4.88 out of 5 average rating, 233 reviews

Oceanfront Condo. Pool & Spa, 1 Br.

DIRECT OCEANFRONT. Oceanfront lawn, panoramic views, full kitchen, washer/dryer, granite counters, oceanfront lanai, all supplies, beach gear, quiet... with pool, jacuzzi/spa, BBQ, TempurPedic queen bed, desk, free wi-fi & parking. Nearby uninhabited 5 mile long beach walk & swim, Rooms have fans and windows /screens that allow cooling breezes along with one A/C unit Peaceful Maalaea neighborhood. Centrally located to explore Maui, 15 minutes to airport. Adults(2) only. No smoking.

Sep 7 – 12

G$47,595 GYD per night

Guest favorite

Home in Maunaloa

4.93 out of 5 average rating, 40 reviews

Tranquility on West Moloka'i

Kick back and relax in this calm, stylish space. This one bedroom, one bathroom condo is located in the Kanaini Kai development on West Molokai. Featuring a spacious floor plan with a full kitchen and an amazing lanai with views of the ocean and Papohaku Beach (longest white sand beach in Hawaii), this unit is just what you need to get away from it all. Cross breezes create a comfortable space to relax, and the lanai is perfect for an evening cocktail while the sun sets on a perfect day.

Aug 30 – Sep 6

G$32,593 GYD per night

Guest favorite

Apartment in Kula

4.91 out of 5 average rating, 948 reviews

Kula Treat - Upcountry Maui with Hot Tub!

Private, gracious apartment in desirable Upcountry Maui. Great home base for exploring, and a quiet country retreat for relaxing. Restaurants, food trucks and farmers’ markets nearby. Beaches, hiking and zipline within an easy drive. Perfectly located for Haleakalā Natʻl Park and day trips to Hana. A wonderful personal chef lives very close by. Dedicated to reducing single use plastics, we provide reusable water bottles for our guests! Fully permitted: BBMP 2015/0003 E komo mai! (Welcome)

Mar 16 – 23

G$32,694 GYD per night

Guest favorite

Condo in Maunaloa

4.97 out of 5 average rating, 234 reviews

Sweet Upstairs Corner Ocean View Studio on Molokai

Top floor corner unit at Kepuhi Beach Resort, on the special island of Molokai....in between Maui and Oahu! Vaulted open ceilings, spacious and airy. Completely remodeled and freshly outfitted. Close to beach and ocean-side pool, views of Kaiaka Rock, ocean surf, vivid sunsets. Fully equipped kitchen, luxurious King sized bed. Fast wireless , 40” SmartTV. Perfect setting to unplug, hike or bike the red dirt trails, explore beaches, and experience Molokai fully.

Dec 2 – 9

G$23,269 GYD per night

Guest favorite

Home in Kaunakakai

4.92 out of 5 average rating, 13 reviews

Getaway at Molokai Shores

Come relax and enjoy everything Molokai has to offer. Newly re modeled, with all new appliances, furnishings and lanai furniture. Queen bed, with fold out couch, with all new linens. Has a excellent view of the water, as well as the property. Comes complete with all you need to cook, bbq, and prepare all your meals. Well maintained pool, putting green and shuffle board with new laundry facilities on site. Located conveniently less than 5 minutes from town.

Aug 19 – 26

G$26,805 GYD per night

Guest favorite

Condo in Kaunakakai

4.94 out of 5 average rating, 180 reviews

Welcome to Hotel Molokai, Unit 102...

*This unit is located on the island of Moloka'i, not MAUI. Welcome to Moloka'i, where time slows down and you're able to relax and unwind. Hotel Moloka'i is a hotel convenient located on the outskirts of Kaunakakai town. Whether you're on Moloka'i for business or pleasure, our unit offers you a comfortable place to stay. Enjoy beaches all to yourself, go on hikes and listen to live music at Hiro's 'Ohana Grill.

Dec 16 – 23

G$22,884 GYD per night

Guest favorite

Guesthouse in Lanai City

4.88 out of 5 average rating, 338 reviews

de Brums Lanai/BBLA 2021/0001

Our one bedroom cottage rests on the hill above Lānaʻi. It offers a complete kitchen and a lovely view from the covered lanai. Shady and cool, we are a 12 minute walk into town. There is no need for either AC or heat. While we do have ceiling fans in every room, you will find Lānaʻi to have a lovely climate with tropical breezes during the day and cool, upcountry temperatures for great sleep in the evenings.

Mar 24 – 31

G$42,641 GYD per night

Guest favorite

Guest suite in Kula

4.99 out of 5 average rating, 173 reviews

Kula Jacaranda Studio on the Slopes of Haleakala

Kula Jacaranda studio is reached by a treehouse walkway. Your private covered deck offers a place to dine and watch the sunset . The shared barbecue area offers a place to prep your own meals. We provide coffee, tea, oil, vinegar and salt. The luxurious walk-in shower offers double shower heads and benches. With years as AirBnb super hosts, we've got everything you need.

Aug 5 – 12

G$59,270 GYD per night