Vacation rentals in Kalaupapa

4.98 out of 5 average rating, 216 reviews

Guesthouse in Kula

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.

Superhost

Cottage in Molokai

4.95 out of 5 average rating, 102 reviews

Oceanview 2-Bedroom Cottage, Stunning Views, Pool

Enjoy stunning sunset views of the Pacific Ocean, Kepuhi Beach, and Kaiaka Rock from this private two-bedroom, two-bathroom, oceanfront cottage with a large covered lanai. This No Smoking two-Level cottage is located at the Kepuhi Beach Resort, close to pristine beaches, trails, and an oceanfront pool. The cottage is a peaceful place to work online, explore or just unplug and relax. You will experience colorful sunsets, breezes, tropical birds, beaches, and breaching whales in the winter.

4.97 out of 5 average rating, 214 reviews

Cabin in Maui

★Rainbow Lookout - PRIVATE HOT TUB+ACCESS TO POOL

This Stunning North Shore Maui hideaway is surrounded with lush fruit and flower gardens, coconut palms, banana trees, and has easy access to all there is to do on this magnificent island. Stargaze … soak in your own private hot tub with a chilled glass of wine and enjoy a once-in-a-lifetime experience. The 'real' Maui:)! ★Jump Start to The to the Road to Hana! ✔ ★New Cold Central AC ✔ ★Cliff Walk ✔ ★Ocean View✔ ★Private Hot Tub ✔ ★44 ft Swimming Pool ★King Bed ✔ ★Sunrise View✔ ★Star Gazing✔

4.99 out of 5 average rating, 133 reviews

Home in Makawao

Private Luxurious Cottage

This marvelous accommodation is for the nature-lover who enjoys luxury. It boasts a lovely deck which looks out onto majestic tall trees and lush green foliage with a romantic soaking tub for two. Centered in the room is a custom-made king-size bed fashioned from cherry wood and adorned with luxurious bedding. There is full kitchen and dining area with views for a tranquil place to share a meal. This is true Hawaiian style where you can enjoy comfortable, elegant and laid-back island living.

4.99 out of 5 average rating, 122 reviews

Condo in Lahaina

NEWLY REMODELED OCEAN VIEW CONDO, STEPS FROM BEACH

Your next relaxing Lahaina escape awaits at this stunning 1-bedroom, 2-bath vacation rental condo - steps away from Kapalua Bay Beach & centrally located next to the Montage Resort. Your group of up to 6 guests will love returning to the comfort of this home, offering over 1,100 sq ft of living space. With easy access to championship golf courses, fine dining, walking/hiking paths, shopping, spas, & several bays/beaches great for snorkeling, surfing, & relaxing, this is the perfect home base.

4.99 out of 5 average rating, 125 reviews

Condo in Lahaina

Luxury Mahana 1bd/2ba-Great Views-Free Park/WiFi

Locally Owned and Operated 1BD/2BA condo with the best direct beachfront location, panoramic Ocean views, sunsets, and seasonal whale watching. The owner’s spared no expense in renovating this unit making it hand’s down one of the nicest units in all of the Mahana. Wake up to the cool tropical breeze and sounds of the shoreline just 50 feet away. Floor to ceiling windows in the living area and bedroom bring the stunning views and warm Maui sun inside while central AC keeps you cool inside.

4.95 out of 5 average rating, 112 reviews

Apartment in Molokai

Peace of Paradise at Kepuhi Beach Resort #2224

(TA#086363955201) Molokai oceanfront condo. View amazing sunsets, beautiful grounds and occasional whale sightings 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. 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!

4.98 out of 5 average rating, 253 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.

4.94 out of 5 average rating, 631 reviews

Farm stay in Haiku

Adorable Garden Gingerbread House, Makawao

Romantic hideaway! This property has the lush beauty and privacy of Hana, without the drive! Only 15-20 minutes to the airport, 10 minutes to beaches, 2 minutes to restaurants and shops...on a private gated property with organic nursery. BEAUTIFUL! Comes with a FREE FARM TOUR and/or LABYRINTH WALK with every booking! Getting married? Renewing your vows? I can perform the ceremony for you as well....free with booking! Permit Number STMP 2015 / 0001 SUP2 2013 / 0013

4.98 out of 5 average rating, 133 reviews

Condo in Lahaina

Kapalua, luxe, ocean view, beach, spa, golf/tennis

KAPALUA - Best location! Welcome to the luxuriously Kapalua Bay Villa #37B1. Bright and airy, with comfortable furniture and modern appliances. Scenic ocean view, a 5-minute walk to Kapalua Bay, Montage Resort, tennis, golf, hiking, zip-lining, amazing restaurants, and a first-class spa. Kapalua Bay Villas is a low-density community within the Kapalua Resort—a 15-minute drive to Kaanapali, and a 40-minute drive to Central Maui to explore the island.

4.93 out of 5 average rating, 224 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.

4.89 out of 5 average rating, 382 reviews

Guesthouse in Lanai City

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.

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Other great vacation rentals in Kalaupapa

4.89 out of 5 average rating, 74 reviews

Home in Molokai

Tranquility on West Moloka'i

HeidiRating, 5 stars2 months ago

You'll probably see wild turkeys, hear tons of birds, watch deer graze at night, and take in a sky full of stars. All that plus a stunning view of a beach, and lots of little walks to take. So so pretty! Plus the pool is very nice, and the condo is great! We had a very comfortable stay and will be back. Mahalo Jon!

Superhost

Home in Maui County

4.84 out of 5 average rating, 75 reviews

Cliff House with Ocean Views in Haiku, Maui jungle

IanRating, 5 stars2 months ago

This place is gorgeous! I am so glad we chose to stay here. The views were perfect. The property was amazing. The place was very comfortable and so peaceful. I would love to come back here some day.

4.92 out of 5 average rating, 38 reviews

Townhouse in Molokai

Kepuhi Hale

MattRating, 5 stars2 months ago

Great host. There were lots of beach supplies and the tropical grounds are beautiful. The couch/bed was comfortable. Short drive to all the well known beaches. The unit was quiet and the little park next door is also nice. Just a fantastic stay, all around!

4.92 out of 5 average rating, 48 reviews

Townhouse in Molokai

Aloha Getaway: Luxe Beachfront 3bdm/2bth townhouse

JadenRating, 5 stars2 months ago

Amazing place to stay with a great host that is easy to communicate with and very responsive. Great views and only a couple minute walk from a very peaceful and natural beach. Plenty to see and do around the area. I highly recommend!

4.97 out of 5 average rating, 74 reviews

Molokai Island Retreat- June is only $109 a night!

ClaireRating, 5 stars4 months ago

Cari was super responsive when we needed a last minute location change, and her space was available for same day check in. Appreciated the little touches here and there that made the stay extra enjoyable!

5 out of 5 average rating, 15 reviews

Molokai Resort with Ocean and West Maui views

IanRating, 5 stars3 months ago

We felt right at home staying here for several days in March 2025. The condo feels very modern and clean - if we were designing a beachfront condo in Hawaii it would hopefully be a lot like this! Before checking in we got a lot of helpful tips and local advice and communication was excellent the whole time. Molokai is a quiet place; there’s not tons to do and you come here to explore a bit and get away from busy-ness. There aren’t that many restaurant options and those that exist aren’t open that much so it was great to have a kitchen to make breakfasts and lunches. Like everywhere in rural Hawaii there are roosters greeting the sunrise so bring earplugs if you are a sensitive sleeper. 5/5 for this stay.

Superhost

4.68 out of 5 average rating, 19 reviews

Ocean View Loft, West Moloka'i

GeorgiaRating, 5 stars3 months ago

Molokai is an amazing island. Loved the view from our deck. We ate every meal outside. Loved it. Beautiful sunsets.