Vacation rentals in Kalaupapa

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Kalaupapa

Guests agree: these stays are highly rated for location, cleanliness, and more.

%{current} / %{total}1 / 1
Top guest favorite
An open living area features a comfortable red leather sofa with decorative pillows. A dining table with wooden chairs is set nearby, and a well-equipped kitchen can be seen in the background. Natural light illuminates the space, enhancing its welcoming ambiance.
Home in Lanai
4.97 out of 5 average rating, 115 reviews

The Artists House

Full renovated 1930s plantation home w/ amenities of comfort: granite counters, dishwasher, wood floor, dryer, 2 head tiled shower, master bath w/ jet tub, outdoor shower, fenced home creating a mini oasis. Home away from home w/great amenities & fabulous Lana'i sunsets. 2 bdrms- master: king bed w/bath & outside shower access, second bdrm: queen bed, pull-out couch w queen available an. Car rental referrals w/booking. $445 INCL: 17.42% TAT & 4.166% GET tax. Permit Number STLA 2017/0002. Aloha

Top guest favorite
A lush green lawn is framed by swaying palm trees, leading toward a vibrant blue ocean. In the background, a thatched-roof structure is visible, alongside tranquil water and distant islands. The bright sky adds to the serene coastal atmosphere.
Condo in Lahaina
4.99 out of 5 average rating, 107 reviews

Ocean View Studio steps away from Napili Bay! w/AC

Beautiful ocean view, air-conditioned studio is located at Napili Shores Resort! Napili Shores is a stunning, beautifully maintained, ocean front resort that offers 2 pools, hot tub, an onsite surf and snorkel rental shop, 2 restaurants, and is steps away from both Napili Bay and Kapalua Bay. The unit is located on the 2nd floor with privacy and an ocean view, with a king size bed, 55" TV, and a full size, fully equipped kitchen. The unit also includes Tommy Bahama beach chairs for guests use.

Top guest favorite
The kitchen features modern white cabinetry with stainless steel appliances, complemented by a blue and green tiled backsplash. A spacious island with a marble countertop provides ample prep space. Natural light streams in through the window, highlighting the kitchen's inviting design.
Home in Lanai
4.85 out of 5 average rating, 344 reviews

Lanai Gem 3-Bdrm Plantation Home Near Town Square

Ideal location. Five-minute walk to Dole Park (Town Square), restaurants, movies, shops, cafe, markets, art gallery. Spacious original plantation home. Full kitchen. Refrigerator/freezer, stove/oven, washer, dryer, kitchen appliances. Free wi-fi. Much lower cost than a small hotel room. Free parking on-property. Nightly rate includes 4.712% GE tax, 10.25% TA tax, 3% MCTA tax. E.g = nightly rate $250.09 + $11.78 GE + $25.63 TA + $7.50 MCTA = $295. Lic: TA-034-244-6080-01. Permit STLA20190001.

Top guest favorite
A spacious living area is furnished with a seven-piece sectional sofa and a comfortable twin daybed. A coffee table rests on a patterned area rug. Floor-to-ceiling windows provide garden views, while a ceiling fan adds comfort to the inviting ambiance.
Condo in Kapalua
4.99 out of 5 average rating, 147 reviews

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.

Guest favorite
A large oceanfront pool area is surrounded by lush tropical landscaping and swaying palm trees. The inviting pool features a gradual entry and a spacious deck for relaxation, with the ocean visible in the background under a clear blue sky.
Cottage in Molokai
4.96 out of 5 average rating, 117 reviews

Oceanside 2-Bedroom 2-Bath Cottage, Stunning Views

Relax & enjoy stunning ocean & sunset views, Kepuhi Beach, and Kaiaka Rock from this private two-bedroom, two-bathroom, two-story oceanfront cottage with a large covered lanai. This no-smoking 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 unplug & relax. You will enjoy blue ocean & beach views, colorful sunsets, breezes, tropical birds, waves, and whales in the winter.

Top guest favorite
A lush outdoor garden area is visible, featuring vibrant green grass and tropical plants. A seating arrangement with a table and chairs can be seen under an overhang, framed by a flowering tree. The ocean glistens in the distance beneath a clear blue sky.
Townhouse in Kapalua
4.95 out of 5 average rating, 176 reviews

Amazing Kapalua ,Stay 7 nights, only pay for 6 !

Our place is close to 3 beautiful beaches, 2 spectacular golf courses, tennis garden, hiking trails, whales, zip line, shops, restaurants, pools, barbecue, and spas. You’ll love our place because of the incredible views from the outdoor garden. It is huge and we call it our living room on the lawn. You'll love the ambiance, neighborhood, people. You will love everything about the Ridge at Kapalua. Our place is good for couples, solo adventurers, business travelers, not suitable for children.

Top guest favorite
The open-concept living space features a modern kitchen with sleek cabinetry and a bar top overlooking a sunlit living area. Floor-to-ceiling windows reveal panoramic ocean views and access to a comfortable seating area, inviting relaxation in a coastal setting.
Condo in Lahaina
4.99 out of 5 average rating, 142 reviews

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.

Guest favorite
Silhouetted palm trees stand against a vibrant sky filled with pink, purple, and orange hues at sunset. The horizon meets the serene ocean, creating a tranquil atmosphere. Fluffy clouds add depth to the colorful backdrop.
Condo in Molokai
4.94 out of 5 average rating, 108 reviews

Molokai Premier Condo & Car Special Package

Kepuhi Beach Resort. Newly remodeled extra large 565 sq. ft. condo with breathtaking sunset and ocean views from the lanai. Master bedroom with a queen bed and full bath on main floor. Open bedroom with full bed, and 1/2 bath in the loft. • Fully supplied with all kitchen appliances, utensils, food storage containers, etc. • Fast WI-FI for working vacationers. • Office space niche • Large flat screen smart TV, clothes washer and dryer FREE CAR TO USE WHILE STAYING AT THE CONDO.

Top guest favorite
An inviting interior is captured from an elevated perspective, featuring a spacious bed with white linens and blue accent pillows. Warm wood floors enhance the cozy ambiance, while large windows frame outdoor views. A dining area with chairs is visible through the glass doors, complemented by soft lighting.
Condo in Molokai
4.98 out of 5 average rating, 264 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.

Top guest favorite
The living room features comfortable seating with a light-colored sectional sofa and matching ottoman. A large wall-mounted TV displays a serene beach scene. Natural light streams in through expansive glass doors, offering views of the outdoors and creating an airy atmosphere.
Condo in Kapalua
4.99 out of 5 average rating, 155 reviews

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.

Guest favorite
A balcony view showcases a table with a decorative vase holding a single flower. Lush green lawn and palm trees frame the scene, leading to a fenced-in pool area. The ocean glistens in the distance, reflecting the clear sky.
Condo in Molokai
4.92 out of 5 average rating, 107 reviews

'Ohana Naeole condo - moloka'i no ka heke

**ALOHA...before booking - our condo is located on Molokai not Maui** B326 is a one bedrm w/ loft and full bath on the 3rd floor fully furnished kitchen - dishwasher, coffeemaker, microwave, blender, crock pot, skillet, rice cooker 1 Queen size bed & 1 Full size bed & 1 full size futon bed New living room furniture, 55in QLED smart TV Board games for the kids, books - pack n play and baby chair Beach chairs, boogie boards and ice chest

Guest favorite
Apartment in Wailuku
4.92 out of 5 average rating, 269 reviews

1929 Restored 1BR Plantation Home | Walk to Town

Experience authentic Maui at The Blue Door on Church Street, a renovated 1930s plantation home in historic Wailuku. This one-bedroom villa features a King-sized Nectar bed, memory foam sleeper sofa, spa-like bath, and a fully equipped bar area. Enjoy the on-site infrared sauna and walk to cafés, restaurants, and shops. Centrally located near ʻĪao Valley, beaches, and top Maui attractions—your perfect base for adventure and relaxation.

Popular amenities for Kalaupapa vacation rentals