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Holiday houses in Kalaupapa

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Top-rated holiday rentals in Kalaupapa

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Top Guest favourite
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, 123 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 favourite
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 Napili-Honokowai
4.99 out of 5 average rating, 127 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 favourite
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, 354 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-079-863-9616-01. Permit STLA20190001.

Top Guest favourite
Townhouse in Kapalua
4.96 out of 5 average rating, 234 reviews

Spectacular views, prime location Kapalua, Maui.

Prime Kapalua location this stylish, romantic two-level villa offers elevated panoramic ocean views. Wake in a luxurious California King bed to stunning Pacific sunrises and fall asleep to the soothing sound of ocean waves. Relax on your private upstairs lanai or spacious patio and take in the breathtaking views. Walk to beaches, scenic trails and dining. Peaceful, magical- your perfect Maui escape. A/C on both levels and bright, airy interiors, this villa is a tranquil upscale Maui retreat.

Guest favourite
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
4.95 out of 5 average rating, 126 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 favourite
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 Kaanapali
4.99 out of 5 average rating, 155 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 favourite
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 Maunaloa
4.94 out of 5 average rating, 112 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 favourite
A spacious balcony features a simple dining table surrounded by two chairs, offering an unobstructed view of the ocean. Palm trees frame the scene, while a bottle and glass sit on the table, reflecting the bright blue sky above and the serene water below.
Apartment in Napili-Honokowai
4.97 out of 5 average rating, 101 reviews

Maui Full Oceanfront Paradise

Indulge in the ultimate Maui getaway at our full oceanfront condo. The cozy balcony beckons you to unwind and marvel at the mesmerizing sea life. Sip on your morning coffee, or relish a sunset cocktail while you watch the ocean's playful inhabitants. For those warm tropical nights, rest easy knowing that the condo is equipped with air conditioning to ensure a comfortable night's sleep. The fully stocked kitchen provides all the essentials for cooking up a delightful island feast.

Top Guest favourite
An aerial view captures the lush green landscaping surrounding the property, featuring palm trees and well-maintained rolling lawns. The ocean sparkles in various shades of blue, while nearby buildings with solar panels are visible, creating a serene atmosphere just steps from the beach.
Condo in Napili-Honokowai
4.98 out of 5 average rating, 110 reviews

Napili Bay Oceanview Resort Hideaway

Welcome to Napili Bay, Maui's hidden gem, and a favorite spot for some of the best snorkeling on Maui. Relax in the ocean breeze from your private lanai. Enjoy ocean views throughout the condo. Lush tropical landscaping, plumerias, monkeypods, and many more plant varieties throughout the property. 2nd floor studio condo, beautiful vaulted ceilings, low density property, old school Hawaiian resort. Easy access to world-class beaches, restaurants, shopping and golfing.

Top Guest favourite
Home in Wailuku
4.92 out of 5 average rating, 287 reviews

The Blue Door on Church Street | Vintage One Bedro

Stay in a restored 1929 plantation-style retreat at The Blue Door on Church Street in historic Wailuku. This private one-bedroom space features a king Helix bed, queen memory foam sleeper sofa, high ceilings, original wood details, kitchenette, rainfall shower, soaking tub, AC, fast WiFi, Smart TV, parking, and access to a shared infrared sauna. Walk to cafés, restaurants, shops, yoga, and the ʻĪao Theater, or drive minutes to ʻĪao Valley, beaches, hikes, and Maui adventures.

Guest favourite
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 Kaunakakai
4.92 out of 5 average rating, 118 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

Top Guest favourite
A set of wooden stairs ascends to a covered porch, flanked by a beige-colored cottage. A green railing provides safety, with the house number displayed prominently on the post. Lush green grass surrounds the area, and trees offer shade.
Guesthouse in Lanai
4.89 out of 5 average rating, 404 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.

Popular amenities for Kalaupapa holiday rentals