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Holiday rentals 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, 119 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
The image captures the exterior of Villa 1615, set within a lush green landscape. Palm trees and other tropical plants surround the two-story villa, which features multiple balconies. The expansive ocean view is visible in the background, highlighting the natural beauty of the location.
Townhouse in Kapalua
4.96 out of 5 average rating, 225 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.

Top guest favourite
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.
Apartment in Lahaina
4.99 out of 5 average rating, 153 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 & located next to The Resort at Kapalua Bay (formerly Montage). 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, spas, & several bays/beaches for snorkeling, surfing, & relaxing, this is the perfect home base.

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
4.96 out of 5 average rating, 121 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
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 Lahaina
4.96 out of 5 average rating, 179 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 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.
Apartment in Lahaina
4.99 out of 5 average rating, 146 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.
Apartment 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 favourite
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.
Apartment in Molokai
4.98 out of 5 average rating, 267 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.

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.
Apartment in Molokai
4.92 out of 5 average rating, 111 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.
Guest house in Lanai
4.89 out of 5 average rating, 399 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.

Guest favourite
Flat in Molokai
4.79 out of 5 average rating, 107 reviews

Molokai sunsets

This beautiful condo is located one mile from the town of Kaunakakai at Molokai Shores, unit 134. Molokai is a laid back destination that has spectacular natural beauty. If you are looking for touristy Hawaii Molokai is not that. Instead you can relax on beaches all to your self and experience Molokai's charm. REMEMBER IT'S UNIT 134 ON THE EASTERN EDGE OF COMPLEX!

Top guest favourite
A spacious lanai offers a stunning ocean view, featuring a glass-top table with two wicker chairs. Bright blue beverages are placed on the table, while blue skies and gentle waves stretch out towards the horizon.
Apartment in Lahaina
4.99 out of 5 average rating, 122 reviews

Stylish Love Hideaway, Maui Kaanapali Oceanfront

Oceanfront studio in one of a kind boutique condominium, on world famous Kaanapali Beach. Wake up to a breathtaking oceanview, take it all in from spacious lanai, fall asleep to the sound of the ocean every night Located on the 3rd floor with close touch to ocean breeze and fantastic views, easy access to world-class beaches, restaurants, shopping and golfing

Popular amenities for Kalaupapa holiday rentals