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Holiday rentals in Kalaupapa

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Top-rated holiday rentals in Kalaupapa

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

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Guest favourite
A serene pool area is surrounded by lush greenery and palm trees, with lounge chairs arranged nearby. Soft lighting highlights the pool and adjacent amenities, while the ocean can be glimpsed in the background under a dusky sky.
Apartment in Lahaina
4.94 out of 5 average rating, 34 reviews

Newly Renovated Kahana Sunset ocean view

Kahana Sunsets is your place for an ocean front resort. This is a ground level condo with ocean views from the patio, bedroom and living room. This condo is fully renovated and all new items with many upgrades. Enjoy the secluded beach, BBQ's (either poolside or oceanfront) all beach essentials provided. Loungers and chairs provided on the oceanfront grass to watch the whales, sunsets and rainbows. A rental agreement will emailed after booking.*Please note there is a payment processing fee charg

Guest favourite
The outdoor view features swaying palm trees against a vibrant blue ocean backdrop. A pool is situated among the lush landscaping, with lounge chairs nearby. The gentle waves are visible in the distance, contributing to the serenity of the coastal environment.
Home in Kapalua
5 out of 5 average rating, 11 reviews

Incredible Oceanviews, Spacious Kapalua Bay Villa!

Stay at Kapalua Bay Villa 16B3 for the perfect mix of luxury, breathtaking views, and unparalleled tranquility in one of Maui’s most exclusive locations. Nestled along the scenic coastline, this ocean view villa offers spacious comforts of home, a private lanai and 3 pools. An ideal unit for creating unforgettable experiences for any romantic getaway to family retreat. Relax or seek adventure, with nearby zip-lining, mountain biking, paddleboarding, surfing, fishing, snorkeling, hiking and more.

Top guest favourite
A private balcony features two comfortable chairs with blue cushions and a small table, overlooking vibrant blue ocean waters. Decorative wall art is displayed nearby, while a distant island and fluffy clouds are visible in the clear sky.
Apartment in Lahaina
4.91 out of 5 average rating, 45 reviews

Stunning Oceanfront Mahana Condo Steps from Beach

"Within minutes of arriving, we saw green sea turtles in the water and on the beach, a breathtaking sunset, and more whales breaching than we could count! Thank you for a magical time and for one of the best Airbnb experiences - we can't wait to return. Cara 2025 "It was a grand slam! Highly recommend, it’s amazing!" -Nancy 2024 "This place is 5 stars. Pura vida paradise. I would stay here for an eternity." Lacy 2024 Add my listing to your wishlist by clicking the ❤ in the upper-right corner

Guest favourite
A dining table is set with plates and utensils, positioned on a lush green lawn. Palm trees surround the area, offering a tropical ambiance with the ocean visible in the background under a partly cloudy sky.
Apartment in Lahaina
4.91 out of 5 average rating, 145 reviews

OCEAN FRONT Condo at Napili Bay, Near Kapalua!

Thank you for checking out my OCEAN FRONT condo located at the Charming Napili Shores resort. This recently renovated condo is in the high demand I building, which is the closest to the ocean in the complex. Imagine every morning you enjoy the brunch ordered from the famous Gazebo restaurant at your own Lanai right beside the ocean; Soak up the sunshine on the Napili beach steps away from the resort during the day, and come back in the evening to watch the stunning sunset in your room!

Superhost
Apartment in Lahaina
4.73 out of 5 average rating, 11 reviews

Kuleana Club #511-Oceanview -1 bd 1 ba- 2nd Floor

Located on Maui's tropical west coast, the Kuleana Club has a panoramic view of the Pacific and the lovely offshore islands of Molokai and Lanai. This unit is a 2nd floor ocean view condo, only steps to the ocean, surrounded by a plush Hawaiian garden. Enjoy swimming in our heated pool, playing tennis on our full sized court, playing shuffle board in the garden, or using our propane gas grills overlooking the ocean at sunset. Everywhere you look at the Kuleana Club is a Hawaiian paradise.

Top guest favourite
Silhouetted palm trees frame a serene ocean view at sunset. Gentle waves roll onto the shore, creating a soft mist. Two figures can be seen sitting close to the water's edge, surrounded by lush greenery, capturing a tranquil moment of nature.
Flat in Molokai
4.95 out of 5 average rating, 119 reviews

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!

Guest favourite
Flat in Kihei
4.8 out of 5 average rating, 35 reviews

Two Bd Grd Fl, AC, Wifi, Pool, Hot Tub, C105

C105 with AC is a Deluxe 2 bedroom, 2 bathroom Ground floor condo with a king size bed, two twin and a sofa bed. C105 has a garden view and faces the cool side of the property. Enjoy quick lanai access to the pool, tennis & pickleball courts & putting green. It is tiled throughout. The C105 floor plan has the largest living room and is very roomy. This apartment is very popular so book way ahead. pool area with hot tub,saunas & 5 gas grills. Tennis and pickleball courts FREE parking

Guest favourite
A hallway leads to an outdoor area with views of the turquoise ocean and swaying palm trees. The scene is framed by a solid railing, showcasing the tropical coastal environment and vibrant colors of the water, with gentle waves visible in the distance.
Apartment in Lahaina
4.89 out of 5 average rating, 338 reviews

TOP FLOOR!!!! Oceanfront, free Wi-Fi, free parking

Honokowai area. Fresh & clean island vibe on the top floor, one unit away from the end. Practically hanging over the water's edge. Beautiful views of Molokai out the screened front door, as well as Lanai off the lanai. Striking floor-ceiling mirrors capture ocean views from virtually anywhere inside. Location in building catches wonderful trade winds. Listen to the sounds of the waves, just steps away & enjoy the endless sea turtle traffic right under your nose.

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, 108 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 favourite
Flat 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.

Superhost
The kitchen features a spacious bar with four high-backed chairs, illuminated by pendant lights. Stainless steel appliances, including a side-by-side refrigerator and gas stove, are visible. Open shelving displays kitchenware and decor, while a ceiling fan is installed above for airflow.
Apartment in Molokai
4.88 out of 5 average rating, 25 reviews

Spacious Molokai Style Condo Locally Owned

Aloha folks, Breezy 1 bedroom 1 bathroom Located on ground floor Plenty of close parking Living room opens to large grassy area Swimming Pool w/ lounge chairs & umbrella tables Shore side picnic tables, bbq & propane grills Shuffle board and mini putting green (equipment provided) Coin laundromat on site (w/ coin and soap dispensers)

Superhost
Apartment in Kapalua
4.81 out of 5 average rating, 42 reviews

Molokai views, refreshed upgrades, relax comfort

Kapalua Bay Villa 11G1 sits at the front of the resort, offering stunning views of Oneloa Bay and the island of Molokai. This one-bedroom, one-and-a-half-bathroom villa is the perfect getaway for a small family or couple, with a maximum occupancy of 3 guests—2 adults and 1 child. A second child may be accommodated upon request.

Popular amenities for Kalaupapa holiday rentals