
Holiday rentals in Kalaupapa
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Top-rated holiday rentals in Kalaupapa
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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
4.97 out of 5 average rating, 126 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.
4.99 out of 5 average rating, 134 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.
4.95 out of 5 average rating, 128 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.
4.95 out of 5 average rating, 182 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.
4.99 out of 5 average rating, 160 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.
4.94 out of 5 average rating, 113 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.
4.97 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
4.92 out of 5 average rating, 120 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.
4.89 out of 5 average rating, 408 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!
4.8 out of 5 average rating, 112 reviews
Kaanapali Fairway Villa 3BR/3BA.
Welcome to this Kaanapali Golf course 3 bedroom 3 bath bed and breakfast. Permit number BBWMT 2021/0003-159 Halelo. This beautiful Mediterranean home is conveniently located on hole number 5 of the Kaanapali Golf Course with a private pool, swim up bar, and ocean view. Recently renovated with many added amenities and features, please see in description below.
4.81 out of 5 average rating, 118 reviews
Oceanfront Paradise! Sea Turtle Cove C24 Napili Pt
Spectacular Ocean & Outer Island views from your Air Conditioned condo! Enjoy snorkeling with Sea Turtles in your backyard, seasonal Whale Watching from your kitchen, and breathtaking Sunsets... Welcome to Paradise! Traveling with family or friends? Please see our other listing just few doors down: Oceanfront Oasis! Sea Turtle Cove B17 Napili Point
4.97 out of 5 average rating, 135 reviewsPopular amenities for Kalaupapa holiday rentals
Other great holiday rentals in Kalaupapa

Pau Hana Paradise Two!
5.0 out of 5 average rating, 7 reviews
Molokai Shores Beachfront Beauty
4.92 out of 5 average rating, 24 reviews
Beachfront Cottage Kepuhi Beach
4.97 out of 5 average rating, 39 reviews
Lush Molokai Island Oasis w/ Pool + Private Beach!
5.0 out of 5 average rating, 6 reviews
1BR+Loft - Mel's Hale at Molokai Shores
4.82 out of 5 average rating, 44 reviews
Getaway at Molokai Shores
4.95 out of 5 average rating, 66 reviews
Oceanfront Condo With Glorious Ocean View
5.0 out of 5 average rating, 71 reviews
Romantic Island Getaway on Beautiful Molokai
4.92 out of 5 average rating, 92 reviewsDestinations to explore
- Maui
- Kaanapali Beach
- Lanikai Beach
- Lahaina Beach
- Whalers Village
- Maui Vista Condominium
- Polo Beach
- Wailea Beach
- Honolua Bay
- Kapalua Bay Beach
- Kepuhi Beach
- Black Rock Beach
- Hanauma Bay Nature Preserve
- KOA Resort
- Old Lahaina Luau
- Ka'anapali Golf Courses
- Kihei Kai Nani
- Aston Mahana at Kaanapali
- Kamaole Beach Park II
- PacWhale Eco-Adventures
- Maui Arts & Cultural Center
- Maui Ocean Center
- Kahana Beach
- Makapuʻu Beach





