Vacation rentals in Lanai

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Top-rated vacation rentals in Lanai

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Top guest favorite
A group of alpacas, varying in color and patterns, stands along a fence in a lush green pasture. Their calm expressions reflect the peaceful environment, with rolling hills and trees visible in the background, creating a serene rural setting.
Guesthouse in Kula
4.98 out of 5 average rating, 234 reviews

Upcountry Alpaca, Llama, and Rabbit working farm

Experience Maui's first working fiber farm, home to Alpacas, Llamas, and Angora rabbits. Sitting at 3300 ft above sea level, Cottontail Farm enjoys perfect weather days and crisp, cool nights. The cooler temperatures are perfect for our wool producing animals that graze just outside your cottage in the back yard. Our alpacas and llamas are quiet observers but also provide plenty of entertainment of their own. Our group of Angora rabbits can be seen out the window hopping around their enclosures.

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 City
4.96 out of 5 average rating, 108 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 charming green cottage is surrounded by lush foliage, featuring a wooden deck with steps leading to the entrance. Large windows reflect the evening light, revealing a cozy interior. Bright blue outdoor chairs are positioned for relaxation amidst the tranquil tropical setting.
Home in Maui
4.97 out of 5 average rating, 246 reviews

Private Hot Tub + Pool Access + AC - Star Lookout

Dreaming of the perfect jungle honeymoon hideaway or retreat? Set amidst a mature coconut grove, (with your own hammock) this private cottage puts you in a romantic world of your own. We have that 'away-from-it-all' feeling but it's only a 20 minute drive to beaches and fabulous restaurants! A perfect romantic hideaway or artist's retreat! ☞ ★Jump Start to The to the Road to Hana! ✔ ☞ ★NEW COLD CENTRAL AC ✔ ★Private Hot Tub ✔ ★Swimming Pool ✔ ★King Bed ✔ ★Sunrise View ✔ ★Outdoor Shower ✔

Guest favorite
A spacious living area provides comfortable seating with tropical-patterned furniture, complemented by large windows offering ocean views. Natural light fills the room, which features a ceiling fan and a wall-mounted television, enhancing the relaxed atmosphere.
Cottage in Molokai
4.95 out of 5 average rating, 111 reviews

Oceanside 2-Bedroom 2-Bath Cottage, Stunning Views

Aloha, relax & enjoy stunning sunset views of the Pacific Ocean, Kepuhi Beach, and Kaiaka Rock from this private two-bedroom, two-bathroom, oceanfront cottage with a large covered lanai. This No Smoking two-Level 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 and relax. You will experience colorful sunsets, breezes, tropical birds, beaches, and whales in the winter.

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 City
4.85 out of 5 average rating, 333 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 charming cottage is nestled among lush tropical foliage, illuminated by warm lights from within. The peaked roof and extensive windows create an inviting atmosphere, while a spacious deck offers a glimpse of the surrounding nature, enhancing a serene setting under the dusk sky.
Home in Makawao
4.99 out of 5 average rating, 143 reviews

Private Luxurious Cottage

This marvelous accommodation is for the nature-lover who enjoys luxury. It boasts a lovely deck which looks out onto majestic tall trees and lush green foliage with a romantic soaking tub for two. Centered in the room is a custom-made king-size bed fashioned from cherry wood and adorned with luxurious bedding. There is full kitchen and dining area with views for a tranquil place to share a meal. This is true Hawaiian style where you can enjoy comfortable, elegant and laid-back island living.

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 Lahaina
4.95 out of 5 average rating, 168 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
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.
Apartment in Maunaloa
4.95 out of 5 average rating, 114 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!

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 Maunaloa
4.98 out of 5 average rating, 260 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 favorite
Home in Kihei
4.96 out of 5 average rating, 442 reviews

Stunning ocean view, heated pool at home by Wailea

Ocean, sunset views, unique home reminiscent of a Victorian villa with heated private pool for guests in the villa, tropical gardens. Home renovated and maintained by designer. Cal King in main, second has twin beds. Pac n play and high chair are available. Open plan living with dining and relaxing on the lanai. Keawakapu beach, Wailea shops and restaurants 5 minutes drive. Your private view retreat. #BBMK 2016/0003

Top guest favorite
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 City
4.89 out of 5 average rating, 392 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.

Top guest favorite
An outdoor deck is surrounded by lush greenery, featuring wooden flooring and multiple seating options. Two wicker chairs and a low table are positioned for relaxation, while a central fire pit adds a gathering point. Landscape elements create a serene environment for outdoor enjoyment.
Guest suite in Kula
5 out of 5 average rating, 286 reviews

Kula Jacaranda Studio on the Slopes of Haleakala

Kula Jacaranda studio is reached by a treehouse walkway. Your private covered deck offers a place to dine and watch the sunset . The shared barbecue area offers a place to prep your own meals. We provide coffee, tea, oil, vinegar and salt. The luxurious walk-in shower offers double shower heads and benches. With years as AirBnb super hosts, we've got everything you need.

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