Vacation rentals in Haleakalā

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.

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 ✔

Oceanview Cottage away from heat! w/ County Permit

Closest Airbnb to Haleakala National Park & Road To Hana. Away from 100 degree heat & traffic & yet still close to food & market! Private Cottage on 2acres of orchard on Haleakala, w/ endless pano Bi-Coastal View (Double Ocean View that no other islands have) & night city view! Stunning sunset & starry nights. Two master suites with ensuite Full Baths. For past guests whom love this home, this AirBnB ends on 12/31/26. Hawaii Supreme Court ruled no more short term rental in agriculture lands.

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.

Kula Jewel - Pool, Hot Tub & Awesome Views!

Pamela has been hosting two fully permitted listings for the last 11 years with over 1,000 five star reviews. BUT this one, Kula Jewel, burned to the ground in the Maui wildfires in 2023. We have recently completed building the NEW Jewel, and it is GORGEOUS! We just had our first guests stay, and this was their review: "Pamela’s place is extraordinary! The views are stunning! The design and decor are fabulous in every detail! I’ve stayed in many Air B&Bs; I give her place my highest rating!"

Ocean View - Private Cabin

NOTE: Many oceanfront condominiums are currently under threat of a phase-out. Farm stays are a "Permissible Use" on agricultural bona fide farms by State of Hawai'i law. Be assured your reservation here will be safe from government interference. Located on a working coffee plantation and food forest, this restored cabin is private but close to lots of upcountry activities. Kitchen, ocean view, open concept, great lanai spaces, plenty of off-street parking, access to private hiking trails.

Adorable Gingerbread House Farm Stay, Makawao

This LEGALLY PERMITTED Farm Stay has the lush beauty and privacy,, without the drive to Hana! Only 15-20 minutes to the airport, 10 minutes to beaches, 2 minutes to restaurants and shops...on a private gated property with organic nursery. Seasonal stream in the back yard. Simply BEAUTIFUL! We gave 8.5 acres of diversified farm-fruit, water lilies, 10,000 sq ft greenhouse) Comes with a FREE FARM TOUR and/or LABYRINTH WALK with every booking! Permit Number STMP 2015 / 0001 SUP2 2013 / 0013

The Farm Cottage -At Olamana Organics

The farm cottage is set at the top of our 5 acre exotic fruit farm. Enjoy your stay by touring the property and relaxing in our cozy home away from home. The cottage is equipt with everything you'll need without the clutter. From the living room, enjoy a view of the ocean, fruit trees, and tropical flowers. Listen to the birds chirp in the morning, and watch the sky turn colors as the sun sets. Our accommodations are licensed with the State of Hawaii. Our license number is BBHA 2020/0001

Romantic Hamoa Bay Bungalow

The Hamoa Bay Bungalow is Hana Maui's most elegant vacation hide-away. Balinese inspired, private, with ocean views, secluded and romantic. Just beyond sleepy Hana Town... this property is tucked in amongst lush ferns, banana trees, bamboo, colorful heliconias, fragrant ginger, papaya, century old trees, and manicured gardens. Enjoy sea views from each verandah. Listen to only the sounds of the birds, the geckos chirping, and the stones rolling in the surf at night.

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

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.

Rustic Upcountry retreat with breathtaking views!

Maui County Permits BBMP2019/0006 & SUP2 2019/0003 This is a BnB not a STRH Owners live on property At this time we are hosting to guests 12 or older. This property is terraced so not optimal for young children. This is a non smoking property. No smoking is allowed. Use of the pool, hot tub and dry sauna are private when reserved with our private calendar. Mahalo!