Vacation rentals in Kaupo

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Top-rated vacation rentals in Kaupo

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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, 225 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.

Guest favorite

A two-story green house is surrounded by lush tropical gardens, showcasing large windows that provide a bright interior. A spacious deck extends from the structure, offering views of the vibrant foliage and the inviting outdoor space.

Cabin in Maui

4.97 out of 5 average rating, 220 reviews

★Rainbow Lookout - PRIVATE HOT TUB+ACCESS TO POOL

This Stunning North Shore Maui hideaway is surrounded with lush fruit and flower gardens, coconut palms, banana trees, and has easy access to all there is to do on this magnificent island. Stargaze … soak in your own private hot tub with a chilled glass of wine and enjoy a once-in-a-lifetime experience. The 'real' Maui:)! ★Jump Start to The to the Road to Hana! ✔ ★New Cold Central AC ✔ ★Cliff Walk ✔ ★Ocean View✔ ★Private Hot Tub ✔ ★44 ft Swimming Pool ★King Bed ✔ ★Sunrise View✔ ★Star Gazing✔

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, 137 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

The cottage is surrounded by lush tropical vegetation with a gravel pathway leading to the entrance. A covered porch welcomes guests, framed by palm trees and vibrant plants, with the ocean visible in the background under a clear blue sky.

Cottage in Hana

4.95 out of 5 average rating, 155 reviews

Solar Cottage With Privacy & Panoramic Ocean Views

Entabeni Cottage sits above the Road to Hana overlooking the Pacific Ocean on the north shore of Maui, Hawaii. Entabeni Cottage is a fully-equipped, 830 square foot home, powered by the sun and beautifully situated on a gorgeous 6.25 acre tropical flower farm. Enjoy ocean views from your bed, kitchen, lanai (covered deck), & private yard. The Kristiansen's offer guests fresh eggs and vegetables from the garden when ready for harvest. License & Permit: BBHA 2013/0006 and SUP2 2012/0011

Top guest favorite

A bright bedroom features a queen bed with a navy blue coverlet, complemented by a decorative yellow pillow. Light streams in through the window, highlighting a wooden chest at the foot of the bed and a bedside table. A comfortable chair and a foldable stool add functionality to the space.

Apartment in Kula

4.92 out of 5 average rating, 1,102 reviews

Kula Treat - Upcountry Maui with Hot Tub!

Private, gracious apartment in desirable Upcountry Maui. Great home base for exploring, and a quiet country retreat for relaxing. Restaurants, food trucks and farmers’ markets nearby. Beaches, hiking and zipline within an easy drive. Perfectly located for Haleakalā Natʻl Park and day trips to Hana. A wonderful personal chef lives very close by. Dedicated to reducing single use plastics, we provide reusable water bottles for our guests! Fully permitted: BBMP 2015/0003 E komo mai! (Welcome)

Top guest favorite

A decorative fruit basket is displayed on a wooden table, featuring an assortment of tropical fruits including bananas, lemons, avocados, and a papaya. Bright pink hibiscus flowers and purple orchids adorn the arrangement, with a silver container visible in the background against a green landscape.

Cottage in Hana

4.99 out of 5 average rating, 427 reviews

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

Guest favorite

A charming cottage is nestled amidst lush tropical foliage, featuring a light-colored exterior with multiple windows. The elevated structure is complemented by a welcoming front porch, surrounded by vibrant palm trees and greenery.

Guesthouse in Hana

4.88 out of 5 average rating, 104 reviews

Hanapapalani-Ohana Cottage, Hana, Maui, HI

Located 10 minutes from Hana town. Literally across the road from Waioka (Venus Pool). The elevated cottage captures tropical breezes passing through aromatic trees; air flows through screen doors on all sides of the cottage. A screened breakfast nook connected to the kitchen. Ceiling fans add additional air flow to comfort on the warmest days and nights. Kitchen amenities include countertop appliances, electric range stove, full size refrigerator & an electric grill. Smart TV / Wifi.

Guest favorite

A vibrant rainbow arcs across the sky, framed by tall palm trees. Lush greenery and distant trees fill the background, enhancing the natural beauty of the surroundings. The scene conveys a sense of tranquility and connection to nature.

Farm stay in Hana

4.94 out of 5 average rating, 312 reviews

JJ’s Hāna Hale - Farm Style Cottage STHA2021/0001

Forget your worries in this spacious serene space. Private air conditioned one bedroom cottage located on a 6 acre farm that is home to many rescued animals. A second bedroom can be made available for a fee please inquire prior to booking. Have as little or as much interaction as you wish. A fully equipped kitchen with a gas stove, full bathroom, a comfy bedroom a spacious living room w Smart TV and separate dining area. Wifi is also provided. Bikes available for two.

Guest favorite

The bungalow is nestled among lush tropical foliage, featuring vibrant banana plants and oversized leaves. A two-story structure with wooden accents is visible in the background, showcasing a welcoming presence within the verdant surroundings.

Bungalow in Hana

4.95 out of 5 average rating, 177 reviews

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.

Guest favorite

A charming studio cottage with a distinctive shingle exterior is set among lush greenery. A golden retriever rests on the pathway in front, alongside large trees that provide shade. A vibrant green door invites guests into the cozy interior.

Farm stay in Makawao

4.94 out of 5 average rating, 640 reviews

Adorable Garden Gingerbread House, Makawao

Romantic hideaway! This property has the lush beauty and privacy of Hana, without the drive! 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. BEAUTIFUL! Comes with a FREE FARM TOUR and/or LABYRINTH WALK with every booking! Getting married? Renewing your vows? I can perform the ceremony for you as well....free with booking! Permit Number STMP 2015 / 0001 SUP2 2013 / 0013

Top guest favorite

A view from the outdoor seating area showcases rolling green lawns leading to a panoramic scene of the ocean and distant islands. Colorful flowers in pots and garden chairs frame the foreground, with an expansive sky filled with clouds adding texture to the landscape.

Guest suite in Kula

4.99 out of 5 average rating, 534 reviews

Charming Art Studio on a Scenic Mountain Slope

Kula Jasmine studio is reached by a bridge pathway. The shared barbecue area just steps from your studio offers a place to prep your own meals. We provide coffee, tea, oil, vinegar, salt and pepper. You can either dine on the waterfall deck or the barbecue area while you watch the sunset. With years as AirBnb super hosts, we've got everything you need. Permit # BBMP20160004

Top guest favorite

A scenic view captures the sunset over a lush landscape, with a pool reflecting the colorful sky. Tall trees frame the scene, and the distant ocean is visible beneath the dramatic clouds. The vibrant greens of the surrounding vegetation provide a serene backdrop.

Cottage in Makawao

4.99 out of 5 average rating, 206 reviews

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. Aloha, sorry but at this time we are not hosting to families with children younger than 16 at this time. 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!