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Holiday rentals in Kaupo

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Top-rated holiday rentals in Kaupo

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

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Top guest favourite
A cozy outdoor fireplace is surrounded by two woven chairs with blue cushions. The stone facade adds texture, while colorful pots with plants adorn the mantel. A lush green landscape is visible in the background, featuring a fenced area with trees.
Guest house in Kula
4.98 out of 5 average rating, 244 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 favourite
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.
Cottage in Hana
4.89 out of 5 average rating, 123 reviews

Hanapapalani - Ohana Cottage, Hana, Maui, HI

Located 10 minutes from Hana town & across the road to Waioka Pond. The elevated cottage captures the breeze passing through aromatic trees; various bird songs, with gentle air flowing 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 favourite
A lush, green landscape is framed by tropical plants, with vibrant flowers adding color throughout. The view extends to the ocean, reflecting clear blue skies. The pathway leads down through the garden, inviting exploration of the serene surroundings.
Cottage in Hana
4.89 out of 5 average rating, 193 reviews

Hana Harvest Cottage

Aloha! The Hana Harvest Cottage is the perfect place to unwind and explore the beauty of Hāna and the surrounding area. Fully renovated and re-furnished including new modern appliances, new organic cotton mattress, WiFi, and upscale modern tropical decor you will feel pampered while nestled in nature. Perched at the level of the treetops, the birds-eye view of the surrounding trees and flowers can be seen from every window and especially enjoyed from the large lanai with beautiful ocean views.

Guest favourite
Home in Hana
4.85 out of 5 average rating, 460 reviews

STHA*2017/0002 TA-061-740-4416-01 Hana Maui Hawaii

STHA 2017/0002 & TA-061-740-4416-01. The Fisher's Hana Hale is located across the street from Hana Bay & Waikoloa Beach. It is within walking distance of Hana Bay & town, Red Sand Beach, and Hana Hotel. Just a short distance down the road is Waianapanapa State Park, Koki & Hamoa beaches. The downstairs features 1 bedroom & 1 bathroom, kitchen, living area, screened in lanai w/ queen bali bed, wireless internet and a small Smart TV. The upstairs can also be booked for more space, please inquire.

Top guest favourite
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, 570 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 reverse osmosis filtered water in the outdoor kitchen sink, so there is no need to buy bottled water. We also 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

Guest favourite
A view from a covered ocean deck is captured, showcasing the tranquil waters of Hana Bay framed by palm trees. A wicker chair with colorful cushions invites relaxation as the landscape reveals a lush shoreline and distant cottage nestled among greenery.
Cottage in Hana
4.96 out of 5 average rating, 107 reviews

Hana Maui Luxe Manini Cottage

Exuding the comfort and ambiance of an authentic Hawaiian beach house and located in a coveted, secluded location, nestled oceanfront on the edge of Hana Bay, it features an open living space and a covered ocean deck with unobstructed ocean views. A one-bedroom, one-bath cottage offers indoor and outdoor living and dining areas. Listening to the sound of the waves crashing on Waikaloa Black Rock beach will be your soundtrack to accompany a front-row view of spectacular sunrises and sunsets.

Top guest favourite
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, 174 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

Guest favourite
The interior of the studio cottage showcases high cathedral ceilings with wooden beams and large windows allowing natural light to fill the space. A kitchenette with modern appliances is visible alongside a cozy seating area. Decorative elements enhance the warm ambiance created by the cedar walls.
Farm stay in Haiku
4.94 out of 5 average rating, 663 reviews

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

Top guest favourite
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.
Flat in Kula
4.92 out of 5 average rating, 1,159 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)

Guest favourite
The cottage exterior features a wooden facade with a welcoming set of steps leading to the entrance. Lush tropical plants, including vibrant foliage and flowers, surround the home, while palm trees provide a natural backdrop.
Cottage in Hana
4.98 out of 5 average rating, 463 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

Top guest favourite
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, 360 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.

Top guest favourite
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, 195 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.

Popular amenities for Kaupo holiday rentals

  1. Airbnb
  2. United States
  3. Hawaii
  4. Maui County
  5. Kaupo