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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, 245 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 Huelo
4.97 out of 5 average rating, 241 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✔

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, 154 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.

Guest favorite
The exterior of the studio is framed by lush green foliage and colorful plants, with a two-story structure visible in the background against the blue sky. Sunlight filters through the leaves, creating a serene and inviting natural setting.
Apartment in Hana
4.88 out of 5 average rating, 466 reviews

Stay in Hana Upstairs

Beautiful studio with 1 queen bed, fridge, microwave, coffee maker, ceiling fan, full private bathroom with bathtub , wraparound covered deck and parking located in front of Unit. You'll be surrounded by trees, flowers, the sounds of the ocean and birds. The property is 2 acres of lush Hana rainforest in a perfect location. * BUGS, MOSQUITOES, ROACHES & other insects are to be EXPECTED * NO A/C * Quiet, serene, tranquil and private, yet close to the best sights Hana has to offer.

Superhost
A cozy living area features warm wood paneling and a decorative sun-shaped design on the wall. A comfortable sofa is positioned across from a sliding glass door, leading to the screened lanai. A coffee table and a bookshelf filled with books add to the inviting atmosphere.
Home in Hana
4.79 out of 5 average rating, 448 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 and within walking distance from Hana Bay and Waikoloa Beach. Just a short distance down the road is Waianapanapa State Park, Red Sand Beach, Koki and Hamoa beaches. The Upstairs unit features one bedroom and one bathroom, full kitchen, living area, screened in lanai with ping pong table, wireless Internet and basic cable TV. For larger parties you can add the downstairs for extra space. Come enjoy Hana!

Guest favorite
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, 111 reviews

Hana Maui Luxury 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 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 Haiku
4.94 out of 5 average rating, 665 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

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
4.98 out of 5 average rating, 466 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 favorite
The cottage exterior is framed by lush greenery and vibrant flowers, complemented by a decorative stone pathway leading to the entrance. A unique circular window and a red door enhance the cottage's character, while balconies offer inviting views of the surrounding landscape.
Farm stay in Haiku
4.99 out of 5 average rating, 364 reviews

Maliko Retreat

NOTE: This farm stay is not being phased out by County regulations. 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. This eclectic antique Hawaiian cottage is perched atop a scenic jungle gorge with breathtaking views in every direction. Open and breezy; attention to detail shines from every facet.

Top 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, 361 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 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, 199 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
Lush tropical greenery is visible, featuring tall palm trees swaying gently in the breeze. The vibrant landscape leads to an expansive view of the ocean, where the water meets the sky in the distance. A serene, rolling lawn invites relaxation.
Bungalow in Hana
4.91 out of 5 average rating, 210 reviews

Ala Type Ocean Vista - Hana Bed & Breakfast

Ala Aina Ocean Vista is a private ohana with its own private front and back entrances. It is situated on an old banana plantation located on an exotic, lush, tropical property. It provides guests with peace & quiet and offers gorgeous vistas of tropical trees, flowers, rolling green lawns and sweeping ocean views in the distance. Permit BBHA2013/002 SUP2-2001/0016

Popular amenities for Kaupo vacation rentals

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