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, 229 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 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, 183 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.

Top 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, 224 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, 141 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 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, 157 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 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, 432 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, 109 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.

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, 320 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, 180 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.

Top guest favorite

A vibrant sunset casts colorful hues across the sky, with layers of pink, orange, and blue blending seamlessly. The foreground features green land and trees. In the background, a cottage rests against the horizon, overlooking a serene coastal landscape.

Cottage in Kula

4.95 out of 5 average rating, 390 reviews

Oceanview Cottage away from heat! w/ County Permit

Closest to the very top 2 Maui attractions (Hana and Haleakala) and away from 100 degree heat & traffic & noises & yet still close to everything! Private Cottage on 2acres of orchard on Haleakala, 1 mile from Kula Lodge, w/ endless pano Bi-Coastal View (Double Ocean View that no other islands have) & night city view! Stunning sunset & starry nights. Approved by Maui County w/ short term rental. The permit #s are listed in the license section.

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, 540 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, 209 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!