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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 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.
Guesthouse in Kula
4.98 out of 5 average rating, 243 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 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.
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 favorite
A clear blue pool is surrounded by palm trees, creating a relaxing atmosphere. Lounge chairs are positioned along the deck, offering spots for sunbathing. Umbrellas provide shade for outdoor dining tables nearby, all with a scenic view of the ocean in the background.
Condo in Wailea
4.95 out of 5 average rating, 218 reviews

Maui's Best - Wailea Ekahi 47A

Ekahi says it all. Don't come all the way to Maui to stay in a bargain space. Unit 47A is a one bedroom (with sleeper sofa), two-bath renovated on the ground floor. This means a larger lanai than upper units. It also means that when you step off that lanai, you step onto A LOT of grass. Our condo is a 5-minute (barefoot) walk to the most wonderful of all Maui beaches; a ten-minute walk to the shops at Wailea. Restaurants nearby. Convenient yet without the road noise.2067153903 Privacy and peace.

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, 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.

Superhost
Home in Hana
4.79 out of 5 average rating, 445 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!

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, 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

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, 1,159 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 favorite
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 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, 194 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 private lanai features a table and two chairs overlooking the tranquil ocean. The expansive view includes gentle waves and the horizon, with a backdrop of serene clouds against a bright blue sky.
Condo in Lahaina
4.99 out of 5 average rating, 209 reviews

Direct Ocean front studio w ocean is ur back yard!

This is a hotel-zoned condo. It will not be affected by potential upcoming county regulations. Book with confidence!! Thank you for considering my direct ocean front studio condo in Kahana, my condo is located minutes outside of Lahaina , Kaanapali , Napili and Kapalua. You'll find the ocean view from my lanai/ room to be breathtaking and serene. This is truly an hidden gem on Maui.

Top guest favorite
Guest suite in Kula
4.99 out of 5 average rating, 300 reviews

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.

Guest favorite
Bungalow in Hana
4.91 out of 5 average rating, 204 reviews

Ala Aina 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