
Holiday rentals in Kaupo
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Top-rated holiday rentals in Kaupo
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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.

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.

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.

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.

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

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.

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

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

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)

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

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.

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
Other great holiday rentals in Kaupo

Tropical Escape to Wailea with Stunning Oceanview

Cliff House w/ Ocean View Haiku, Maui Road to Hana

Peaceful Hideaway to Begin All Your Maui Journeys

Home Hana Hale $415. per night for 6 people

Kihei Maui Getaway

Jasmine at Ekena

*Newly Refurnished* Coastal Condo — Paia, Maui

Cottage on tropical flower farm
Destinations to explore
- Maui
- Kamaole Beach Park II
- Kaanapali Beach
- Hapuna Beach
- Lahaina Beach
- Honolua Bay
- Kapalua Bay Beach
- Wailea Beach
- Polo Beach
- Maui Ocean Center
- Hāmoa Beach
- Ka'anapali Golf Courses
- Old Lahaina Luau
- Ulua Beach
- Black Rock Beach
- Big Beach
- Whalers Village
- Haleakala National Park
- Spencer Beach Park
- Maui Vista Condominium
- Kahana Beach
- Maui Arts & Cultural Center
- Maui Sunset
- Kihei Kai Nani




