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Upcountry Maui with Paniolo Roots
Makawao is a laid-back town in Maui's Upcountry region, famous for its cowboy roots, art galleries, and refreshing high-elevation setting. Located on the slopes of Haleakala, this area is right for travelers seeking tranquility, cooler weather, and a touch of rural Hawaiian culture. Vacation rentals range from rustic cottages to renovated plantation homes, ideal for couples, solo adventurers, and families wanting a more local experience.
Makawao offers a refreshing alternative to Maui's coastal resorts, allowing visitors to settle in and connect with nature and culture. Whether you're watching stars from your lanai or exploring nearby farms and forests, this Upcountry destination has a unique rhythm. Browse Makawao vacation rentals below and find your personal stay in Maui's highlands.
Rental Listings
Map View
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many...From $526/night · Sleeps 10
Luxury Upcountry retreat with breathtaking views!From $395/night · Sleeps 2
Ocean View Cabin located on Organic Coffee Farm with Hiking...From $340/night · Sleeps 4
Pualani Hale: Upcountry Maui Villa with Breathtaking ViewsFrom $577/night · Sleeps 6
Historic Upcountry Ranch HomeFrom $450/night · Sleeps 6
Relaxing Hawaiian Suite for a Exiting Getaway in the Upcountry...From $450/night · Sleeps 2
Spacious Hawaiian Cottage Suite in the Upcountry of Maui!From $475/night · Sleeps 2
Spacious Hawaiian Suite for a Romatic Getaway in the Upcountry...From $425/night · Sleeps 2
Adorable 1930's Gingerbread House....Permitted!From $275/night · Sleeps 2
Upcountry Short Term Rental Home with Ocean and Mt Views,...From $375/night · Sleeps 6
Quiet 1-bd cottage retreat with sleeping loft & work spaceFrom $199/night · Sleeps 4
From $526/night
Our Maui home is quiet vacation escape. The upstairs has a master bedroom with a California King mattress with a bathroom having a Jacuzzi tub...
From $395/night
PermitsBBMP2019/0006 & SUP2 2019/0003GE-081-730-0480-01 & TA-081-730-0480-01This is a BnB not a STRHOwners live on property.Aloha, sorry but at this...
From $340/night
This is a beautiful jewel of a house. It's all one level and close to shopping, activities such as hiking, biking, zip lines, farm tours, horseback...
From $577/night
Pualani Hale is a peaceful 3-bedroom, 2-bath retreat nestled on 2.5 acres along the slopes of Haleakala, offering sweeping views of Maui's ranchlands...
From $450/night
PERMITS: SUP2 2019/0015 and STMP T2019/0002MAUI’S VRBOS ARE NOW OPEN TO TRAVELERS FROM THE MAINLAND AND ELSEWHERE. FOR LATEST INFORMATION PLEASE GO...
From $450/night
The Makani suite is named after the wonderful trade winds we receive here on Maui! Enjoy the breeze in the front lanai rocking chairs while sipping...
From $475/night
This very spacious ocean and pool view cottage has everything you need to truly relax andenjoy the serenity of Maui. Designed in a vintage Hawaiian...
From $425/night
This Hawaiian plantation style suite is one of our largest and most spacious. It is very relaxing and romantic, especially in the evening when stars...
From $275/night
This renovated and adorable "Gingerbread House" is a studio cottage nestled amongst beautiful trees and tropical flowers and an organic farm growing...
From $375/night
Please note, this is a permitted vacation rental property. Maui County Permit: STMP 2016/0002, Hawaii Tax Numbers: TA-042-382-9504-01,...
From $199/night
Quiet, secluded cottage with 2 private decks. Equipped with everything you need for a weekend escape or longer retreat. The cottage has outdoor &...
Makawao rentals are in Upcountry Maui, with cooler air, local-town character, galleries, cafes and mountain roads instead of beach access outside the door.
Rentals usually include cottages, private homes, guest suites, small inns and farm-style rentals. They vary more than condo resorts, so each property should be reviewed closely.
Makawao is in Upcountry Maui, with convenient access to Kula, Pukalani and routes toward Haleakala. Driving time depends on the exact rental location.
Yes. Makawao is higher in elevation than Maui's beach areas, so evenings can feel cooler. Visitors may want warmer layers, especially in winter.
Elevation, driveway access, parking, kitchen setup, heating, outdoor space, laundry, cell service and driving time to beaches or restaurants can shape the visit.