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Makawao Upcountry Town
Makawao vacation rentals sit in Upcountry Maui near galleries, ranch country, farms, Haleakala routes and cooler hillside roads. This area works well for travelers who want a town setting away from the beach resorts.
Rental Listings
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Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many...From $526/night · Sleeps 10
Luxury Upcountry retreat with breathtaking views!From $356/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 $608/night · Sleeps 6
Historic Upcountry Ranch HomeFrom $450/night · Sleeps 6
Relaxing Hawaiian Suite for a Exiting Getaway in the Upcountry...From $375/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 $381/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 $356/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 $608/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 $375/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 $381/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 &...