Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenitiesFrom $526/night · Sleeps 10
Upcountry Maui with Paniolo Roots
Makawao Vacation Rentals
Makawao Vacation Rentals – Upcountry Charm and Mountain Serenity
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.
Why Choose Makawao?
- Cooler climate and mountain air
- Quiet, non-touristy Upcountry charm
- Proximity to Haleakala Crater, Kula, and Pukalani
- Charming town center with galleries, cafés, and boutiques
Key Features and Amenities of Makawao Rentals
- Cozy cottages and custom homes with lanais and gardens
- Full kitchens, high-speed Wi-Fi, and scenic views
- Close access to hiking trails and nature preserves
- Right for stargazing and sunrise trips to Haleakala
Who It's Ideal For
- Nature lovers and hikers
- Artists, writers, and remote workers
- Couples seeking peace and privacy
- Travelers wanting to explore beyond the beach
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
Makawao Vacation Rentals Listings
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Makawao Vacation Rentals Map
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenitiesFrom $526/night · Sleeps 10
Luxury Upcountry retreat with breathtaking views!From $320/night · Sleeps 2
Pualani Hale: Upcountry Maui Villa with Breathtaking ViewsFrom $577/night · Sleeps 6
Relaxing Hawaiian Suite for a Exiting Getaway in the Upcountry of Maui!From $550/night · Sleeps 2
Spacious Hawaiian Cottage Suite in the Upcountry of Maui!From $550/night · Sleeps 2
Spacious Hawaiian Suite for a Romatic Getaway in the Upcountry of Maui!From $550/night · Sleeps 2
Adorable 1930's Gingerbread House....Permitted!From $316/night · Sleeps 2
Upcountry Short Term Rental Home with Ocean and Mt Views, Close to Makawao Town.From $371/night · Sleeps 6
Hale Aku Bed and BreakfastFrom $197/night · Sleeps 2
Quiet 1-bd cottage retreat with sleeping loft & work spaceFrom $199/night · Sleeps 4
Historic 5-Bedroom Home in Upcountry MauiFrom $1,295/night · Sleeps 12
From $526/night
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
Makawao, Hawaii
★★★★★ 10.0/10 · 250 reviews
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 $320/night
Luxury Upcountry retreat with breathtaking views!
Makawao, Hawaii
★★★★★ 10.0/10 · 101 reviews
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 $577/night
Pualani Hale: Upcountry Maui Villa with Breathtaking Views
Makawao, Hawaii
★★★★★ 10.0/10 · 55 reviews
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 $550/night
Relaxing Hawaiian Suite for a Exiting Getaway in the Upcountry of Maui!
Makawao, Hawaii
★★★★★ 10.0/10 · 26 reviews
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 $550/night
Spacious Hawaiian Cottage Suite in the Upcountry of Maui!
makawao, Hawaii
★★★★★ 10.0/10 · 9 reviews
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 $550/night
Spacious Hawaiian Suite for a Romatic Getaway in the Upcountry of Maui!
makawao, Hawaii
★★★★★ 10.0/10 · 7 reviews
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 $316/night
Adorable 1930's Gingerbread House....Permitted!
Makawao, Hawaii
★★★★★ 9.8/10 · 13 reviews
This renovated and adorable "Gingerbread House" is a studio cottage nestled amongst beautiful trees and tropical flowers and an organic farm growing...
From $371/night
Upcountry Short Term Rental Home with Ocean and Mt Views, Close to Makawao Town.
Makawao, Hawaii
★★★★★ 9.4/10 · 98 reviews
Please note, this is a permitted vacation rental property. Maui County Permit: STMP 2016/0002, Hawaii Tax Numbers: TA-042-382-9504-01,...
From $197/night
Hale Aku Bed and Breakfast
Makawao, Hawaii
Make yourself at home in this 1-bedroom Makawao apartment. The space features a queen bed that promises restful nights and a soothing bathroom...
From $199/night
Quiet 1-bd cottage retreat with sleeping loft & work space
Makawao, Hawaii
Quiet, secluded cottage with 2 private decks. Equipped with everything you need for a weekend escape or longer retreat. The cottage has outdoor &...
From $1,295/night
Historic 5-Bedroom Home in Upcountry Maui
Makawao, Hawaii
Located in Makawao, enjoy what this 5-bedroom/5 Bath house has to offer. The perfect retreat features three queen beds, one king bed, and three twin...