Makawao Vacation Rentals – Upcountry Charm and Mountain Serenity
Makawao vacation rentals offer peaceful stays in Maui's Upcountry, featuring cottages, homes, and farm retreats with sweeping views, cooler temperatures, and close access to Haleakala and artistic town life.
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 perfect 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
- Perfect 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 unwind 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 retreat in Maui's highlands.
Spacious Hawaiian Cottage Suite in the Upcountry of Maui!
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 theme with a modern twist, thisroom offers a unique tribute to the great Hawaiian Surfer, Duke Kahanamoku. The cottage...
Luxury Upcountry retreat with breathtaking views!
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 time we are not hosting to families with children younger than 12 Mahalo.This is a NO SMOKING property. Mahalo. Our...
Historic Upcountry Ranch Home
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 TO travel.hawaii.gov. WE PROVIDE: 1. ENHANCED CLEANING PROCEDURES BETWEEN GUESTS 2. HAND SANITIZER AND DISINFECTING...
Ocean View Cabin located on Organic Coffee Farm with Hiking Trails
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 riding, art school, dining and Haleakala National Park. Just an eight to ten minute drive to white sand beaches.This...
Relaxing Hawaiian Suite for a Exiting Getaway in the Upcountry of Maui!
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 your cup of coffee. Though this is our economy suite it is spacious and has all the comforts and amenities. Designed in a...
Spacious Hawaiian Suite for a Romatic Getaway in the Upcountry of Maui!
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 can be seen. This suite was named Hoku, meaning star in Hawaiian. You will find all sorts of star gazing tools in this...
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
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 separate from shower. The secondary bedroom also has a California King mattress with a 3/4 bath. The kitchen has all amenities...
Pualani Hale: Upcountry Maui Villa with Breathtaking Views
Aloha, sorry but at this time we are not hosting to families with children younger than 12 Mahalo.PermitsBBMP2019/0006 & SUP2 2019/0003GE-081-730-0480-01 & TA-081-730-0480-01This is a BnB not a STRHOwners live on property.We encourage you to respectfully enjoy our...
Adorable 1930's Gingerbread House....Permitted!
This renovated and adorable "Gingerbread House" is a studio cottage nestled amongst beautiful trees and tropical flowers and an organic farm growing Turmeric, Ginger, Papaya, Tangerines, Avocado, Oranges, Lemons, Grapefruit, Macadamia Nuts, Lychee, coffee and tropical...
Up Country spacious Newly remodeled kitchen close to beach, airport, UpCountry
Our open beamed 3 bedroom 2 bath home is surrounded by trees with windows full of light and airiness to let the trade winds blow. Conveniently near Haleakala highway, shopping, beaches, airport with a Maui country lifestyle. Sleeps six comfortably. Open kitchen, dining...
Upcountry Short Term Rental Home with Ocean and Mt Views, Close to Makawao Town.
Please note, this is a permitted vacation rental property. Maui County Permit: STMP 2016/0002, Hawaii Tax Numbers: TA-042-382-9504-01, GE-042-382-9504-01. Maui County Tax Number: TA-042-382-9504-01, Maui County TMK: (2) 2-4-007:017Welcome to the perfect location! This...