Makawao Vacation Rentals

Makawao is an artistic Upcountry Maui town offering peaceful vacation rentals in cottages, cabins, and homes with mountain views, cool breezes, and access to hiking, Haleakala, and local culture.

Makawao is a charming Upcountry town on the slopes of Haleakala, known for its paniolo (Hawaiian cowboy) heritage, vibrant arts scene, and peaceful mountain setting. Vacation rentals in Makawao include rustic cottages, plantation-style homes, and farm stays - ideal for travelers seeking a quieter, more authentic Maui experience away from the resort crowds. With cool breezes and wide-open views, Makawao offers a refreshing retreat from the coast.

Guests can explore the town's art galleries, local shops, and cafés, or venture into nearby forests and hiking trails. Makawao is also just a short drive from Haleakala National Park, the towns of Kula and Pukalani, and other Upcountry attractions. Whether you're interested in stargazing, horseback riding, or simply relaxing in a rural setting, Makawao delivers a unique and memorable stay. Take your time, breathe in the mountain air, and browse below to find the perfect Makawao rental for your Upcountry escape.

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Spacious Hawaiian Cottage Suite in the Upcountry of Maui!

Spacious Hawaiian Cottage Suite in the Upcountry of Maui!

This very spacious ocean and pool view cottage has everything you need to truly relax and
enjoy the serenity of Maui. Designed in a vintage Hawaiian theme with a modern twist, this
room offers a unique tribute to the great Hawaiian Surfer, Duke Kahanamoku.

1 bedroom
1 bathroom
Sleeps 2

from $501

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Charming Country Cottage with WiFi and Smart TV in Kula!!!

Charming Country Cottage with WiFi and Smart TV in Kula!!!

Stay comfortably in lower Kula at this 1-bedroom cottage. Located in lower Kula, this property is situated on a small 2-acre organic fruit orchard. Enjoy views of Haleakala, Maui’s Central Valley, West Maui mountains, Maalaea Harbor, and parts of North Kihei as you walk around the orchard.

1 bedroom
1 bathroom
Sleeps 3

from $350

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Charming 2-bedroom cottage in Kula with AC, WiFi. Relax and unwind

Charming 2-bedroom cottage in Kula with AC, WiFi. Relax and unwind

Located in lower Kula, this cottage is a dream. It is situated on a small 2+ acres organic fruit orchard with 6 varieties of avocados, 28 varieties of citrus, with other exotics like soursop, lychee and longan. There are 2 king beds in the cozy bedrooms and a living room with a very comfortable queen sofa bed, this retreat is perfect for small groups or families.

2 bedroom
1 bathroom
Sleeps 6

from $588

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Luxury Upcountry retreat with breathtaking views!

Luxury Upcountry retreat with breathtaking views!

Permits
BBMP2019/0006 & SUP2 2019/0003
GE-081-730-0480-01 & TA-081-730-0480-01
This is a BnB not a STRH
Owners live on property.

Aloha, sorry but at this time we are not hosting to families with children younger than 16. Mahalo.

1 bedroom
1 bathroom
Sleeps 2

from $601

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Historic Upcountry Ranch Home

PERMITS: SUP2 2019/0015 and STMP T2019/0002

MAUI’S VRBOS ARE NOW OPEN TO TRAVELERS FROM THE MAINLAND AND ELSEWHERE. gov.

WE PROVIDE:
1. ENHANCED CLEANING PROCEDURES BETWEEN GUESTS
2.

3 bedroom
2 bathroom
Sleeps 6

from $639

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Upcountry Single Level Private 3 Bedroom Home in Marvelous Kula!!!

Upcountry Single Level Private 3 Bedroom Home in Marvelous Kula!!!

Experience upcountry Kula like a local in this enchanting 3-bedroom single level home. With 2 king beds and 1 queen bed, our organically tended fruit orchard offers a delightful stay for guests.

Situated in one of the most sought-out upcountry neighborhoods, this property is situated in lower Kula on a small 2-acre family farm/fruit orchard.

3 bedroom
1 bathroom
Sleeps 8

from $720

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Ocean View Cabin located on Organic Coffee Farm with Hiking Trails

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.

1 bedroom
1 bathroom
Sleeps 4

from $442

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Relaxing Hawaiian Suite for a Exiting Getaway in the Upcountry of Maui!

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.

1 bedroom
1 bathroom
Sleeps 2

from $383

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Spacious Hawaiian Suite for a Romatic Getaway in the Upcountry of Maui!

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 room to explore and cozy up on the lanai at night.

1 bedroom
1 bathroom
Sleeps 2

from $442

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Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

Our Maui home is permitted with the County of Maui #STMP 2013-0001.
The upstairs has a master bedroom with a California King mattress with adjoining bathroom having a Jacuzzi tub separate from shower. The secondary bedroom also has a California King mattress with an adjoining secondary 3/4 bath.

4 bedroom
3 bathroom
Sleeps 10

from $751

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Beautifully Appointed 2-Bedroom Home in Upcountry Kula with AC, WiFi

Beautifully Appointed 2-Bedroom Home in Upcountry Kula with AC, WiFi

Escape to this marvelous modern country home in picturesque Kula. This charming property features 2 cozy bedrooms with a king and queen beds, 2 lovely bathrooms with a bathtub and shower, and an additional living room space with a queen sofa bed.

2 bedroom
2 bathroom
Sleeps 6

from $682

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Luxury Upcountry Villa with breathtaking views

Luxury Upcountry Villa with breathtaking views

Aloha, sorry but at this time we are not hosting to families with children younger than 13. Mahalo.

Permits
BBMP2019/0006 & SUP2 2019/0003
GE-081-730-0480-01 & TA-081-730-0480-01
This is a BnB not a STRH
Owners live on property.

3 bedroom
2 bathroom
Sleeps 6

from $942

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Adorable 1930's Gingerbread House....Permitted!

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 flowers.

1 bedroom
1 bathroom
Sleeps 2

from $591

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Up Country spacious Newly remodeled kitchen close to beach, airport, UpCountry

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.

3 bedroom
1 bathroom
Sleeps 6

from $460

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Upcountry Short Term Rental Home with Ocean and Mt Views, Close to Makawao Town.

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) 2-4-007:017

Welcome to the perfect location!

3 bedroom
2 bathroom
Sleeps 6

from $412

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Beautifully Appointed 2-bedroom cottage in Lower Kula with AC, WiFi, & Smart TV

Beautifully Appointed 2-bedroom cottage in Lower Kula with AC, WiFi, & Smart TV

This 2-bedroom cottage is perfect for your escape to Makawao. Nestled in a tranquil setting, this nice property features 2 king beds, a cozy living room with a sofa bed, and a bathroom with a bidet and shower. With amenities like heating, cooling, SmartTV, WiFi, washer and dryer, your stay here will be pleasant and worry-free.

2 bedroom
1 bathroom
Sleeps 6

from $564

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Charming 4-Bedroom Cottage with AC, Smart TVs, and WiFi in Lower Kula

Charming 4-Bedroom Cottage with AC, Smart TVs, and WiFi in Lower Kula

Escape to this wonderful cottage in picturesque Kula. This cozy retreat features 4 king bedrooms, 2 bathrooms with showers, and 2 additional living spaces with queen beds. Guests can enjoy the convenience of amenities like AC, WiFi, Smart TVs, Washer and Dryer, etc.

4 bedroom
2 bathroom
Sleeps 12

from $1,078

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