82+ Private Villas and Holiday Rentals in Upcountry Maui |
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Upcountry Maui Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Upcountry Maui

Discover more than 82 vacation rentals available in Upcountry Maui. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Upcountry Maui.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Upcountry Maui, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Upcountry Maui. On average, places to stay near Upcountry Maui offer 685.98 ft², with nightly prices averaging ZA R9,034.

With Casai, finding and comparing holiday rentals in Upcountry Maui is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Upcountry Maui

Type Count
Vacation Homes 37
Cottages 15
Holiday Apartments 9
Villas 4

Use these Quick Filters to Find a Holiday Rental in Upcountry Maui

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Upcountry Maui.

Weather in Upcountry Maui, HI

View the weather forecast for Upcountry Maui before booking your Upcountry Maui Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Upcountry Maui, HI

Casai offers a large selection of top attractions around Upcountry Maui . Research things to do on your vacation before you visit Upcountry Maui.


Haleakala National Park
Haleakala Crater
Hana Forest Reserve
Kahikinui Forest Reserve
Bamboo Forest
Maui Spa Retreat
Ho'omana Spa Maui
Maui's Winery
Lani Kai Snorkeling
Hosmer Grove
Makaluapuna Point
Kalahaku Overlook
Maui Agricultural Research Center
Hanawi Natural Forest Reserve
Haleakala Bike Company
Hali imaile Farmer's Market
Enlighten Up Massage
Makawao Park
Puuulaula
Maunalei Arboretum

Other Places to Stay in Upcountry Maui, HI


Maui 14,272 Properties
Waiakoa 8,283 Properties
Aliʻi Kula Lavender 7,678 Properties
Kula 7,115 Properties
Sun Yat-sen Park 5,483 Properties
Kaiser Permanente 5,304 Properties
East Maui 236 Properties
Makawao 125 Properties
Pukalani 96 Properties
Haiku 85 Properties
Haiku 73 Properties
Haliimaile 25 Properties

Frequently Asked Questions About Upcountry Maui?

What are the top holiday rentals in Upcountry Maui?

With numerous options available in Upcountry Maui, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Upcountry Maui:

How many holiday rentals have private pools in Upcountry Maui?

Discover a selection of holiday rentals with private pools near Upcountry Maui with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Upcountry Maui are best for families?

If you're searching for a family-friendly holiday home in Upcountry Maui, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Upcountry Maui:

How many Casai.co.za holiday rentals are available in Upcountry Maui?

As of 2025, Casai boasts over 82 properties listed in the Upcountry Maui area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Upcountry Maui.

Nearby Neighborhood (2) 
Neighborhood Property Count
Wailea Vacation Rentals in Hawaii 1394
Haiku Vacation Rentals in Hawaii 73

People Also Ask

There are 82 Upcountry Maui, HI Holiday Rentals

Recently Booked Holiday Rentals in Upcountry Maui