Explore Upcountry Maui Vacation Rentals
About Upcountry Maui Vacation Rentals
Explore more than 85 vacation rentals available in Upcountry Maui. These accommodations, including vacation homes and HawaiiVillas properties, boast excellent amenities and exceptional value, blending comfort and luxury. Enjoy spaciousness and convenience at a HawaiiVillas property in Upcountry Maui.
Looking for last-minute deals or the best available offers on cottages, condos, private villas, and large vacation homes? With HawaiiVillas in Upcountry Maui, you can effortlessly compare various options with a simple click. Whether you seek properties with swimming pools, hot tubs, pet-friendly policies, or expansive master suites with large screen TVs, you'll find vacation rentals by owner (RBOs) and other popular Airbnb-style accommodations near Upcountry Maui. The average room size in accommodations near Upcountry Maui is 583.05 ft². Prices average US $503 per night.
HawaiiVillas streamlines and secures your search for vacation rentals in Upcountry Maui, often offering savings of 30-40% compared to hotel prices. Start your search today and book with confidence.
Top Rental Accommodation Types in Upcountry Maui
| Type | Count |
|---|---|
| Vacation Homes | 41 |
| Cottages | 11 |
| Holiday Apartments | 7 |
| Villas | 6 |
Use these Quick Filters to Find a Vacation Rental in Upcountry Maui
★ Pro Tip: HawaiiVillas simplifies comparison of top listings across various online vacation rental platforms like Booking.com and others. Use the Advanced Filter feature to switch effortlessly between HawaiiVillas homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, property types, cancellation policies, prices, and more. These tools streamline the search for your 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.
Top Attractions Around Upcountry Maui, HI
HawaiiVillas offers a wide selection of top attractions nearby Upcountry Maui . Research things to do on your vacation before you visit Upcountry Maui.
Other Places to Stay in Upcountry Maui, HI
Frequently Asked Questions About Upcountry Maui?
What are the top vacation rentals in Upcountry Maui?
Currently, HawaiiVillas lists over 85 properties in the Upcountry Maui area for 2026, with more being added continuously. By consolidating listings from various websites, HawaiiVillas provides a wide selection of top properties in Upcountry Maui.
- Haleakala Cottage - private hot tub, pool access
- Rustic yet modern Upcountry retreat with breathtaking views!
- Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
- Bed and Breakfast on the Slopes of Haleakala
- PERMITTED Charming LOG HOUSE in REAL Upcountry Maui. Magical and Peaceful!
- Exceptional Upcountry Villa with breathtaking views
- Historic Upcountry Ranch Home
- Jump start The Road to Hana at The Lookout House!
- Best Location! Beachy 3 BR Home, 4 miles to Ho'okipa, Permit #STPH2015/0006
- Mahina Cottage, Mahina Cottage
How many vacation rentals have private pools in Upcountry Maui?
Discover 2 vacation rentals featuring private pools near Upcountry Maui. Highly-rated HawaiiVillas properties with swimming pool access include:
- Private Home with Pool & Fruit Trees, on the Way to Haleakala National Park!
- Maui Tropical Paradise - Vacation Home In Haiku - Pool/Spa
Which vacation homes in Upcountry Maui are best for families?
If you're searching for a family-friendly vacation residence in Upcountry Maui, explore one of these highly-rated properties, all praised for their excellent reviews among families or groups visiting Upcountry Maui:
- Garden Room Farm Stay in Haiku on Road to Hana
- Lotus Room Farm Stay in Haiku on Road to Hana
- Lumeria Maui Educational Retreat Center
How many Hawaii.Villas vacation rentals are available in Upcountry Maui?
At present, HawaiiVillas showcases more than 85 properties available in the Upcountry Maui area for 2026, with new listings added regularly. By aggregating listings from multiple sources, HawaiiVillas offers a diverse range of premier properties in Upcountry Maui.
Nearby Neighborhood (2)
| Neighborhood | Property Count |
|---|---|
| Wailea Vacation Rentals in Hawaii | 1312 |
| Haiku Vacation Rentals in Hawaii | 85 |
