A barren volcanic landscape with rugged terrain and distant mountains.

Search Holiday Rentals in Upcountry Maui

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Upcountry Maui holiday rentals

1. 2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
3.0 star property
Haiku
The price is 11.669.400 ₫
28.502.380 ₫ total
includes taxes & fees
16 Sept - 17 Sept
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

2. Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (968 reviews)
"Dennis and the entire staff made our trip so enjoyable. We will forever have a special place in our hearts for this place. Celebrated our 10 year wedding anniversary here!"
United States
Arleen
The price is 7.950.346 ₫
9.438.014 ₫ total
includes taxes & fees
11 Oct - 12 Oct
Aston Maui Hill

3. Kihei Ali'i Kai Condos with Free Parking

Kihei Ali'i Kai Condos with Free Parking
4.0 star property
South Kihei
9.6 out of 10, Exceptional, (52 reviews)
"The property was exactly as shown in the pictures. Very clean and the washer and dryer was a big plus. Would definitely stay here again."
United States
Monica Ivette
The price is 5.730.972 ₫
14.776.510 ₫ total
includes taxes & fees
12 Sept - 13 Sept
Kihei Ali'i Kai Condos with Free Parking
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Upcountry Maui Hotel Reviews

Explore a world of travel with Expedia