
Upcountry Maui Vacation Rentals
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check prices for these dates
Our top choices for Upcountry Maui vacation rentals

Haiku Hale - 3 Bedroom Maui Getaway!
Haiku Hale - 3 Bedroom Maui Getaway!
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access
Hana Homestead by the Beach
Hana Homestead by the Beach
Fisher's Hana Bay Hale, Across from Hana Bay
Fisher's Hana Bay Hale, Across from Hana BayFind vacation rentals that suit your style
Top Upcountry Maui Hotel Reviews

OUTRIGGER Kaanapali Beach Resort
Find out more about Upcountry Maui
You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Upcountry Maui. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.
Explore a world of travel with Expedia
- Hotels with Kitchenettes in Maui
- Adults Only Resorts & in Maui
- Marriott Hotels & Resorts in Maui
- Family Hotels in Maui
- Beach Hotel Hotels in Maui
- All Inclusive Resorts and in Maui
- Outrigger Hotels in Maui
- Cottages in Maui
- Hotels with Waterslides in Maui
- Hotels near Haleakala National Park
- Romantic Hotels in Maui
- Condo Rentals in Kihei
- Wailea Hotels
- Apartments in Maui
- Exceptional Ocean Views
- Hilton Hotels in Maui
- Hotels with Free Breakfast in Maui
- 5 Star Hotels in Maui
- Golf Hotels in Maui
- Kaanapali Hotels
- Hilton Grand Vacations Club Maui Bay Villas
- Hana Hotels
- Vacation Homes in Upcountry Maui
- B&B in Maui
- B&B in Upcountry Maui
- Condo Rentals in Maui
- Villas in Maui
- Oceanfront Hotels in Maui
- Wyndham Hotels in Maui
- Kula Hotels
- Luxury Hotels in Maui
- Hotels near Haleakala Crater
- Cheap Hotels in Maui
- 5 Star Hotels in Upcountry Maui
- Honeymoon Resorts and in Maui
- Boutique Hotels in Maui
- Hotels near Kahului
- Kihei Hotels
- Hotels with Free Airport Shuttle in Maui
- Pet-Friendly Hotels in Maui
- Kahului Hotels
- Hostels in Maui
- Hotels with a Lazy River in Maui
- Best Western Hotels in Maui
- Flights from Honolulu (HNL) to Kahului (OGG)
- Flights from Toronto (YYZ) to Kahului (OGG)
- Flights from Victoria (YYJ) to Kahului (OGG)
- Flights from Vancouver (YVR) to Kahului (OGG)
- Flights from Kahului
- Flights from Los Angeles (LAX) to Kahului (OGG)
- Flights from Seattle (SEA) to Kahului (OGG)
- Flights from Maui
- Flights from Calgary (YYC) to Kahului (OGG)
- Flights from Kelowna (YLW) to Kahului (OGG)
- Flights from Edmonton (YEG) to Kahului (OGG)
- Flights to Maui
- Rent A Wreck Rental Cars in Maui
- Car rentals near Haleakala National Park
- Car rental Kihei
- Advantage Rent-A-Car Rental Cars in Maui
- Rental cars Kahului airport
- Enterprise Rental Cars in Maui
- Thrifty Car Rental Rental Cars in Maui
- Car rental Kahului
- Budget Rental Cars in Maui
- Avis Rental Cars in Maui
- Alamo Rent A Car Rental Cars in Maui
- Nü Car Rentals Rental Cars in Upcountry Maui

















































































