Owner Direct Vacation
Rentals in Upcountry Maui
The Best Owner Direct Vacation Rentals in Upcountry Maui. Explore thousands of vacation home rentals, large cabins, and villas near Upcountry Maui
GUESTS
Explore the Best Upcountry Maui Vacation Homes
Looking for the perfect place to stay in Upcountry Maui? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Upcountry Maui character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
Owner Direct to
Find Upcountry Maui Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Upcountry Maui
- Air Conditioner
- Parking
- Pool
- Parking
- Pool
- TV
- Parking
- Designated Smoking Area
- Balcony/Terrace
- Parking
- Pool
- Designated Smoking Area
- Air Conditioner
- Parking
- Pool
- Parking
- Pool
- View
- Parking
- Pool
- TV
- Parking
- Pool
- View
Popular Neighborhoods for Upcountry Maui Vacation Rentals
Discover the top neighborhoods in Upcountry Maui and choose a place that suits your stay.
Wednesday Jul 29
Upcountry Maui, Hawaii
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Upcountry Maui vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Upcountry Maui
- Air Conditioner
- Pool
- TV
- Parking
- View
- Ocean View
- Air Conditioner
- Pool
- TV
- Air Conditioner
- Pool
- TV
- Parking
- Pool
- View
- Parking
- Pet Friendly
- TV
- Parking
- Pool
- View
How to Reserve Your Upcountry Maui Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Upcountry Maui Vacation Rental FAQs
There are a lot of options in Upcountry Maui. If you plan on staying in the Upcountry Maui area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals 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 Farm Stay! Upcountry Maui. Magical and Peaceful!
- Exceptional Upcountry Villa with breathtaking views
- Historic Upcountry Ranch Home
- Best Location! Beachy 3 BR Home, 4 miles to Ho'okipa, Permit #STPH2015/0006
- ★Rainbow Lookout - PRIVATE HOT TUB+ACCESS TO POOL
- Mahina Cottage, Mahina Cottage
There are 1 vacation rentals with private pools near Upcountry Maui. Top-rated homes that have access to a swimming pool include:
If you are looking for a family-friendly vacation home in Upcountry Maui, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Upcountry Maui:
Currently, the total number of properties listed in 2026 is over 79 in the Upcountry Maui area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Upcountry Maui.
