Upcountry Maui Holiday Rentals

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Our top choices for Upcountry Maui holiday rentals

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Makawao
10.0 out of 10, Exceptional, (72)
"We had an amazing vacation here. We had 4 generations ranging from 4 months to 81 years and everyone had a great time. There was room to spread out and room to all gather together. Having the private pool and spa was perfect. Host was available when we needed her and the B and B was well stocked. We also loved the Maui feel of the accommodations and being out of the busier parts of Maui. I highly recommend this venue for larger groups! "
United States
Kari L.
The price is AU$4,452
includes taxes & fees
6 Jan - 7 Jan 2026
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views

Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views
Kula
10.0 out of 10, Exceptional, (185)
"Great stay"
United States
Peter A.
The price is AU$1,768
includes taxes & fees
14 Jan - 15 Jan 2026
Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views

Haiku Hale - 3 Bedroom Maui Getaway!

Haiku Hale - 3 Bedroom Maui Getaway!
Haiku
10.0 out of 10, Exceptional, (4)
"Clean, well lit, private, Haiku is a sweet town. Note that there are a few steep steps to master bedroom."
United States
Linda S.
The price is AU$1,847
includes taxes & fees
5 Jan - 6 Jan 2026
Haiku Hale - 3 Bedroom Maui Getaway!

Fisher's Hana Bay Hale, Across from Hana Bay

Fisher's Hana Bay Hale, Across from Hana Bay
Hana Town Center
9.6 out of 10, Exceptional, (409)
"Wonderful place to spend a few days in paradise! Would definitely stay again!"
United States
Steve K.
The price is AU$600
includes taxes & fees
22 Jan - 23 Jan 2026
Fisher's Hana Bay Hale, Across from Hana Bay

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Hana Town Center
9.6 out of 10, Exceptional, (414)
"Great stay. "
United States
Anthony A.
The price is AU$528
includes taxes & fees
24 Jan - 25 Jan 2026
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Hana Town Center
9.6 out of 10, Exceptional, (192)
"Super lovely place, I wish we were staying longer! Has everything you need. "
United States
Nicole
The price is AU$880
includes taxes & fees
15 Jan - 16 Jan 2026
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
4.5 star property
South Kihei
9.6 out of 10, Exceptional, (4)
"Wonderful experience. Clean, convenient, great location, pool, hot tub, beautiful property, and safe. Had a great time."
United States
Melinda
The price is AU$871
includes taxes & fees
1 Jan - 2 Jan 2026
Signature Residences at Maui Banyan

Oceanview #101 at Hana Kai Maui - 1 Bedroom Corner Unit, Amazing View!

Oceanview #101 at Hana Kai Maui - 1 Bedroom Corner Unit, Amazing View!
Hana Town Center
9.6 out of 10, Exceptional, (76)
"Nice easy check in. Easy access to black sand beach (not the State Park)."
United States
Brett
The price is AU$900
includes taxes & fees
11 Jan - 12 Jan 2026
Oceanview #101 at Hana Kai Maui - 1 Bedroom Corner Unit, Amazing View!

Relaxing home away from home- honeymoon friendly

Relaxing home away from home- honeymoon friendly
Hana
10.0 out of 10, Exceptional, (281)
"Lovely property with enormous views. Very quiet and relaxing. "
United States
caren w.
The price is AU$801
includes taxes & fees
17 Jan - 18 Jan 2026
Relaxing home away from home- honeymoon friendly

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hana
10.0 out of 10, Exceptional, (90)
"Very unique property near Hana. Great experience!"
United States
Keith R.
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

Stay in Hana #2

Stay in Hana #2
Hana Town Center
9.6 out of 10, Exceptional, (47)
"Staying here was a pleasure - from the ease of the check in process, to the cleanliness of the room, amenities and location, we're so glad we chose this home!"
United States
Jenny E.
The price is AU$524
includes taxes & fees
31 Dec - 1 Jan 2026
Stay in Hana #2

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 Town Center
9.6 out of 10, Exceptional, (111)
"Everything Good "
United States
Marc
The price is AU$900
includes taxes & fees
9 Jan - 10 Jan 2026
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
Kuau
9.4 out of 10, Exceptional, (196)
"Very quiet safe place. "
Canada
Monica
The price is AU$660
includes taxes & fees
7 Jan - 8 Jan 2026
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
Kaʻeleku
9.8 out of 10, Exceptional, (77)
"Phenomenal property for your stay in Hana - especially for a large group "
United States
Logan G.
The price is AU$1,522
includes taxes & fees
12 Jan - 13 Jan 2026
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

Secluded cottage on Tropical flower farm

Secluded cottage on Tropical flower farm
Kaʻeleku
9.4 out of 10, Exceptional, (281)
"This was a great location, comfortable cute little cottage."
United States
Briana B.
The price is AU$840
includes taxes & fees
7 Jan - 8 Jan 2026
Secluded cottage on Tropical flower farm

Oceanview Condo in Hana-Let the ocean lull you to sleep

Oceanview Condo in Hana-Let the ocean lull you to sleep
Hana Town Center
9.2 out of 10, Wonderful, (118)
"A good place to stay "
United States
Xiaohong
The price is AU$701
includes taxes & fees
9 Jan - 10 Jan 2026
Oceanview Condo in Hana-Let the ocean lull you to sleep

Kuau Surf 2.0 Maui North Shore Locally-Owned

Kuau Surf 2.0 Maui North Shore Locally-Owned
Paia
9.2 out of 10, Wonderful, (19)
"Clean and convenient"
United States
Ilya L
The price is AU$568
includes taxes & fees
22 Jan - 23 Jan 2026
Kuau Surf 2.0 Maui North Shore Locally-Owned

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (329)
"Amazing resort second time being here will definitely be back next year "
United States
David
The price is AU$1,135
includes taxes & fees
27 Jan - 28 Jan 2026
The Whaler Resort Kaanapali Beach

Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (647)
"Location was excellent"
United States
Polly
The price is AU$497
includes taxes & fees
1 Jan - 2 Jan 2026
Napili Sunset on the Beach

Hana Homestead by the Beach

Hana Homestead by the Beach
Hana Town Center
9.8 out of 10, Exceptional, (138)
"This property is amazing! Not right on the water but great view of the ocean, can hear the ocean and 3minute walk to the beach!! Beautiful property and plenty of extras such as a jacuzzi, sauna, boogie boards, beach chairs, beach toys for the kids, and an on-site private outside shower to clean up after walking or playing in the beach. "
United States
Christopher
The price is AU$2,005
includes taxes & fees
13 Jan - 14 Jan 2026
Hana Homestead by the Beach
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.
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Top Upcountry Maui Hotel Reviews

Find out more about Upcountry Maui

Everything you need to know about Upcountry Maui holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Upcountry Maui holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Upcountry Maui holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Upcountry Maui holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Upcountry Maui. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Upcountry Maui holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Upcountry Maui holiday rentals we have selected for you start as low as AU$551 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Upcountry Maui rentals

At Expedia, we put the best Upcountry Maui holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Upcountry Maui rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Upcountry Maui holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Upcountry Maui. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.