A barren volcanic landscape with rugged terrain and distant mountains.

Upcountry Maui Vacation Rentals

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Our top choices for Upcountry Maui vacation rentals

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 CA $559
CA $1,463 total
includes taxes & fees
Aug 12 - Aug 13
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

Haiku Hale - 3 Bedroom Maui Getaway!

Haiku Hale - 3 Bedroom Maui Getaway!
Haiku
10.0 out of 10, Exceptional, (6 reviews)
"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 CA $568
CA $1,212 total
includes taxes & fees
Jul 28 - Jul 29
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!
Haiku
9.0 out of 10, Wonderful, (2 reviews)
"Very comfortable "
United States
Tanya N.
The price is CA $466
CA $1,475 total
includes taxes & fees
Aug 12 - Aug 13
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
Makawao
10.0 out of 10, Exceptional, (80 reviews)
"Great stay with Heleina and John! The property was spacious, very clean, and comfortable. Despite the terrible weather in Hawaii, they went above and beyond to accommodate us, even offering a complimentary extra night in case we got stuck. Truly thoughtful hosts. Would definitely stay again and I highly recommend! "
United States
Anna H.
The price is CA $2,018
CA $4,190 total
includes taxes & fees
Jul 28 - Jul 29
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!
Hana Town Center
9.6 out of 10, Exceptional, (80 reviews)
"Great view, excellent location. 2 -3 nights is the perfect amount of time in Hana."
United States
Jim
The price is CA $440
CA $634 total
includes taxes & fees
Jul 17 - Jul 18
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 Town Center
9.6 out of 10, Exceptional, (119 reviews)
"Beautiful place to stay in Hana and super nice people. "
United States
Tanya L.
The price is CA $468
CA $671 total
includes taxes & fees
Jul 16 - Jul 17
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

Hana Homestead by the Beach

Hana Homestead by the Beach
Hana Town Center
9.8 out of 10, Exceptional, (143 reviews)
"We loved are quiet, peaceful stay in Hāna! So much fun! Beautiful property!"
United States
Justin
The price is CA $1,024
CA $2,208 total
includes taxes & fees
Jul 28 - Jul 29
Hana Homestead by the Beach

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, (445 reviews)
"Great stay thanks! "
United States
Stephanie C.
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, (459 reviews)
"Great place to stay while exploring Hana"
Canada
Igor G.
The price is CA $289
CA $560 total
includes taxes & fees
Aug 3 - Aug 4
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, (200 reviews)
"Comfortable, clean, well equipped cottage in the heart of Hana. Great place, highly recommend! "
United States
Michelle S.
The price is CA $325
CA $706 total
includes taxes & fees
Jul 15 - Jul 16
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

Secluded cottage on Tropical flower farm

Secluded cottage on Tropical flower farm
Kaʻeleku
9.4 out of 10, Exceptional, (305 reviews)
"Beautiful secluded property. Great instuctions provided by the host. The cottage had everything we needed for our stay. "
United States
Lokahi
Secluded cottage on Tropical flower farm

Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
Kaʻeleku
9.8 out of 10, Exceptional, (247 reviews)
"I appreciated everything as advertised. Would have preferred mini splits or AC in the bedrooms, but still a nice peaceful spot."
United States
Robert
The price is CA $495
CA $936 total
includes taxes & fees
Aug 3 - Aug 4
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

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, (90 reviews)
"Beautiful property. Our second time here, it is one of our favorite places to stay. "
United States
Myra P.
The price is CA $720
CA $1,341 total
includes taxes & fees
Aug 12 - Aug 13
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

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

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hāna
10.0 out of 10, Exceptional, (101 reviews)
"Beautiful grounds, great location close to secluded beach."
United States
Mark S.
The price is CA $436
CA $771 total
includes taxes & fees
Jul 28 - Jul 29
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

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, (80 reviews)
"Great beach view lovely gardens"
United States
Dianne
The price is CA $502
CA $717 total
includes taxes & fees
Jul 19 - Jul 20
Oceanview #101 at Hana Kai Maui - 1 Bedroom Corner Unit, Amazing View!

Oceanview #104 at Hana Kai Maui - 1 Bedroom, Easy Access, no steps, Great View!

Oceanview #104 at Hana Kai Maui - 1 Bedroom, Easy Access, no steps, Great View!
Hana Town Center
9.6 out of 10, Exceptional, (79 reviews)
"Hana Kai is very convenient place to stay. Lanai is big and great place to hang out."
United States
Ann E.
The price is CA $471
CA $676 total
includes taxes & fees
Jul 19 - Jul 20
Oceanview #104 at Hana Kai Maui - 1 Bedroom, Easy Access, no steps, Great View!

Oceanview #201 at Hana Kai Maui - 1 Bedroom Upper Floor Corner, Panoramic View!

Oceanview #201 at Hana Kai Maui - 1 Bedroom Upper Floor Corner, Panoramic View!
Hana Town Center
9.4 out of 10, Exceptional, (62 reviews)
"This condo was exactly as advertised! Wonderful property! Would definitely stay here again. This side of Maui is a must see!"
United States
Lisa S.
The price is CA $502
CA $713 total
includes taxes & fees
Jul 20 - Jul 21
Oceanview #201 at Hana Kai Maui - 1 Bedroom Upper Floor Corner, Panoramic View!

Partial Oceanview #107 at Hana Kai Maui - 1 Bedroom, corner unit

Partial Oceanview #107 at Hana Kai Maui - 1 Bedroom, corner unit
Hana Town Center
9.6 out of 10, Exceptional, (64 reviews)
"Nice location "
United States
janie h.
The price is CA $459
CA $655 total
includes taxes & fees
Jul 20 - Jul 21
Partial Oceanview #107 at Hana Kai Maui - 1 Bedroom, corner unit

Oceanview #203 at Hana Kai Maui - 1 Bedroom Upper Floor, Stunning View!

Oceanview #203 at Hana Kai Maui - 1 Bedroom Upper Floor, Stunning View!
Hana Town Center
9.4 out of 10, Exceptional, (69 reviews)
"Staff was amazing great location "
United States
ric m.
The price is CA $512
CA $732 total
includes taxes & fees
Jul 23 - Jul 24
Oceanview #203 at Hana Kai Maui - 1 Bedroom Upper Floor, Stunning View!

Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens
Hana
10.0 out of 10, Exceptional, (519 reviews)
"Beautiful place. Excellent host. "
United States
Darryl S.
The price is CA $295
CA $554 total
includes taxes & fees
Jul 28 - Jul 29
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens
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

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.

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