Upcountry Maui Holiday Rentals

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Holiday Rentals in Upcountry Maui

Ocean View Cabin located on Organic Coffee Farm with Hiking Trails

Makawao
10.0 out of 10, Exceptional, (88)
"Enjoyed the property. More rustic than I am used to. "
United States
Thomas S.
The price is NZ$1,089
includes taxes & fees
3 Dec - 4 Dec
Ocean View Cabin located on Organic Coffee Farm with Hiking Trails

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

Kula
10.0 out of 10, Exceptional, (184)
"Great place !!"
United States
adrian p.
The price is NZ$2,038
includes taxes & fees
21 Nov - 22 Nov
Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views

Haiku Hale - 3 Bedroom Maui Getaway!

Haiku
10.0 out of 10, Exceptional, (4)
"The neighborhood is a nice quiet area, with shops & places to eat within a minute walk. The driveway is a bit tricky, but opens up to a beautiful property with plenty of outdoor space. The house itself was very clean & neat, and the rooms all fit our needs. We only stayed one night but wish we could have stayed a week! I would highly recommend this property to anyone looking to stay off the beaten path but still be able to see everything you want!"
United States
Nate G.
The price is NZ$1,740
includes taxes & fees
18 Nov - 19 Nov
Haiku Hale - 3 Bedroom Maui Getaway!

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

Haiku
The price is NZ$2,271
includes taxes & fees
23 Nov - 24 Nov
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

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

Makawao
10.0 out of 10, Exceptional, (70)
"There is absolutely nothing we could think of that was missing from our week at Banyon Tree! The property is beautiful, lovingly maintained, and made this our best trip to Hawaii ever!! Actually, our best-ever family vacation! Plenty of room for swimming, playing Capture the Flag, enjoying family dinners, playing card and table games, and just hanging out. We enjoyed seeing the turtles at Ho’okepa Beach, playing in the river at Íao State Park, and shopping local markets. Comfortable island...
United States
Sheridan B.
The price is NZ$4,920
includes taxes & fees
18 Nov - 19 Nov
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
Lahaina
8.8 out of 10, Excellent, (2865)
"Very clean and convenient, great location and great beaches"
United States
Kevin William
The price is NZ$1,475
includes taxes & fees
1 Dec - 2 Dec
OUTRIGGER Honua Kai Resort & Spa

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

Hana
9.6 out of 10, Exceptional, (408)
"Nice space with a good location. Comfy beds. "
United States
Dannielle P.
The price is NZ$627
includes taxes & fees
5 Dec - 6 Dec
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Fisher's Hana Bay Hale, Across from Hana Bay

Kahului
9.6 out of 10, Exceptional, (408)
"We only stayed one night but it was fantastic, clean and cozy! Check in was super simple and we were able to get in and out quickly to enjoy the rest of our trip."
United States
Jarah A.
The price is NZ$702
includes taxes & fees
17 Dec - 18 Dec
Fisher's Hana Bay Hale, Across from Hana Bay

Aston Maui Hill

3.0 star property
South Kihei
9.0 out of 10, Wonderful, (841)
"Great atmosphere. Quite community and great front desk service."
United States
Cassandra Nicole
The price is NZ$524
includes taxes & fees
19 Nov - 20 Nov
Aston Maui Hill

Aston Kaanapali Shores

3.5 star property
Lahaina
8.6 out of 10, Excellent, (3867)
"Was a great place to stay"
United States
Christine
The price is NZ$558
includes taxes & fees
18 Nov - 19 Nov
Aston Kaanapali Shores

Napili Village Hotel

3.0 star property
Lahaina
9.0 out of 10, Wonderful, (131)
"check in process was super easy. friendly staff "
United States
Nicholas
The price is NZ$332
includes taxes & fees
11 Dec - 12 Dec
Napili Village Hotel

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

Hana
9.6 out of 10, Exceptional, (190)
"Super lovely place, I wish we were staying longer! Has everything you need. "
United States
Nicole
The price is NZ$713
includes taxes & fees
24 Nov - 25 Nov
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

Signature Residences at Maui Banyan

4.5 star property
South Kihei
The price is NZ$1,095
includes taxes & fees
18 Nov - 19 Nov
Signature Residences at Maui Banyan

The Westin Nanea Ocean Villas, Ka'anapali

4.0 star property
Lahaina
9.2 out of 10, Wonderful, (470)
"Spacious rooms and fun pools"
United States
Vanessa
The price is NZ$1,161
includes taxes & fees
4 Dec - 5 Dec
The Westin Nanea Ocean Villas, Ka'anapali

Napili Sunset on the Beach

2.5 star property
Lahaina
9.2 out of 10, Wonderful, (647)
"Extremely clean, quiet and well maintained property. Would stay again."
United States
Paul
The price is NZ$584
includes taxes & fees
18 Nov - 19 Nov
Napili Sunset on the Beach

Napili Shores Maui by OUTRIGGER

3.0 star property
Lahaina
9.0 out of 10, Wonderful, (1697)
"Enjoyed our stay."
United States
MARTIN
The price is NZ$642
includes taxes & fees
18 Nov - 19 Nov
Napili Shores Maui by OUTRIGGER

Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

Hana
9.6 out of 10, Exceptional, (75)
"Amazing views!"
United States
Alexander
The price is NZ$758
includes taxes & fees
19 Nov - 20 Nov
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

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

Hana
10.0 out of 10, Exceptional, (89)
"The place was beautiful and the gardens are absolutely breathtaking!!! It was so peaceful and perfect for my husband and I after a VERY long day making the drive to Hana and hiking the Pipiwai Trail to see the Waimoku Falls!!! Only wish we could have stayed here longer on our trip!"
United States
Dena V.
The price is NZ$954
includes taxes & fees
24 Nov - 25 Nov
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

Aston Maui Kaanapali Villas

3.0 star property
Lahaina
8.8 out of 10, Excellent, (2494)
"We left feeling very refreshed! Beautiful beach and the staff are awesome! "
United States
ERIC
The price is NZ$728
includes taxes & fees
18 Nov - 19 Nov
Aston Maui Kaanapali Villas

The Whaler Resort Kaanapali Beach

4.0 star property
Lahaina
9.6 out of 10, Exceptional, (295)
"We loved our stay at the Whaler"
United States
Kris Leann
The price is NZ$1,227
includes taxes & fees
17 Dec - 18 Dec
The Whaler Resort Kaanapali 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 favorite 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 depends 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 NZ$421 per night. Entering your travel dates in the search wizard you might find 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.