Holiday Rentals in Upcountry Maui

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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, (87)
"Enjoyed the property. More rustic than I am used to. "
United States
Thomas S.
The price is €588
includes taxes & fees
3 Dec - 4 Dec
Ocean View Cabin located on Organic Coffee Farm with Hiking Trails

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 €2,625
includes taxes & fees
18 Nov - 19 Nov
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

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

Kula
10.0 out of 10, Exceptional, (182)
"Great place !!"
United States
adrian p.
The price is €1,026
includes taxes & fees
14 Nov - 15 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 €864
includes taxes & fees
10 Nov - 11 Nov
Haiku Hale - 3 Bedroom Maui Getaway!

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

Haiku
The price is €1,143
includes taxes & fees
23 Nov - 24 Nov
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

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

Hana
9.6 out of 10, Exceptional, (404)
"Very clean, excellent directions and instructions, loved the lanai, fans helped keep one comfortable "
United States
Jean J.
The price is €314
includes taxes & fees
8 Dec - 9 Dec
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

Hana
9.6 out of 10, Exceptional, (189)
"Super lovely place, I wish we were staying longer! Has everything you need. "
United States
Nicole
The price is €360
includes taxes & fees
10 Nov - 11 Nov
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

Hana
9.2 out of 10, Wonderful, (145)
"We liked the flat very much. Clean, cosy, like described."
Germany
Petra W.
The price is €439
includes taxes & fees
23 Nov - 24 Nov
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

Fisher's Hana Bay Hale, Across from Hana Bay

Kahului
9.6 out of 10, Exceptional, (407)
"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.
Fisher's Hana Bay Hale, Across from Hana Bay

Napili Village Hotel

3.0 star property
Lahaina
9.0 out of 10, Wonderful, (128)
"check in process was super easy. friendly staff "
United States
Nicholas
The price is €171
includes taxes & fees
9 Dec - 10 Dec
Napili Village Hotel

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 €480
includes taxes & fees
24 Nov - 25 Nov
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
Lahaina
8.8 out of 10, Excellent, (2861)
"Great stay"
United States
Andrea
The price is €695
includes taxes & fees
22 Nov - 23 Nov
OUTRIGGER Honua Kai Resort & Spa

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

Kuau
9.4 out of 10, Exceptional, (194)
"This condo was a great location right near mamas fish house and the beach. The air conditioning worked really well unlike some condos we’ve stayed in while in Hawaii. "
United States
Lindsey K.
The price is €392
includes taxes & fees
25 Nov - 26 Nov
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

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 €415
includes taxes & fees
19 Nov - 20 Nov
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

Hana
9.6 out of 10, Exceptional, (109)
"Beautiful spot in the ocean. Couldn’t have been more relaxing and beautiful"
United States
Tim S.
The price is €405
includes taxes & fees
13 Nov - 14 Nov
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

Secluded cottage on Tropical flower farm

Hana
9.4 out of 10, Exceptional, (274)
"The cottage was great. Check-in was stress-free and Ms. Rebecca was always responsive. "
United States
La Tecia P.
The price is €494
includes taxes & fees
11 Nov - 12 Nov
Secluded cottage on Tropical flower farm

Relaxing home away from home- honeymoon friendly

Hana
10.0 out of 10, Exceptional, (280)
"Great location. We had a great stay."
United States
Ernest H.
The price is €468
includes taxes & fees
18 Nov - 19 Nov
Relaxing home away from home- honeymoon friendly

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

Hana
9.2 out of 10, Wonderful, (111)
"This was the most beautiful condo I've ever stayed. The ocean view was absolutely breathtaking. No ac, but didn't really need it. I highly recommend this property. Access to black sand beach was a short walk, it was rough, but naturally beautiful. Sunrise was just perfect. "
United States
Richard
The price is €412
includes taxes & fees
11 Nov - 12 Nov
Oceanview Condo in Hana-Let the ocean lull you to sleep

Ocean front condo at Ma'alaea just a few steps to the ocean and harbor.

Wailuku
9.8 out of 10, Exceptional, (56)
"Really nice owners and great location."
United States
Robin D.
The price is €367
includes taxes & fees
14 Nov - 15 Nov
Ocean front condo at Ma'alaea just a few steps to the ocean and harbor.

OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC

Wailuku
9.6 out of 10, Exceptional, (156)
"Everything was great. Kitchen well stocked, beautiful view. "
United States
Eric S.
The price is €310
includes taxes & fees
15 Nov - 16 Nov
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC
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, apart-hotels, 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 €171 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.