A barren volcanic landscape with rugged terrain and distant mountains.

Upcountry Maui Holiday Rentals

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Our top choices for Upcountry Maui holiday rentals

1. Adorable 1930's Gingerbread House....Permitted!

Adorable 1930's Gingerbread House....Permitted!
Makawao
9.8 out of 10, Exceptional, (13 reviews)
"a beautiful property and a nice cottage! We completely enjoyed our time here."
United States
Kathy W.
The price is NZ$920
includes taxes & fees
4 Sept - 5 Sept
Adorable 1930's Gingerbread House....Permitted!

2. 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 NZ$1,865
includes taxes & fees
31 Aug - 1 Sept
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

3. Haiku Hale - 3 Bedroom Maui Getaway!

Haiku Hale - 3 Bedroom Maui Getaway!
Haiku
10.0 out of 10, Exceptional, (8 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 NZ$1,390
includes taxes & fees
18 Aug - 19 Aug
Haiku Hale - 3 Bedroom Maui Getaway!

4. 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 NZ$1,869
includes taxes & fees
31 Aug - 1 Sept
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

5. 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, (82 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 NZ$4,854
includes taxes & fees
21 Aug - 22 Aug
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

6. Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (958 reviews)
"Everything was perfect and clean"
United States
Kathy
The price is NZ$573
includes taxes & fees
16 Sept - 17 Sept
Aston Maui Hill

7. 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, (524 reviews)
"Absolutely wonderful place in paradise. Hosts were amazing. Brough us fresh eggs and fruit. Amazing view and love the kitty too!"
United States
Diann
The price is NZ$651
includes taxes & fees
20 Aug - 21 Aug
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

8. 10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
North Kihei
9.8 out of 10, Exceptional, (279 reviews)
"Absolutely perfect stay! Kevin was very kind and very communicative. I highly recommend staying here when visiting Kīhei."
United States
Sylvia
The price is NZ$658
includes taxes & fees
18 Aug - 19 Aug
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

9. Yonegan Maui Getaways - Haiku - Unit 6

Yonegan Maui Getaways - Haiku - Unit 6
Haiku-Pauwela
9.2 out of 10, Wonderful, (40 reviews)
"Everything was great."
United States
Bryan
The price is NZ$517
includes taxes & fees
23 Aug - 24 Aug
Yonegan Maui Getaways - Haiku - Unit 6

10. 10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
North Kihei
10.0 out of 10, Exceptional, (315 reviews)
"Kevin was a great host! Communication was prompt and he gave wonderful suggestions on places to eat, things to do.The condo was beautiful, very cozy and clean.We would definitely stay here again"
United States
Janet M.
The price is NZ$671
includes taxes & fees
11 Sept - 12 Sept
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

11. 10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
North Kihei
9.8 out of 10, Exceptional, (306 reviews)
"Awesome stay, all you need around there, very quiet place, good neighbors, excellent Host and amazing commons area."
United States
pablo
The price is NZ$659
includes taxes & fees
9 Sept - 10 Sept
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

12. 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, (215 reviews)
"We had a great time! Everything was perfect. "
United States
Samantha S.
The price is NZ$753
includes taxes & fees
30 Aug - 31 Aug
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

13. Wonderful South Maui Beach Condos

Wonderful South Maui Beach Condos
3.5 star property
South Kihei
9.2 out of 10, Wonderful, (43 reviews)
"Excellent location with all that you need in the condo. "
United States
Karen
The price is NZ$800
includes taxes & fees
31 Aug - 1 Sept
Wonderful South Maui Beach Condos

14. 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, (462 reviews)
"Great place to stay while exploring Hana"
Canada
Igor G.
The price is NZ$639
includes taxes & fees
31 Aug - 1 Sept
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

15. Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View

Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View
North Kihei
10.0 out of 10, Exceptional, (43 reviews)
"Had lots of great and useful amenities "
United States
Rochelle P.
The price is NZ$724
includes taxes & fees
24 Aug - 25 Aug
Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View

16. SUMMER SPECIAL! Walk to Beach! Cute Beachy Ground Floor Getaway! Pool Access

SUMMER SPECIAL! Walk to Beach! Cute Beachy Ground Floor Getaway! Pool Access
South Kihei
9.8 out of 10, Exceptional, (133 reviews)
"Location; proximity to beach and stores/restaurants"
United States
Sharon O.
The price is NZ$881
includes taxes & fees
31 Aug - 1 Sept
SUMMER SPECIAL! Walk to Beach! Cute Beachy Ground Floor Getaway! Pool Access

17. Beautiful, Renovated, Hale Kamaole 159

Beautiful, Renovated, Hale Kamaole 159
South Kihei
10.0 out of 10, Exceptional, (113 reviews)
"Excellent room"
United States
Rene
The price is NZ$579
includes taxes & fees
18 Aug - 19 Aug
Beautiful, Renovated, Hale Kamaole 159

18. Sugar Beach Resort Oceanview 1 bed/1 bath

Sugar Beach Resort Oceanview 1 bed/1 bath
North Kihei
9.6 out of 10, Exceptional, (120 reviews)
"Great location, great property and great condo. "
Canada
DIANNE V.
The price is NZ$696
includes taxes & fees
19 Aug - 20 Aug
Sugar Beach Resort Oceanview 1 bed/1 bath

19. 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, (82 reviews)
"Great place! Had everything we needed.Very attentive reception staff."
United States
Kari T.
The price is NZ$711
includes taxes & fees
23 Aug - 24 Aug
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

20. 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, (150 reviews)
"Our stay was for one night and the condo was clean, well equipped, and the ocean waves lulled us to sleep. If doing the road to Hana an overnight stay here is recommended "
United States
Jaime C.
The price is NZ$729
includes taxes & fees
30 Aug - 31 Aug
Oceanview Condo in Hana-Let the ocean lull you to sleep
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Upcountry Maui holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Upcountry Maui. 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 Upcountry Maui. 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 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 holiday 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 Upcountry Maui short-term rentals, that won’t be hard to do.

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