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

1. 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 CA $539
CA $1,179 total
includes taxes & fees
Oct 18 - Oct 19
Haiku Hale - 3 Bedroom Maui Getaway!

2. 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)
"This place was perfect for our big group!"
United States
Lisa B.
The price is CA $2,050
CA $4,256 total
includes taxes & fees
Oct 30 - Oct 31
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

3. 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 $817
CA $1,775 total
includes taxes & fees
Oct 31 - Nov 1
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

4. 2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
Haiku
8.8 out of 10, Excellent, (3 reviews)
"Holly was a great host! Beautiful views from the back lanai! We loved our time in Maui!"
United States
Amy C.
The price is CA $696
CA $1,791 total
includes taxes & fees
Oct 31 - Nov 1
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

5. 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, (535 reviews)
"Beautiful scenery and hostess!"
United States
Sonja W.
The price is CA $299
CA $562 total
includes taxes & fees
Oct 18 - Oct 19
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

6. Yonegan Maui Getaways - Haiku - Unit 6

Yonegan Maui Getaways - Haiku - Unit 6
Haiku-Pauwela
9.2 out of 10, Wonderful, (42 reviews)
"Everything was great."
United States
Bryan
The price is CA $176
CA $443 total
includes taxes & fees
Nov 2 - Nov 3
Yonegan Maui Getaways - Haiku - Unit 6

7. 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, (224 reviews)
"Great location for our last night. Walk to the beach and close enough to the airport for an early flight."
United States
jeff s.
The price is CA $264
CA $640 total
includes taxes & fees
Oct 24 - Oct 25
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

8. Maui Modern North Shore Beach Condo - Walk to Mamas Fish House! AC, Fast WiFi

Maui Modern North Shore Beach Condo - Walk to Mamas Fish House! AC, Fast WiFi
Paia
9.8 out of 10, Exceptional, (99 reviews)
"Close walk to a beach. Owner took care of maintenance problem quickly."
United States
David
The price is CA $243
CA $606 total
includes taxes & fees
Oct 18 - Oct 19
Maui Modern North Shore Beach Condo - Walk to Mamas Fish House! AC, Fast WiFi

9. 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, (308 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 CA $154
CA $573 total
includes taxes & fees
Nov 2 - Nov 3
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10. Romantic 1 BR Condo with King Tempurpedic

Romantic 1 BR Condo with King Tempurpedic
Wailea
9.6 out of 10, Exceptional, (64 reviews)
"The condo property was beautiful and in a great location. We had to book last minute due to storms affecting our initial booking and host was very responsive. "
United States
Kathryn R.
The price is CA $216
CA $528 total
includes taxes & fees
Oct 20 - Oct 21
Romantic 1 BR Condo with King Tempurpedic

11. Condo w/ Lanai at Beginning of Road to Hana!

Condo w/ Lanai at Beginning of Road to Hana!
Paia
9.2 out of 10, Wonderful, (45 reviews)
"The property was very clean and well-appointed. It was a great location that allowed us to walk in to Mama's Fish House. The host was extremely helpful and proactive and checked to make sure we had everything we needed. If you are looking for a place to stay in Paia, this is it."
United States
Martin S.
The price is CA $180
CA $599 total
includes taxes & fees
Oct 18 - Oct 19
Condo w/ Lanai at Beginning of Road to Hana!

12. 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, (280 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 CA $148
CA $571 total
includes taxes & fees
Oct 22 - Oct 23
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

13. 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, (320 reviews)
"This condo was perfect for my husband and I. Very clean, right across from the beach. We truly enjoyed our week at this place."
United States
stacey w.
The price is CA $161
CA $588 total
includes taxes & fees
Oct 24 - Oct 25
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

14. Oceanside condo, full kitchen, ocean view. Fully renovated 2023

Oceanside condo, full kitchen, ocean view. Fully renovated 2023
Central Kihei
9.6 out of 10, Exceptional, (89 reviews)
The price is CA $154
CA $491 total
includes taxes & fees
Oct 16 - Oct 17
Oceanside condo, full kitchen, ocean view. Fully renovated 2023

15. Top Floor Beachfront Condo with Ocean view

Top Floor Beachfront Condo with Ocean view
North Kihei
9.6 out of 10, Exceptional, (64 reviews)
"It was a beautiful place and very cozy"
United States
Stephanie T.
The price is CA $203
CA $654 total
includes taxes & fees
Oct 18 - Oct 19
Top Floor Beachfront Condo with Ocean view

16. 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, (47 reviews)
"Had lots of great and useful amenities "
United States
Rochelle P.
The price is CA $142
CA $617 total
includes taxes & fees
Oct 16 - Oct 17
Tracy’s Tropical Treasure #4 "Best in Kihei" 4 times and “#1 in Maui” Ocean View

17. Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
North Kihei
9.8 out of 10, Exceptional, (110 reviews)
" Kīhei Casita House Stay (above the Main House): just lovely - would stay there again - reasonably priced - fully functioning everything - and easy outside access - we actually stayed in the Main House for one week and then one week in the Casita - while in the Main House the Casita was occupied and no noise issues at all. Fairly easy access to beaches and beach shopping. Excellent communication with host."
United States
Michael C.
The price is CA $146
CA $720 total
includes taxes & fees
Oct 22 - Oct 23
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

18. Steps to the Beach! Cute Beachy Ground Floor Getaway! Pool Access

Steps to the Beach! Cute Beachy Ground Floor Getaway! Pool Access
South Kihei
9.6 out of 10, Exceptional, (135 reviews)
"Location; proximity to beach and stores/restaurants"
United States
Sharon O.
The price is CA $157
CA $746 total
includes taxes & fees
Nov 2 - Nov 3
Steps to the Beach! Cute Beachy Ground Floor Getaway! Pool Access

19. Beautiful, Renovated, Hale Kamaole 159

Beautiful, Renovated, Hale Kamaole 159
South Kihei
10.0 out of 10, Exceptional, (113 reviews)
"Great location and value!"
United States
Christopher
The price is CA $161
CA $502 total
includes taxes & fees
Oct 23 - Oct 24
Beautiful, Renovated, Hale Kamaole 159

20. Oceanfront, Hale Kai O Kihei, incredible sunsets, King bed, AC, remodeled 2023

Oceanfront, Hale Kai O Kihei, incredible sunsets, King bed, AC, remodeled 2023
Central Kihei
10.0 out of 10, Exceptional, (127 reviews)
"Well appointed and clean. The place is in a great location and has a very serene restful vibe."
United States
Tiffany
The price is CA $217
CA $653 total
includes taxes & fees
Oct 14 - Oct 15
Oceanfront, Hale Kai O Kihei, incredible sunsets, King bed, AC, remodeled 2023
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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