A barren volcanic landscape with rugged terrain and distant mountains.

Upcountry Maui Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Upcountry Maui vacation rentals

A rustic wooden house with a large window and a door, surrounded by lush greenery and palm trees.

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 ￥39,192
￥88,377 total
includes taxes & fees
Nov 16 - Nov 17
Adorable 1930's Gingerbread House....Permitted!
A bamboo structure with a sloped roof, surrounded by rocks and plants.

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 ￥227,311
￥471,854 total
includes taxes & fees
Nov 18 - Nov 19
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
A spacious kitchen with a large island, wooden flooring, and modern lighting fixtures.

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 ￥90,735
￥197,167 total
includes taxes & fees
Nov 30 - Dec 1
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
A spacious kitchen with a large island, wooden flooring, and modern lighting fixtures.

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.
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
A residential street with a white car parked on the side, surrounded by lush greenery and palm trees.

5. Haiku Hale - 3 Bedroom Maui Getaway!

Haiku Hale - 3 Bedroom Maui Getaway!
Haiku
10.0 out of 10, Exceptional, (8 reviews)
"Great spot and a nice rental. Wonderful outdoor space as well. We will be back!"
United States
Will W.
The price is ￥70,545
￥139,530 total
includes taxes & fees
Nov 6 - Nov 7
Haiku Hale - 3 Bedroom Maui Getaway!
A paved pathway leading to a gate with red pillars, surrounded by lush greenery and palm trees, with a view of the ocean in the background.

6. 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, (537 reviews)
"Beautiful scenery and hostess!"
United States
Sonja W.
The price is ￥33,254
￥62,088 total
includes taxes & fees
Nov 11 - Nov 12
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens
A resort with a swimming pool, palm trees, and ocean views.

7. Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (1,003 reviews)
"Such a beautiful place, lots to do, close to local beaches, tons of yummy food nearby"
United States
Megan
The price is ￥49,805
￥59,125 total
includes taxes & fees
Dec 6 - Dec 7
Aston Maui Hill
A beach resort with rows of palm trees, a sandy beach, and a view of the ocean.

8. Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.8 out of 10, Excellent, (41 reviews)
"Absolutely loved our room. The kitchen was spacious and had all of the necessities. The best part was the lawn chairs, umbrella and tote bag provided in the room. Rooms large enough to relax and not feel so crowded."
United States
Mai
The price is ￥9,369
￥85,814 total
includes taxes & fees
Nov 15 - Nov 16
Signature Residences at Maui Banyan
Beach

9. 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 ￥29,295
￥70,601 total
includes taxes & fees
Nov 9 - Nov 10
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
A beach with a palm tree, rocky shoreline, and a wooden bench.

10. Across from Sandy Beaches! Island Paradise- Special Rates Book Now!

Across from Sandy Beaches! Island Paradise- Special Rates Book Now!
South Kihei
9.4 out of 10, Exceptional, (28 reviews)
"Perfect location, close to the beach and all amenities. The apartment was clean and included beach chairs and a bodyboard. Free parking was a great bonus.The owner was very responsive and helpful throughout our stay.We had a great time and would happily stay here again."
United States
Ewa L.
The price is ￥17,577
￥59,823 total
includes taxes & fees
Nov 13 - Nov 14
Across from Sandy Beaches! Island Paradise- Special Rates Book Now!
A beach with palm trees, clear blue water, and rocky shoreline.

11. 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
Maui Modern North Shore Beach Condo - Walk to Mamas Fish House! AC, Fast WiFi
A balcony with a table set for two, featuring a bottle of wine and two glasses.

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, (309 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 ￥20,269
￥68,346 total
includes taxes & fees
Dec 3 - Dec 4
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
A beach with clear blue water, rocky shore, and palm trees.

13. 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)
"Great location and good ammenities"
United States
Zachary S.
The price is ￥19,952
￥63,714 total
includes taxes & fees
Nov 12 - Nov 13
Condo w/ Lanai at Beginning of Road to Hana!
A table with a bottle and glasses on a red mat, surrounded by red chairs on a balcony with a view of palm trees and a tennis court.

14. 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
10.0 out of 10, Exceptional, (281 reviews)
"Very good place to stay. Very clean 100% recommend."
United States
john
The price is ￥16,397
￥63,251 total
includes taxes & fees
Nov 8 - Nov 9
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
A pathway leading to a beach with dense green foliage on either side.

15. #239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed

#239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed
South Kihei
9.6 out of 10, Exceptional, (99 reviews)
"Kitchen was fully equipped. Condo was very clean and host was promt with replys. Loved our stay "
Canada
Lori D.
The price is ￥17,696
￥86,353 total
includes taxes & fees
Dec 1 - Dec 2
#239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed
A balcony with wicker chairs and a wooden table, overlooking a beach with palm trees and the ocean.

16. Oceanfront, Exceptionally Remodeled, Split A/C, King bed, OH the sunsets

Oceanfront, Exceptionally Remodeled, Split A/C, King bed, OH the sunsets
Central Kihei
10.0 out of 10, Exceptional, (212 reviews)
"We loved this place! Was perfect for what we were needing:)"
United States
Alana C.
Oceanfront, Exceptionally Remodeled, Split A/C, King bed, OH the sunsets
A resort with multiple buildings, a swimming pool, and a view of the ocean and mountains.

17. 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, (323 reviews)
"Clean and comfortable base for our vacation. Convenient location with easy parking."
United States
Luukia R.
The price is ￥17,751
￥65,023 total
includes taxes & fees
Nov 12 - Nov 13
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
A modern kitchen with a granite countertop, wooden cabinets, and a large island. There is a dining area with a gray sofa and a table, and a view of a garden through large glass doors.

18. Sugar Beach 102 Gorgeous Remodeled Home Beachfront Condo Home

Sugar Beach 102 Gorgeous Remodeled Home Beachfront Condo Home
North Kihei
9.4 out of 10, Exceptional, (48 reviews)
"The hot tub and the in unit washer and dryer were a huge bonus. The condo was well stocked, and very clean. The only thing I wish it had, and maybe I missed it would be a tray to carry items out to the bbq area. The pool area and proximity to the beach was wonderful. Overall we had a great stay!!"
United States
Angie W.
The price is ￥35,040
￥92,033 total
includes taxes & fees
Nov 19 - Nov 20
Sugar Beach 102 Gorgeous Remodeled Home Beachfront Condo Home
A swimming pool area with lounge chairs and a covered patio.

19. Beautiful Ocean View Studio!

Beautiful Ocean View Studio!
South Kihei
9.6 out of 10, Exceptional, (20 reviews)
"We loved the location and partial ocean view from the balcony. Easy walk to the beach and we had everything available that we needed for a comfortable stay. "
United States
Susan C.
The price is ￥16,896
￥65,044 total
includes taxes & fees
Nov 6 - Nov 7
Beautiful Ocean View Studio!
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

Hyatt Regency Maui Resort & Spa

Hyatt Regency Maui Resort & Spa

10/10 Excellent
"Good location, friendly staffs, good room rate."
KHOA THANH 3-night trip
Posted 2 hours ago
Hyatt Regency Maui Resort & Spa

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