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Upcountry Maui Vacation Rentals

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Our top choices for Upcountry Maui vacation 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.
$464 nightly
The price is $545
Nov 16 - Nov 17
Total with taxes and fees
Adorable 1930's Gingerbread House....Permitted!

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.
$2,481 nightly
The price is $2,910
Nov 17 - Nov 18
Total with taxes and fees
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
$1,049 nightly
The price is $1,245
Nov 30 - Dec 1
Total with taxes and fees
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

4. 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.
$729 nightly
The price is $860
Nov 15 - Nov 16
Total with taxes and fees
Haiku Hale - 3 Bedroom Maui Getaway!

5. 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.
$971 nightly
The price is $1,148
Nov 30 - Dec 1
Total with taxes and fees
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

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, (538 reviews)
"Beautiful scenery and hostess!"
United States
Sonja W.
$326 nightly
The price is $383
Nov 11 - Nov 12
Total with taxes and fees
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

7. Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.8 out of 10, Excellent, (42 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
$443 nightly
The price is $526
Nov 10 - Nov 11
Total with taxes and fees
Signature Residences at Maui Banyan

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, (309 reviews)
"Awesome stay, all you need around there, very quiet place, good neighbors, excellent Host and amazing commons area."
United States
pablo
$353 nightly
The price is $414
Dec 3 - Dec 4
Total with taxes and fees
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

9. 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.
$333 nightly
The price is $393
Nov 12 - Nov 13
Total with taxes and fees
Condo w/ Lanai at Beginning of Road to Hana!

10. 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, (225 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.
$368 nightly
The price is $432
Nov 10 - Nov 11
Total with taxes and fees
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

11. 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
$283 nightly
The price is $336
Dec 8 - Dec 9
Total with taxes and fees
Aston Maui Hill

12. #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.
$442 nightly
The price is $522
Dec 1 - Dec 2
Total with taxes and fees
#239 Steps to Kamaole III Beach, New Kitchen 'Solid Gold Value' Maui Revealed

13. 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, (282 reviews)
"Very good place to stay. Very clean 100% recommend."
United States
john
$333 nightly
The price is $390
Nov 10 - Nov 11
Total with taxes and fees
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

14. 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
$293 nightly
The price is $344
Nov 12 - Nov 13
Total with taxes and fees
Beautiful, Renovated, Hale Kamaole 159

15. 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.
$342 nightly
The price is $401
Nov 12 - Nov 13
Total with taxes and fees
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!

16. 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.
$362 nightly
The price is $426
Dec 7 - Dec 8
Total with taxes and fees
Beautiful Ocean View Studio!

17. 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, (137 reviews)
"A cozy place just right for us to stay while visiting family in town. Minutes away from groceries, beach, food trucks, and other attractions in town. Loved having all the beach chairs, boogie boards and other fun family activities like available for us to use during our stay. They even provided an electric pump, which we used to blow up our own floaties for our kids to use. Others on the property were friendly and greeted us when passing. Pool is just steps away from the gated back patio. View...
United States
Tricia B.
$437 nightly
The price is $513
Nov 29 - Nov 30
Total with taxes and fees
Steps to the Beach! Cute Beachy Ground Floor Getaway! Pool Access

18. Bingo! KKN's TROPHY Unit! Deluxe Renovation, Central Split A/C & Ground Floor.

Bingo! KKN's TROPHY Unit! Deluxe Renovation, Central Split A/C & Ground Floor.
South Kihei
10.0 out of 10, Exceptional, (229 reviews)
"The location right next to the water and the wonderful amenities were just what we needed! Might have to come here again!"
United States
Paulina B.
$319 nightly
The price is $375
Dec 1 - Dec 2
Total with taxes and fees
Bingo! KKN's TROPHY Unit! Deluxe Renovation, Central Split A/C & Ground Floor.

19. Beachfront condo in Maalaea - 2 Bedroom 2 Bath - Ground floor, AC!!!

Beachfront condo in Maalaea - 2 Bedroom 2 Bath - Ground floor, AC!!!
Wailuku
9.4 out of 10, Exceptional, (71 reviews)
"Great location to harbor for whale watching and good distance between airport and beaches. "
United States
Kellie B.
$429 nightly
The price is $503
Nov 16 - Nov 17
Total with taxes and fees
Beachfront condo in Maalaea - 2 Bedroom 2 Bath - Ground floor, AC!!!

20. Bingo! Maui Vista Favorite 170 reviews, pool front w/central split A/C.

Bingo! Maui Vista Favorite 170 reviews, pool front w/central split A/C.
South Kihei
9.8 out of 10, Exceptional, (202 reviews)
"Great location for our Maui stay! Just a block off the beach and within walking distance of a good many park areas, restaurants, and shops. We dud have occasion to communicate with our host and he was always prompt and helpful."
United States
Scott F.
$339 nightly
The price is $399
Nov 15 - Nov 16
Total with taxes and fees
Bingo! Maui Vista Favorite 170 reviews, pool front w/central split A/C.
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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