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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.
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.
The price is AU$4,176
includes taxes & fees
19 Nov - 20 Nov
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 AU$1,799
includes taxes & fees
30 Nov - 1 Dec
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.
The price is AU$1,269
includes taxes & fees
15 Nov - 16 Nov
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.
The price is AU$1,677
includes taxes & fees
30 Nov - 1 Dec
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, (539 reviews)
"Beautiful scenery and hostess!"
United States
Sonja W.
The price is AU$557
includes taxes & fees
4 Dec - 5 Dec
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
The price is AU$821
includes taxes & fees
15 Nov - 16 Nov
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
The price is AU$581
includes taxes & fees
3 Dec - 4 Dec
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.
The price is AU$574
includes taxes & fees
12 Nov - 13 Nov
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, (227 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 AU$629
includes taxes & fees
11 Nov - 12 Nov
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
The price is AU$511
includes taxes & fees
9 Dec - 10 Dec
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.
The price is AU$757
includes taxes & fees
1 Dec - 2 Dec
#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
The price is AU$560
includes taxes & fees
11 Nov - 12 Nov
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
The price is AU$495
includes taxes & fees
12 Nov - 13 Nov
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.
The price is AU$565
includes taxes & fees
12 Nov - 13 Nov
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.
The price is AU$601
includes taxes & fees
8 Dec - 9 Dec
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, (138 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.
The price is AU$742
includes taxes & fees
6 Dec - 7 Dec
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, (230 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.
The price is AU$545
includes taxes & fees
1 Dec - 2 Dec
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 vacation. Location was perfect for our plans."
United States
Jennifer C.
The price is AU$729
includes taxes & fees
16 Nov - 17 Nov
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.
The price is AU$580
includes taxes & fees
15 Nov - 16 Nov
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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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, 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 favourite 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 depend 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 AU$322 per night. Entering your travel dates in the search wizard might find you 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. 

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