A barren volcanic landscape with rugged terrain and distant mountains.

Holiday Rentals in Upcountry Maui

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Our top choices for Upcountry Maui holiday rentals

1. 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 €2,654
includes taxes & fees
30 Oct - 31 Oct
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

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 €1,111
includes taxes & fees
31 Oct - 1 Nov
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

3. 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!

4. 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 €742
includes taxes & fees
21 Oct - 22 Oct
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 €1,124
includes taxes & fees
31 Oct - 1 Nov
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

6. Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (999 reviews)
"Such a beautiful place, lots to do, close to local beaches, tons of yummy food nearby"
United States
Megan
The price is €309
includes taxes & fees
20 Nov - 21 Nov
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, (535 reviews)
"Beautiful scenery and hostess!"
United States
Sonja W.
The price is €360
includes taxes & fees
21 Oct - 22 Oct
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens

8. Villa, Garden View, 2-bedroom

Villa, Garden View, 2-bedroom
5.0 star property
Wailea
The price is €1,463
includes taxes & fees
27 Oct - 28 Oct
Villa, Garden View, 2-bedroom

9. Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.8 out of 10, Excellent, (40 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 €537
includes taxes & fees
21 Oct - 22 Oct
Signature Residences at Maui Banyan

10. 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 €283
includes taxes & fees
2 Nov - 3 Nov
Yonegan Maui Getaways - Haiku - Unit 6

11. Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝

Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝
Wailea
10.0 out of 10, Exceptional, (165 reviews)
"Beautiful area and great location with walking distance to dining and shopping."
United States
Teri S.
The price is €583
includes taxes & fees
29 Oct - 30 Oct
Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝

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 €361
includes taxes & fees
22 Oct - 23 Oct
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

13. 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 €316
includes taxes & fees
23 Oct - 24 Oct
Beautiful, Renovated, Hale Kamaole 159

14. 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 €403
includes taxes & fees
24 Oct - 25 Oct
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

15. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,392 reviews)
"Great Stay"
United States
Roopa Rani
The price is €271
includes taxes & fees
28 Oct - 29 Oct
Aston Kaanapali Shores

16. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Kannapali Beach Area
8.8 out of 10, Excellent, (2,650 reviews)
"Amazing and relaxing resort"
United States
Mariano
The price is €309
includes taxes & fees
6 Nov - 7 Nov
Aston Maui Kaanapali Villas

17. Exceptionally Remodeled Oceanfront, Sunsets, A/C, King bed Hale Kai O Kihei

Exceptionally Remodeled Oceanfront, Sunsets, A/C, King bed Hale Kai O Kihei
Central Kihei
10.0 out of 10, Exceptional, (181 reviews)
"AMAZING location!! Great beach and close to everything you need in Kihei. Would absolutely stay again!"
United States
Kendall P.
Exceptionally Remodeled Oceanfront, Sunsets, A/C, King bed Hale Kai O Kihei

18. Direct Beachfront Newly Remodeled!

Direct Beachfront Newly Remodeled!
North Kihei
9.2 out of 10, Wonderful, (34 reviews)
"Very nice right on the beach "
United States
MATILDA
The price is €334
includes taxes & fees
24 Oct - 25 Oct
Direct Beachfront Newly Remodeled!

19. 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, (90 reviews)
"Awesome spot for our honeymoon. Would recommend."
United States
Jack
The price is €331
includes taxes & fees
10 Nov - 11 Nov
Oceanside condo, full kitchen, ocean view. Fully renovated 2023

20. 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, (322 reviews)
"Clean and comfortable base for our vacation. Convenient location with easy parking."
United States
Luukia R.
The price is €388
includes taxes & fees
20 Nov - 21 Nov
10% 7 Day Discount! Kihei 1Br Top Floor - Split AC, Clean, Free WiFi, Turtles!
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, apart-hotels, 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 favorite 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 depends 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 €183 per night. Entering your travel dates in the search wizard you might find 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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