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 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Upcountry Maui vacation rentals

A bamboo structure with a sloped roof, surrounded by rocks and plants.

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.
$2,548 nightly
The price is $2,980
Oct 30 - Oct 31
Total with taxes and fees
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
A spacious kitchen with a large island, wooden flooring, and modern lighting fixtures.

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
$1,049 nightly
The price is $1,245
Oct 31 - Nov 1
Total with taxes and fees
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
A rustic wooden house with a large window and a door, surrounded by lush greenery and palm trees.

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.
$480 nightly
The price is $561
Nov 16 - Nov 17
Total with taxes and fees
Adorable 1930's Gingerbread House....Permitted!
A residential street lined with palm trees and houses.

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.
$708 nightly
The price is $829
Oct 21 - Oct 22
Total with taxes and fees
Haiku Hale - 3 Bedroom Maui Getaway!
A spacious kitchen with a large island, wooden flooring, and modern lighting fixtures.

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.
$1,067 nightly
The price is $1,249
Oct 31 - Nov 1
Total with taxes and fees
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
A resort with a swimming pool, palm trees, and 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
$263 nightly
The price is $312
Nov 20 - Nov 21
Total with taxes and fees
Aston Maui Hill
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.

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.
$327 nightly
The price is $384
Oct 21 - Oct 22
Total with taxes and fees
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens
A resort pool area with a hot tub, lounge chairs, and palm trees.

8. Villa, Garden View, 2-bedroom

Villa, Garden View, 2-bedroom
5.0 star property
Wailea
$1,249 nightly
The price is $1,482
Oct 25 - Oct 26
Total with taxes and fees
Villa, Garden View, 2-bedroom
A beach resort with rows of palm trees, a sandy beach, and a view of the ocean.

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
$526 nightly
The price is $625
Oct 21 - Oct 22
Total with taxes and fees
Signature Residences at Maui Banyan
A two-story house with a balcony, surrounded by well-maintained lawns and tropical vegetation.

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
$311 nightly
The price is $313
Oct 26 - Oct 27
Total with taxes and fees
Yonegan Maui Getaways - Haiku - Unit 6
A beach with palm trees and a clear sky.

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.
$536 nightly
The price is $630
Oct 29 - Oct 30
Total with taxes and fees
Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝
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.

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
$342 nightly
The price is $399
Oct 22 - Oct 23
Total with taxes and fees
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
A balcony with a view of a sunset over palm trees and a row of modern buildings.

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
$297 nightly
The price is $347
Oct 23 - Oct 24
Total with taxes and fees
Beautiful, Renovated, Hale Kamaole 159
Beach

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.
$380 nightly
The price is $445
Oct 24 - Oct 25
Total with taxes and fees
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
A tropical garden with a waterfall, lush greenery, and a gazebo.

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
$240 nightly
The price is $285
Oct 28 - Oct 29
Total with taxes and fees
Aston Kaanapali Shores
A swimming pool with a curved design, surrounded by palm trees and lounge chairs, with a building in the background.

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
$270 nightly
The price is $321
Nov 20 - Nov 21
Total with taxes and fees
Aston Maui Kaanapali Villas
A balcony with a view of palm trees and the ocean.

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.
$479 nightly
The price is $560
Oct 29 - Oct 30
Total with taxes and fees
Exceptionally Remodeled Oceanfront, Sunsets, A/C, King bed Hale Kai O Kihei
An aerial view of a coastal hotel with multiple buildings, a beach, and a mountainous backdrop.

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
$338 nightly
The price is $366
Oct 24 - Oct 25
Total with taxes and fees
Direct Beachfront Newly Remodeled!
A beach with clear blue water, a sandy shore, and a distant mountain.

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
$309 nightly
The price is $361
Nov 3 - Nov 4
Total with taxes and fees
Oceanside condo, full kitchen, ocean view. Fully renovated 2023
A resort with multiple buildings, a swimming pool, and a view of the ocean and mountains.

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.
$342 nightly
The price is $399
Oct 24 - Oct 25
Total with taxes and fees
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

Maui Coast Hotel

Maui Coast Hotel

8/10 Good
"Room was a bit run down- terrible lighting. Tub faucet was practically falling off and shower head did not pull from the tub spout very well. They tried to fix it but it was like this last year so it’s not a one off."
Susan 5-night trip
Posted 1 hour ago
Maui Coast Hotel

Find out more about Upcountry Maui

Everything you need to know about Upcountry Maui vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Upcountry Maui vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Upcountry Maui vacation 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 low season months. For more hustle and bustle, you may prefer to visit Upcountry Maui in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $189 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Upcountry Maui rentals

At Expedia, we put the best Upcountry Maui vacation 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 vacation.

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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