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 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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.
$480 nightly
The price is $561
Nov 16 - Nov 17
Total with taxes and fees
Adorable 1930's Gingerbread House....Permitted!
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 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!
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.
$1,058 nightly
The price is $1,239
Oct 31 - Nov 1
Total with taxes and fees
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.

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.
$988 nightly
The price is $1,157
Oct 30 - Oct 31
Total with taxes and fees
Haiku Hale - 3 Bedroom Maui Getaway!
A swimming pool with a wooden deck, surrounded by palm trees and tropical plants.

5. 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
Nov 17 - Nov 18
Total with taxes and fees
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
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, (1,000 reviews)
"Such a beautiful place, lots to do, close to local beaches, tons of yummy food nearby"
United States
Megan
$248 nightly
The price is $294
Nov 29 - Nov 30
Total with taxes and fees
Aston Maui Hill
A green house with a porch, surrounded by lush greenery.

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, (537 reviews)
"Beautiful scenery and hostess!"
United States
Sonja W.
$324 nightly
The price is $381
Nov 11 - Nov 12
Total with taxes and fees
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens
A breakfast table set on a balcony with a view of a tropical landscape.

8. 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
$447 nightly
The price is $531
Oct 30 - Oct 31
Total with taxes and fees
Signature Residences at Maui Banyan
Living area

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.
$378 nightly
The price is $443
Oct 31 - Nov 1
Total with taxes and fees
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
A balcony with a view of palm trees and the ocean.

10. 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 30 - Oct 31
Total with taxes and fees
Exceptionally Remodeled Oceanfront, Sunsets, A/C, King bed Hale Kai O Kihei
A modern kitchen with a central island, built-in appliances, and a sliding glass door leading to a balcony.

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
$375 nightly
The price is $439
Oct 30 - Oct 31
Total with taxes and fees
Maui Modern North Shore Beach Condo - Walk to Mamas Fish House! AC, Fast WiFi
A wooden staircase leading to a balcony of a blue building surrounded by lush greenery and flowering plants.

12. Yonegan Maui Getaways - Haiku - Unit 3

Yonegan Maui Getaways - Haiku - Unit 3
Haiku-Pauwela
9.2 out of 10, Wonderful, (24 reviews)
"Clean and comfortable. Enjoyed having the balconies. On the road to Hana. In a quiet neighborhood. Would definitely stay again."
United States
Gennessa R.
$308 nightly
The price is $310
Nov 1 - Nov 2
Total with taxes and fees
Yonegan Maui Getaways - Haiku - Unit 3
A hotel with a pool, a lawn, and a view of the ocean.

13. Oceanview #101 at Hana Kai Maui - 1 Bedroom King/Twins , Amazing View!

Oceanview #101 at Hana Kai Maui - 1 Bedroom King/Twins , Amazing View!
Hana Town Center
9.6 out of 10, Exceptional, (86 reviews)
"Great beach view lovely gardens"
United States
Dianne
$381 nightly
The price is $446
Oct 30 - Oct 31
Total with taxes and fees
Oceanview #101 at Hana Kai Maui - 1 Bedroom King/Twins , Amazing View!
A golf course with a clear view of the ocean and a row of houses in the background.

14. 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.
$553 nightly
The price is $648
Oct 30 - Oct 31
Total with taxes and fees
Traveler Favorite! Spacious, comfortable, updated 5-STAR Wailea Retreat. 🏝
A balcony with a view of the ocean, a pool, and tropical plants.

15. Ocean Front Sugar Beach Resort 3rd floor 1 Bedroom condo ~ Unit 311

Ocean Front Sugar Beach Resort 3rd floor 1 Bedroom condo ~ Unit 311
North Kihei
10.0 out of 10, Exceptional, (144 reviews)
"We really enjoy staying here at Sugar Beach!! This condo is always perfect in every way! We have stayed here multiple times and it is always a great experience. Would highly recommend this condo!!"
United States
Lela N.
$570 nightly
The price is $667
Nov 17 - Nov 18
Total with taxes and fees
Ocean Front Sugar Beach Resort 3rd floor 1 Bedroom condo ~ Unit 311
A kitchen with wooden cabinets, stainless steel appliances, and a view of the ocean.

16. Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!

Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!
North Kihei
9.8 out of 10, Exceptional, (227 reviews)
"Has everything you need and you cannot beat the location. Everything works, slept great, would definitely book again"
United States
Michelle S.
$399 nightly
The price is $467
Oct 30 - Oct 31
Total with taxes and fees
Beachfront ,Ground floor, Sugar Beach, Corner unit 114 - Steps to the Ocean!!!
A hotel room with a balcony, leather sofas, and a view of the ocean.

17. ~~OceanFRONT complex~~on the BEACH~~Luxury Remodel~~

~~OceanFRONT complex~~on the BEACH~~Luxury Remodel~~
North Kihei
9.8 out of 10, Exceptional, (140 reviews)
"Great location and facilities. Very convenient to all the great places on Maui."
United States
Tom
$509 nightly
The price is $595
Oct 30 - Oct 31
Total with taxes and fees
~~OceanFRONT complex~~on the BEACH~~Luxury Remodel~~
A balcony with a table set for two, overlooking a beach with palm trees and the ocean.

18. 🤙 Oct-Nov-Dec SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE

🤙 Oct-Nov-Dec SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE
North Kihei
10.0 out of 10, Exceptional, (145 reviews)
"We enjoyed the resort and the condo was perfect"
United States
Shelley S.
$632 nightly
The price is $740
Nov 17 - Nov 18
Total with taxes and fees
🤙 Oct-Nov-Dec SPECIALS PLUS VRBO discounts 🏝️ at the LIVE ALOHA SUITE
A balcony with a table set for two, featuring a bottle of wine and two glasses.

19. 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
$342 nightly
The price is $399
Oct 30 - Oct 31
Total with taxes and fees
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
A covered porch with a table and four chairs, a potted plant, and a view of tropical foliage.

20. Beautiful Home in paradise!

Beautiful Home in paradise!
Kaʻeleku
9.6 out of 10, Exceptional, (179 reviews)
"Loved everything about it. As advertised. Will do it again."
United States
Monafou M.
$564 nightly
The price is $661
Oct 30 - Oct 31
Total with taxes and fees
Beautiful Home in paradise!
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

The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

10/10 Excellent
"Great location on Ka’anapali Beach area. Lots of restaurants and shops nearby."
Stephen 5-night trip
Posted 1 hour ago
The Westin Maui Resort & Spa, Ka'anapali

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 $195 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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