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.
The price is ￥39,021
￥88,488 total
includes taxes & fees
Nov 16 - Nov 17
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
The price is ￥90,339
￥196,307 total
includes taxes & fees
Nov 30 - Dec 1
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.
The price is ￥76,780
￥188,269 total
includes taxes & fees
Nov 30 - Dec 1
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.
The price is ￥98,616
￥183,341 total
includes taxes & fees
Nov 5 - Nov 6
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.
The price is ￥226,321
￥469,798 total
includes taxes & fees
Nov 17 - Nov 18
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, (1,001 reviews)
"Such a beautiful place, lots to do, close to local beaches, tons of yummy food nearby"
United States
Megan
The price is ￥40,478
￥48,054 total
includes taxes & fees
Nov 29 - Nov 30
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.
The price is ￥33,109
￥59,999 total
includes taxes & fees
Nov 11 - Nov 12
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
The price is ￥10,728
￥88,477 total
includes taxes & fees
Nov 1 - Nov 2
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.
The price is ￥29,167
￥69,798 total
includes taxes & fees
Nov 10 - Nov 11
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.
The price is ￥36,129
￥88,386 total
includes taxes & fees
Oct 31 - Nov 1
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
The price is ￥28,663
￥69,530 total
includes taxes & fees
Nov 4 - Nov 5
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.
The price is ￥19,424
￥48,851 total
includes taxes & fees
Nov 1 - Nov 2
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
The price is ￥49,348
￥70,361 total
includes taxes & fees
Oct 31 - Nov 1
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.
The price is ￥39,916
￥101,147 total
includes taxes & fees
Nov 8 - Nov 9
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.
The price is ￥47,180
￥105,161 total
includes taxes & fees
Nov 20 - Nov 21
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.
The price is ￥33,652
￥77,736 total
includes taxes & fees
Nov 7 - Nov 8
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
The price is ￥39,415
￥93,853 total
includes taxes & fees
Oct 31 - Nov 1
~~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.
The price is ￥49,032
￥116,608 total
includes taxes & fees
Nov 17 - Nov 18
🤙 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
The price is ￥16,326
￥62,976 total
includes taxes & fees
Nov 4 - Nov 5
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.
The price is ￥55,181
￥104,147 total
includes taxes & fees
Oct 31 - Nov 1
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 Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua

10/10 Excellent
"Warm and courteous staff✅ Clean and convenient amenities✅ Secluded and walkable beach✅ Would definitely come back for another visit✅"
Bryan Patrick 4-night trip
Posted 5 hours ago
The Ritz-Carlton Maui, Kapalua

Find out more about Upcountry Maui

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