A barren volcanic landscape with rugged terrain and distant mountains.

Upcountry Maui Holiday Rentals

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Check prices for these dates

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

Our top choices for Upcountry Maui holiday 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.
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 HK$4,496
HK$9,769 total
includes taxes & fees
31 Oct - 1 Nov
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 HK$3,821
HK$9,722 total
includes taxes & fees
31 Oct - 1 Nov
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 HK$4,907
HK$9,074 total
includes taxes & fees
31 Oct - 1 Nov
Haiku Hale - 3 Bedroom Maui Getaway!
A bamboo structure with a sloped roof, surrounded by rocks and 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 HK$11,262
HK$23,378 total
includes taxes & fees
17 Nov - 18 Nov
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 HK$2,289
HK$2,717 total
includes taxes & fees
29 Nov - 30 Nov
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, (537 reviews)
"Beautiful scenery and hostess!"
United States
Sonja W.
The price is HK$1,648
HK$2,986 total
includes taxes & fees
11 Nov - 12 Nov
Paradise Ocean View Private Cottage Solar Power Tropical Flower Gardens
A beach resort with rows of palm trees, a sandy beach, and a view of the ocean.

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 HK$516
HK$4,362 total
includes taxes & fees
1 Nov - 2 Nov
Signature Residences at Maui Banyan
Beach

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 HK$1,451
HK$3,498 total
includes taxes & fees
3 Nov - 4 Nov
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 HK$1,797
HK$4,395 total
includes taxes & fees
31 Oct - 1 Nov
Exceptionally Remodeled Oceanfront, Sunsets, A/C, King bed Hale Kai O Kihei
A beach with palm trees, clear blue water, and rocky shoreline.

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 HK$1,426
HK$3,444 total
includes taxes & fees
31 Oct - 1 Nov
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 HK$967
HK$2,431 total
includes taxes & fees
1 Nov - 2 Nov
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 HK$2,456
HK$3,501 total
includes taxes & fees
31 Oct - 1 Nov
Oceanview #101 at Hana Kai Maui - 1 Bedroom King/Twins , Amazing View!
A beach with palm trees and a clear sky.

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)
"Everything was amazing, I enjoyed all the amenities the room had to offer. Will definitely book again in the future."
United States
Rojelio G.
The price is HK$1,985
HK$5,030 total
includes taxes & fees
8 Nov - 9 Nov
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 HK$2,348
HK$5,209 total
includes taxes & fees
27 Nov - 28 Nov
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 HK$1,673
HK$3,866 total
includes taxes & fees
7 Nov - 8 Nov
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 HK$1,961
HK$4,670 total
includes taxes & fees
31 Oct - 1 Nov
~~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 HK$2,440
HK$5,803 total
includes taxes & fees
17 Nov - 18 Nov
🤙 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 HK$812
HK$3,134 total
includes taxes & fees
31 Oct - 1 Nov
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
A coastal landscape with clear turquoise waters, a sandy beach, and lush greenery.

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 HK$2,746
HK$5,183 total
includes taxes & fees
31 Oct - 1 Nov
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

Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

10/10 Excellent
"Our room was very clean and had a beautiful view of the ocean! In the evening, if we weren't busy doing something else, we could sit on our balcony and listen to the Hawaiian Luau. The menu in the restaurant was great, especially the Pineapple Upside Down Pancakes! Just outside of the Restaurant/Bar was one of the two pools and then just steps away from the Ocean! We went on the Maui Pineapple Tour, that came with a box of 3 fresh Pineapples, and the restaurant downstairs cut it up for us and we ate it by the pool. We had a great time and definitely would stay here again!!"
Joann 7-night trip
Posted 4 hours ago
Royal Lahaina Resort & Bungalows

Find out more about Upcountry Maui

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