A barren volcanic landscape with rugged terrain and distant mountains.

Holiday Homes in Upcountry Maui

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Upcountry Maui holiday homes

A residential street lined with palm trees and houses.

1. 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 AU$1,168
includes taxes & fees
29 Sept - 30 Sept
Haiku Hale - 3 Bedroom Maui Getaway!
A wooden deck with a chair, surrounded by lush tropical vegetation and a clear blue sky.

2. Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.8 out of 10, Excellent, (37 reviews)
"Good location for the Road to Hana and exploring Paia, hot tub was enjoyable."
United States
Matt
The price is AU$427
includes taxes & fees
4 Oct - 5 Oct
Yonegan Maui Getaways - Haiku
A beach with red sand, scattered rocks, and a distant rocky island.

3. Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Hana Town Center
9.6 out of 10, Exceptional, (469 reviews)
"Great place to stay while exploring Hana"
Canada
Igor G.
The price is AU$605
includes taxes & fees
16 Oct - 17 Oct
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
A beach with clear turquoise waters, rocky shoreline, and distant mountains under a clear sky.

4. Hale Nihi - Paia, Maui

Hale Nihi - Paia, Maui
Paia
9.6 out of 10, Exceptional, (65 reviews)
"Very convenient place to stay within walking distance to activities and beach. "
United States
Chameil H.
The price is AU$662
includes taxes & fees
30 Sept - 1 Oct
Hale Nihi - Paia, Maui
An aerial view of a coastal area with a clear pathway leading to a beach, surrounded by lush greenery and rocky coastline.

5. Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
North Kihei
9.8 out of 10, Exceptional, (110 reviews)
"This place was in a good location in Kihei. You are within 5 mins of dozen of beaches. All the beach gear a person needs is provided(towels, chairs, snorkels, flippers, coolers and more)! Jon is super friendly and a great host!"
United States
Troy s.
The price is AU$705
includes taxes & fees
30 Sept - 1 Oct
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
A beach with clear turquoise waters, rocky shoreline, and distant mountains under a clear sky.

6. HALE NIHI, Paia, Maui

HALE NIHI, Paia, Maui
Paia
9.6 out of 10, Exceptional, (106 reviews)
"great location, great host"
United States
Peter M.
The price is AU$711
includes taxes & fees
30 Sept - 1 Oct
HALE NIHI, Paia, Maui
A house with a lawn and tropical plants.

7. Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
Kaʻeleku
9.8 out of 10, Exceptional, (253 reviews)
"Beautiful place to stay!"
United States
Mary B.
The price is AU$846
includes taxes & fees
30 Sept - 1 Oct
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
A beach with red sand, waves, and a rocky outcrop in the distance.

8. Fisher's Hana Bay Hale, Across from Hana Bay

Fisher's Hana Bay Hale, Across from Hana Bay
Hana Town Center
9.4 out of 10, Exceptional, (465 reviews)
"This property was as advertised. Not having air conditioning was uncomfortable especially in an upper apartment. Some window units would help."
United States
Jane
The price is AU$608
includes taxes & fees
5 Oct - 6 Oct
Fisher's Hana Bay Hale, Across from Hana Bay
A beach with clear blue water, a sandy shore, and greenery.

9. Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!!

Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!!
South Kihei
9.2 out of 10, Wonderful, (63 reviews)
"Our vacation was amazing! The place was even better than we expected — super clean, cozy, and had everything we needed in the kitchen. The AC worked great, and the view from the patio was just beautiful. The beach is right across the street and honestly one of the best around. We already know where we’ll stay next time — we loved it!"
United States
Olga T.
The price is AU$824
includes taxes & fees
29 Sept - 30 Sept
Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!!
A spacious living room with a piano, wicker furniture, and a large mirror.

10. Pikake Suite - Historic Elegance, Wailuku

Pikake Suite - Historic Elegance, Wailuku
Wailuku
10.0 out of 10, Exceptional, (9 reviews)
"Easy parking"
United States
Quinten M.
The price is AU$441
includes taxes & fees
29 Sept - 30 Sept
Pikake Suite - Historic Elegance, Wailuku
A coastal landscape with clear turquoise waters, a sandy beach, and lush greenery.

11. 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 AU$950
includes taxes & fees
29 Sept - 30 Sept
Beautiful Home in paradise!
An outdoor lounge area with wooden furniture and green cushions, a pool, and a view of the surrounding greenery.

12. Villa 8

Villa 8
South Kihei
9.8 out of 10, Exceptional, (74 reviews)
The price is AU$949
includes taxes & fees
7 Oct - 8 Oct
Villa 8
A lush green lawn with a gazebo, a large rock, and a view of a forested hill under a partly cloudy sky.

13. 3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
Kaʻeleku
9.8 out of 10, Exceptional, (101 reviews)
"Beautiful property. Our second time here, it is one of our favorite places to stay. "
United States
Myra P.
The price is AU$1,208
includes taxes & fees
29 Sept - 30 Sept
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
A hot tub on a deck with a view of palm trees and a sunset.

14. Private Hot Tub + Pool Access + AC - Star Lookout

Private Hot Tub + Pool Access + AC - Star Lookout
Haiku
9.8 out of 10, Exceptional, (18 reviews)
"This is an incredible home base for everything special Maui has to offer. On site laundry makes it homey and comfortable leg of any long vacation. Some great local food within a quick 5-15 minute drive and major cities/towns within 20-30 minutes. "
United States
Michael V.
The price is AU$1,218
includes taxes & fees
7 Oct - 8 Oct
Private Hot Tub + Pool Access + AC - Star Lookout
A wooden fence with a sign reading "WOODSTOCK" and a peace sign.

15. Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub

Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub
North Kihei
9.6 out of 10, Exceptional, (110 reviews)
"We had a great stay! Everything was as described and perfect for our family vacation. "
United States
Kristin P.
The price is AU$1,571
includes taxes & fees
30 Sept - 1 Oct
Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub
An aerial view of a beachfront property with a sandy beach, a few palm trees, and a few houses.

16. Beach front Honu Cottage

Beach front Honu Cottage
South Kihei
9.4 out of 10, Exceptional, (10 reviews)
"Perfect location with a private beach a few steps outside the back door. All kitchen essentials available and a bbq included. Perfect place to relax and beautiful scenery. "
United States
JESSICA S.
The price is AU$1,457
includes taxes & fees
29 Sept - 30 Sept
Beach front Honu Cottage
A wooden deck with outdoor furniture, a hanging lantern, and a stone fireplace.

17. Featured on Staycation TV Stunning Modern Home Surrounded by Nature

Featured on Staycation TV Stunning Modern Home Surrounded by Nature
Haiku-Pauwela
10.0 out of 10, Exceptional, (13 reviews)
"Great location and nice clean and quiet"
Canada
Greg B.
The price is AU$2,073
includes taxes & fees
29 Sept - 30 Sept
Featured on Staycation TV Stunning Modern Home Surrounded by Nature
A swimming pool with lounge chairs and palm trees.

18. Penthouse II

Penthouse II
South Kihei
10.0 out of 10, Exceptional, (24 reviews)
"Wonderful stay in a desirable location! We absolutely loved it! "
United States
Lindsay T.
The price is AU$1,960
includes taxes & fees
29 Sept - 30 Sept
Penthouse II
A modern bedroom with a large bed, a wooden bench, and a tray with breakfast items.

19. Tropical Garden Family Home & Penthouse - Sleeps 8 Walk to Beach, BBQ, Hot Tub

Tropical Garden Family Home & Penthouse - Sleeps 8 Walk to Beach, BBQ, Hot Tub
North Kihei
9.6 out of 10, Exceptional, (7 reviews)
"Great place to stay!"
United States
Lori R.
The price is AU$1,966
includes taxes & fees
30 Sept - 1 Oct
Tropical Garden Family Home & Penthouse - Sleeps 8 Walk to Beach, BBQ, Hot Tub
A modern living room with a sofa, coffee table, and a dining area with chairs and a table.

20. Kapalua Golf Villas Resort by KBM

Kapalua Golf Villas Resort by KBM
4.0 star property
Lahaina
9.0 out of 10, Wonderful, (16 reviews)
"Absolute gem. Wife and I love this place and location. "
United States
Joe
The price is AU$1,128
includes taxes & fees
29 Sept - 30 Sept
Kapalua Golf Villas Resort by KBM
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

Aston Kaanapali Shores

Aston Kaanapali Shores

10/10 Excellent
"We had the penthouse we celebrated my birthday, and it was absolutely amazing. The scenery is beautiful and I enjoyed it very much."
Philly 2-night trip
Posted 4 hours ago
Aston Kaanapali Shores

Find out more about Upcountry Maui

Upcountry Maui Holiday Homes information

Number of reviews
2,018
Accommodation
185 Holiday Homes
Lowest Price
AU$427
Highest Price
AU$2,073

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