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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Upcountry Maui holiday homes

Property grounds

1. Haiku Hale - 3 Bedroom Maui Getaway!

Haiku Hale - 3 Bedroom Maui Getaway!
Haiku
10.0 out of 10, Exceptional, (7 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$1,210
includes taxes & fees
16 Aug - 17 Aug
Haiku Hale - 3 Bedroom Maui Getaway!
Property grounds

2. 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, (81 reviews)
"Great stay with Heleina and John! The property was spacious, very clean, and comfortable. Despite the terrible weather in Hawaii, they went above and beyond to accommodate us, even offering a complimentary extra night in case we got stuck. Truly thoughtful hosts. Would definitely stay again and I highly recommend! "
United States
Anna H.
The price is AU$4,046
includes taxes & fees
31 Aug - 1 Sept
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Outdoor dining

3. 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$1,960
includes taxes & fees
20 Aug - 21 Aug
Featured on Staycation TV Stunning Modern Home Surrounded by Nature
Studio, Garden View (Haiku #6) | Terrace/patio

4. Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.8 out of 10, Excellent, (36 reviews)
"Large room and bathroom. Nice little kitchen area. We had a room with two balconies so great air flow through to cool the room. Beautiful area of Hawaii to explore"
Canada
Amanda
The price is AU$425
includes taxes & fees
23 Aug - 24 Aug
Yonegan Maui Getaways - Haiku
Beach towels

5. 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, (460 reviews)
"Great place to stay while exploring Hana"
Canada
Igor G.
The price is AU$539
includes taxes & fees
14 Aug - 15 Aug
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Beach towels

6. 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, (454 reviews)
"Great stay thanks! "
United States
Stephanie C.
The price is AU$560
includes taxes & fees
24 Aug - 25 Aug
Fisher's Hana Bay Hale, Across from Hana Bay
Property grounds

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, (249 reviews)
"Beautiful place to stay!"
United States
Mary B.
The price is AU$832
includes taxes & fees
24 Aug - 25 Aug
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
Sun-loungers, beach towels

8. 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$809
includes taxes & fees
17 Aug - 18 Aug
HALE NIHI, Paia, Maui
Beach nearby, sun-loungers, beach towels

9. Hale Nihi - Paia, Maui

Hale Nihi - Paia, Maui
Paia
9.6 out of 10, Exceptional, (64 reviews)
"Very convenient place to stay within walking distance to activities and beach. "
United States
Chameil H.
The price is AU$809
includes taxes & fees
13 Aug - 14 Aug
Hale Nihi - Paia, Maui
Sun-loungers, beach towels

10. 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$716
includes taxes & fees
4 Sept - 5 Sept
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
2 bedrooms, iron/ironing board, free WiFi, bed sheets

11. Romantic Hana Hideaway, Big Ocean Views, Old Hawaii Charm

Romantic Hana Hideaway, Big Ocean Views, Old Hawaii Charm
Hana
9.8 out of 10, Exceptional, (151 reviews)
"Nice place to stay."
United States
chris
The price is AU$915
includes taxes & fees
26 Aug - 27 Aug
Romantic Hana Hideaway, Big Ocean Views, Old Hawaii Charm
Exterior

12. Kamaole Sands 3104-Bright and Fresh!

Kamaole Sands 3104-Bright and Fresh!
South Kihei
10.0 out of 10, Exceptional, (51 reviews)
"Beautiful and comfortable ground unit in a great Kihei complex."
United States
Shaun C.
The price is AU$662
includes taxes & fees
28 Aug - 29 Aug
Kamaole Sands 3104-Bright and Fresh!
Beach

13. 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, (62 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$834
includes taxes & fees
13 Aug - 14 Aug
Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!!
Property grounds

14. 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, (96 reviews)
"Beautiful property. Our second time here, it is one of our favorite places to stay. "
United States
Myra P.
The price is AU$1,209
includes taxes & fees
18 Aug - 19 Aug
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
Interior

15. 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$513
includes taxes & fees
13 Aug - 14 Aug
Pikake Suite - Historic Elegance, Wailuku
Property grounds

16. Hana Homestead by the Beach

Hana Homestead by the Beach
Hana Town Center
9.8 out of 10, Exceptional, (145 reviews)
"We loved are quiet, peaceful stay in Hāna! So much fun! Beautiful property!"
United States
Justin
The price is AU$2,130
includes taxes & fees
20 Aug - 21 Aug
Hana Homestead by the Beach
Exterior detail

17. 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, (111 reviews)
"We had a great stay! Everything was as described and perfect for our family vacation. "
United States
Kristin P.
The price is AU$1,416
includes taxes & fees
13 Aug - 14 Aug
Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub
Interior

18. Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!

Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!
Hana Town Center
9.6 out of 10, Exceptional, (35 reviews)
"The view, the location, the rooms, tha kitchen all were wonderful. A great place, If we get back to Hana we will definitely stay here again. "
United States
Bruce B.
The price is AU$1,468
includes taxes & fees
24 Aug - 25 Aug
Oceanfront Hana Bay Beach Cottage. 5-Minute Walk to Hana town & beaches!
4 bedrooms, in-room safe, blackout curtains, iron/ironing board

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)
"The house is an easy walk to a quiet beach and any easy drive to a grocery store and restaurants. The house was clean and well stocked. "
United States
Kimberly F.
The price is AU$2,117
includes taxes & fees
4 Sept - 5 Sept
Tropical Garden Family Home & Penthouse - Sleeps 8 Walk to Beach, BBQ, Hot Tub
Interior

20. Mamane Suite - Historic charm and views

Mamane Suite - Historic charm and views
Wailuku
10.0 out of 10, Exceptional, (5 reviews)
"This was my 2nd time staying here and I love it. Super nice rooms, yummy breakfast."
United States
Jane D.
The price is AU$497
includes taxes & fees
13 Aug - 14 Aug
Mamane Suite - Historic charm and views
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
"Ideal for families! We are a family of 5, 3 teenagers. We could spend time as a family and had separate spaces for down time. The property is amazing! So beautiful! Two pool areas and the beach front offers much for fun and relaxation! Would return in a heartbeat!"
Nathan 1-night trip
Posted 9 hours ago
Aston Kaanapali Shores

Find out more about Upcountry Maui

Upcountry Maui Holiday Homes information

Number of reviews
2,216
Accommodation
185 Holiday Homes
Lowest Price
AU$425
Highest Price
AU$4,046

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