A barren volcanic landscape with rugged terrain and distant mountains.

Holiday Homes in Upcountry Maui

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Our top choices for Upcountry Maui holiday homes

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 NZ$1,456
includes taxes & fees
17 Aug - 18 Aug
Haiku Hale - 3 Bedroom Maui Getaway!

2. 2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
Haiku
9.0 out of 10, Wonderful, (2 reviews)
"Very comfortable "
United States
Tanya N.
The price is NZ$1,846
includes taxes & fees
10 Sept - 11 Sept
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

3. 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)
"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 NZ$4,888
includes taxes & fees
31 Aug - 1 Sept
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

4. 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 NZ$2,452
includes taxes & fees
7 Sept - 8 Sept
Featured on Staycation TV Stunning Modern Home Surrounded by Nature

5. 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 NZ$513
includes taxes & fees
23 Aug - 24 Aug
Yonegan Maui Getaways - Haiku

6. 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 NZ$819
includes taxes & fees
23 Aug - 24 Aug
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

7. 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, (461 reviews)
"Great place to stay while exploring Hana"
Canada
Igor G.
The price is NZ$643
includes taxes & fees
16 Aug - 17 Aug
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

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, (454 reviews)
"Great stay thanks! "
United States
Stephanie C.
The price is NZ$682
includes taxes & fees
18 Aug - 19 Aug
Fisher's Hana Bay Hale, Across from Hana Bay

9. 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 NZ$816
includes taxes & fees
28 Aug - 29 Aug
Kamaole Sands 3104-Bright and Fresh!

10. 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 NZ$944
includes taxes & fees
25 Aug - 26 Aug
HALE NIHI, Paia, Maui

11. 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 NZ$973
includes taxes & fees
21 Aug - 22 Aug
Hale Nihi - Paia, Maui

12. 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 NZ$983
includes taxes & fees
24 Aug - 25 Aug
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

13. 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 NZ$1,118
includes taxes & fees
10 Sept - 11 Sept
Romantic Hana Hideaway, Big Ocean Views, Old Hawaii Charm

14. 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 NZ$593
includes taxes & fees
20 Aug - 21 Aug
Pikake Suite - Historic Elegance, Wailuku

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, (111 reviews)
"We had a great stay! Everything was as described and perfect for our family vacation. "
United States
Kristin P.
The price is NZ$1,701
includes taxes & fees
16 Aug - 17 Aug
Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub

16. 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, (98 reviews)
"Beautiful property. Our second time here, it is one of our favorite places to stay. "
United States
Myra P.
The price is NZ$1,444
includes taxes & fees
17 Aug - 18 Aug
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

17. 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 NZ$2,206
includes taxes & fees
23 Aug - 24 Aug
Tropical Garden Family Home & Penthouse - Sleeps 8 Walk to Beach, BBQ, Hot Tub

18. New! The Aloha Cottage in Puamana, Maui Hawaii

New! The Aloha Cottage in Puamana, Maui Hawaii
Lahaina
9.8 out of 10, Exceptional, (99 reviews)
"Excellent quiet location in a HOA neighborhood, two pools one on the lake. Just beyond where the fires hit years ago as they’re just starting to rebuild, but this unit and that half of the neighborhood was spared. Nicely remodeled on the inside."
United States
Jason D.
The price is NZ$1,526
includes taxes & fees
15 Aug - 16 Aug
New! The Aloha Cottage in Puamana, Maui Hawaii

19. Beach front Honu Cottage

Beach front Honu Cottage
South Kihei
9.4 out of 10, Exceptional, (9 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 NZ$1,945
includes taxes & fees
24 Aug - 25 Aug
Beach front Honu Cottage

20. Penthouse I

Penthouse I
South Kihei
10.0 out of 10, Exceptional, (19 reviews)
"Great place. Great location. "
United States
Lars B.
Penthouse I
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

Find out more about Upcountry Maui

Upcountry Maui Holiday Homes information

Number of reviews
15
Accommodation
185 Holiday Homes
Lowest Price
NZ$513
Highest Price
NZ$4,161

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