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Our top choices for Upcountry Maui holiday homes
1. Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16Makawao
10.0 out of 10, Exceptional, (82 reviews)
"This place was perfect for our big group!"
Lisa B.
The price is NZ$5,568
includes taxes & fees
17 Nov - 18 Nov
2. Haiku Hale - 3 Bedroom Maui Getaway!
Haiku Hale - 3 Bedroom Maui Getaway!Haiku
10.0 out of 10, Exceptional, (8 reviews)
"Great spot and a nice rental. Wonderful outdoor space as well. We will be back!"
Will W.
The price is NZ$1,573
includes taxes & fees
15 Nov - 16 Nov
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!"
Amy C.
The price is NZ$2,064
includes taxes & fees
30 Nov - 1 Dec
4. Yonegan Maui Getaways - Haiku
Yonegan Maui Getaways - HaikuHaiku
8.8 out of 10, Excellent, (42 reviews)
"The place was just as described. The host was great. Definitely recommend."
Nancy
The price is NZ$540
includes taxes & fees
17 Nov - 18 Nov
5. Fisher's Hana Bay Hale, Across from Hana Bay
Fisher's Hana Bay Hale, Across from Hana BayHana Town Center
9.4 out of 10, Exceptional, (471 reviews)
"Great stay!"
Val S.
The price is NZ$760
includes taxes & fees
18 Nov - 19 Nov
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 KiheiNorth Kihei
9.8 out of 10, Exceptional, (111 reviews)
" Kīhei Casita House Stay (above the Main House): just lovely - would stay there again - reasonably priced - fully functioning everything - and easy outside access - we actually stayed in the Main House for one week and then one week in the Casita - while in the Main House the Casita was occupied and no noise issues at all. Fairly easy access to beaches and beach shopping. Excellent communication with host."
Michael C.
The price is NZ$851
includes taxes & fees
16 Nov - 17 Nov
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 0002Hana Town Center
9.6 out of 10, Exceptional, (478 reviews)
"The bed on the front porch was a hit! Watching sunset from the porch bed was a great experience"
Jennifer
The price is NZ$744
includes taxes & fees
21 Nov - 22 Nov
8. Hale Nihi - Paia, Maui
Hale Nihi - Paia, MauiPaia
9.6 out of 10, Exceptional, (65 reviews)
"Very convenient place to stay within walking distance to activities and beach. "
Chameil H.
The price is NZ$921
includes taxes & fees
14 Nov - 15 Nov
9. HALE NIHI, Paia, Maui
HALE NIHI, Paia, MauiPaia
9.6 out of 10, Exceptional, (108 reviews)
"great location, great host"
Peter M.
The price is NZ$984
includes taxes & fees
16 Nov - 17 Nov
10. Kamaole Sands 3104-Bright and Fresh!
Kamaole Sands 3104-Bright and Fresh!South Kihei
10.0 out of 10, Exceptional, (53 reviews)
"Fantastic stay. The condo was clean, comfortable, and perfectly located. It was a short walk to the beach and restaurants, and we appreciated all the thoughtful touches throughout the property. The hosts were wonderful and made check‑in easy. Would absolutely stay here again."
Koree L.
The price is NZ$921
includes taxes & fees
6 Dec - 7 Dec
11. 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, (256 reviews)
"Beautiful place to stay!"
Mary B.
The price is NZ$1,068
includes taxes & fees
17 Nov - 18 Nov
12. 3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006Kaʻeleku
9.8 out of 10, Exceptional, (103 reviews)
"The property was clean, and we enjoyed our stay in this beautiful home. The host was responsive when we asked questions. The only downside I would say was no AC as it was very hot and humid, but there is fans all around the house that helped cool us down. Overall was a good experience."
Nancy
The price is NZ$1,497
includes taxes & fees
14 Nov - 15 Nov
13. Beautiful Home in paradise!
Beautiful Home in paradise!Kaʻeleku
9.6 out of 10, Exceptional, (181 reviews)
"Loved everything about it. As advertised. Will do it again."
Monafou M.
The price is NZ$1,154
includes taxes & fees
14 Nov - 15 Nov
14. The Pikake Suite at The Historic Wailuku Inn
The Pikake Suite at The Historic Wailuku InnWailuku
10.0 out of 10, Exceptional, (9 reviews)
"Easy parking"
Quinten M.
The price is NZ$566
includes taxes & fees
14 Nov - 15 Nov
15. 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, (64 reviews)
"The location was perfect. Family had a perfect stay."
Elizabeth M.
16. Featured on Staycation TV Stunning Modern Home Surrounded by Nature
Featured on Staycation TV Stunning Modern Home Surrounded by NatureHaiku-Pauwela
10.0 out of 10, Exceptional, (13 reviews)
"Great location and nice clean and quiet"
Greg B.
The price is NZ$2,609
includes taxes & fees
11 Dec - 12 Dec
17. Private Hot Tub + Pool Access + AC - Star Lookout
Private Hot Tub + Pool Access + AC - Star LookoutHaiku
9.8 out of 10, Exceptional, (20 reviews)
"Great host, amazing location and views. This place is like its own little resort without all the hustle and bustle of resort life. We loved the privacy and quiet nights and the cliff walk is breathtaking ! So clean and well maintained that we are already looking to book it again ! "
Bob E.
19. Tropical Vacation Rental Near Hana Bay & Waianapanapa State Park, Hawaii
Tropical Vacation Rental Near Hana Bay & Waianapanapa State Park, HawaiiHana Town Center
The price is NZ$902
includes taxes & fees
16 Nov - 17 Nov
20. Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub
Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot TubNorth Kihei
9.6 out of 10, Exceptional, (111 reviews)
"We had a great stay! Everything was as described and perfect for our family vacation. "
Kristin P.
The price is NZ$1,839
includes taxes & fees
16 Nov - 17 Nov
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.
Learn more about Upcountry Maui
Venture to top sights like Haleakala National Park as you discover Upcountry Maui—a relaxing city also notable for its island views.
Photo by Project Forever
Open Photo by Project Forever