A barren volcanic landscape with rugged terrain and distant mountains.

Holiday Homes in Upcountry Maui

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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 €805
includes taxes & fees
10 Sept - 11 Sept
Haiku Hale - 3 Bedroom Maui Getaway!
Coffee/tea maker, fridge, microwave, oven

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 €951
includes taxes & fees
31 Aug - 1 Sept
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
Property grounds

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, (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 €2,564
includes taxes & fees
21 Aug - 22 Aug
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Interior

4. Historic 5-Bedroom Home in Upcountry Maui

Historic 5-Bedroom Home in Upcountry Maui
Makawao
Historic 5-Bedroom Home in Upcountry Maui
Outdoor dining

5. 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.
Featured on Staycation TV Stunning Modern Home Surrounded by Nature
Studio, Garden View (Haiku #6) | Terrace/patio

6. 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 €260
includes taxes & fees
23 Aug - 24 Aug
Yonegan Maui Getaways - Haiku
Sun-loungers, beach towels

7. 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 €429
includes taxes & fees
23 Aug - 24 Aug
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
Beach towels

8. 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 €340
includes taxes & fees
14 Aug - 15 Aug
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Exterior

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.
Kamaole Sands 3104-Bright and Fresh!
Beach towels

10. 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 €353
includes taxes & fees
18 Aug - 19 Aug
Fisher's Hana Bay Hale, Across from Hana Bay
Beach

11. 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.
Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!!
Sun-loungers, beach towels

12. 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 €500
includes taxes & fees
19 Aug - 20 Aug
HALE NIHI, Paia, Maui
Beach nearby, sun-loungers, beach towels

13. 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 €500
includes taxes & fees
24 Aug - 25 Aug
Hale Nihi - Paia, Maui
Interior

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.
Pikake Suite - Historic Elegance, Wailuku
Property grounds

15. 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 €525
includes taxes & fees
13 Aug - 14 Aug
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
2 bedrooms, iron/ironing board, free WiFi, bed sheets

16. 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 €582
includes taxes & fees
13 Aug - 14 Aug
Romantic Hana Hideaway, Big Ocean Views, Old Hawaii Charm
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 €909
includes taxes & fees
10 Sept - 11 Sept
Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub
Property grounds

18. 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 €748
includes taxes & fees
18 Aug - 19 Aug
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
Interior

19. Elegant Puakenikeni Suite- Historic & Ground Floor

Elegant Puakenikeni Suite- Historic & Ground Floor
Wailuku
10.0 out of 10, Exceptional, (7 reviews)
"I liked the quaint ambiance of the property, beautiful landscape and the room was great."
United States
Wayne
Elegant Puakenikeni Suite- Historic & Ground Floor
Interior

20. Experience luxury at The Ulu Suite | Garden patio

Experience luxury at The Ulu Suite | Garden patio
Wailuku
10.0 out of 10, Exceptional, (5 reviews)
"We enjoyed the room very much! It’s perfect size confortable and very clean!Josie"
United States
Josie H.
Experience luxury at The Ulu Suite | Garden patio
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Upcountry Maui Hotel Reviews

Maui Seaside Hotel

Maui Seaside Hotel

10/10 Excellent
"Fabulous experience, mahalo to the staff for being so helpful! The room and property were super clean, and having a laundromat on site was awesome!"
Danielle 4-night trip
Posted 2 hours ago
Maui Seaside Hotel

Find out more about Upcountry Maui

Upcountry Maui Holiday Homes information

Number of reviews
2,031
Accommodation
185 Holiday Homes
Lowest Price
€260
Highest Price
€2,564

Explore a world of travel with Expedia