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
10 July - 12 July
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Upcountry Maui holiday homes

Property grounds

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, (77 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$4,262
includes taxes & fees
29 June - 30 June
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Property grounds

Haiku Hale - 3 Bedroom Maui Getaway!

Haiku Hale - 3 Bedroom Maui Getaway!
Haiku
10.0 out of 10, Exceptional, (5 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$1,247
includes taxes & fees
6 July - 7 July
Haiku Hale - 3 Bedroom Maui Getaway!
TV

Kapalua Golf Villas Resort by KBM

Kapalua Golf Villas Resort by KBM
4.0 star property
Lahaina
9.4 out of 10, Exceptional, (15 reviews)
"The property was in exquisite shape and the unit was very well kept. Great location! Just a short walk down a hill to beach access. Many restaurants nearby. Easy to drive to the unit."
United States
Clark
The price is AU$5,443
includes taxes & fees
4 July - 5 July
Kapalua Golf Villas Resort by KBM
Studio, Garden View (Haiku #6) | Terrace/patio

Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.8 out of 10, Excellent, (31 reviews)
"Good location for the Road to Hana and exploring Paia, hot tub was enjoyable."
United States
Matt
The price is AU$460
includes taxes & fees
29 June - 30 June
Yonegan Maui Getaways - Haiku
Property grounds

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, (247 reviews)
"I appreciated everything as advertised. Would have preferred mini splits or AC in the bedrooms, but still a nice peaceful spot."
United States
Robert
The price is AU$870
includes taxes & fees
1 July - 2 July
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
Beach towels

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, (455 reviews)
"Great place to stay while exploring Hana"
Canada
Igor G.
The price is AU$580
includes taxes & fees
1 July - 2 July
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Property grounds

Hana Homestead by the Beach

Hana Homestead by the Beach
Hana Town Center
9.8 out of 10, Exceptional, (143 reviews)
"We loved are quiet, peaceful stay in Hāna! So much fun! Beautiful property!"
United States
Justin
The price is AU$2,244
includes taxes & fees
1 July - 2 July
Hana Homestead by the Beach
Beach towels

Fisher's Hana Bay Hale, Across from Hana Bay

Fisher's Hana Bay Hale, Across from Hana Bay
Hana Town Center
9.6 out of 10, Exceptional, (440 reviews)
"Great stay thanks! "
United States
Stephanie C.
The price is AU$583
includes taxes & fees
11 July - 12 July
Fisher's Hana Bay Hale, Across from Hana Bay
Sun-loungers, beach towels

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, (109 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$692
includes taxes & fees
6 July - 7 July
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei
Property grounds

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, (89 reviews)
"Beautiful property. Our second time here, it is one of our favorite places to stay. "
United States
Myra P.
The price is AU$1,239
includes taxes & fees
5 July - 6 July
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006
Beach nearby, sun-loungers, beach towels

Hale Nihi - Paia, Maui

Hale Nihi - Paia, Maui
Paia
9.6 out of 10, Exceptional, (63 reviews)
"Very convenient place to stay within walking distance to activities and beach. "
United States
Chameil H.
The price is AU$642
includes taxes & fees
29 June - 30 June
Hale Nihi - Paia, Maui
Pool

Haleakala Cottage - private hot tub, pool access

Haleakala Cottage - private hot tub, pool access
Haiku
10.0 out of 10, Exceptional, (106 reviews)
"Wonderful Retreat. The privacy is amazing including private hot tub for two. Comfortable layout & well appointed. Only complaint is not understanding how far removed / isolated it is l. That said, we figured it out! The “welcome” solved our breakfast—fresh eggs/bread/a pineapple & more got us started "
Canada
laura
Haleakala Cottage - private hot tub, pool access
Sun-loungers, beach towels

Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b
Hana Town Center
9.4 out of 10, Exceptional, (158 reviews)
"The host communicated clearly and the accommodations were exactly what we were looking for. "
United States
Angie F.
The price is AU$745
includes taxes & fees
1 July - 2 July
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b
2 bedrooms, iron/ironing board, free WiFi, bed sheets

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, (146 reviews)
"Nice place to stay."
United States
chris
The price is AU$964
includes taxes & fees
1 July - 2 July
Romantic Hana Hideaway, Big Ocean Views, Old Hawaii Charm
Interior

Pikake Suite - Historic Elegance, Wailuku

Pikake Suite - Historic Elegance, Wailuku
Wailuku
10.0 out of 10, Exceptional, (9 reviews)
"We arrived after hours. Everything was clean. Very Happy and would stay again "
United States
Tiffany A.
The price is AU$514
includes taxes & fees
23 July - 24 July
Pikake Suite - Historic Elegance, Wailuku
Fridge, microwave, oven, stovetop

New! The Aloha Cottage in Puamana, Maui Hawaii

New! The Aloha Cottage in Puamana, Maui Hawaii
Lahaina
9.8 out of 10, Exceptional, (97 reviews)
"Welcoming host. Great location. Beautiful home. "
United States
Charles W.
The price is AU$1,490
includes taxes & fees
15 July - 16 July
New! The Aloha Cottage in Puamana, Maui Hawaii
Beach nearby

Walk to Beach, Luxury, Great Location! Sleeps 8

Walk to Beach, Luxury, Great Location! Sleeps 8
Lahaina
10.0 out of 10, Exceptional, (181 reviews)
"Communication, location and all amenities were top notch. "
United States
Gary S.
The price is AU$1,857
includes taxes & fees
20 July - 21 July
Walk to Beach, Luxury, Great Location! Sleeps 8
Exterior detail

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)
"Nice property with plenty of space, great location on the island, super communicative and polite host, and such a great backyard/outdoor area. Would highly recommend!"
United States
Michael B.
The price is AU$1,456
includes taxes & fees
10 July - 11 July
Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub
Outdoor pool, pool loungers

HALE VISTA Tropical Getaway at 4BR Kaanapali House to Relax

HALE VISTA Tropical Getaway at 4BR Kaanapali House to Relax
Lahaina
9.8 out of 10, Exceptional, (100 reviews)
"Great stay!"
United States
Zak D.
The price is AU$2,934
includes taxes & fees
29 June - 30 June
HALE VISTA Tropical Getaway at 4BR Kaanapali House to Relax
Terrace/patio

Villa 8

Villa 8
South Kihei
9.8 out of 10, Exceptional, (74 reviews)
"Had a nice time, close to beach and restraunts."
Canada
Jessica M.
The price is AU$1,100
includes taxes & fees
14 July - 15 July
Villa 8
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

Aston Kaanapali Shores

Aston Kaanapali Shores

10/10 Excellent
"We stayed in a two bedroom garden view room but we’re still be able to see the ocean from the room and had a plenty room for five of us."
KUMIKO 4-night trip
Posted 2 hours ago
Aston Kaanapali Shores

Find out more about Upcountry Maui

Upcountry Maui Holiday Homes information

Number of reviews
2,257
Accommodation
185 Holiday Homes
Lowest Price
AU$460
Highest Price
AU$5,443

Explore a world of travel with Expedia