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

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 €2,642
includes taxes & fees
29 Jun - 30 Jun
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

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 €765
includes taxes & fees
29 Jun - 30 Jun
Haiku Hale - 3 Bedroom Maui Getaway!

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 €3,297
includes taxes & fees
3 Jul - 4 Jul
Kapalua Golf Villas Resort by KBM

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 €264
includes taxes & fees
2 Jul - 3 Jul
Yonegan Maui Getaways - Haiku

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 €527
includes taxes & fees
1 Jul - 2 Jul
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

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 €351
includes taxes & fees
1 Jul - 2 Jul
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

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 €1,393
includes taxes & fees
1 Jul - 2 Jul
Hana Homestead by the Beach

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, (439 reviews)
"Great stay thanks! "
United States
Stephanie C.
The price is €358
includes taxes & fees
11 Jul - 12 Jul
Fisher's Hana Bay Hale, Across from Hana Bay

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 €426
includes taxes & fees
6 Jul - 7 Jul
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

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 €861
includes taxes & fees
14 Jul - 15 Jul
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

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 €393
includes taxes & fees
28 Jun - 29 Jun
Hale Nihi - Paia, Maui

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

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 €458
includes taxes & fees
30 Jun - 1 Jul
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

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 €586
includes taxes & fees
2 Jul - 3 Jul
Romantic Hana Hideaway, Big Ocean Views, Old Hawaii Charm

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 €319
includes taxes & fees
28 Jun - 29 Jun
Pikake Suite - Historic Elegance, Wailuku

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 €924
includes taxes & fees
5 Jul - 6 Jul
New! The Aloha Cottage in Puamana, Maui Hawaii

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 €1,278
includes taxes & fees
28 Jul - 29 Jul
Walk to Beach, Luxury, Great Location! Sleeps 8

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 €914
includes taxes & fees
10 Jul - 11 Jul
Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub

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 €1,813
includes taxes & fees
28 Jun - 29 Jun
HALE VISTA Tropical Getaway at 4BR Kaanapali House to Relax

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 €685
includes taxes & fees
14 Jul - 15 Jul
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.
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Top Upcountry Maui Hotel Reviews

Find out more about Upcountry Maui

Upcountry Maui Holiday Homes information

Number of reviews
2,256
Accommodation
185 Holiday Homes
Lowest Price
€264
Highest Price
€3,297

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