Upcountry Maui Holiday Rentals

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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sept - 13 Sept

Our top choices for Upcountry Maui holiday rentals

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)
"Absolutely incredible, the property and the host exceeded all expectations! "
Canada
Marley L.
The price is HK$11,245
HK$23,120 total
includes taxes & fees
26 May - 27 May
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 HK$3,165
HK$6,812 total
includes taxes & fees
28 May - 29 May
Haiku Hale - 3 Bedroom Maui Getaway!
Terrace/patio

Stay in Hana #2

Stay in Hana #2
Hana Town Center
9.6 out of 10, Exceptional, (56 reviews)
"Clean and quiet spot in Hana! A great base for exploring the road to Hana without having to do it all in a day."
United States
Paul John Van de
The price is HK$1,637
HK$2,944 total
includes taxes & fees
5 Jun - 6 Jun
Stay in Hana #2
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, (450 reviews)
"Nice and quiet stay, very peaceful. "
United States
Kari H.
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Property grounds

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hāna
10.0 out of 10, Exceptional, (101 reviews)
"This bungalow is perfect! It is beautiful and peaceful. I would come to Hāna just to stay here. And the host provided excellent information and was very gracious. "
United States
Catherine R.
The price is HK$2,428
HK$4,296 total
includes taxes & fees
11 Jun - 12 Jun
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
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, (246 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 HK$2,330
HK$4,645 total
includes taxes & fees
1 Jun - 2 Jun
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!
Property grounds

Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access
Hana Town Center
9.6 out of 10, Exceptional, (118 reviews)
"Great view, enjoyed location. "
United States
Tony E.
The price is HK$2,992
HK$4,170 total
includes taxes & fees
27 May - 28 May
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access
Property grounds

Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!
Hana Town Center
9.6 out of 10, Exceptional, (78 reviews)
"Great view, excellent location. 2 -3 nights is the perfect amount of time in Hana."
United States
Jim
The price is HK$3,055
HK$4,253 total
includes taxes & fees
28 May - 29 May
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!
Beach towels

A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
Kuau
9.4 out of 10, Exceptional, (207 reviews)
"Great location near Paia shops and short walk to Mama's Fish House, & beach. Enjoyed our stay at Kuau Plaza. The condo was just as described and pictured. Nicely furnished & decorated. Comfy bed, everything you could need in the kitchen, nice bathroom...all looked brand new! Although right next to the road, we barely heard the traffic. We would stay here again."
United States
Kimberly
The price is HK$1,449
HK$3,468 total
includes taxes & fees
6 Jun - 7 Jun
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach
Exterior

Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.6 out of 10, Excellent, (24 reviews)
"Thank you for hosting us! The place was very clean and the location was fantastic, close to the beach, shops and restaurants!"
United States
Julie
The price is HK$366
HK$4,037 total
includes taxes & fees
23 May - 24 May
Signature Residences at Maui Banyan
Exterior detail

Yonegan Maui Getaways - Haiku - Unit 3

Yonegan Maui Getaways - Haiku - Unit 3
Haiku-Pauwela
9.0 out of 10, Wonderful, (21 reviews)
"Great spot in my old home town. Very well kept yard & beautiful place to stay"
United States
Ryan H.
The price is HK$1,017
HK$2,520 total
includes taxes & fees
2 Jun - 3 Jun
Yonegan Maui Getaways - Haiku - Unit 3
Fridge, microwave, oven, stovetop

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 HK$5,092
HK$11,455 total
includes taxes & fees
3 Jun - 4 Jun
Hana Homestead by the Beach
Fridge, microwave, oven, stovetop

Paia 2 Bedroom 2 Bathroom

Paia 2 Bedroom 2 Bathroom
Paia
9.2 out of 10, Wonderful, (12 reviews)
"The house was perfect for the 6 of us and near a beautiful cove. "
United States
Vanessa C.
The price is HK$2,429
HK$5,175 total
includes taxes & fees
23 May - 24 May
Paia 2 Bedroom 2 Bathroom
Outdoor dining

OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC

OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC
Wailuku
9.6 out of 10, Exceptional, (170 reviews)
"Great location on the island, nice accommodations. "
United States
Chris P.
The price is HK$697
HK$2,657 total
includes taxes & fees
25 May - 26 May
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC
On the beach

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,798 reviews)
"Beautiful condo to stay at and the staff was wonderful"
United States
Rina Kaur
The price is HK$1,856
HK$2,203 total
includes taxes & fees
4 Jun - 5 Jun
Napili Shores Maui by OUTRIGGER
Outdoor pool, open 8:00 AM to 9:30 PM, pool loungers

Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (911 reviews)
"Staff was amazing and nice! The GM is a huge Kansas City Chiefs fan. The property is beautiful and is a perfect walking distance for anything Kīhei/Wailea. Great TV channels as well. There are cute roosters, lizards and birds everywhere. Will be staying here again for sure! "
Canada
Ethan
The price is HK$2,057
HK$2,442 total
includes taxes & fees
28 May - 29 May
Aston Maui Hill
Beach nearby, white sand, beach towels

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (183 reviews)
"The property is beautiful and located just steps away from the beach."
United States
Patricia
The price is HK$1,430
HK$1,698 total
includes taxes & fees
24 May - 25 May
Napili Village Hotel
Garden view

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (406 reviews)
"From check-in to check-out and all days in between the staff and property were wonderful.Clean, beautiful property located in the hub of Kaanapali Beach. Always a great place to stay."
United States
Ralph
The price is HK$2,392
HK$5,702 total
includes taxes & fees
22 May - 23 May
The Whaler Resort Kaanapali Beach
Outdoor dining

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!

10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
North Kihei
10.0 out of 10, Exceptional, (274 reviews)
"Perfectly situated on Maui island to easily visit everything and come back to condo to sleep."
Canada
Jean-Philippe R.
The price is HK$944
HK$3,303 total
includes taxes & fees
12 Jun - 13 Jun
10% 7 Day Discount! Kihei Studio - Split AC, Clean, Free WiFi, Turtles!
Smart TV, DVD player, books, streaming services

This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!

This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!
North Kihei
10.0 out of 10, Exceptional, (40 reviews)
"Had lots of great and useful amenities "
United States
Rochelle P.
The price is HK$979
HK$3,560 total
includes taxes & fees
22 May - 23 May
This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!
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

Maui Coast Hotel

Maui Coast Hotel

8/10 Good
"I appreciated that the hotel offered complimentary self-service laundry facilities, which can be very helpful for travelers. Unfortunately, the experience became frustrating when the washing machine was not operating properly and I asked for assistance. What disappointed me most was not the machine itself, but the response from management. When I approached the hotel for help, I was essentially told to “Google the solution” instead of being offered assistance, troubleshooting guidance, or support. Even if the laundry area is self-service, basic hospitality would suggest helping guests navigate an issue with an amenity provided by the hotel. Problems can happen anywhere, and most guests understand that. What leaves a lasting impression is how staff and management respond when assistance is requested. In this case, the interaction felt dismissive and lacking in customer service professionalism. I hope management takes this as constructive feedback and improves the level of guest support moving forward."
German 3-night trip
Posted 3 hours ago
Maui Coast Hotel

Find out more about Upcountry Maui

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