Upcountry Maui Holiday Rentals

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Our top choices for Upcountry Maui holiday rentals

Haiku Hale - 3 Bedroom Maui Getaway!

Haiku Hale - 3 Bedroom Maui Getaway!
Haiku
10.0 out of 10, Exceptional, (4 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$1,238
includes taxes & fees
5 Apr - 6 Apr
Haiku Hale - 3 Bedroom Maui Getaway!

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, (76 reviews)
"Absolutely incredible, the property and the host exceeded all expectations! "
Canada
Marley L.
The price is AU$4,214
includes taxes & fees
29 Mar - 30 Mar
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Hana Town Center
9.6 out of 10, Exceptional, (199 reviews)
"Had a very nice stay. The cottage was well equipped. I spent 8 days there. Loved this location in Hana."
United States
Lon S.
The price is AU$618
includes taxes & fees
30 Mar - 31 Mar
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

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
9.2 out of 10, Wonderful, (155 reviews)
"The location was fantastic and the house was very comfortable, especially the beds."
United States
Lisa H.
The price is AU$726
includes taxes & fees
29 Mar - 30 Mar
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

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, (423 reviews)
"Very peaceful place to stay. Enjoyed location and would stay again if I come to Hana!"
United States
Nicholas
The price is AU$578
includes taxes & fees
29 Mar - 30 Mar
Fisher's Hana Bay Hale, Across from Hana Bay

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, (437 reviews)
"Enjoyed the screened in porch"
United States
Thomas
The price is AU$554
includes taxes & fees
24 Apr - 25 Apr
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Oceanview Condo in Hana-Let the ocean lull you to sleep

Oceanview Condo in Hana-Let the ocean lull you to sleep
Hana Town Center
9.4 out of 10, Exceptional, (138 reviews)
"Great location."
United States
John
The price is AU$668
includes taxes & fees
3 Apr - 4 Apr
Oceanview Condo in Hana-Let the ocean lull you to sleep

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, (239 reviews)
"30 yr anniversary - perfectly relaxing for us - would stay here again for sure."
United States
Trent H.
The price is AU$866
includes taxes & fees
5 Apr - 6 Apr
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

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, (201 reviews)
"Recently renovated and spotless! This condo had everything we needed and was comfortable and conveniently located. Highly recommend!"
United States
Allison H.
The price is AU$639
includes taxes & fees
3 Apr - 4 Apr
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

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, (77 reviews)
"Great view, excellent location. 2 -3 nights is the perfect amount of time in Hana."
United States
Jim
The price is AU$730
includes taxes & fees
29 Mar - 30 Mar
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

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

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hāna
10.0 out of 10, Exceptional, (97 reviews)
"The view was beautiful! Location was fantastic and secluded! Outdoor shower was awesome! Will certainly come again. "
United States
Rustin S.
The price is AU$778
includes taxes & fees
22 Apr - 23 Apr
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

Relaxing home away from home- honeymoon friendly

Relaxing home away from home- honeymoon friendly
Hana
10.0 out of 10, Exceptional, (283 reviews)
"It was such a cute little place. Quite and charming with a spectacular view. Loved our stay here."
Canada
Marjorie
Relaxing home away from home- honeymoon friendly

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)
"Everything Good "
United States
Marc
The price is AU$793
includes taxes & fees
31 Mar - 1 Apr
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

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, (81 reviews)
"Plenty of room for our family of 5. Clean and cozy. Lots of fruits to try on the farm. "
United States
Nikki R.
The price is AU$1,239
includes taxes & fees
5 Apr - 6 Apr
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

The Ocean View Residence

The Ocean View Residence
3.0 star property
South Kihei
10.0 out of 10, Exceptional, (1 review)
"Very nice condo for a longer-term stay. We loved being able to cook. "
United States
John
The price is AU$900
includes taxes & fees
30 Mar - 31 Mar
The Ocean View Residence

Kuau Surf 2.0 Maui North Shore Locally-Owned

Kuau Surf 2.0 Maui North Shore Locally-Owned
Paia
9.2 out of 10, Wonderful, (23 reviews)
"Clean and convenient"
United States
Ilya L
The price is AU$509
includes taxes & fees
27 Apr - 28 Apr
Kuau Surf 2.0 Maui North Shore Locally-Owned

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, (167 reviews)
"Great location on the island, nice accommodations. "
United States
Chris P.
The price is AU$495
includes taxes & fees
1 Apr - 2 Apr
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC

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$743
includes taxes & fees
13 Apr - 14 Apr
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

Hana Homestead by the Beach

Hana Homestead by the Beach
Hana Town Center
9.8 out of 10, Exceptional, (142 reviews)
"We loved are quiet, peaceful stay in Hāna! So much fun! Beautiful property!"
United States
Justin
The price is AU$1,939
includes taxes & fees
21 Apr - 22 Apr
Hana Homestead by the Beach

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, (39 reviews)
"we really enjoyed our stay here. It is clean and maintained well and close to the beach."
United States
stuti s.
The price is AU$685
includes taxes & fees
29 Mar - 30 Mar
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

Find out more about Upcountry Maui

Everything you need to know about Upcountry Maui holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Upcountry Maui holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Upcountry Maui holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Upcountry Maui holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Upcountry Maui. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Upcountry Maui holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Upcountry Maui holiday rentals we have selected for you start as low as AU$560 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Upcountry Maui rentals

At Expedia, we put the best Upcountry Maui holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Upcountry Maui rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Upcountry Maui holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Upcountry Maui. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.