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 NZ$1,407
includes taxes & fees
22 Feb - 23 Feb
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, (73 reviews)
"We had an amazing vacation here. We had 4 generations ranging from 4 months to 81 years and everyone had a great time. There was room to spread out and room to all gather together. Having the private pool and spa was perfect. Host was available when we needed her and the B and B was well stocked. We also loved the Maui feel of the accommodations and being out of the busier parts of Maui. I highly recommend this venue for larger groups! "
United States
Kari L.
The price is NZ$4,864
includes taxes & fees
4 Mar - 5 Mar
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

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
9.2 out of 10, Wonderful, (133 reviews)
"Great location."
United States
John
The price is NZ$793
includes taxes & fees
12 Mar - 13 Mar
Oceanview Condo in Hana-Let the ocean lull you to sleep

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, (193 reviews)
"Super lovely place, I wish we were staying longer! Has everything you need. "
United States
Nicole
The price is NZ$803
includes taxes & fees
24 Feb - 25 Feb
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

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, (418 reviews)
"Very peaceful place to stay. Enjoyed location and would stay again if I come to Hana!"
United States
Nicholas
The price is NZ$661
includes taxes & fees
24 Feb - 25 Feb
Fisher's Hana Bay Hale, Across from Hana Bay

MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA

MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA
Hana
10.0 out of 10, Exceptional, (253 reviews)
"We loved staying here! It had all the amenities, was so comfortable and very easy for check in and check out. Perfect place for a quiet and relaxing stay in Hana. Also, SO close to the most gorgeous beach, only a two minute drive!"
United States
Kristi O.
The price is NZ$989
includes taxes & fees
8 Mar - 9 Mar
MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA

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, (113 reviews)
"Everything Good "
United States
Marc
The price is NZ$989
includes taxes & fees
7 Mar - 8 Mar
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

Oceanview #101 at Hana Kai Maui - 1 Bedroom Corner Unit, Amazing View!

Oceanview #101 at Hana Kai Maui - 1 Bedroom Corner Unit, Amazing View!
Hana Town Center
9.6 out of 10, Exceptional, (77 reviews)
"Nice easy check in. Easy access to black sand beach (not the State Park)."
United States
Brett
The price is NZ$989
includes taxes & fees
1 Mar - 2 Mar
Oceanview #101 at Hana Kai Maui - 1 Bedroom Corner Unit, Amazing View!

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, (150 reviews)
"The location was fantastic and the house was very comfortable, especially the beds."
United States
Lisa H.
The price is NZ$930
includes taxes & fees
22 Feb - 23 Feb
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

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, (197 reviews)
"Such a great place to stay! Location could not have been better. Quiet neighbors, walking distance to Mama’s Fish house and the beach. Traffic can be a little loud, but that has nothing do to with the owner or space. We would stay here again!"
United States
Allison S.
The price is NZ$737
includes taxes & fees
24 Feb - 25 Feb
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

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

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hāna
10.0 out of 10, Exceptional, (92 reviews)
"Very unique property near Hana. Great experience!"
United States
Keith R.
The price is NZ$934
includes taxes & fees
6 Mar - 7 Mar
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

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, (22 reviews)
"Clean and convenient"
United States
Ilya L
The price is NZ$568
includes taxes & fees
2 Mar - 3 Mar
Kuau Surf 2.0 Maui North Shore Locally-Owned

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (357 reviews)
"Location is absolutely perfect…lots of space and nice kitchen amenities "
United States
Scott
The price is NZ$1,717
includes taxes & fees
18 Mar - 19 Mar
The Whaler Resort Kaanapali Beach

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (164 reviews)
"Amazing place to stay, loved it. "
United States
Jacqueline
The price is NZ$454
includes taxes & fees
9 Mar - 10 Mar
Napili Village Hotel

OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (2,917 reviews)
"Wonderful vacation apot Everyone was amazing. "
United States
Michael
The price is NZ$1,593
includes taxes & fees
15 Mar - 16 Mar
OUTRIGGER Honua Kai Resort & Spa

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, (79 reviews)
"Phenomenal property for your stay in Hana - especially for a large group "
United States
Logan G.
The price is NZ$1,669
includes taxes & fees
24 Feb - 25 Feb
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (650 reviews)
"Great Hotel! Super clean! Has everything you need for perfect vacation!"
United States
Sergii
The price is NZ$553
includes taxes & fees
17 Feb - 18 Feb
Napili Sunset on the Beach

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
Hana Homestead by the Beach

Bright, Beautiful, Remodeled Island Sands 505 Condo

Bright, Beautiful, Remodeled Island Sands 505 Condo
Wailuku
9.6 out of 10, Exceptional, (54 reviews)
"Very clean, quiet, nice people all around. Good location."
Canada
Betty T.
The price is NZ$1,250
includes taxes & fees
4 Mar - 5 Mar
Bright, Beautiful, Remodeled Island Sands 505 Condo

Ocean Front Sugar Beach Resort 3rd floor 1 Bedroom condo ~ Unit 311

Ocean Front Sugar Beach Resort 3rd floor 1 Bedroom condo ~ Unit 311
North Kihei
10.0 out of 10, Exceptional, (141 reviews)
"Wonderful! This was steps from a beautiful uncrowded beach where my family had a blast. We enjoyed watching the sunrise from the balcony every morning. I wish we could have stayed longer. "
United States
Sharon
The price is NZ$1,045
includes taxes & fees
3 Mar - 4 Mar
Ocean Front Sugar Beach Resort 3rd floor 1 Bedroom condo ~ Unit 311
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 favorite 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 depends 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 NZ$454 per night. Entering your travel dates in the search wizard you might find 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.