Holiday Rentals in Upcountry Maui

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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.
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, (74 reviews)
"Absolutely incredible, the property and the host exceeded all expectations! "
Canada
Marley L.
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, (135 reviews)
"Great location."
United States
John
The price is €396
includes taxes & fees
1 Apr - 2 Apr
Oceanview Condo in Hana-Let the ocean lull you to sleep

MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA

MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA
Hana
10.0 out of 10, Exceptional, (254 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.
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, (115 reviews)
"Everything Good "
United States
Marc
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

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

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hāna
10.0 out of 10, Exceptional, (93 reviews)
"Very unique property near Hana. Great experience!"
United States
Keith R.
The price is €484
includes taxes & fees
19 Mar - 20 Mar
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

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, (79 reviews)
"Nice easy check in. Easy access to black sand beach (not the State Park)."
United States
Brett
Oceanview #101 at Hana Kai Maui - 1 Bedroom Corner Unit, Amazing View!

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, (198 reviews)
"Recently renovated and spotless! This condo had everything we needed and was comfortable and conveniently located. Highly recommend!"
United States
Allison H.
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

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 €553
includes taxes & fees
22 Mar - 23 Mar
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

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 €312
includes taxes & fees
17 Mar - 18 Mar
Kuau Surf 2.0 Maui North Shore Locally-Owned

Kuleana Club - 513

Kuleana Club - 513
3.0 star property
Lahaina
10.0 out of 10, Exceptional, (1 review)
"Clean room, easy check in process, great property with great pool and little beach area to see turtles. We were on the third floor and had to carry all our suitcases up the flights of stairs but being able to see the whales off the Lanai every morning was worth it "
Australia
Andrea
The price is €398
includes taxes & fees
26 Mar - 27 Mar
Kuleana Club - 513

Beautiful Home in paradise!

Beautiful Home in paradise!
Kaʻeleku
9.6 out of 10, Exceptional, (173 reviews)
"Beautiful and quiet location, close to town. Perfect for a rural experience. "
United States
Matt D.
Beautiful Home in paradise!

Bright, Beautiful, Remodeled Island Sands 505 Condo

Bright, Beautiful, Remodeled Island Sands 505 Condo
Wailuku
9.6 out of 10, Exceptional, (54 reviews)
"Stay was great, condo was well equipped, great location and beautiful view."
United States
Tara C.
The price is €673
includes taxes & fees
30 Mar - 31 Mar
Bright, Beautiful, Remodeled Island Sands 505 Condo

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (364 reviews)
"Location is absolutely perfect…lots of space and nice kitchen amenities "
United States
Scott
The price is €712
includes taxes & fees
6 Apr - 7 Apr
The Whaler Resort Kaanapali Beach

Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (885 reviews)
"The location was great, staff provided clean towels and bedding daily. "
United States
Christine
The price is €315
includes taxes & fees
1 Apr - 2 Apr
Aston Maui Hill

Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (653 reviews)
"Great Hotel! Super clean! Has everything you need for perfect vacation!"
United States
Sergii
The price is €287
includes taxes & fees
7 Mar - 8 Mar
Napili Sunset on the Beach

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, (80 reviews)
"Phenomenal property for your stay in Hana - especially for a large group "
United States
Logan G.
The price is €886
includes taxes & fees
19 Mar - 20 Mar
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (2,924 reviews)
"Great place nice people very clean and great food"
Canada
Dalen L
The price is €738
includes taxes & fees
12 Mar - 13 Mar
OUTRIGGER Honua Kai Resort & Spa

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, (166 reviews)
"Great location on the island, nice accommodations. "
United States
Chris P.
The price is €289
includes taxes & fees
8 Mar - 9 Mar
OCEANFRONT Spectacular 60 ft to the water, Recently Re-modeled! HDTV,WiFi,AC

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
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, apart-hotels, 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 €305 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.