Upcountry Maui Vacation Rentals

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Our top choices for Upcountry Maui vacation rentals

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.
The price is CA $1,963
CA $4,076 total
includes taxes & fees
Mar 4 - Mar 5
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, (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 CA $553
CA $1,195 total
includes taxes & fees
Mar 2 - Mar 3
Haiku Hale - 3 Bedroom Maui Getaway!

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, (194 reviews)
"Super lovely place, I wish we were staying longer! Has everything you need. "
United States
Nicole
The price is CA $302
CA $665 total
includes taxes & fees
Mar 1 - Mar 2
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, (419 reviews)
"Very peaceful place to stay. Enjoyed location and would stay again if I come to Hana!"
United States
Nicholas
Fisher's Hana Bay Hale, Across from Hana Bay

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 CA $357
CA $661 total
includes taxes & fees
Mar 12 - Mar 13
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.
The price is CA $479
CA $822 total
includes taxes & fees
Mar 8 - Mar 9
MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA

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, (151 reviews)
"The location was fantastic and the house was very comfortable, especially the beds."
United States
Lisa H.
The price is CA $363
CA $778 total
includes taxes & fees
Mar 6 - Mar 7
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

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, (78 reviews)
"Nice easy check in. Easy access to black sand beach (not the State Park)."
United States
Brett
The price is CA $490
CA $701 total
includes taxes & fees
Mar 8 - Mar 9
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.
The price is CA $253
CA $610 total
includes taxes & fees
Feb 28 - Mar 1
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, (93 reviews)
"Very unique property near Hana. Great experience!"
United States
Keith R.
The price is CA $445
CA $777 total
includes taxes & fees
Mar 3 - Mar 4
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

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, (114 reviews)
"Everything Good "
United States
Marc
The price is CA $490
CA $701 total
includes taxes & fees
Mar 8 - Mar 9
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, (80 reviews)
"Phenomenal property for your stay in Hana - especially for a large group "
United States
Logan G.
The price is CA $682
CA $1,278 total
includes taxes & fees
Mar 30 - Mar 31
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

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 CA $287
CA $504 total
includes taxes & fees
Mar 17 - Mar 18
Kuau Surf 2.0 Maui North Shore Locally-Owned

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 CA $268
CA $1,141 total
includes taxes & fees
Mar 13 - Mar 14
The Ocean View Residence

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 CA $830
CA $1,928 total
includes taxes & fees
Mar 24 - Mar 25
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)
"Stay was great, condo was well equipped, great location and beautiful view."
United States
Tara C.
The price is CA $165
CA $1,034 total
includes taxes & fees
Mar 4 - Mar 5
Bright, Beautiful, Remodeled Island Sands 505 Condo

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)
"It was a really nice stay. "
Canada
KATHRYN M.
The price is CA $190
CA $557 total
includes taxes & fees
Mar 8 - Mar 9
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 CA $119
CA $657 total
includes taxes & fees
Mar 2 - Mar 3
Tropical Honeymoon Suite - BBQ, Hot Tub - Walk 2 Beach - In the Heart Of Kihei

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 CA $374
CA $862 total
includes taxes & fees
Mar 1 - Mar 2
Ocean Front Sugar Beach Resort 3rd floor 1 Bedroom condo ~ Unit 311

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 CA $494
CA $703 total
includes taxes & fees
Mar 1 - Mar 2
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing 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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Upcountry Maui. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.