Upcountry Maui Vacation Rentals

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Our top choices for Upcountry Maui vacation rentals

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.
$738 nightly
The price is $864
Apr 28 - Apr 29
Total with taxes and fees
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, (77 reviews)
"Absolutely incredible, the property and the host exceeded all expectations! "
Canada
Marley L.
$2,730 nightly
The price is $3,193
May 26 - May 27
Total with taxes and fees
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.
$413 nightly
The price is $483
Apr 29 - Apr 30
Total with taxes and fees
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

Stay in Hana #2

Stay in Hana #2
Hana Town Center
9.6 out of 10, Exceptional, (55 reviews)
"Great location and comfy!"
United States
Lindsay B.
$297 nightly
The price is $348
Apr 30 - May 1
Total with taxes and fees
Stay in Hana #2

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, (446 reviews)
"Food truck near."
United States
Neal
$326 nightly
The price is $382
May 2 - May 3
Total with taxes and fees
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!

Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!
Hana Town Center
9.6 out of 10, Exceptional, (27 reviews)
"I would stay again "
United States
Bruce H.
$416 nightly
The price is $487
Apr 30 - May 1
Total with taxes and fees
Oceanview #206 at Hana Kai Maui - Lofted Studio, Upper floor, Great View!

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, (243 reviews)
"30 yr anniversary - perfectly relaxing for us - would stay here again for sure."
United States
Trent H.
$490 nightly
The price is $573
Apr 29 - Apr 30
Total with taxes and fees
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

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
$439 nightly
The price is $514
Apr 28 - Apr 29
Total with taxes and fees
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

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, (426 reviews)
"Very peaceful place to stay. Enjoyed location and would stay again if I come to Hana!"
United States
Nicholas
$338 nightly
The price is $397
May 2 - May 3
Total with taxes and fees
Fisher's Hana Bay Hale, Across from Hana Bay

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.
$436 nightly
The price is $511
Apr 29 - Apr 30
Total with taxes and fees
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.8 out of 10, Excellent, (23 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
$447 nightly
The price is $531
Apr 28 - Apr 29
Total with taxes and fees
Signature Residences at Maui Banyan

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.
$459 nightly
The price is $538
May 1 - May 2
Total with taxes and fees
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

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, (204 reviews)
"Recently renovated and spotless! This condo had everything we needed and was comfortable and conveniently located. Highly recommend!"
United States
Allison H.
$378 nightly
The price is $443
Apr 28 - Apr 29
Total with taxes and fees
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

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, (142 reviews)
"Great location."
United States
John
$384 nightly
The price is $450
Apr 30 - May 1
Total with taxes and fees
Oceanview Condo in Hana-Let the ocean lull you to sleep

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, (86 reviews)
"Great tropical location with ocean view. "
United States
Myra S.
$732 nightly
The price is $857
Apr 30 - May 1
Total with taxes and fees
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
9.0 out of 10, Wonderful, (26 reviews)
"Clean and convenient"
United States
Ilya L
$352 nightly
The price is $354
May 5 - May 6
Total with taxes and fees
Kuau Surf 2.0 Maui North Shore Locally-Owned

Yonegan Maui Getaways - Haiku - Unit 6

Yonegan Maui Getaways - Haiku - Unit 6
Haiku-Pauwela
9.0 out of 10, Wonderful, (36 reviews)
"Great location, comfortable bed and room. "
United States
kimo
$316 nightly
The price is $318
Apr 28 - Apr 29
Total with taxes and fees
Yonegan Maui Getaways - Haiku - Unit 6

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, (169 reviews)
"Great location on the island, nice accommodations. "
United States
Chris P.
$309 nightly
The price is $362
Apr 30 - May 1
Total with taxes and fees
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
$1,276 nightly
The price is $1,390
May 27 - May 28
Total with taxes and fees
Hana Homestead by the Beach

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
$574 nightly
The price is $681
May 13 - May 14
Total with taxes and fees
The Ocean View Residence
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Upcountry Maui vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Upcountry Maui vacation 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 low season months. For more hustle and bustle, you may prefer to visit Upcountry Maui in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $312 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Upcountry Maui rentals

At Expedia, we put the best Upcountry Maui vacation 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 vacation.

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.