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, (76 reviews)
"Absolutely incredible, the property and the host exceeded all expectations! "
Canada
Marley L.
The price is CA $1,979
CA $4,091 total
includes taxes & fees
Apr 23 - Apr 24
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, (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.
The price is CA $557
CA $1,205 total
includes taxes & fees
Apr 21 - Apr 22
Haiku Hale - 3 Bedroom Maui Getaway!

Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
9.0 out of 10, Wonderful, (19 reviews)
"Perfect location, clean room, and friendly staff! "
United States
Krystel
The price is CA $74
CA $731 total
includes taxes & fees
Apr 15 - Apr 16
Signature Residences at Maui Banyan

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 CA $304
CA $673 total
includes taxes & fees
Apr 21 - Apr 22
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, (426 reviews)
"Very peaceful place to stay. Enjoyed location and would stay again if I come to Hana!"
United States
Nicholas
The price is CA $269
CA $563 total
includes taxes & fees
May 3 - May 4
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, (444 reviews)
"Enjoyed the screened in porch"
United States
Thomas
The price is CA $269
CA $534 total
includes taxes & fees
Apr 27 - Apr 28
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

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, (203 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 $255
CA $615 total
includes taxes & fees
Apr 19 - Apr 20
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

Great location between Hana Town and Hamoa Beach, private, family-friendly

Great location between Hana Town and Hamoa Beach, private, family-friendly
Hana Town Center
9.8 out of 10, Exceptional, (237 reviews)
"Great location in Hana. Cozy and private. "
United States
Heather F.
The price is CA $367
CA $713 total
includes taxes & fees
May 7 - May 8
Great location between Hana Town and Hamoa Beach, private, family-friendly

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, (241 reviews)
"30 yr anniversary - perfectly relaxing for us - would stay here again for sure."
United States
Trent H.
The price is CA $416
CA $833 total
includes taxes & fees
Apr 26 - Apr 27
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

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

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hāna
10.0 out of 10, Exceptional, (99 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.
The price is CA $427
CA $756 total
includes taxes & fees
Apr 22 - Apr 23
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, (80 reviews)
"Fantastic experience! Staff was helpful and genuinely nice people Condo and view were perfect. So relaxing and we'll be back! "
United States
Bill
The price is CA $527
CA $750 total
includes taxes & fees
Apr 21 - Apr 22
Oceanview #101 at Hana Kai Maui - 1 Bedroom Corner Unit, Amazing View!

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
The price is CA $172
CA $435 total
includes taxes & fees
Apr 19 - Apr 20
Yonegan Maui Getaways - Haiku - Unit 6

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 CA $529
CA $750 total
includes taxes & fees
Apr 19 - Apr 20
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

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, (24 reviews)
"Clean and convenient"
United States
Ilya L
The price is CA $276
CA $492 total
includes taxes & fees
Apr 28 - Apr 29
Kuau Surf 2.0 Maui North Shore Locally-Owned

Relaxing home away from home- honeymoon friendly

Relaxing home away from home- honeymoon friendly
Hana
10.0 out of 10, Exceptional, (284 reviews)
"It was such a cute little place. Quite and charming with a spectacular view. Loved our stay here."
Canada
Marjorie
The price is CA $385
CA $735 total
includes taxes & fees
May 6 - May 7
Relaxing home away from home- honeymoon friendly

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, (82 reviews)
"Great tropical location with ocean view. "
United States
Myra S.
The price is CA $688
CA $1,289 total
includes taxes & fees
Apr 30 - May 1
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

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 $725
CA $1,760 total
includes taxes & fees
Apr 28 - Apr 29
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)
"The host was very welcoming, the condo was well stocked with everything needed for the stay, it was super clean and everything worked really well. "
United States
Ellen B.
The price is CA $179
CA $632 total
includes taxes & fees
Apr 25 - Apr 26
This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (177 reviews)
"Great location "
United States
John Roger
The price is CA $286
CA $339 total
includes taxes & fees
Apr 19 - Apr 20
Napili Village Hotel

Paia 2 Bedroom 2 Bathroom

Paia 2 Bedroom 2 Bathroom
Paia
9.0 out of 10, Wonderful, (10 reviews)
"The house was perfect for the 6 of us and near a beautiful cove. "
United States
Vanessa C.
The price is CA $418
CA $910 total
includes taxes & fees
Apr 21 - Apr 22
Paia 2 Bedroom 2 Bathroom
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.