Upcountry Maui Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Browse Select Upcountry Maui Vacation Homes

Our top choices for Upcountry Maui vacation homes

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

10.0 out of 10, Exceptional, (67)
"16 of us stayed at this beautiful property. Two Families, 12 children total. We have nothing bad to say. All of our expectations were met. The listing is true and accurate. Communication with the property manager was always prompt and efficient.We would definitely stay her again."
The price is CA $2,207
CA $4,186 total
includes taxes & fees
Sep 10 - Sep 11
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Haiku Hale - 3 Bedroom Maui Getaway!

10.0 out of 10, Exceptional, (4)
"Clean, well lit, private, Haiku is a sweet town. Note that there are a few steep steps to master bedroom."
The price is CA $684
CA $1,365 total
includes taxes & fees
Sep 5 - Sep 6
Haiku Hale - 3 Bedroom Maui Getaway!

Yonegan Maui Getaways - Haiku

3.0 star property
9.0 out of 10, Wonderful, (4)
"It was a last minute stay and it had what we needed. "
The price is CA $188
CA $358 total
includes taxes & fees
Aug 28 - Aug 29
Yonegan Maui Getaways - Haiku

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

9.6 out of 10, Exceptional, (394)
"The property was excellent, highly recommend. "
The price is CA $241
CA $493 total
includes taxes & fees
Sep 9 - Sep 10
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Fisher's Hana Bay Hale, Across from Hana Bay

9.4 out of 10, Exceptional, (399)
"Lovely getaway after our long on the road to Hana drive. Provided everything we needed with kitchen, 1bedroom and nice full-size bed tucked in the corner off the TV room. Loved the woody walls, plenty of ceiling fans and distant view of the bay. Check this place out folks!"
The price is CA $270
CA $549 total
includes taxes & fees
Sep 8 - Sep 9
Fisher's Hana Bay Hale, Across from Hana Bay

Romantic Hana Hideaway, Big Ocean Views, Old Hawaii Charm

9.8 out of 10, Exceptional, (140)
"Wonderful property and so beautiful! "
The price is CA $484
CA $914 total
includes taxes & fees
Aug 28 - Aug 29
Romantic Hana Hideaway, Big Ocean Views, Old Hawaii Charm

Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

9.8 out of 10, Exceptional, (229)
"Wonderful location!"
The price is CA $415
CA $869 total
includes taxes & fees
Aug 28 - Aug 29
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

Locally-owned, eco-friendly condo on Road to Hāna. 2-min walk to beach & seafood

The price is CA $249
CA $378 total
includes taxes & fees
Aug 30 - Aug 31
Locally-owned, eco-friendly condo on Road to Hāna. 2-min walk to beach & seafood

3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

9.8 out of 10, Exceptional, (76)
"This place was more than enough for our family of 5! We could have fit another family with us! Very clean, easy check in. The instructions on finding the place were spot on. We would definitely stay here again!"
The price is CA $759
CA $1,364 total
includes taxes & fees
Sep 8 - Sep 9
3 Bedroom Ocean View Private Home in Hana Permit#SUP2 2019/0006

Hana Homestead by the Beach

9.8 out of 10, Exceptional, (134)
"This property is amazing! Not right on the water but great view of the ocean, can hear the ocean and 3minute walk to the beach!! Beautiful property and plenty of extras such as a jacuzzi, sauna, boogie boards, beach chairs, beach toys for the kids, and an on-site private outside shower to clean up after walking or playing in the beach. "
The price is CA $714
CA $1,752 total
includes taxes & fees
Sep 22 - Sep 23
Hana Homestead by the Beach

Charming Direct Oceanfront North Shore Beach House

9.0 out of 10, Wonderful, (33)
"We had a great time at this VRBO! It was so clean and was the perfect lay out for our family. The beds were comfortable and the views were gorgeous! We will definitely be staying again. "
The price is CA $914
CA $1,106 total
includes taxes & fees
Sep 1 - Sep 2
Charming Direct Oceanfront North Shore Beach House

Hotel-zoned OCEAN FRONT GROUND FLOOR! Menehune Shores 121

10.0 out of 10, Exceptional, (186)
"The property was amazing and was well stocked in both the kitchen as well as for all supplies. We loved our stay here and the immediate access from the patio to the beach area was amazing. We would stay here again!"
The price is CA $328
CA $947 total
includes taxes & fees
Aug 28 - Aug 29
Hotel-zoned OCEAN FRONT GROUND FLOOR! Menehune Shores 121

Sugar Beach PH17 - Direct Oceanfront 1 bedroom

The price is CA $311
CA $797 total
includes taxes & fees
Aug 28 - Aug 29
Sugar Beach PH17 - Direct Oceanfront 1 bedroom

Sugar Beach 106 - Ground Floor next to the 5 Miles of Sandy Beach

The price is CA $256
CA $729 total
includes taxes & fees
Sep 2 - Sep 3
Sugar Beach 106 - Ground Floor next to the 5 Miles of Sandy Beach

Oceanview Retreat in Puamana – Steps from the Beach & Surf

10.0 out of 10, Exceptional, (1)
"This property had everything you would want in a vacation home. Great location. We enjoyed the beach, community pool and grounds. The photos were exactly as pictured. We had a great time in your home. Thank you for hosting us."
The price is CA $450
CA $1,632 total
includes taxes & fees
Aug 30 - Aug 31
Oceanview Retreat in Puamana – Steps from the Beach & Surf

Sugar Beach 417 Direct Row Beach Views in Beautifully Upgraded Ocean front Condo Home

The price is CA $311
CA $801 total
includes taxes & fees
Aug 31 - Sep 1
Sugar Beach 417 Direct Row Beach Views in Beautifully Upgraded Ocean front Condo Home

NEW LUXURY REMODEL W/POOL | Panoramic Ocean Views!

10.0 out of 10, Exceptional, (26)
"Excellent location, beautiful view, modern and updated interior, well equipped kitchen, plenty of room, and easy communication with property manager. Would stay again. "
The price is CA $371
CA $1,212 total
includes taxes & fees
Sep 3 - Sep 4
NEW LUXURY REMODEL W/POOL | Panoramic Ocean Views!

New! The Aloha Cottage in Puamana, Maui Hawaii

9.8 out of 10, Exceptional, (86)
"Great place to stay. We all enjoyed the area and Lahaina was incredible."
The price is CA $347
CA $1,169 total
includes taxes & fees
Aug 28 - Aug 29
New! The Aloha Cottage in Puamana, Maui Hawaii

Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!!

9.4 out of 10, Exceptional, (58)
"Everything you need in the condo and enough beaches to try one every day!"
The price is CA $206
CA $810 total
includes taxes & fees
Aug 28 - Aug 29
Kihei Akahi A102: Maui Ocean Front Town House - Location, Location, Location!!!

Historic Maui Estate: 10 Suites & Chef Breakfast

2.0 star property
The price is CA $4,220
CA $5,425 total
includes taxes & fees
Sep 26 - Sep 27
Historic Maui Estate: 10 Suites & Chef Breakfast
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Upcountry Maui Hotel Reviews

Find out more about Upcountry Maui

Find out more about Upcountry Maui

Upcountry Maui Vacation Homes information

Number of reviews
1,947
Accommodation
174 Vacation Homes
Lowest Price
CA $188
Highest Price
CA $270

Explore a world of travel with Expedia

Explore a world of travel with Expedia