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, (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 €745
includes taxes & fees
23 Apr - 24 Apr
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.
The price is €2,542
includes taxes & fees
23 Apr - 24 Apr
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (902 reviews)
"We really enjoyed the pool & hot tub area. The staff was very friendly & helpful & everything was great, we really enjoyed our stay at Maui Hill."
United States
Kelly
The price is €264
includes taxes & fees
26 Apr - 27 Apr
Aston Maui Hill

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 €438
includes taxes & fees
23 Apr - 24 Apr
Oceanview #103 at Hana Kai Maui - 1 Bedroom, Amazing View - Easy Access

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,790 reviews)
"Ocean view, comfortable room, nice bar on property, well located"
United States
Rosanne Marie
The price is €343
includes taxes & fees
5 May - 6 May
Napili Shores Maui by OUTRIGGER

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 €412
includes taxes & fees
30 Apr - 1 May
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

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, (238 reviews)
"Great location in Hana. Cozy and private. "
United States
Heather F.
The price is €438
includes taxes & fees
7 May - 8 May
Great location between Hana Town and Hamoa Beach, private, family-friendly

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 €438
includes taxes & fees
23 Apr - 24 Apr
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

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 €329
includes taxes & fees
24 Apr - 25 Apr
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,067 reviews)
"Beautiful location and friendly helpful staff. Nice clean rooms and resort. "
Canada
Megan Ruth
The price is €298
includes taxes & fees
11 May - 12 May
Aston Kaanapali Shores

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (384 reviews)
"Beautiful views, wonderful staff, clean & spacious room! Would love to stay again someday. "
United States
Sophia
The price is €617
includes taxes & fees
23 Apr - 24 Apr
The Whaler Resort Kaanapali Beach

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 €346
includes taxes & fees
24 Apr - 25 Apr
Fisher's Hana Bay Hale, Across from Hana Bay

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 €314
includes taxes & fees
26 Apr - 27 Apr
Napili Village Hotel

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
The price is €341
includes taxes & fees
25 Apr - 26 Apr
Oceanview Condo in Hana-Let the ocean lull you to sleep

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

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui
Hāna
10.0 out of 10, Exceptional, (100 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 €463
includes taxes & fees
25 Apr - 26 Apr
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

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
Relaxing home away from home- honeymoon 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, (242 reviews)
"30 yr anniversary - perfectly relaxing for us - would stay here again for sure."
United States
Trent H.
The price is €493
includes taxes & fees
3 May - 4 May
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

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.
The price is €376
includes taxes & fees
20 May - 21 May
A/C North Shore Maui - Paia/Kuau <br>Just steps away to Mama’s and beach

Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (654 reviews)
"Clean room amd friendly staff."
United States
Chris
The price is €283
includes taxes & fees
23 Apr - 24 Apr
Napili Sunset on the Beach

OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (2,952 reviews)
"Nice staff/clean rooms. Overall very nice"
Canada
Anastassiya
The price is €748
includes taxes & fees
28 Apr - 29 Apr
OUTRIGGER Honua Kai Resort & Spa
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 €264 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.