Upcountry Maui Holiday Rentals

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Our top choices for Upcountry Maui holiday 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, (77 reviews)
"Absolutely incredible, the property and the host exceeded all expectations! "
Canada
Marley L.
The price is AU$3,977
includes taxes & fees
26 May - 27 May
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 AU$1,188
includes taxes & fees
27 May - 28 May
Haiku Hale - 3 Bedroom Maui Getaway!

Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (907 reviews)
"Staff was amazing and nice! The GM is a huge Kansas City Chiefs fan. The property is beautiful and is a perfect walking distance for anything Kīhei/Wailea. Great TV channels as well. There are cute roosters, lizards and birds everywhere. Will be staying here again for sure! "
Canada
Ethan
The price is AU$418
includes taxes & fees
16 May - 17 May
Aston Maui Hill

Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,095 reviews)
"Pools were great had available seating and kids loved the waterfall and hot tub."
United States
Doreen
The price is AU$561
includes taxes & fees
17 May - 18 May
Aston Kaanapali Shores

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,794 reviews)
"Super clean room with fantastic view of the sea. Short walk to Napili beach. Great breakfast at the Gazebo restaurant "
United States
Mark
The price is AU$364
includes taxes & fees
4 June - 5 June
Napili Shores Maui by OUTRIGGER

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, (78 reviews)
"Great view, excellent location. 2 -3 nights is the perfect amount of time in Hana."
United States
Jim
The price is AU$745
includes taxes & fees
19 May - 20 May
Oceanview #204 at Hana Kai Maui - 1 Bedroom Upper Floor, Amazing View!

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (182 reviews)
"The property is beautiful and located just steps away from the beach."
United States
Patricia
The price is AU$418
includes taxes & fees
14 May - 15 May
Napili Village Hotel

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (400 reviews)
"Great service, clean rooms, friendly staff, and perfectly located. We had a great time."
United States
Forest Daniel
The price is AU$1,004
includes taxes & fees
17 May - 18 May
The Whaler Resort Kaanapali Beach

Stay in Hana #2

Stay in Hana #2
Hana Town Center
9.6 out of 10, Exceptional, (56 reviews)
"Clean and quiet spot in Hana! A great base for exploring the road to Hana without having to do it all in a day."
United States
Paul John Van de
The price is AU$485
includes taxes & fees
18 May - 19 May
Stay in Hana #2

Beautiful Home in paradise!

Beautiful Home in paradise!
Kaʻeleku
9.6 out of 10, Exceptional, (174 reviews)
"Beautiful and quiet location, close to town. Perfect for a rural experience. "
United States
Matt D.
Beautiful Home in paradise!

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, (244 reviews)
"I appreciated everything as advertised. Would have preferred mini splits or AC in the bedrooms, but still a nice peaceful spot."
United States
Robert
The price is AU$828
includes taxes & fees
19 May - 20 May
Special quiet, romantic, cozy home in a special place, Heavenly Hana. Lucky you!

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 AU$460
includes taxes & fees
16 May - 17 May
Napili Sunset on the Beach

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 AU$1,968
includes taxes & fees
29 May - 30 May
Hana Homestead by the Beach

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.
The price is AU$744
includes taxes & fees
11 June - 12 June
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

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 AU$690
includes taxes & fees
28 May - 29 May
Oceanview Condo in Hana-Let the ocean lull you to sleep

OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (2,961 reviews)
"Everything about this place was great!"
United States
Jag
The price is AU$1,404
includes taxes & fees
18 May - 19 May
OUTRIGGER Honua Kai Resort & Spa

Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Lahaina
8.8 out of 10, Excellent, (2,566 reviews)
"Great location for beach lovers and family vacation. "
United States
meryem
The price is AU$711
includes taxes & fees
16 May - 17 May
Aston Maui Kaanapali Villas

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, (449 reviews)
"Food truck near."
United States
Neal
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Paia 2 Bedroom 2 Bathroom

Paia 2 Bedroom 2 Bathroom
Paia
9.2 out of 10, Wonderful, (11 reviews)
"The house was perfect for the 6 of us and near a beautiful cove. "
United States
Vanessa C.
The price is AU$916
includes taxes & fees
19 May - 20 May
Paia 2 Bedroom 2 Bathroom

Honua Kai Konea Resort by KBM

Honua Kai Konea Resort by KBM
4.5 star property
Kaanapali
9.6 out of 10, Exceptional, (88 reviews)
"Amazing stayThis was our honeymoon. I would definitely come back again"
United States
Annette
The price is AU$2,827
includes taxes & fees
16 May - 17 May
Honua Kai Konea Resort by KBM
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, 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 favourite 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 depend 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 AU$364 per night. Entering your travel dates in the search wizard might find you 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.