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Top Holiday Rentals in Upcountry Maui

Our top choices for Upcountry Maui holiday rentals

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 £2,131
includes taxes & fees
10 Sept - 11 Sept
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

10.0 out of 10, Exceptional, (228)
"Lovely property and very enjoyable place to stay. Great location."
Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities

Aston Kaanapali Shores

3.5 star property
8.6 out of 10, Excellent, (3689)
"Great area and great place to stay"
The price is £168
includes taxes & fees
1 Sept - 2 Sept
Aston Kaanapali Shores

Aston Maui Kaanapali Villas

3.0 star property
8.8 out of 10, Excellent, (2448)
"Great place! Room was a good size, very clean spacious, full kitchen, nice staff. We enjoyed our stay! "
The price is £192
includes taxes & fees
12 Sept - 13 Sept
Aston Maui Kaanapali Villas

Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014

10.0 out of 10, Exceptional, (263)
"Great location for whale watching, comfortable condo with well equipped kitchen, easy check in and check out"
The price is £571
includes taxes & fees
1 Sept - 2 Sept
Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014

The Whaler Resort Kaanapali Beach

4.0 star property
9.6 out of 10, Exceptional, (223)
"Location was excellent "
The price is £520
includes taxes & fees
27 Sept - 28 Sept
The Whaler Resort Kaanapali Beach

Napili Shores Maui by OUTRIGGER

3.0 star property
9.0 out of 10, Wonderful, (1653)
"Check-in was easy, the staff were very friendly and helpful. The room was clean and comfortable. Great place to stay."
The price is £219
includes taxes & fees
13 Sept - 14 Sept
Napili Shores Maui by OUTRIGGER

Aston Maui Hill

3.0 star property
9.0 out of 10, Wonderful, (817)
"Everything was perfect. The staff was super kind. The swimming pool was nice. Parking is easy in front of the apartment. I would like to come back here if again in Maui "
Aston Maui Hill

Maui Beach Vacation Club

2.5 star property
8.2 out of 10, Very good, (792)
"Just a great stay! "
Maui Beach Vacation Club

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
8.8 out of 10, Excellent, (2826)
"Beautiful resort! "
The price is £643
includes taxes & fees
5 Sept - 6 Sept
OUTRIGGER Honua Kai Resort & Spa

Aston at The Whaler on Kaanapali Beach

4.0 star property
9.2 out of 10, Wonderful, (1483)
"It was a nice place to stay"
Aston at The Whaler on Kaanapali Beach

Aston at Papakea Resort

3.0 star property
8.2 out of 10, Very good, (1381)
"A208 was terrific. We loved the view and the sound of ocean and accessibility to the beach. Would love to see a few more hooks in place to hang towels and some written information about sites and where to go etc. - like a welcome notebook "
Aston at Papakea Resort

AEI at Kaanapali Shores

4.0 star property
8.8 out of 10, Excellent, (428)
"Was an absolute beautiful place! "
AEI at Kaanapali Shores

Kahana Falls Maui by VRI Americas

3.5 star property
8.0 out of 10, Very good, (911)
"Great Aloha spirit and a great location and pool."
Kahana Falls Maui by VRI Americas

#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool

2.0 star property
10.0 out of 10, Exceptional, (11)
"We had an amazing vacation with our kids and grandkids. We have already booked again for next year"
#1 Luxury BEACHFRONT! Pickleball, Sand Volleyball, 2 Gyms, Pool

The Westin Ka'anapali Ocean Resort Villas

4.0 star property
8.6 out of 10, Excellent, (1113)
"The resort was beautiful. The hospitality in all seas was top notch. "
The price is £391
includes taxes & fees
4 Sept - 5 Sept
The Westin Ka'anapali Ocean Resort Villas

Aston Mahana at Kaanapali

3.5 star property
9.0 out of 10, Wonderful, (1643)
"Beautiful location "
Aston Mahana at Kaanapali

Kapalua Villas Maui

4.0 star property
8.8 out of 10, Excellent, (952)
"The view of the ocean was great and I was happy just to be there. It was old and a little poorly built, windows or doors were hard to open, etc. Some renovated parts were comfortable. The dryer was broken, which was inconvenient, but housekeeping provided new towels daily and offered to do laundry for free. Cooking utensils were very well stocked"
The price is £606
includes taxes & fees
26 Sept - 27 Sept
Kapalua Villas Maui

The Westin Nanea Ocean Villas, Ka'anapali

4.0 star property
9.2 out of 10, Wonderful, (466)
"Very nice place to stay"
The price is £419
includes taxes & fees
12 Sept - 13 Sept
The Westin Nanea Ocean Villas, Ka'anapali

Castle Kama'ole Sands

3.0 star property
8.0 out of 10, Very good, (2254)
"Great location for beach with beautiful garden views and easy close parking."
Castle Kama'ole Sands
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

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 £168 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.