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Upcountry Maui Vacation Rentals

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Vacation Rentals in Upcountry Maui

OUTRIGGER Honua Kai Resort & Spa

4.0 star property
Lahaina
8.8 out of 10, Excellent, (2879)
"Wonderful stay! "
United States
Quiauna
$813 nightly
The price is $871
Dec 11 - Dec 12
Total with taxes and fees
OUTRIGGER Honua Kai Resort & Spa

The Whaler Resort Kaanapali Beach

4.0 star property
Lahaina
9.6 out of 10, Exceptional, (312)
"great time, great resort, helpful staff"
Canada
Prableen
$561 nightly
The price is $662
Dec 11 - Dec 12
Total with taxes and fees
The Whaler Resort Kaanapali Beach

Napili Shores Maui by OUTRIGGER

3.0 star property
Lahaina
9.0 out of 10, Wonderful, (1708)
"Excellent stay. "
United States
casey william
$329 nightly
The price is $388
Dec 8 - Dec 9
Total with taxes and fees
Napili Shores Maui by OUTRIGGER

Kahana Beach Vacation Club

3.0 star property
Lahaina
8.4 out of 10, Very Good, (749)
"Excellent Resort from all areas "
United States
Kausik
Kahana Beach Vacation Club

Maui Beach Vacation Club

2.5 star property
North Kihei
8.2 out of 10, Very Good, (817)
"A excelent service in the office. Nice and clean room y all the hotel. I recommend this hotel."
United States
Blanca I
Maui Beach Vacation Club

Aston Kaanapali Shores

3.5 star property
Lahaina
8.6 out of 10, Excellent, (3901)
"Was a great place to stay"
United States
Christine
$379 nightly
The price is $447
Dec 8 - Dec 9
Total with taxes and fees
Aston Kaanapali Shores

Aston Maui Kaanapali Villas

3.0 star property
Lahaina
8.8 out of 10, Excellent, (2511)
"Great place! Very clean, friendly staff, beautiful grounds, lots to do with in walking distance. The best part that we enjoyed was the beach it was outstanding! highly recommend."
Canada
Natalia
$390 nightly
The price is $462
Jan 1 - Jan 2, 2026
Total with taxes and fees
Aston Maui Kaanapali Villas

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

Lahaina
10.0 out of 10, Exceptional, (271)
"It was perfect! When we come back we will definitely use this condo again!"
United States
Jeffrey J.
$806 nightly
The price is $939
Dec 15 - Dec 16
Total with taxes and fees
Mahana at Kaanapali, Spectacular Oceanfront, Amazing Sunsets & Sea Life Unit1014

Sands of Kahana

3.0 star property
Lahaina
8.2 out of 10, Very Good, (458)
"Size for the price was great"
United States
Ben
Sands of Kahana

Kahana Falls Maui by VRI Americas

3.5 star property
Lahaina
8.2 out of 10, Very Good, (973)
"The Entire staff of Kahana Falls Resort was very welcoming and very attentive to our needs. "
United States
Greg
Kahana Falls Maui by VRI Americas

Aston Maui Hill

3.0 star property
South Kihei
9.0 out of 10, Wonderful, (848)
"The accommodations were comfortable, very roomy, nice view from the balcony, and staff was helpful and friendly."
United States
David
$289 nightly
The price is $341
Dec 9 - Dec 10
Total with taxes and fees
Aston Maui Hill

Castle Kama'ole Sands

3.0 star property
South Kihei
8.0 out of 10, Very Good, (2276)
"great stay for my family"
United States
Jasmin
Castle Kama'ole Sands

The Westin Nanea Ocean Villas, Ka'anapali

4.0 star property
Lahaina
9.4 out of 10, Exceptional, (472)
"Spacious rooms and fun pools"
United States
Vanessa
$559 nightly
The price is $660
Dec 21 - Dec 22
Total with taxes and fees
The Westin Nanea Ocean Villas, Ka'anapali

The Westin Ka'anapali Ocean Resort Villas

4.0 star property
Lahaina
8.6 out of 10, Excellent, (1124)
"Clean room, amazing staff and great location and beach access "
United States
Amanda
$447 nightly
The price is $527
Dec 14 - Dec 15
Total with taxes and fees
The Westin Ka'anapali Ocean Resort Villas

Royal Kahana Maui by OUTRIGGER

3.0 star property
Lahaina
8.0 out of 10, Very Good, (1399)
"Room was beautiful and had an amazing view"
United States
Becky
Royal Kahana Maui by OUTRIGGER

Aston at Papakea Resort

3.0 star property
Lahaina
8.2 out of 10, Very Good, (1396)
"Everything was great very good stay "
Canada
Paul
Aston at Papakea Resort

Kapalua Villas Maui

4.0 star property
Lahaina
8.8 out of 10, Excellent, (958)
"Gorgeous property, the staff, beach, hiking close by, restaurants in area all were great. Room was spotless and we were able to check in early."
United States
Arturo
Kapalua Villas Maui

Signature Residences at Maui Banyan

4.5 star property
South Kihei
10.0 out of 10, Exceptional, (4)
"Wonderful experience. Clean, convenient, great location, pool, hot tub, beautiful property, and safe. Had a great time."
United States
Melinda
$492 nightly
The price is $581
Dec 8 - Dec 9
Total with taxes and fees
Signature Residences at Maui Banyan

Kahana Villa

3.0 star property
Lahaina
8.0 out of 10, Very Good, (352)
" Great stay!!! Easy and quiet place next to beach.Feels like home"
United States
Jose
Kahana Villa

The Gardens at West Maui

3.0 star property
Lahaina
8.4 out of 10, Very Good, (519)
"We stayed here for 4 days easy check in and check out process "
United States
Relda
The Gardens at West Maui
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Upcountry Maui vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Upcountry Maui vacation 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 low season months. For more hustle and bustle, you may prefer to visit Upcountry Maui in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $341 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Upcountry Maui rentals

At Expedia, we put the best Upcountry Maui vacation 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 vacation.

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.