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Holiday Rentals in Upcountry Maui

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Our top choices for Upcountry Maui holiday rentals

Condo resort in Lahaina

OUTRIGGER Honua Kai Resort & Spa
4.0 star property
8.8 out of 10, Excellent, (2886)
"Wonderful stay! "
United States
Quiauna
The price is €863
includes taxes & fees
15 Jan - 16 Jan 2026
OUTRIGGER Honua Kai Resort & Spa

Aparthotel in Lahaina

Aston Maui Kaanapali Villas
3.0 star property
8.8 out of 10, Excellent, (2521)
"We enjoyed the property "
United States
Therese
The price is €393
includes taxes & fees
1 Jan - 2 Jan 2026
Aston Maui Kaanapali Villas

Aparthotel in Lahaina

Aston Kaanapali Shores
3.5 star property
8.8 out of 10, Excellent, (3928)
"Loved the 2 pools and 2 hot tub, staff is great…thank you!"
United States
Candida
The price is €346
includes taxes & fees
2 Jan - 3 Jan 2026
Aston Kaanapali Shores
4.0 star property
9.6 out of 10, Exceptional, (327)
"great time, great resort, helpful staff"
Canada
Prableen
The price is €652
includes taxes & fees
24 Jan - 25 Jan 2026
The Whaler Resort Kaanapali Beach

Aparthotel in Lahaina

Napili Sunset on the Beach
2.5 star property
9.2 out of 10, Wonderful, (647)
"Location was excellent"
United States
Polly
The price is €283
includes taxes & fees
6 Jan - 7 Jan 2026
Napili Sunset on the Beach

Holiday Home in Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
9.0 out of 10, Wonderful, (12)
"Loved having the hot tub to come home to!!"
United States
Pedro
The price is €238
includes taxes & fees
5 Jan - 6 Jan 2026
Yonegan Maui Getaways - Haiku
4.0 star property
8.6 out of 10, Excellent, (1126)
"Perfect stay"
United States
hao
The price is €491
includes taxes & fees
2 Jan - 3 Jan 2026
The Westin Ka'anapali Ocean Resort Villas

Aparthotel in Lahaina

Napili Village Hotel
3.0 star property
9.0 out of 10, Wonderful, (145)
"Exactly what we were looking for! Close walking distance to beach and dining!"
United States
Tessa
The price is €289
includes taxes & fees
19 Jan - 20 Jan 2026
Napili Village Hotel

Condo resort in South Kihei

Signature Residences at Maui Banyan
4.5 star property
9.6 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
The price is €501
includes taxes & fees
31 Dec - 1 Jan 2026
Signature Residences at Maui Banyan
4.0 star property
8.4 out of 10, Very good, (237)
"Room was clean. Hotel staff were pleasant and competent. Construction was a little inconvenient noise and no carpeting by elevators was weird."
United States
Ron
The price is €507
includes taxes & fees
12 Jan - 13 Jan 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Aparthotel in Lahaina

Napili Shores Maui by OUTRIGGER
3.0 star property
9.0 out of 10, Wonderful, (1719)
"Excellent stay. "
United States
casey william
The price is €434
includes taxes & fees
13 Jan - 14 Jan 2026
Napili Shores Maui by OUTRIGGER

Aparthotel in South Kihei

Aston Maui Hill
3.0 star property
9.0 out of 10, Wonderful, (854)
"Clean room, attentive staff, and tons of things for kids and adults alike to do! "
United States
Misty
The price is €360
includes taxes & fees
28 Dec - 29 Dec
Aston Maui Hill

Condo resort in Lahaina

Paki Maui 103
2.0 star property
Paki Maui 103

Apartment in South Kihei

The Ocean View Residence
3.0 star property
10.0 out of 10, Exceptional, (1)
"Very nice condo for a longer-term stay. We loved being able to cook. "
United States
John
The price is €758
includes taxes & fees
30 Dec - 31 Dec
The Ocean View Residence
4.0 star property
9.0 out of 10, Wonderful, (21)
"I loved that it was a short walk to the beach and there were grocery stores nearby. Lots of options of places to eat and shop and explore the island!"
United States
Emma
Kihei Ali'i Kai Condos with Free Parking

Aparthotel in Lahaina

Royal Lahaina Bungalows & Spa
5.0 star property
9.0 out of 10, Wonderful, (2)
"Clean room and staff is super friendly. Would stay here again "
United States
Rene
The price is €398
includes taxes & fees
9 Jan - 10 Jan 2026
Royal Lahaina Bungalows & Spa
4.0 star property
9.4 out of 10, Exceptional, (474)
"Spacious rooms and fun pools"
United States
Vanessa
The price is €628
includes taxes & fees
9 Jan - 10 Jan 2026
The Westin Nanea Ocean Villas, Ka'anapali
3.0 star property
9.2 out of 10, Wonderful, (7)
"Room was perfect, staff extremely friendly and views were amazing!"
United States
Elizabeth
Timeshare Oceanview Studio in Maui
10.0 out of 10, Exceptional, (1)
"Beautiful place"
United States
Armando
The price is €1,112
includes taxes & fees
4 Jan - 5 Jan 2026
Wailea Ekahi One Bedrooms - Garden View by Coldwell Banker Island Vacations
4.0 star property
8.8 out of 10, Excellent, (198)
"It was a great place to spend a vacation for the whole family. "
United States
Melanie
The price is €491
includes taxes & fees
8 Jan - 9 Jan 2026
Marriott's Maui Ocean Club - Lahaina & Napili Towers
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 €346 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.