A barren volcanic landscape with rugged terrain and distant mountains.

Upcountry Maui Holiday Rentals

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Our top choices for Upcountry Maui holiday rentals

1. Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
8.8 out of 10, Excellent, (37 reviews)
"Good location for the Road to Hana and exploring Paia, hot tub was enjoyable."
United States
Matt
The price is NZ$533
includes taxes & fees
6 Oct - 7 Oct
Yonegan Maui Getaways - Haiku

2. Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (979 reviews)
"The property was very welcoming and respectful. Love the swimming pool . We went in it every day. We meet a lot of people who has timeshares and respect their surroundings. Mahalo 🌺"
United States
Lisa
The price is NZ$608
includes taxes & fees
1 Nov - 2 Nov
Aston Maui Hill

3. Kihei Ali'i Kai Condos with Free Parking

Kihei Ali'i Kai Condos with Free Parking
4.0 star property
South Kihei
9.6 out of 10, Exceptional, (54 reviews)
"Absolutely an amazing place. Very nice, clean, comfortable. We stayed in B104 and it is a perfect spot to get in and out. Definitely come back again."
United States
Angeline
The price is NZ$918
includes taxes & fees
10 Oct - 11 Oct
Kihei Ali'i Kai Condos with Free Parking

4. Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.6 out of 10, Excellent, (40 reviews)
"It was as good as a motel 6 bed was comfortable and my beach front condo as it was described was a room facing a mountain that you couldn’t see passed the forest of plants in front of back patio and the ac unit was very old and loud but served its purpose"
United States
Roark
The price is NZ$923
includes taxes & fees
7 Oct - 8 Oct
Signature Residences at Maui Banyan

5. The Residences at Kamaole Sands Resort

The Residences at Kamaole Sands Resort
4.5 star property
South Kihei
10.0 out of 10, Exceptional, (5 reviews)
"Bonus was there were beach chairs, towels and an umbrella. We only used two chairs as our family were busy snorkeling or boarding away while 1-2 sat out and rested. Clean, right down from beach park 3...stocked pantry got some add-ons and pots and pans enough to allow us making most of our meals. Great times and great communication from host. Thanks! Lucas"
United States
George Lucas
The price is NZ$1,116
includes taxes & fees
8 Oct - 9 Oct
The Residences at Kamaole Sands Resort

6. Condo w/ Lanai at Beginning of Road to Hana!

Condo w/ Lanai at Beginning of Road to Hana!
3.0 star property
Paia
The price is NZ$743
includes taxes & fees
5 Oct - 6 Oct
Condo w/ Lanai at Beginning of Road to Hana!

7. The Kalama Residence

The Kalama Residence
3.0 star property
South Kihei
8.0 out of 10, Very good, (3 reviews)
"My stay was okay. "
United States
Rosalba
The price is NZ$1,601
includes taxes & fees
5 Oct - 6 Oct
The Kalama Residence

8. Grand Champions by KBM

Grand Champions by KBM
3.5 star property
Wailea
10.0 out of 10, Exceptional, (5 reviews)
"Clean everything great time great location! "
United States
Sean
The price is NZ$1,584
includes taxes & fees
7 Oct - 8 Oct
Grand Champions by KBM

9. Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (240 reviews)
"thank you for the best stay! perfect location, stunning beach with walking distance to beach, cafe, and rentals. room had everything we needed, recommend upgrading to ocean view it was a treat!"
United States
ASHLEY
The price is NZ$361
includes taxes & fees
2 Nov - 3 Nov
Napili Village Hotel

10. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,347 reviews)
"Great Stay"
United States
Roopa Rani
The price is NZ$560
includes taxes & fees
5 Oct - 6 Oct
Aston Kaanapali Shores

11. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.6 out of 10, Exceptional, (482 reviews)
"Great place"
United States
Alessio
The price is NZ$1,172
includes taxes & fees
7 Oct - 8 Oct
The Whaler Resort Kaanapali Beach

12. Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa
5.0 star property
Lahaina
7.8 out of 10, Good, (27 reviews)
"Place was beautiful and I really enjoyed the live music under the stats every night"
United States
AURA MARINA
The price is NZ$801
includes taxes & fees
5 Oct - 6 Oct
Royal Lahaina Bungalows & Spa

13. Waiohuli Beach Hale Ocean View Condos with Parking

Waiohuli Beach Hale Ocean View Condos with Parking
3.0 star property
Central Kihei
9.8 out of 10, Exceptional, (6 reviews)
"Easy access to the beach, nice kitchen, view of the water"
United States
Phillip J
The price is NZ$934
includes taxes & fees
4 Oct - 5 Oct
Waiohuli Beach Hale Ocean View Condos with Parking

14. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,888 reviews)
"Love this place!"
United States
Diana
The price is NZ$555
includes taxes & fees
3 Oct - 4 Oct
Napili Shores Maui by OUTRIGGER

15. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Kannapali Beach Area
8.8 out of 10, Excellent, (2,639 reviews)
"The property was a fantastic place to stay. The beach that is in front of the property is excellent for swimming and snorkeling."
United States
Marie
The price is NZ$626
includes taxes & fees
1 Nov - 2 Nov
Aston Maui Kaanapali Villas

16. Lanai & Steps to Beach! Stunning South Maui Condo

Lanai & Steps to Beach! Stunning South Maui Condo
3.5 star property
North Kihei
The price is NZ$889
includes taxes & fees
15 Oct - 16 Oct
Lanai & Steps to Beach! Stunning South Maui Condo

17. Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (656 reviews)
"Nice and clean stay! "
United States
Beverly
The price is NZ$593
includes taxes & fees
4 Oct - 5 Oct
Napili Sunset on the Beach

18. Villa, Garden View, 2-bedroom

Villa, Garden View, 2-bedroom
5.0 star property
Wailea
The price is NZ$2,360
includes taxes & fees
6 Oct - 7 Oct
Villa, Garden View, 2-bedroom

19. Kuleana Club - 608

Kuleana Club - 608
3.5 star property
Lahaina
Kuleana Club - 608

20. Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
4.0 star property
Kannapali Beach Area
8.6 out of 10, Excellent, (254 reviews)
"Great property very close to everything"
United States
Carroll M
The price is NZ$1,077
includes taxes & fees
17 Oct - 18 Oct
Marriott's Maui Ocean Club - Molokai, Maui & Lanai 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, 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 NZ$361 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. 

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