A barren volcanic landscape with rugged terrain and distant mountains.

Holiday Rentals in Upcountry Maui

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Our top choices for Upcountry Maui holiday rentals

1. 2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
3.0 star property
Haiku
The price is €946
includes taxes & fees
16 Sept - 17 Sept
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!

2. Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (964 reviews)
"Dennis and the entire staff made our trip so enjoyable. We will forever have a special place in our hearts for this place. Celebrated our 10 year wedding anniversary here!"
United States
Arleen
The price is €337
includes taxes & fees
4 Oct - 5 Oct
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, (51 reviews)
"The property was exactly as shown in the pictures. Very clean and the washer and dryer was a big plus. Would definitely stay here again."
United States
Monica Ivette
The price is €490
includes taxes & fees
6 Sept - 7 Sept
Kihei Ali'i Kai Condos with Free Parking

4. 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 €273
includes taxes & fees
8 Sept - 9 Sept
Yonegan Maui Getaways - Haiku

5. Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
3.5 star property
South Kihei
8.8 out of 10, Excellent, (37 reviews)
"Thank you for hosting us! The place was very clean and the location was fantastic, close to the beach, shops and restaurants!"
United States
Julie
The price is €445
includes taxes & fees
7 Sept - 8 Sept
Signature Residences at Maui Banyan

6. Makena Surf - CoralTree Residence Collection

Makena Surf - CoralTree Residence Collection
4.0 star property
Wailea
9.4 out of 10, Exceptional, (117 reviews)
"Most beautiful view"
United States
Vesselina
The price is €1,037
includes taxes & fees
14 Sept - 15 Sept
Makena Surf - CoralTree Residence Collection

7. The Ocean View Residence

The Ocean View Residence
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (2 reviews)
"Very nice condo for a longer-term stay. We loved being able to cook. "
United States
John
The price is €555
includes taxes & fees
6 Sept - 7 Sept
The Ocean View Residence

8. Ocean-view Kihei Condo w/ Lanai: Steps to Beach!

Ocean-view Kihei Condo w/ Lanai: Steps to Beach!
3.0 star property
North Kihei
The price is €666
includes taxes & fees
25 Sept - 26 Sept
Ocean-view Kihei Condo w/ Lanai: Steps to Beach!

9. 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 €534
includes taxes & fees
9 Sept - 10 Sept
The Residences at Kamaole Sands Resort

10. Polo Beach Club POL-109 by KBM

Polo Beach Club POL-109 by KBM
3.5 star property
Wailea
8.0 out of 10, Very good, (1 review)
"The property location was exactly what we wanted, easy access to the Wailea beachfront walking path and directly on the beach. We had a great time but if you are considering this place you need to go in with your eyes wide open. It was very pricey for how tired this unit is. It badly needs a full renovation. The tile is from the 1980's, the carpet is gross and crunchy. When we arrived late, it appeared someone had tried to break in the sliding doors and that set off numerous R&M emails...
Canada
PAMELA
The price is €3,770
includes taxes & fees
15 Sept - 16 Sept
Polo Beach Club POL-109 by KBM

11. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,867 reviews)
"Love this place!"
United States
Diana
The price is €264
includes taxes & fees
14 Sept - 15 Sept
Napili Shores Maui by OUTRIGGER

12. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Kannapali Beach Area
8.8 out of 10, Excellent, (2,625 reviews)
"Loved the waterfront cafe and beautiful beach!"
United States
Sabrina
The price is €300
includes taxes & fees
8 Sept - 9 Sept
Aston Maui Kaanapali Villas

13. Kuau Plaza Paia Condo with Parking

Kuau Plaza Paia Condo with Parking
3.0 star property
Paia
The price is €869
includes taxes & fees
6 Sept - 7 Sept
Kuau Plaza Paia Condo with Parking

14. Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (223 reviews)
"Great stay, thank you"
United States
Elizabeth
The price is €222
includes taxes & fees
15 Sept - 16 Sept
Napili Village Hotel

15. Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (4,291 reviews)
"Great location!"
United States
Shad
The price is €204
includes taxes & fees
10 Sept - 11 Sept
Aston Kaanapali Shores

16. Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (656 reviews)
"Clean room amd friendly staff."
United States
Chris
The price is €287
includes taxes & fees
10 Sept - 11 Sept
Napili Sunset on the Beach

17. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.6 out of 10, Exceptional, (460 reviews)
"Clean room, friendly staff, great location and views!"
United States
Luis A
The price is €559
includes taxes & fees
1 Oct - 2 Oct
The Whaler Resort Kaanapali Beach

18. 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 €337
includes taxes & fees
16 Sept - 17 Sept
Lanai & Steps to Beach! Stunning South Maui Condo

19. OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (3,039 reviews)
"Beautiful property, kind staff, Dukes restaurant was awesome & located on property!! Will definitely come back again!!"
United States
Diana
The price is €805
includes taxes & fees
7 Sept - 8 Sept
OUTRIGGER Honua Kai Resort & Spa

20. 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 €1,904
includes taxes & fees
8 Sept - 9 Sept
Grand Champions 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, 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 €204 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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