A barren volcanic landscape with rugged terrain and distant mountains.

Search Holiday Rentals in Upcountry Maui

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Upcountry Maui holiday rentals

A wooden deck with a chair, surrounded by lush tropical vegetation and a clear blue sky.

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 Rp2.263.169
Rp5.370.754 total
includes taxes & fees
4 Oct - 5 Oct
Yonegan Maui Getaways - Haiku
A resort with a swimming pool, palm trees, and ocean views.

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 Rp5.511.070
Rp6.542.303 total
includes taxes & fees
1 Nov - 2 Nov
Aston Maui Hill
A modern kitchen with a large island, a dining area with a view, and a living room with a sofa and chairs.

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 Rp3.377.608
Rp9.533.524 total
includes taxes & fees
10 Oct - 11 Oct
Kihei Ali'i Kai Condos with Free Parking
A beach resort with rows of palm trees, a sandy beach, and a view of the ocean.

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 Rp849.920
Rp9.250.936 total
includes taxes & fees
7 Oct - 8 Oct
Signature Residences at Maui Banyan
A balcony with a table set for breakfast, overlooking a residential area with palm trees and modern buildings.

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 Rp1.901.283
Rp11.497.505 total
includes taxes & fees
3 Oct - 4 Oct
The Residences at Kamaole Sands Resort
A beach with clear blue water, rocky shore, and palm trees.

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 Rp3.024.086
Rp7.487.744 total
includes taxes & fees
5 Oct - 6 Oct
Condo w/ Lanai at Beginning of Road to Hana!
A beach with clear blue water, a sandy shore, and palm trees.

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 Rp4.388.503
Rp16.812.239 total
includes taxes & fees
4 Oct - 5 Oct
The Kalama Residence
A balcony with wicker furniture, a wooden table, and a view of a lush landscape and distant buildings.

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 Rp6.052.592
Rp15.958.235 total
includes taxes & fees
7 Oct - 8 Oct
Grand Champions by KBM
A beach with clear blue water, palm trees, and a resort in the background.

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 Rp3.258.556
Rp3.868.297 total
includes taxes & fees
1 Nov - 2 Nov
Napili Village Hotel
A tropical garden with a waterfall, lush greenery, and a gazebo.

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 Rp4.280.245
Rp5.612.258 total
includes taxes & fees
10 Oct - 11 Oct
Aston Kaanapali Shores
A view of a beach with palm trees and a sailboat on the water.

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 Rp4.408.856
Rp11.798.146 total
includes taxes & fees
7 Oct - 8 Oct
The Whaler Resort Kaanapali Beach
A resort with multiple bungalow-style buildings, a swimming pool, and a 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 Rp5.994.490
Rp8.071.983 total
includes taxes & fees
5 Oct - 6 Oct
Royal Lahaina Bungalows & Spa
A tropical beach scene with palm trees, a clear blue sky, and a view of the ocean.

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 Rp3.292.496
Rp9.410.351 total
includes taxes & fees
3 Oct - 4 Oct
Waiohuli Beach Hale Ocean View Condos with Parking
A beach with clear turquoise water, sandy shore, palm trees, and a resort building in the background.

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 Rp4.683.754
Rp5.560.177 total
includes taxes & fees
3 Oct - 4 Oct
Napili Shores Maui by OUTRIGGER
A swimming pool with a curved design, surrounded by palm trees and lounge chairs, with a building in the background.

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 Rp3.961.503
Rp6.302.113 total
includes taxes & fees
1 Nov - 2 Nov
Aston Maui Kaanapali Villas
A beach with a building on the left, a rocky breakwater, and a clear blue sky.

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 Rp4.222.984
Rp8.911.033 total
includes taxes & fees
15 Oct - 16 Oct
Lanai & Steps to Beach! Stunning South Maui Condo
A beach view with lounge chairs and a clear sky.

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 Rp5.031.256
Rp5.972.838 total
includes taxes & fees
3 Oct - 4 Oct
Napili Sunset on the Beach
A resort pool area with a hot tub, lounge chairs, and palm trees.

18. Villa, Garden View, 2-bedroom

Villa, Garden View, 2-bedroom
5.0 star property
Wailea
The price is Rp11.496.430
Rp23.780.230 total
includes taxes & fees
6 Oct - 7 Oct
Villa, Garden View, 2-bedroom
A patio with a round table and two chairs, overlooking a grassy area with a view of the ocean and a clear sky.

19. Kuleana Club - 608

Kuleana Club - 608
3.5 star property
Lahaina
Kuleana Club - 608
A resort with a pool, palm trees, and a night scene with fire torches.

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 Rp9.143.834
Rp10.854.829 total
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Upcountry Maui Hotel Reviews

AEI at Maui Kaanapali Villas Resort

AEI at Maui Kaanapali Villas Resort

10/10 Excellent
"Room was clean and spacious. Staff was very helpful. Rain at the front desk is amazing!"
Sasha 5-night trip
Posted 7 hours ago
AEI at Maui Kaanapali Villas Resort

Find out more about Upcountry Maui

Search for holiday rentals in Upcountry Maui on Expedia.co.id! You can easily find your home rentals, villas, holiday apartments in Upcountry Maui using one of the methods below:

  • View our selection of featured holiday rentals in Upcountry Maui
  • Use the map to find apartments and other holiday homes in the Upcountry Maui neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Upcountry Maui while they last

Look no further and take a look at our great range of rental properties in Upcountry Maui!