A barren volcanic landscape with rugged terrain and distant mountains.

Upcountry Maui Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Upcountry Maui vacation rentals

A spacious kitchen with a large island, wooden flooring, and modern lighting fixtures.

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 NT$14,238
NT$34,776 total
includes taxes & fees
Sep 16 - Sep 17
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
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, (965 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 NT$10,417
NT$12,367 total
includes taxes & fees
Oct 4 - Oct 5
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, (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 NT$6,992
NT$18,029 total
includes taxes & fees
Sep 6 - Sep 7
Kihei Ali'i Kai Condos with Free Parking
A wooden deck with a chair, surrounded by lush tropical vegetation and a clear blue sky.

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 NT$4,465
NT$10,047 total
includes taxes & fees
Sep 10 - Sep 11
Yonegan Maui Getaways - Haiku
A beach resort with rows of palm trees, a sandy beach, and a view of the ocean.

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 NT$1,252
NT$15,822 total
includes taxes & fees
Sep 6 - Sep 7
Signature Residences at Maui Banyan
A room with a large window overlooking the ocean, wicker furniture, a sofa, and a table with a lamp.

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 NT$25,257
NT$38,306 total
includes taxes & fees
Sep 16 - Sep 17
Makena Surf - CoralTree Residence Collection
A dining area with a table set for breakfast, including bread, fruit, and orange juice.

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 NT$3,395
NT$20,400 total
includes taxes & fees
Sep 6 - Sep 7
The Ocean View Residence
A covered patio with a table and chairs, overlooking a well-maintained lawn and palm trees.

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 NT$7,117
NT$24,599 total
includes taxes & fees
Sep 25 - Sep 26
Ocean-view Kihei Condo w/ Lanai: Steps to Beach!
A balcony with a table set for breakfast, overlooking a residential area with palm trees and modern buildings.

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 NT$2,940
NT$19,428 total
includes taxes & fees
Sep 9 - Sep 10
The Residences at Kamaole Sands Resort
A glass-top table with chairs, a bottle of wine, and a vase of flowers.

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 NT$100,207
NT$138,640 total
includes taxes & fees
Sep 15 - Sep 16
Polo Beach Club POL-109 by KBM
A beach with clear turquoise water, sandy shore, palm trees, and a resort building in the background.

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 NT$8,173
NT$9,702 total
includes taxes & fees
Sep 8 - Sep 9
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.

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 NT$6,935
NT$11,050 total
includes taxes & fees
Sep 8 - Sep 9
Aston Maui Kaanapali Villas
A coastal resort with beachfront properties, palm trees, and a view of distant mountains.

13. Kuau Plaza Paia Condo with Parking

Kuau Plaza Paia Condo with Parking
3.0 star property
Paia
The price is NT$17,465
NT$31,964 total
includes taxes & fees
Sep 7 - Sep 8
Kuau Plaza Paia Condo with Parking
A beach with clear blue water, palm trees, and a resort in the background.

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 NT$6,570
NT$7,799 total
includes taxes & fees
Sep 17 - Sep 18
Napili Village Hotel
A tropical garden with a waterfall, lush greenery, and a gazebo.

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 NT$5,515
NT$7,486 total
includes taxes & fees
Sep 11 - Sep 12
Aston Kaanapali Shores
A beach view with lounge chairs and a clear sky.

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 NT$8,896
NT$10,561 total
includes taxes & fees
Sep 6 - Sep 7
Napili Sunset on the Beach
A view of a beach with palm trees and a sailboat on the water.

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 NT$7,575
NT$20,552 total
includes taxes & fees
Oct 1 - Oct 2
The Whaler Resort Kaanapali Beach
A beach with a building on the left, a rocky breakwater, and a clear blue sky.

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 NT$4,619
NT$12,376 total
includes taxes & fees
Sep 16 - Sep 17
Lanai & Steps to Beach! Stunning South Maui Condo
A resort pool with red umbrellas, palm trees, and a view of the ocean.

19. OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (3,040 reviews)
"Beautiful property, kind staff, Dukes restaurant was awesome & located on property!! Will definitely come back again!!"
United States
Diana
The price is NT$11,000
NT$29,913 total
includes taxes & fees
Sep 10 - Sep 11
OUTRIGGER Honua Kai Resort & Spa
A balcony with wicker furniture, a wooden table, and a view of a lush landscape and distant buildings.

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 NT$41,501
NT$70,038 total
includes taxes & fees
Sep 8 - Sep 9
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

Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

10/10 Excellent
"The resort was amazing. Beautiful views, spacious rooms and they worked very hard at keeping the grounds clean. The staff throughout were very helpful and friendly. So many pools to choose from and easy access to beach."
Doug 5-night trip
Posted 2 hours ago
Wailea Beach Resort - Marriott, Maui

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