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Check prices for these dates

In two weeks
25 Sep - 27 Sep
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Upcountry Maui holiday rentals

House (3 Bedrooms) | Interior

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 14.852.160 ₫
32.273.770 ₫ total
includes taxes & fees
16 Sept - 17 Sept
2 Mi to Hana Hwy: Haiku Home w/ Ocean Views!
Outdoor pool, open 8:00 AM to 9:30 PM, pool umbrellas, pool loungers

2. Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (971 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 7.950.960 ₫
9.438.745 ₫ total
includes taxes & fees
13 Oct - 14 Oct
Aston Maui Hill
Terrace/patio

3. 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 33.998.693 ₫
57.376.421 ₫ total
includes taxes & fees
15 Sept - 16 Sept
Grand Champions by KBM
Condo, 2 Bedrooms, Oceanfront (F304) | 2 bedrooms, hypo-allergenic bedding, in-room safe, iron/ironing board

4. 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 20.603.290 ₫
31.248.673 ₫ total
includes taxes & fees
16 Sept - 17 Sept
Makena Surf - CoralTree Residence Collection
Exterior

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)
"Wonderful location, a short walk to restaurants, shops and beaches. The condo and property grounds were VERY well taken care of and groomed. Beautiful gardens and waterfalls. The pools were very relaxing and our experience was definitely one we will remember. A++"
United States
Patrick
The price is 1.317.643 ₫
13.585.111 ₫ total
includes taxes & fees
17 Sept - 18 Sept
Signature Residences at Maui Banyan
Studio, Garden View (Haiku #6) | Terrace/patio

6. 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 3.278.269 ₫
7.779.699 ₫ total
includes taxes & fees
15 Sept - 16 Sept
Yonegan Maui Getaways - Haiku
Family Apartment, 1 King Bed with Sofa bed, Garden View (1 BR 1011) | Living area

7. 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, (53 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 5.728.320 ₫
14.769.672 ₫ total
includes taxes & fees
15 Sept - 16 Sept
Kihei Ali'i Kai Condos with Free Parking
Deluxe Apartment, Partial Ocean View | Balcony

8. 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 2.894.422 ₫
16.954.399 ₫ total
includes taxes & fees
17 Sept - 18 Sept
The Residences at Kamaole Sands Resort
Apartment (1 Bedroom) | Interior

9. 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 6.117.120 ₫
12.907.901 ₫ total
includes taxes & fees
16 Sept - 17 Sept
Lanai & Steps to Beach! Stunning South Maui Condo
Elite Apartment, Balcony, Ocean View | Dining room

10. 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 1.308.651 ₫
13.565.900 ₫ total
includes taxes & fees
15 Sept - 16 Sept
The Ocean View Residence
Aerial view

11. 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 8.683.200 ₫
11.692.512 ₫ total
includes taxes & fees
30 Sept - 1 Oct
Royal Lahaina Bungalows & Spa
On the beach

12. Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.5 star property
Lahaina
9.0 out of 10, Wonderful, (1,873 reviews)
"Love this place!"
United States
Diana
The price is 7.756.560 ₫
9.207.967 ₫ total
includes taxes & fees
15 Sept - 16 Sept
Napili Shores Maui by OUTRIGGER
Villa, 2 Bedrooms (Ocean View, Sleeps 6 (POL-109)) | Outdoor dining

13. 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 82.091.465 ₫
113.575.978 ₫ total
includes taxes & fees
15 Sept - 16 Sept
Polo Beach Club POL-109 by KBM
Property grounds

14. The Westin Ka'anapali Ocean Resort Villas

The Westin Ka'anapali Ocean Resort Villas
4.0 star property
Kannapali Beach Area
8.6 out of 10, Excellent, (1,158 reviews)
"All in all , it was an amazing experience, staff was great, room clean, trip was amazing."
United States
Brenda
The price is 12.830.400 ₫
15.231.224 ₫ total
includes taxes & fees
20 Sept - 21 Sept
The Westin Ka'anapali Ocean Resort Villas
Suite, Multiple Beds, Garden View (2 Baths) | Garden view

15. The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Kannapali Beach Area
9.6 out of 10, Exceptional, (466 reviews)
"Clean room, friendly staff, great location and views!"
United States
Luis A
The price is 6.049.728 ₫
16.652.241 ₫ total
includes taxes & fees
5 Oct - 6 Oct
The Whaler Resort Kaanapali Beach
TV

16. Kapalua Golf Villas Resort by KBM

Kapalua Golf Villas Resort by KBM
4.0 star property
Lahaina
9.0 out of 10, Wonderful, (16 reviews)
"Absolute gem. Wife and I love this place and location. "
United States
Joe
The price is 42.999.103 ₫
63.199.303 ₫ total
includes taxes & fees
15 Sept - 16 Sept
Kapalua Golf Villas Resort by KBM
On the beach, white sand, beach towels

17. 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 5.961.600 ₫
15.046.603 ₫ total
includes taxes & fees
16 Sept - 17 Sept
Waiohuli Beach Hale Ocean View Condos with Parking
4 outdoor pools, open 8:00 AM to 10:00 PM, pool cabanas (surcharge)

18. OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.5 star property
Lahaina
8.8 out of 10, Excellent, (3,041 reviews)
"Beautiful property, kind staff, Dukes restaurant was awesome & located on property!! Will definitely come back again!!"
United States
Diana
The price is 9.231.408 ₫
24.766.632 ₫ total
includes taxes & fees
21 Sept - 22 Sept
OUTRIGGER Honua Kai Resort & Spa
Apartment (2 Bedrooms) | Front of property

19. 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 5.806.080 ₫
20.066.746 ₫ total
includes taxes & fees
25 Sept - 26 Sept
Ocean-view Kihei Condo w/ Lanai: Steps to Beach!
Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, pool loungers

20. Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Kannapali Beach Area
8.8 out of 10, Excellent, (2,628 reviews)
"Loved the waterfront cafe and beautiful beach!"
United States
Sabrina
The price is 5.715.360 ₫
9.092.217 ₫ total
includes taxes & fees
10 Oct - 11 Oct
Aston Maui Kaanapali Villas
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

The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

10/10 Excellent
"Hotel facility is perfect But things to do(ex haleakela iao valley etc) faraway) ."
DOO IL 3-night trip
Posted 4 hours ago
The Westin Maui Resort & Spa, Ka'anapali

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