Photo by Project Forever

Search Holiday Rentals in Upcountry Maui

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Tonight
10 Dec - 11 Dec
Tomorrow
11 Dec - 12 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Our top choices for Upcountry Maui holiday rentals

4 outdoor pools, open 8:00 AM to 10:00 PM, pool cabanas (surcharge)
OUTRIGGER Honua Kai Resort & Spa

Condo resort in Lahaina

OUTRIGGER Honua Kai Resort & Spa
4.0 star property
8.8 out of 10, Excellent, (2881)
"Wonderful stay! "
United States
Quiauna
The price is 7.784.424 ₫
21.351.892 ₫ total
includes taxes & fees
15 Dec - 16 Dec
OUTRIGGER Honua Kai Resort & Spa
Suite, Multiple Beds, Garden View (2 Baths) | Garden view
The Whaler Resort Kaanapali Beach

Condo in Lahaina

The Whaler Resort Kaanapali Beach
4.0 star property
9.6 out of 10, Exceptional, (314)
"great time, great resort, helpful staff"
Canada
Prableen
The price is 8.456.068 ₫
19.673.272 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
The Whaler Resort Kaanapali Beach
On the beach
Napili Shores Maui by OUTRIGGER

Aparthotel in Lahaina

Napili Shores Maui by OUTRIGGER
3.0 star property
9.0 out of 10, Wonderful, (1710)
"Excellent stay. "
United States
casey william
The price is 9.730.530 ₫
11.478.327 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Napili Shores Maui by OUTRIGGER
Terrace/patio
Kahana Beach Vacation Club

Condo in Lahaina

Kahana Beach Vacation Club
3.0 star property
8.4 out of 10, Very good, (750)
"Excellent Resort from all areas "
United States
Kausik
Kahana Beach Vacation Club
Suite, 2 Bedrooms | Living area | TV
Maui Beach Vacation Club

Aparthotel in North Kihei

Maui Beach Vacation Club
2.5 star property
8.2 out of 10, Very good, (818)
"A excelent service in the office. Nice and clean room y all the hotel. I recommend this hotel."
United States
Blanca I
Maui Beach Vacation Club
Property amenity
Aston Kaanapali Shores

Aparthotel in Lahaina

Aston Kaanapali Shores
3.5 star property
8.6 out of 10, Excellent, (3909)
"Best hotel I stayed at "
United States
Nohely
The price is 8.407.883 ₫
10.695.110 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Aston Kaanapali Shores
2 outdoor pools
Aston Maui Kaanapali Villas

Aparthotel in Lahaina

Aston Maui Kaanapali Villas
3.0 star property
8.8 out of 10, Excellent, (2513)
"Great place! Very clean, friendly staff, beautiful grounds, lots to do with in walking distance. The best part that we enjoyed was the beach it was outstanding! highly recommend."
Canada
Natalia
The price is 8.306.550 ₫
12.193.035 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Aston Maui Kaanapali Villas
Garden
Sands of Kahana

Aparthotel in Lahaina

Sands of Kahana
3.0 star property
8.2 out of 10, Very good, (458)
"Size for the price was great"
United States
Ben
Sands of Kahana
Outdoor pool, pool loungers
Kahana Falls Maui by VRI Americas

Aparthotel in Lahaina

Kahana Falls Maui by VRI Americas
3.5 star property
8.2 out of 10, Very good, (974)
"The Entire staff of Kahana Falls Resort was very welcoming and very attentive to our needs. "
United States
Greg
Kahana Falls Maui by VRI Americas
Outdoor pool, open 8:00 AM to 9:30 PM, pool loungers
Aston Maui Hill

Aparthotel in South Kihei

Aston Maui Hill
3.0 star property
9.0 out of 10, Wonderful, (850)
"The accommodations were comfortable, very roomy, nice view from the balcony, and staff was helpful and friendly."
United States
David
The price is 7.617.173 ₫
8.985.368 ₫ total
includes taxes & fees
12 Dec - 13 Dec
Aston Maui Hill
Property grounds
Castle Kama'ole Sands

Condo in South Kihei

Castle Kama'ole Sands
3.0 star property
8.0 out of 10, Very good, (2276)
"great stay for my family"
United States
Jasmin
Castle Kama'ole Sands
Exterior
The Westin Nanea Ocean Villas, Ka'anapali

Condo resort in Lahaina

The Westin Nanea Ocean Villas, Ka'anapali
4.0 star property
9.4 out of 10, Exceptional, (472)
"Spacious rooms and fun pools"
United States
Vanessa
The price is 16.433.784 ₫
19.508.873 ₫ total
includes taxes & fees
5 Jan - 6 Jan 2026
The Westin Nanea Ocean Villas, Ka'anapali
Property grounds
The Westin Ka'anapali Ocean Resort Villas

Condo resort in Lahaina

The Westin Ka'anapali Ocean Resort Villas
4.0 star property
8.6 out of 10, Excellent, (1125)
"Clean room, amazing staff and great location and beach access "
United States
Amanda
The price is 11.787.390 ₫
13.904.642 ₫ total
includes taxes & fees
17 Dec - 18 Dec
The Westin Ka'anapali Ocean Resort Villas
Condo, 2 Bedrooms, 2 Bathrooms, Oceanfront (Unit 1110) | Living area | 65-inch Smart TV with cable channels
Royal Kahana Maui by OUTRIGGER

Aparthotel in Lahaina

Royal Kahana Maui by OUTRIGGER
3.0 star property
8.0 out of 10, Very good, (1399)
"Room was beautiful and had an amazing view"
United States
Becky
Royal Kahana Maui by OUTRIGGER
Suite, 2 Bedrooms (2 story unit) | Living area | TV
Kahana Villa

Condo in Lahaina

Kahana Villa
3.0 star property
8.0 out of 10, Very good, (352)
" Great stay!!! Easy and quiet place next to beach.Feels like home"
United States
Jose
Kahana Villa
Villa, 2 Bedrooms, Oceanfront (Bay 27B2 Gold 2.5 bath) | Beach/ocean view
Kapalua Villas Maui

Aparthotel in Lahaina

Kapalua Villas Maui
4.0 star property
8.8 out of 10, Excellent, (959)
"Gorgeous property, the staff, beach, hiking close by, restaurants in area all were great. Room was spotless and we were able to check in early."
United States
Arturo
Kapalua Villas Maui
Surfing/boogie boarding
Aston at Papakea Resort

Aparthotel in Lahaina

Aston at Papakea Resort
3.0 star property
8.2 out of 10, Very good, (1396)
"Everything was great very good stay "
Canada
Paul
Aston at Papakea Resort
Exterior
Signature Residences at Maui Banyan

Condo resort in South Kihei

Signature Residences at Maui Banyan
4.5 star property
10.0 out of 10, Exceptional, (4)
"Wonderful experience. Clean, convenient, great location, pool, hot tub, beautiful property, and safe. Had a great time."
United States
Melinda
The price is 2.988.512 ₫
17.232.857 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Signature Residences at Maui Banyan
Suite, 1 Bedroom | Iron/ironing board, free WiFi
The Gardens at West Maui

Condo in Lahaina

The Gardens at West Maui
3.0 star property
8.4 out of 10, Very good, (520)
"We stayed here for 4 days easy check in and check out process "
United States
Relda
The Gardens at West Maui
Condo, 2 Bedrooms (1115) | Property amenity
Kaanapali Alii

Aparthotel in Lahaina

Kaanapali Alii
4.0 star property
9.6 out of 10, Exceptional, (956)
"Views were fantastic, as were beach and pool access, hotel was very clean."
Canada
Ryan
Kaanapali Alii
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

OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa

10/10 Excellent
"Amazing staff so friendly. Very clean. Definitely going back and staying there again."
Nicole 5-night trip
Posted 2 days ago
OUTRIGGER Honua Kai Resort & Spa