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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

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

OUTRIGGER Honua Kai Resort & Spa

OUTRIGGER Honua Kai Resort & Spa
4.0 star property
Lahaina
8.8 out of 10, Excellent, (2886)
"Wonderful stay! "
United States
Quiauna
The price is ฿13,694
฿30,750 total
includes taxes & fees
10 Jan - 11 Jan 2026
OUTRIGGER Honua Kai Resort & Spa
Exterior
Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas
3.0 star property
Lahaina
8.8 out of 10, Excellent, (2518)
"We enjoyed the property "
United States
Therese
The price is ฿11,118
฿15,894 total
includes taxes & fees
22 Dec - 23 Dec
Aston Maui Kaanapali Villas
Exterior
Aston Kaanapali Shores

Aston Kaanapali Shores

Aston Kaanapali Shores
3.5 star property
Lahaina
8.8 out of 10, Excellent, (3925)
"Best hotel I stayed at "
United States
Nohely
The price is ฿8,763
฿11,263 total
includes taxes & fees
22 Dec - 23 Dec
Aston Kaanapali Shores
Exterior
The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach
4.0 star property
Lahaina
9.6 out of 10, Exceptional, (321)
"great time, great resort, helpful staff"
Canada
Prableen
The price is ฿10,467
฿23,902 total
includes taxes & fees
20 Jan - 21 Jan 2026
The Whaler Resort Kaanapali Beach
Sun deck
Napili Sunset on the Beach

Napili Sunset on the Beach

Napili Sunset on the Beach
2.5 star property
Lahaina
9.2 out of 10, Wonderful, (647)
"Location was excellent"
United States
Polly
The price is ฿8,831
฿10,417 total
includes taxes & fees
22 Dec - 23 Dec
Napili Sunset on the Beach
Garden
Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku

Yonegan Maui Getaways - Haiku
3.0 star property
Haiku
9.0 out of 10, Wonderful, (12)
"Loved having the hot tub to come home to!!"
United States
Pedro
The price is ฿4,793
฿8,799 total
includes taxes & fees
5 Jan - 6 Jan 2026
Yonegan Maui Getaways - Haiku
2 outdoor pools, pool cabanas (surcharge), pool umbrellas
The Westin Ka'anapali Ocean Resort Villas

The Westin Ka'anapali Ocean Resort Villas

The Westin Ka'anapali Ocean Resort Villas
4.0 star property
Lahaina
8.6 out of 10, Excellent, (1126)
"Perfect stay"
United States
hao
The price is ฿15,296
฿18,158 total
includes taxes & fees
2 Jan - 3 Jan 2026
The Westin Ka'anapali Ocean Resort Villas
Beach nearby, white sand, beach towels
Napili Village Hotel

Napili Village Hotel

Napili Village Hotel
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (142)
"Exactly what we were looking for! Close walking distance to beach and dining!"
United States
Tessa
The price is ฿8,329
฿9,888 total
includes taxes & fees
21 Jan - 22 Jan 2026
Napili Village Hotel
Exterior
Signature Residences at Maui Banyan

Signature Residences at Maui Banyan

Signature Residences at Maui Banyan
4.5 star property
South Kihei
9.6 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 ฿1,658
฿16,487 total
includes taxes & fees
22 Dec - 23 Dec
Signature Residences at Maui Banyan
3 outdoor pools, pool cabanas (surcharge), pool loungers
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
4.0 star property
Lahaina
8.4 out of 10, Very good, (237)
"Room was clean. Hotel staff were pleasant and competent. Construction was a little inconvenient noise and no carpeting by elevators was weird."
United States
Ron
The price is ฿15,798
฿18,754 total
includes taxes & fees
3 Jan - 4 Jan 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
On the beach
Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER

Napili Shores Maui by OUTRIGGER
3.0 star property
Lahaina
9.0 out of 10, Wonderful, (1715)
"Excellent stay. "
United States
casey william
The price is ฿11,590
฿13,671 total
includes taxes & fees
22 Dec - 23 Dec
Napili Shores Maui by OUTRIGGER
Outdoor pool, open 8:00 AM to 9:30 PM, pool loungers
Aston Maui Hill

Aston Maui Hill

Aston Maui Hill
3.0 star property
South Kihei
9.0 out of 10, Wonderful, (854)
"Clean room, attentive staff, and tons of things for kids and adults alike to do! "
United States
Misty
The price is ฿13,003
฿15,338 total
includes taxes & fees
23 Dec - 24 Dec
Aston Maui Hill
Beach/ocean view
Paki Maui 103

Paki Maui 103

Paki Maui 103
2.0 star property
Lahaina
The price is ฿28,239
฿42,734 total
includes taxes & fees
22 Dec - 23 Dec
Paki Maui 103
Elite Apartment, Balcony, Ocean View | Blackout curtains, iron/ironing board, free WiFi
The Ocean View Residence

The Ocean View Residence

The Ocean View Residence
3.0 star property
South Kihei
10.0 out of 10, Exceptional, (1)
"Very nice condo for a longer-term stay. We loved being able to cook. "
United States
John
The price is ฿2,827
฿18,969 total
includes taxes & fees
24 Dec - 25 Dec
The Ocean View Residence
Beach nearby, white sand, beach towels
Kihei Ali'i Kai Condos with Free Parking

Kihei Ali'i Kai Condos with Free Parking

Kihei Ali'i Kai Condos with Free Parking
4.0 star property
South Kihei
9.0 out of 10, Wonderful, (21)
"I loved that it was a short walk to the beach and there were grocery stores nearby. Lots of options of places to eat and shop and explore the island!"
United States
Emma
Kihei Ali'i Kai Condos with Free Parking
Exterior
Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa
5.0 star property
Lahaina
9.0 out of 10, Wonderful, (2)
"I had a wonderful stay here! The location is perfect, right by a peaceful beach that made the whole experience incredibly relaxing. I stayed in the bungalows, which were amazing—spacious, comfortable, and not crowded at all. The atmosphere felt private and serene. The staff were outstanding—friendly, attentive, and always ready to help. Their hospitality truly made the stay special. Overall, this is the ideal place if you’re looking for relaxation, great service, and a beautiful setting."
United States
Karina Soto
The price is ฿9,983
฿13,518 total
includes taxes & fees
5 Jan - 6 Jan 2026
Royal Lahaina Bungalows & Spa
2 outdoor pools, pool cabanas (surcharge), pool umbrellas
The Westin Nanea Ocean Villas, Ka'anapali

The Westin Nanea Ocean Villas, Ka'anapali

The Westin Nanea Ocean Villas, Ka'anapali
4.0 star property
Lahaina
9.4 out of 10, Exceptional, (474)
"Spacious rooms and fun pools"
United States
Vanessa
The price is ฿19,573
฿23,236 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Westin Nanea Ocean Villas, Ka'anapali
Exterior
Timeshare Oceanview Studio in Maui

Timeshare Oceanview Studio in Maui

Timeshare Oceanview Studio in Maui
3.0 star property
Lahaina
9.2 out of 10, Wonderful, (7)
"Room was perfect, staff extremely friendly and views were amazing!"
United States
Elizabeth
Timeshare Oceanview Studio in Maui
Condo, 1 Bedroom | Pool
Wailea Ekahi One Bedrooms - Garden View by Coldwell Banker Island Vacations

Wailea Ekahi One Bedrooms - Garden View by Coldwell Banker Island Vacations

Wailea Ekahi One Bedrooms - Garden View by Coldwell Banker Island Vacations
3.0 star property
Wailea
10.0 out of 10, Exceptional, (1)
"Beautiful place"
United States
Armando
The price is ฿11,558
฿41,149 total
includes taxes & fees
6 Jan - 7 Jan 2026
Wailea Ekahi One Bedrooms - Garden View by Coldwell Banker Island Vacations
3 outdoor pools, pool cabanas (surcharge), pool loungers
Marriott's Maui Ocean Club - Lahaina & Napili Towers

Marriott's Maui Ocean Club - Lahaina & Napili Towers

Marriott's Maui Ocean Club - Lahaina & Napili Towers
4.0 star property
Lahaina
8.8 out of 10, Excellent, (198)
"It was a great place to spend a vacation for the whole family. "
United States
Melanie
The price is ฿15,296
฿18,158 total
includes taxes & fees
6 Jan - 7 Jan 2026
Marriott's Maui Ocean Club - Lahaina & Napili 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.
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Top Upcountry Maui Hotel Reviews

Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

10/10 Excellent
"Excellent resort environment, Beautiful beach and nice staff. "
dewei 5-night trip
Posted 2 days ago
Royal Lahaina Resort & Bungalows

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