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Find Hotels with a Pool in Upcountry Maui, HI
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Our top choices for Upcountry Maui hotels with a pool
8.6 out of 10, Excellent, (209)
"The staff were kind and helpful. The rooms were comfortable and the property is gorgeous and well maintained. "
Sarah Catherine
The price is ￥61,683
￥86,155 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16Makawao
10.0 out of 10, Exceptional, (72)
"We had an amazing vacation here. We had 4 generations ranging from 4 months to 81 years and everyone had a great time. There was room to spread out and room to all gather together. Having the private pool and spa was perfect. Host was available when we needed her and the B and B was well stocked. We also loved the Maui feel of the accommodations and being out of the busier parts of Maui. I highly recommend this venue for larger groups! "
Kari L.
The price is ￥224,756
￥463,434 total
includes taxes & fees
Jan 6 - Jan 7, 2026
9.6 out of 10, Exceptional, (2355)
"Always a great stay for business!!"
Stephen
The price is ￥38,328
￥52,701 total
includes taxes & fees
Jan 22 - Jan 23, 2026
8.4 out of 10, Very Good, (1598)
"Excellent resort environment, Beautiful beach and nice staff. "
dewei
The price is ￥42,133
￥58,328 total
includes taxes & fees
Jan 11 - Jan 12, 2026
9.0 out of 10, Wonderful, (1202)
"Cute little beach nice pool and sweet little restaurant attached with amazing food on property."
Cody
The price is ￥34,560
￥45,673 total
includes taxes & fees
Jan 11 - Jan 12, 2026
9.0 out of 10, Wonderful, (166)
"Great staff, clean rooms. It was a pleasant stay."
Mary
The price is ￥52,106
￥66,504 total
includes taxes & fees
Jan 13 - Jan 14, 2026
7.2 out of 10, Good, (1124)
"Everything was great! The location, lawn, beach access, staff were all excellent."
Jiaqiu
The price is ￥33,138
￥43,032 total
includes taxes & fees
Jan 4 - Jan 5, 2026
9.0 out of 10, Wonderful, (1003)
"Clean room and nice staff"
Joseph
The price is ￥57,148
￥67,841 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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.
Top Upcountry Maui Hotel Reviews
OUTRIGGER Kaanapali Beach Resort
10/10 Excellent
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