Book Hotels in Kaupo, HI
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Top Kaupo hotels

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16
Makawao
This vacation home features an outdoor pool and a hot tub. A terrace, a garden, and a picnic area are also on offer.
"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. ..."
Reviewed on Sep 19, 2025

Exceptional Upcountry Villa with breathtaking views
Makawao
This vacation home features an outdoor pool and a hot tub. Enjoy the sauna and conveniences like a garden and laundry facilities.
Amazing!
"We had the most amazing experience in Hawaii and was mostly due to where we stayed! David and Dawn were the most amazing hosts! Very responsive and helpful with restaurants, things to do and made our stay very comfortable! This place was perfect for our family of 5 and the views - stunning!! We plan ..."
Reviewed on Jul 24, 2025

Private lush 2 Acre Mountain Home Maui Permitted#STMP 2013-0001 many amenities
Makawao
A hot tub is featured at this vacation home, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.
"This home was fantastic! The kitchen was stocked with all we needed for meal prep. The beds were spacious and comfortable. Tasey was quick to respond to texts. The entrance key code made it super simple to come and go from the home. The location of the house was perfectly in between beaches and the ..."
Reviewed on Aug 17, 2025

Island Sunset Villa: Your Maui Escape with Ocean & Stunning Sunsets Views
Kula
$988 nightly
The price is $1,149 total per night from Oct 27 to Oct 28
$1,149 total
Oct 27 - Oct 28
Total with taxes and fees
This villa features a garden, laundry facilities, and barbecue grills.
"This was an astounding property for our stay! The view, the bedrooms, and the bathrooms/showers are fantastic! Wonderful wonderful wonderful!"
Reviewed on Sep 1, 2025

Couples & Honeymooners. Privacy & Romance! 7 Sacred Pools
Hana
This apartment includes a garden and barbecue grills.
"Beautiful stay on a beautiful property. This one is truly special & the hosts are great. Make sure you check out the stars at night magical! Thank you guys. :)Ryan & Mabel"
Reviewed on Aug 23, 2025

Hotel Wailea, Relais & Chateaux - Adults Only
555 Kaukahi Street, Kihei, HI
Fully refundableReserve now, pay when you stay
$949 nightly
The price is $1,119 total per night from Sep 29 to Sep 30
$1,119 total
Sep 29 - Sep 30
Total with taxes and fees
This luxury resort includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the business center, laundry service, and valet ...
"Great resort with great amenities! Very convenient to downtown wailea and the beaches and the staff are super friendly and attentive!"
Reviewed on Aug 27, 2025

Oceanview Condo in Hana-Let the ocean lull you to sleep
Hana
$341 nightly
The price is $397 total per night from Oct 2 to Oct 3
$397 total
Oct 2 - Oct 3
Total with taxes and fees
This apartment includes a garden and laundry facilities.
"This was a delightful unit - easy to access and enjoy the views and the ocean breezes. The fan was awesome. Appreciated the firm mattress and new pillows. Clean and updated."
Reviewed on Sep 6, 2025

Hana-Maui Resort, a Destination by Hyatt Residence
5031 Hana Hwy, Hana, HI
Fully refundableReserve now, pay when you stay
$584 nightly
The price is $689 total per night from Oct 27 to Oct 28
$689 total
Oct 27 - Oct 28
Total with taxes and fees
This resort features a full-service spa, 2 outdoor pools, and a restaurant. Families will appreciate the mini golf and onsite laundry facilities. Enjoy the gym ...
"A Wonderful Anniversary Experience at the Hana Maui Resort by Hyatt!! The entire staff at breakfast was great! Since we had an extended stay, we meet and got to know many of the staff at the resort and restaurant. They were very sweet and made us feel like family. All the drivers were very helpful ..."
Reviewed on Sep 14, 2025

Wailea Ekolu - CoralTree Residence Collection
10 Wailea Ekolu Place, Kihei, HI
$616 nightly
The price is $722 total per night from Sep 28 to Sep 29
$722 total
Sep 28 - Sep 29
Total with taxes and fees
This condo doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a picnic area, and dry cleaning are also on offer.
"It’s a great place to Stay for the family vacation."
Reviewed on Aug 22, 2025
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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Recent Kaupo hotel reviews by fellow wanderers

Hale Akua Garden Farm & Eco-Retreat
5 out of 5
Posted 4 days ago
Travelocity Verified Review
"Stayed in the 1800sq ft house and was awesome! Was so nice having our own pool and hot tub overlooking the valley and a waterfall. Perfect way to end our Maui trip. Round bed needs a new mattress now. Very soft and not easy to get out of. The shower outside I didn't mind but my wife didn't like much. You're rather far from places but that was the point of staying there. Loved the little geckos climbing the walls. Huge comfy place "
A verified traveler stayed at Hale Akua Garden Farm & Eco-Retreat
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