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Compare 17 Cottages in Kaupo with updated reviews, rates, and availability.

Secluded cottage on Tropical flower farm

9.6 out of 10, Exceptional, (240)
"Had a wonderful time staying in this lovely cottage set in the midst of all the Hawaiian trees and flowers. Was just a visual delight. The house was clean and wonderful. Thank You"
The price is SAR 1,258
SAR 2,281 total
includes taxes & fees
19 Jan - 20 January 2025
Secluded cottage on Tropical flower farm

Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

9.6 out of 10, Exceptional, (172)
"Enjoyed our stay at this spot in Hana. The owners do a great job at providing essentials and even had beach chairs which came in so handy! Loved the stay and a perfect way for us to rest after doing the Highway to Hana. The only thing: the GPS didn’t quite bring us here but we figured it out!"
The price is SAR 1,108
SAR 2,070 total
includes taxes & fees
10 Jan - 11 January 2025
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

10.0 out of 10, Exceptional, (64)
"We had an amazing time in Hana! The cabin"
The price is SAR 1,220
SAR 2,122 total
includes taxes & fees
7 Jan - 8 January 2025
Tropical Romance... Lush Gardens.... in Heavenly Hana, Maui

Heaven on Earth in Upcountry Maui

10.0 out of 10, Exceptional, (93)
"Star Lookout is located in upland Maui - the cottage has spectacular views of both east and west maui and amazing views of the night sky - so wonderful we deliberately got up in the middle of the night to see it "
Heaven on Earth in Upcountry Maui

Hana Harvest Cottage

9.4 out of 10, Exceptional, (63)
"The Hana harvest cottage is a great place to stay. The cottage was very comfortable, and nicely kept. The location was absolutely beautiful, surrounded by trees and a river. Would highly recommend for travelers looking to unplug and enjoy the Hana area."
Hana Harvest Cottage

Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

10.0 out of 10, Exceptional, (136)
"The property is absolutely incredible. Elaine provided all the information in advance and instructions were all very clear. The place itself is nicely setup. The kitchen had all the things needed for some quick meals and probably more if you wanted to do some additional cooking. For us at least, the proximity to amazing local food kept us largely out of the kitchen. The rooms were nicely setup, and the owners even had a pack'n'play for our toddler which was great. The pool was of course the...
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

Great location between Hana Town and Hamoa Beach, private, family-friendly

9.8 out of 10, Exceptional, (217)
"We loved this little spot. Fabulous view that we enjoyed with the moon reflecting off the ocean, a huge lawn to play on and super close to Koki, Hamoa and Hana. We would have loved to stay longer! "
The price is SAR 1,014
SAR 1,928 total
includes taxes & fees
25 Jan - 26 January 2025
Great location between Hana Town and Hamoa Beach, private, family-friendly

Remodeled cottage with AC, ocean views, yard & lanai - near beach, golf & dining

9.4 out of 10, Exceptional, (31)
"Very comfortable and a great location. We enjoyed our stay."
Remodeled cottage with AC, ocean views, yard & lanai - near beach, golf & dining

MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA

10.0 out of 10, Exceptional, (230)
"It was perfect! We loved Hāna, the bungalow, the people, the location. Truly magical! The property managers were fantastic, helped with navigating the area. It’s so perfect you don’t want it to get spoiled. Hana is special, and the bungalow was perfect! "
MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA

Luxury Upcountry retreat with breathtaking views!

10.0 out of 10, Exceptional, (74)
"Stayed here a few years ago, and we loved our return stay. Very peaceful in a beautiful setting with incredible views, this is a unique and fantastic way to experience Maui. Great, clear and concise communications with David. We look forward to returning…mahalo!"
Luxury Upcountry retreat with breathtaking views!

Beautiful Hana, Near Waianapanapa State Park. STR 216/0003 TA186-656-9728-01

9.8 out of 10, Exceptional, (184)
"The property was exactly as described. Beautiful large fruit tree garden property within walking distance to Waianapanapa State Park's black sand beach. Home was very clean and well-stocked. The owner's housekeeper left fresh fruit for us on the day we checked in. Owner was very responsive to questions before our arrival."
Beautiful Hana, Near Waianapanapa State Park. STR 216/0003 TA186-656-9728-01

Adorable 1930's Gingerbread House....Permitted!

9.8 out of 10, Exceptional, (11)
"My wife and I stayed in the Gingerbread House for a week in June. Eve welcomed us and helped us get oriented with the area, even suggesting places to visit and restaurants to check out. She was very quick to respond to questions. The location of the Gingerbread House itself is generally located in the middle of Maui away from the resorts, where we were able to enjoy a more authentic Hawaiian experience. The grounds are beautiful, and the house had everything we needed for a lovely stay. Very...
The price is SAR 1,250
SAR 2,518 total
includes taxes & fees
3 Jan - 4 January 2025
Adorable 1930's Gingerbread House....Permitted!

Bamboo Bliss: Ocean Views & Waterfalls Await!

Bamboo Bliss: Ocean Views & Waterfalls Await!

Cozy cottage nestled on our 5 acre Organic fruit farm

10.0 out of 10, Exceptional, (2)
"Absolutely great stay here! We stayed one night to break up our “Road to Hana” trip but we could have easily stay a couple more nights. Don’t hesitate to book here. Ola and Monyca are great hosts and the cottage is really nicely done. This cottage is 5 minutes from town and just a couple minutes from Hana Farms where they have outdoor seating with some really good wood fired pizza. When we come back to Hana, we will 100% be back here."
Cozy cottage nestled on our 5 acre Organic fruit farm

Honeymoon Bliss: Bamboo Temple with Ocean Views at Maui Eco Retreat

Honeymoon Bliss: Bamboo Temple with Ocean Views at Maui Eco Retreat

Cozy Cottage in Beautiful Wailea

Cozy Cottage in Beautiful Wailea

Quiet 1-bd cottage retreat with sleeping loft & work space

Quiet 1-bd cottage retreat with sleeping loft & work space
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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Other property types in Kaupo

Wailea Ekolu - CoralTree Residence Collection

3.5 star property
8.8 out of 10, Excellent, (246)
"We loved this property! It was more then what we were expected, so comfortable and quiet and super clean and very spacious, we will stay here again."
Wailea Ekolu - CoralTree Residence Collection

STHA-2017/0002 Across from Hana Bay

9.6 out of 10, Exceptional, (337)
"This is an older place that has been kept in excellent condition. Very nice, clean, and comfortable. Everything in the place is neat and clean. The instructions from the owner, impeccable. Anything and everything you could possibly need to know is described. Good location to food and beach. "
STHA-2017/0002 Across from Hana Bay

Fisher's Hana Bay Hale, Across from Hana Bay

9.6 out of 10, Exceptional, (342)
"Great place. Wish we had coffee too"
The price is SAR 732
SAR 1,494 total
includes taxes & fees
2 Jan - 3 January 2025
Fisher's Hana Bay Hale, Across from Hana Bay
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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