Search Kaupakulua Cottage Rentals

Plan, book, stay with confidence

Be picky

Search almost a million properties worldwide

Treat yourself

Change your mind

Book hotels with free cancellation

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Compare 42 Cottages in Kaupakulua with updated reviews, rates, and availability.

"It was a very centralized location albeit on a busy road. It was close to the airport and shopping and not too far from the beach. We enjoyed doing The Road to Hana, a Luau in Lahaina and Baldwin Beach. "

"Waking up with the birds singing with coffee on the deck in a quiet neighborhood…applause.Elaine is a wonderful host and very accommodating. We will recommend this property to all of our friends and family. We will likely stay here again on our next trip!Mahalo"

1 bedroom, iron/ironing board, travel crib, free WiFi

"Very clean and well maintained. Kitchen well equipped, linens and towels first rate. A pleasant find was the South Maui Gardens, just 4 blocks down the street, dont miss the food trucks.. Just another block to the beach, grocery store and more shopping. "

￥69,567 total

includes taxes & fees

Apr 27 - Apr 28

"Thank you for sharing your beautiful little paradise with us. The kids had a blast! We loved Haiku. The grocery store there had everything we needed. Colleens was a nice place to go for a big breakfast! Baby beach (near baldwin beach) was one of my favorite spots to visit. "

"We enjoyed our week at the cottage. It was so nice to have our own private space. It was quiet and comfy with all the amenities you could possibly need. The view of the water from the patio was awesome and it was an easy little trail to get to the beach for a walk on the sand. We got to see a turtle resting our first day! The cottage was clean and well stocked with linens, towels, beach necessities and all our kitchen needs. We had easy access to all of Kihei and Wailea, a lot of things...

"Amazing place and great host, highly recommended."

"This is exactly as listed, a spacious, tall ceiling town house with charming yard, a roofed porch, spacious kitchen, fast internet and well stocked. We very much appreciated to be in a local neighborhood rather than the tourist mile :-) Mahalo for sharing your house with us!"

"This was the perfect upcountry spot, with the most beautiful views of Maui - from the balcony, from the hot tub, from the bed! 10/10 will definitely stay here again"

"This was a great place to stay. We loved coming home to it. The owners were very nice. The little grey cat was so welcoming and we appreciated his company. Our only "complaint" would be the beds. They are a tad uncomfortable. But we all survived unscathed. Thanks Jon and Jody"

"Everything about the cottage is perfect, you won't even want to leave. The backyard is your private oasis and is perfect for kids. Everything was clean, well cared for, and a great host."

"We couldn’t recommend Jenni and Dave’s luxury Kehei cottage more! Such a beautiful slice of Maui. Lots of activities, restaurants, shopping, etc to do within a 10-15 minute walk. The cottage itself was extremely clean and very comfortable. We hope to be back!"

￥61,917 total

includes taxes & fees

Apr 18 - Apr 19

"The property was perfect for our family with an 8 and 10 year old. The kids slept on the lanai and were very comfortable. It really felt like you were out in nature. John was welcoming and the fresh bananas were great. We split our trip up with one week here and one week on the south shore and we’re very happy we did. "

"All what we wanted quiet, private, clean. Hank and Carol Ann provided fresh fruit and a juicer for the oranges too. A wonderful time here."

"Just a wonderful spot away from hustle and bustle. Cabin has a thoughtful and personalized style that makes home rentals so special. Sydney gave us an incredible tour of the property and the knowledge and care she displayed is very commendable. An incredible view off the deck let us watch the weather every morning and evening. We would come back for sure. "

"It had everything we needed. Close to the beaches, restaurants, shopping, and main roads. Comfortable beds, and a nice kitchen. Pamela is very helpful. We had very good time."

"We loved everything about our stay. The place was adorable with lots of little touches. The patio was amazing and we enjoyed sitting and reading. The location was perfect for everything. Seriously great place!"

"Second year we have stayed here. Very quiet on dead end street in Maui Meadows. Beautiful view. Really no issues at all. Will stay here again next year when we return to Maui!"