Holiday Homes in Kaupo

"Auntie Kali's cottage is magical. Plain and simple. I knew it would be special just looking at the pictures, but even those can't capture just how wonderful it is. It is a private oasis; we found it hard to leave and explore Maui on any given day! Of course the pool is incredible, and we enjoyed using the grill and fire pit to make s'mores. The home is so incredibly comfortable, with quite literally anything you could possibly need to make your stay perfect. We arrived to an abundance of fruit (some grown right on the property!), homemade banana bread, and such wonderful hospitality from Carrie, the owner. It is located close to beaches, shopping, and restaurants, but when you're behind those doors, it is as if you are far, far away in your own special resort that is 100% yours! There is no doubt...this place is very special. "

"This property was indescribable! Our stay was amazing and the host was so very accommodating! Check-in was a breeze and every room was meticulously cleaned, arranged, and ready for our group. "

"Check-in was easy, home was fun to stay and prepare our meals. At first we were concerned upon arrival as the home doesn’t have air conditioning. The home cooled down after opening windows & doors. Two fans, plus a ceiling fan kept us comfortable at night. There is a general store nearby which was helpful. Sunrise was beautiful and we enjoyed the walk to the beach from this home. Recommend staying here and thank you to our host and owner."

"I have Been coming out here for yrs, and My family and my self for the past 3 yrs out for are family vacation and we love this place!!! The best ABB we have stayed at!! Amazing view every morning, very peaceful atmosphere and overall beautiful and amazing home, very clean and roomy place feels like home most definitely looking to book for next yr July 2026! "

"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 to come back and know exactly where we would stay!! "

"After each day of snorkeling we would come back to relax poolside, soak in hot tub, grill together, play games, watch the changing sky into the evening sunset and end with star gazing. It felt like our home away from home. Thank you Dianna & Troy. We look forward to a return visit hopefully soon. "

"It was an amazing boutique resort the property is beautiful and very relaxing a different vibe from the other Wailea resorts the staff is great and the amenities are nice including the shuttles to anywhere in the Wailea area. Definitely would come back and say if you get a chance to check it out loved our suite"

"The oldest hotel on Maui. Beautifully manicured grounds, very peaceful. Our room was quite sizable in one of the cottages. Quite pricey, but as it is remote and you get the 5* experience despite the fact that you can see the hotel isn’t the most modern. Overall wonderfull and very friendly staff!"

"Very clean, excellent directions and instructions, loved the lanai, fans helped keep one comfortable "