Monthly Rentals in Kaupo

We had a wonderful time staying at Michael's and Terry's cottage. The setting was amazing, with a view of the ocean and having entire botanical gardens to ourselves. The cottage was in great condition and well-equipped. We really appreciated fresh eggs from their chickens and tomatoes from their garden that they left us. Having read that it was off the grid, I had concerns about electricity and hot water, but we had no issues with them. The internet worked very well too. There was an orange cat who was very friendly and stayed on the patio the entire time we were there. The only thing that was less than ideal was the mattress, which was too soft for me. Communicating with Terry and Michael and their guests who were house sitting for them was a pleasure! If you stay there, please follow their advise and get groceries ahead of time, since the place is really remote and almost all food stands nearby closed very early.

We stayed at Christine’s place for five nights and had an amazing time. The apartment was great to directly feel like home and it’s located in a quiet area with a great view. We had the chance to see the Alpacas Asher, Cal & Gabriel every day on our way to get to the car since they were “mowing” the grass in that area. We travelled around Maui from here and everything was accessible within a maximum drive of ~1h. Christine was always responsive and allowed us to feed the Alpacas (Apple or Banana) and invited us to see other animals on the farm. Overall, we highly recommend Christine’s place and would always stay at her house the next time we visit Maui.

A lovely location with an amazing host! This is a good starting point for lots of hot spots on Maui, and you can’t beat the view. Very comfortable and peaceful.

A Hidden Gem in Makawao – Truly Unforgettable I had an absolutely amazing time staying at Sydney’s cottage in Makawao. From the moment I arrived, the space felt warm and inviting—a true home away from home. The cottage is cozy, beautifully kept, and surrounded by serene, peaceful landscapes that instantly put you at ease. One of the highlights of my stay was the incredible connection to nature. The surrounding wildlife made it feel like I was truly one with the land, offering moments of quiet reflection and a deeper appreciation for the natural beauty of the area. Sydney is a phenomenal host. Her warmth and hospitality go above and beyond. She gave me a tour of the property and shared a thoughtful and informative history of both the land and local island culture. That experience made me feel less like a tourist and more like a welcomed guest in a very special place. This was an authentic, peaceful, and enriching escape. I can’t recommend this stay enough—thank you Sydney.