I'm writing this review from the perspective of a parent traveling with an almost-3-yr-old.
The good:
Tradewind Bungalow is on a very nice, quiet residential street. We chose it for its intersection of price/proximity to beach/proximity to shops and restaurants.
Leonard provided just about everything we could need which allowed us to pack very light! The beach chairs were super convenient, and my daughter loved the life jacket and sand toys.
Leonard lives on site and is available to answer any questions or help with anything required.
There is laundry access, which was soooo helpful!
Kailua Town Center is roughly a mile walk...not too far for Target and dinner runs. There are also a few decent food options closer if you want something faster/easier.
The not-as-good:
Because of the way the roads go, it is a half mile walk (which takes 20 minutes with a toddler walking) to the part of the beach with the bathrooms/showers. There is no shortcut. (Without kids and accessing the beach at the very first available point might be 8-10ish minutes. I think you'd have to jog to make it in 5.)
You have to walk through one of the bedrooms to reach the other bedroom and bathroom. We would have chosen the back bedroom for ourselves bc it has a tv/patio access/AC unit...That obviously doesn't work well when a kidlet needs to go to bed early! We wound up switching rooms, and it was fine...just not my first choice. :-D
There is no bathtub...only an issue if your almost-3-yr-old is terrified of showers!
Overall, it was a great trip! I wouldn't book this place again *until* my kid was a few years older and could keep up when walking to the beach (or was in a stroller/baby carrier for the commute.) If none of those drawbacks are an issue for you, hurry up and book this place already!