I stayed at Diamond Head for two night. Hosts Joanne and Sumiko were welcoming and helpful. I arrived there quite early in the morning; Joanne offered me breakfast and allowed me to check in much earlier than I had expected. Knowing I was coming in early, she had arranged the room to be cleaned the day before. Throughout my stay, both Joanne and Sumiko were extremely helpful and full of interesting and useful information about the island and things to do.
Yes, the B&B is a little worn. It's not a standard hotel. It's a private home that's been turned into a B&B. Joanne has lived here for a long time and it's reflected in the decor and furnishing. However, the room (the Princess Ruth) was huge, and the lanai large and private. The furnishing have seen better days, but personally I felt the size, privacy, and quiet made up for it. It's not a place to stay for travelers who want lots of amenities or need many special accommodations. It's about a 15 minute walk to Waikiki Beach, but there is a bus stop relatively close (I didn't try it). The birds will wake you up in the morning, which I enjoyed. Something to keep in mind is that the two rooms (not Grandpa's Apartment) are upstairs and travelers will need to carry their bags up the stairs, a consideration for travelers with heavy bags or bad backs. There isn't anyone to help you with that. A car would probably be helpful if you plan to see anything other than Waikiki beach or the downtown area.
During my stay, breakfast consisted of plenty of fresh fruit and bread, as well as something hot (one day eggs, one day stuffed peppers, one day fried plantains). It was all healthy and hearty. Joanne joins guests for breakfast and is full of suggestions of places to visit, based on travelers' preferences. Sumiko was kind and helpful to me.
Overall, this was one of the quirkier travel experiences I've had; however, once I got over my initial surprise and took the experience for what it was, I enjoyed it. I recommend it for travelers who are looking for a slightly offbeat experience and don't mind sacrificing a little privacy for a more personal view of Hawaii.
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.