Let's see, I think that would be Fiveman, GoGoFive, Magiranger, and Ninninger as an extended family (2 siblings and 3 cousins). Some older, some newer. I guess there haven't been many examples of more than one family member being a Rider. The only cases of two siblings being main Riders at the same time were Zangetsu and Ryugen in Gaim and the Shindai siblings in Saber. There are a few cases of family members becoming Riders temporarily or at different times. Kiva's father was briefly Ixa before Kiva was born, and two of Ixa's other wielders were a mother and daughter, a generation apart. Specter's father and sister became Zero Specter and Kanon Specter in movies/specials after the end of Ghost proper. And Build's father was a prototype Build. A couple of near-misses: Black's villain Shadow Moon, who was sort of a pseudo-Rider, was Black's stepbrother. And Zeronos is the younger version of the man who nearly became Den-O's brother-in-law.