A wraparound inflatable headboard apparatus (100) includes a headboard portion (104), first and second arms (106, 108), and a plurality of accessories (138, 140,142, 144, 148), wherein the headboard portion (104) and the first and second arms (106, 108) are configured to accommodate plurality of accessories (138, 140,142, 144, 148), at least one of which is fixedly attached to the at least one of the headboard portion (104), the first arm (106), and the second arm (108), and at least one of which is removable from the at least one of the headboard portion (104), the first arm (106), and the second arm (108). An inflatable bed system (122) includes an inflatable headboard apparatus (100) comprised of a headboard (104), arms (106, 108), an inflatable mattress (102), and at least one accessory (138, 140,142, 144, 148), wherein the headboard (104) and arms (106, 108) are configured in a bracket shape, the inflatable mattress (102) comprises a shape complementary to the bracket shape of the headboard (104) and arms (106, 108) such that the inflatable headboard apparatus (100) at least partially surrounds the inflatable mattress (102), and the at least one accessory (138, 140,142, 144, 148) is supplied proximal to a user when the inflatable headboard apparatus (100) is arranged about the inflatable mattress (102).