Put on rubber gloves.
Mix three parts water with one part bleach in a large bucket.
Remove any mildew, using a scrub brush and the diluted bleach solution.
Wash the surface with dish soap, water and a rag. The soapy water will get rid of any grime and remove bleach residue. Let the surface dry before sanding.
Sand the vinyl surface with 220-grit sandpaper if the surface is slick and glossy. The biggest problem with painting exterior vinyl is its glossy finish, according to "Complete Painting," by Larry Johnston. Glossy coatings and exterior sealants make it harder for new paint to adhere. If the surface is already matte, you don't need to sand.
Rinse the surface with a garden hose, getting rid of any remaining soapy residue and sanding dust.
Dry the vinyl surface with a towel, or let it air dry.
Protect nearby items with painter's tape or plastic sheets.
Prime the vinyl with general-purpose exterior primer. For large items, use an airless sprayer. Prime smaller pieces with a synthetic-bristle paintbrush. Wait for the primer to dry, according to the drying times specified on the primer's container.
Paint the vinyl with exterior latex acrylic paint. Use an airless spray gun for large surfaces and a synthetic-bristle paintbrush for smaller exterior vinyl surfaces.
Apply a second coat of paint, if necessary, after the first coat dries.
Remove the protective painter's tape and plastic sheets after 24 hours.