Clean the vinyl siding thoroughly to remove dirt, dust and debris. There are several different ways to do this. If the siding isn’t too dirty, combine three parts warm water and one part liquid bleach in a 5-gallon bucket. Add 1 teaspoon of dishwashing liquid. Don a pair of rubber gloves to protect your hands. Dip a sponge, rag or stiff-bristled brush into the water-and-bleach mixture, and scrub the vinyl siding clean. You can also use vinyl siding wash concentrate attached to your garden hose and spray the area clean. Use a power washer as a last resort -- be careful because a power washer can inject water behind the siding and cause leaking.
Rinse the vinyl siding with a water hose to remove the soap and loosened dirt.
Allow the vinyl siding to dry at least four days before painting. The vinyl siding has to be completely dry or the paint won’t adhere to the surface.
Inspect the surface for nail holes and dents. Fill any holes and dents with exterior-grade spackling. For cracks, use a paintable acrylic caulk for vinyl siding. Use your finger to smooth the caulk, being careful to not cut yourself. Don't caulk under the laps of the siding -- the siding needs to be able to expand and contract.
Tape off any areas with blue painters tape to protect areas you don’t want painted. Put a tarp over plants, deck or sidewalks to catch paint drops.
Stir the paint with a drill with a paint stirring attachment for 7 minutes or until well mixed. Beginning at the top corner of the wall, apply a thin coat of paint, brushing in the direction of the grain of the siding. Do not use a glob of paint to cover the surface, because it will not dry well. Use long, even strokes. One coat may not cover the siding completely. Wait at least 24 hours before applying another coat. Allow the final coat of paint to dry for 3 days.
Inspect the vinyl siding for any places you may not have covered completely with paint. With a small brush, touch up those areas with paint.