Vinyl siding isn't designed for painting -- and painting yours may void its warranty -- but sometimes painting is your only recourse for a refresh. Years of exposure to sun damages vinyl, fading the original color and transforming the sheen from glossy to washed-out. Use acrylic latex paint, which remains flexible enough after it cures to move with the vinyl. It's essential to stick with light colors, because dark ones absorb enough light and heat to actually cause vinyl siding to buckle. This is why you rarely see dark-colored vinyl siding. A good cleaning should precede your paint job.
Set up scaffolding or get a ladder high enough to allow you to work comfortably without overreaching.
Wash the siding, using a mixture of 30 percent vinegar and 70 percent water -- or, if you need stronger cleaning, a mixture of 1/3 cup laundry detergent, 2/3 cup powdered household cleaner and 1 quart liquid bleach per gallon of water. Wearing rubber gloves, brush or sponge the cleaner on the siding and wash it off with a garden hose.
Cover the windows and doors, as well as all the trim around them, using masking tape and plastic sheeting. Cover the shrubs and anything else you don't want to paint with plastic.
Use acrylic latex paint or, for better adhesion, a paint with a mixture of urethane and acrylic resins. Paint early in the morning, in the evening or on a cloudy day. Avoid painting in full sun -- the paint is likely to shrink and crack.
Spray the paint with a hand-held airless spray gun. This tool gives you more control than a conventional airless sprayer, and you won't get brush marks as you would with a paintbrush. Move the gun parallel to the siding, ensuring you get paint in the space between the bottom of each slat and the top of the one below it. Apply a single coat to one side of the house at a time, either working from a scaffold or moving a ladder as needed.
Allow the paint to dry overnight, then apply a second coat, if needed. Let the last coat cure for a day or two before painting the door and window trim.