If you want to paint vinyl siding and cost is the main concern, here are the figures you need to keep in mind. The rough estimate of exterior painting can vary from $1 to $3 a square foot, depending on the labor, materials, and prep work required. The total cost of painting can range from $1,500 to $5,000, depending on the size of your home. Therefore, if you are planning to do such a venture, make sure you have the right budget available.