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Google Maps has a URL call that can create a polygon and create an image with this information. I am trying to find something similar for Bing. I read their static image documentation and it just talks about pushpins.

See Google Maps example: enter image description here

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Yes on bing maps you can add shapes like polygons to the map. It also seems you have been looking at the wrong Bing page.

www.bing.com/maps/shapes

This link tells you how to add polygons. On Bing the only way to do it is to edit some code but that page fully explains it!!!

Example: [in XAML] use this to make a triangle.

<Window x:Class="WPFTestApplication.MainWindow"
xmlns="http://schemas.microsoft.com/winfx/2006/xaml/presentation" 
xmlns:x="http://schemas.microsoft.com/winfx/2006/xaml"
xmlns:m="clr-namespace:Microsoft.Maps.MapControl.WPF;assembly=Microsoft.Maps.MapControl.WPF"
Width="1024" Height="768">
<Grid x:Name="LayoutRoot" Background="White">
    <m:Map CredentialsProvider="<strong>InsertYourBingMapsKey</strong>" Center="47.640,-122.125" ZoomLevel="11">
        <m:MapPolygon Fill="Blue" Stroke="Green" StrokeThickness="5" 
                      Locations="47.6424,-122.3219 47.8424,-122.1747 47.5814,-122.1747"
                      Opacity="0.7"/>
    </m:Map>
</Grid>

the locations line of code above is the only code you need to edit. Change the longitude and latitude to the position you want and it will add it with this code.

You can also make a custom polygon one but it requires you to do more and you'll find that code if you read the article above.

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