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There is some undocumented functionality in Graphics`Mesh that may help.

• SimplePolygonPartition will break apart a self-intersecting polygon into non-self-intersecting components (the components include the "holes" in the original)
• PolygonCombine will merge those components into a single polygon (note that while free of interior holes this polygon may still intersect itself)
• FindIntersections will find any self-intersections and can therefore be used to filter out such polygons

.

Graphics`Mesh`MeshInit[]; randompoly := Module[{poly}, While[Length[FindIntersections[ poly = PolygonCombine @ SimplePolygonPartition @ Polygon[RandomReal[{-1, 1}, {25, 2}]]]] > 0]; poly] Graphics[{EdgeForm[Red], Yellow, randompoly}]