Kentucky is about 1,131 times bigger than Anguilla.

Anguilla is approximately 91 sq km, while Kentucky is approximately 102,896 sq km, making Kentucky 112,973% larger than Anguilla. Meanwhile, the population of Anguilla is ~18,741 people (4.3 million more people live in Kentucky).
Tip: This to-scale comparison of Anguilla vs. Kentucky uses the Mercator projection, which distorts the size of regions near the poles.