Prior to the 1950s, the term "Kendall" was used to describe a region centered around U.S.-1, bounded by Snapper Creek to the north, the Everglades to the west, Old Cutler Road to the east, and the former community of Rockdale to the south. This area was largely uninhabited, generally consisting of pine rockland interspersed with fields and groves.
As the region experienced rapid development in the 1950s, the moniker "Kendall" came to refer to the various communities built in the vicinity of present-day Pinecrest and the eastern half of the current Kendall CDP. When growth shifted west in the 1970s, 80s, and 90s, the usage of the term steadily shifted west concurrently, and today it is most often applied to the area more formally known as West Kendall.
Prior to incorporation in 1996, the Village of Pinecrest was still included in the official boundaries of Kendall CDP.
According to the United States Census Bureau, the Kendall region has an approximate total area of 16.3 sq mi (42.3 km2); 16.1 sq mi (41.8 km2) of it is land and 0.23 sq mi (0.6 km2) of it (1.35%) is water.