Swimming Pool
From Homestar Runner Wiki
The Swimming Pool is where Homestar Runner characters are ocassionally seen swimming and lounging. It appears to be located somewhere in The Field, walking distance from the Contest Area. It also must be near an outlet, as a radio with a power cord supposedly connected to an outlet has been seen here. It first appeared in A Jumping Jack Contest, when Strong Bad was seen reclining in a pool chair while waiting for Homestar to fail at the jumping jack contest. It later appeared in the Theme Song Video, with a newly-added diving board that Homestar jumps off of.
In the book Where My Hat Is At?, a different pool belonging to Homestar was seen.