We report the discovery of five transiting companions near the hydrogen-burning mass limit in close orbits around main sequence stars originally identified by the Transiting Exoplanet Survey Satellite (TESS) as TESS objects of interest (TOIs): TOI-148, TOI-587, TOI-681, TOI-746, and TOI-1213. Using TESS and ground-based photometry as well as radial velocities from the CORALIE, CHIRON, TRES, and FEROS spectrographs, we found the companions have orbital periods between 4.8 and 27.2 days, masses between 77 and 98 MJup, and radii between 0.81 and 1.66 RJup. These targets have masses near the uncertain lower limit of hydrogen core fusion (~73-96 MJup), which separates brown dwarfs and low-mass stars. We constrained young ages for TOI-587 (0.2 ± ...