The prevalence of deep endometriosis invading the bowel is unknown but has been estimated to affect between 3.8% and 37% of women with endometriosis. The most common locations of bowel endometriosis are the sigmoid colon and rectum. Endometriosis affecting the small bowel is exceedingly rare. Laparoendoscopic single-site port surgery (LESS) and robotic-assisted LESS (R-LESS) offer potential advantages in cosmesis and surgical recovery while safely and effectively treating disease. R-LESS is an effective and safe technique for surgical excision of deep endometriosis of the small bowel while utilizing the same access incision as a retrieval site for the surgical specimen. We present a case of a surgical excision of double nodules of deep endometriosis of the small bowel, that was managed using the R-LESS technique, and discuss the proposed advantages and technical challenges.