Little is known about the location and consistency of sleeping arrangements among youth experiencing homelessness (YEH) and how this is linked to their well-being. This study addresses this gap using ecological momentary assessment (EMA) via short message service (SMS) surveying with 150 YEH over 30 days, to examine how various sleeping arrangements are associated with depression, marijuana use, support received, and service utilization. Results revealed that the average number of consecutive days youth stayed at any particular location varied considerably. Youth who stayed more frequently with a friend/partner or in a transitional living facility (TLF) reported fewer days of being depressed, whereas staying with a friend/partner was associated with using marijuana more frequently. Finally, youth staying with a friend/partner, stranger, or TLF reported using services on fewer days. Because sleeping arrangements change almost daily, on average, this has important public health implications for agencies finding permanent housing for YEH.