Yes, in most cases you can anchor urban outdoor furniture to a deck without drilling holes—but it depends on the furniture, the deck surface, and how much wind or public use it will face. For lighter pieces, the safest no-drill approach is usually a combination of weight and friction: weighted bases, sand- or water-filled ballast boxes, non-marking rubber pads, and anti-slip feet. For benches, tables, and planters, choose hollow bases you can fill with sand or gravel, or use low-profile steel plates hidden underneath.
For railings and posts, clamp-on brackets and ratchet straps can secure furniture temporarily without damaging the deck. Modular furniture with interlocking feet or linking clips also works well in cafes and rooftop spaces where layouts change. I would not rely on suction cups or removable adhesive alone for anything tall, such as umbrellas or heaters; those need a properly weighted base and, in exposed locations, a manufacturer-approved tie-down.
Before you commit, check lease or HOA rules, deck load limits, and the furniture’s wind rating. Avoid trapping moisture under weights, use pads to protect the surface, and inspect straps and clamps regularly. In high-wind or public-safety settings, ask a professional to confirm the setup. So yes—no-drill anchoring is often possible, but it should be planned around weight, wind uplift, and surface protection rather than just convenience.