We investigate the possibility of realizing a loophole-free violation of Bell's inequality using deterministic single-photon sources. We provide a detailed analysis of a scheme to achieve such violations over long distances with immediate extensions to device-independent quantum key distribution. We investigate the effect of key experimental imperfections that are unavoidable in real-world single-photon sources including the finite degree of photon indistinguishability, single-photon purity, and the overall source efficiency. We benchmark the performance requirements to state-of-the-art deterministic single-photon sources based on quantum dots in photonic nanostructures and find that experimental realizations appear to be within reach. We also evaluate the requirements for a postselected version of the protocol, which relaxes the demanding requirements with respect to the source efficiency.