Provided are a continuous contents reproduction service providing server, a user device, and a method of providing a continuous contents reproduction service for continuously providing contents to a plurality of devices. The server may include: a device management unit to store identification information of a first device and a second device; a service interruption monitoring unit to determine whether reproducing of contents in the first device is interrupted; a continuous reproduction information message transceiving unit to generate a continuous reproduction information message when the reproducing of the contents is interrupted, and to transmit the generated continuous reproduction information message to the second device; a continuous reproduction management unit to receive a request for a continuous reproduction service and to determine whether to continuously provide the contents to the second device; and a contents providing unit to provide the contents to the second device based on the determination.