In recent years, short-term rentals through online booking platforms such as Airbnb, has experienced increasing popularity as alternative tourist accommodations. The growing maturity of online hosting platforms under the expansion of peer-to-peer network and the context of sharing economy allow this innovative accommodation model to flourish. It is noted a significant proportion of listings are operated in historic properties. Historic-related keywords often appear in the names and descriptions of short-term rental listings as ways to attract interested guests. Despite its popularity, short-term rental is frequently criticized for its adverse impacts on local housing market and neighborhood characters. In the past few years, many major cities in the U.S. have adopted ordinances to address issues caused by this innovative industry but the specific focus on historic preservation and its impact on historic properties is, however, limited. This thesis offers a preliminary analysis on this connection by synthesizing short-term rental and historic preservation, identifying opportunities and challenges for operating short-term rentals in historic properties through the assessment of existing regulatory frameworks, and developing recommendations narrowly tailored towards guiding this specialized use. Three case-study cities are chosen and analyzed in this thesis: San Francisco, Boston, and New Orleans. While recognizing the need for regulations, this thesis explores how short-term rental can be used an effective tool for encouraging public engagement in historic preservation and recommends cities to adopt strategic approaches based on assessments of market conditions and neighborhood needs and to coordinate short-term rental regulations with broader city efforts.