The purpose of this paper is to demonstrate the impact of lease duration and lease break options on the optimal holding period for a real estate asset or portfolio. Methodology/approach We use a Monte Carlo simulation framework to simulate a real estate asset's cash flows in which lease structures (rent, indexation pattern, overall lease duration and break options) are explicitly taken into account. We assume that a tenant exercises his/her option to break a lease if the rent paid is higher than the market rental value of similar properties. We also model vacancy duration stochastically. Finally, capital values and market rental values, assumed to be correlated, are simulated using specific stochastic processes. We derive the optimal holding period for the asset as the value that maximises its discounted value. Findings We demonstrate that, consistent with existing capital markets literature and real estate business practice, break options in leases can dramatically alter optimal holding periods for real estate assets and, by extension, portfolios. We show that, everything else being equal, shorter lease durations, higher market rental value volatility, increasing negative rental reversion, higher vacancy duration, more break options, all tend to decrease the optimal holding period of a real estate asset. The converse is also true. Practical implications