You don't need any additional conditions beyond those already stated in the question. That is, for any isometry $V: A \rightarrow A\otimes B$ and any unit vector $|\psi\rangle_B$, there will always be a unitary $U$ satisfying the equation in the question (simultaneously for every choice of $\rho_A$).
One way to see this is to first pick any orthonormal basis $\{|1\rangle,\ldots,|n\rangle\}$ for $A$, and then consider the two sets $\{|1\rangle\otimes|\psi\rangle, \ldots, |n\rangle\otimes|\psi\rangle\}$ and $\{V|1\rangle,\ldots,V|n\rangle\}$. These are orthonormal sets (using the fact that $V$ is an isometry in the second case), so you can extend them both to be orthonormal bases of $A\otimes B$ and choose a unitary $U$ that maps the first completed basis to the second. Of course there are many ways to do this in general, but in particular you can choose $U$ so that it maps $|k\rangle\otimes|\psi\rangle$ to $V|k\rangle$ for each $k \in \{1,\ldots,n\}$. This implies that the equation in the question is satisfied.
Note that if what you really want is $S(A)_{\rho} = S(AB)_{V\rho V^{\dagger}}$, then it is simpler to conclude that this is always true from the observation that $\rho$ and $V \rho V^{\dagger}$ must agree on their nonzero eigenvalues.