Some context: the orbit you are describing is called a Krylov Subspace.
For the case where $ V = \mathbb{R}^n$:
Consider a diagonalizable $A$: since the eigenvectors of $A$ span $\mathbb{R}^n$, we can write
$$ v = \sum_i^n c_i \mathbf{u}_i, \; \mathbf{u}_i \text{ eigenvector of $A$} $$
Then, for every power of $A$, we have
$$ A^k v = A^k \left( \sum_i c_i \mathbf{u}_i \right) = \sum_i c_i A^k \mathbf{u}_i = \sum_i c_i (\lambda_i)^k \mathbf{u}_i $$
Based on the above observation, we may write $\left\{ v, Av, \dots, A^{n-1} v \right\}$ in compact form as
$$ \{ v, Av, \dots, A^{n-1}v\} = \underbrace{\begin{pmatrix} c_1 \mathbf{u}_1 & \dots & c_n \mathbf{u}_n \end{pmatrix}}_{\displaystyle=: U_c, \in \mathbb{R}^{n \times n}} \underbrace{\begin{pmatrix} 1 & \lambda_1 & \dots & \lambda_1^{n-1} \\ 1 & \dots & \dots & \dots \\ 1 & \lambda_n & \dots & \lambda_n^{n-1} \end{pmatrix}}_{\Lambda} $$
In order for the above to be a basis of $V$, we want its determinant to be nonzero, which means that we want $$ \det(\Lambda) \neq 0 \Rightarrow \prod_{i \neq j} (\lambda_i - \lambda_j) \neq 0 \Leftrightarrow \lambda_i \neq \lambda_j, i \neq j, \; \\ \det(U_c) \neq 0 \Rightarrow c_i \neq 0, \; \forall i $$ where the first equality follows from the fact that $\Lambda$ is a Vandermonde Matrix. If $v$ is representable as a linear combination of $d < n$ eigenvectors, one of the $c_i$'s above will be $0$, making $\det(U_c) = 0$. On the other hand, if all the eigenvectors are necessary to represent $v$, the resulting subspace spans $V = \mathbb{R}^n$.