We present radiation transfer simulations of evolutionary sequences of massive protostars forming from massive dense cores in environments of high mass surface densities, based on the Turbulent Core model (McKee & Tan 2003). The protostellar evolution is calculated with a multi-zone numerical model, with accretion rate regulated by feedback from an evolving disk-wind outflow cavity. Disk evolution is calculated assuming a fixed ratio of disk to protostellar mass, while core envelope evolution assumes inside-out collapse of the core of fixed outer radius. In this framework, an evolutionary track is determined by three environmental initial conditions: core mass M c , mass surface density of the ambient clump Σ cl , and ratio of the core's initial rotational to gravitational energy β c . Evolutionary sequences with various M c , Σ cl , β c are constructed. We find that in a fiducial model with M c = 60 M ⊙ , Σ cl = 1 g cm −2 and β c = 0.02, the final mass of the protostar reaches at least ∼ 26 M ⊙ , making the final star formation efficiency 0.43. For each of the evolutionary tracks, radiation transfer simulations are performed at selected stages, with temperature profiles, spectral energy distributions (SEDs), and multi-wavelength images produced. At a given stage, envelope temperature is depends strongly on Σ cl , with higher temperatures in a higher Σ cl core, but only weakly on M c . The SED and MIR images depend sensitively on the evolving outflow cavity, which gradually widens as the protostar grows. The fluxes at 100 µm increase dramatically, and the far-IR peaks move to shorter wavelengths. The influence of Σ cl and β c (which determines disk size) are discussed. We find that, despite scatter caused by different M c , Σ cl , β c , and inclinations, sources at a given evolutionary stage appear in similar regions of color-color diagrams, especially when using colors with fluxes at 70 µm, where scatter due to inclination is minimized, implying that such diagrams can be useful diagnostic tools of evolutionary stages of massive protostars. We discuss how intensity profiles along or perpendicular to the outflow axis are affected by environmental conditions and source evolution, and can thus act as additional diagnostics of the massive star formation process.