Self‐assembly and supramolecular inclusion complexations between telechelic polymers bearing one or double adamantane groups and linear poly(β‐cyclodextrin) (P(β‐CD)) were investigated in water. An adamantane (Ada) attached to poly (acrylic acid) (PAA) was prepared by reversible addition‐fragmentation chain transfer polymerization using s‐1‐dodecyl‐s″ ‐(α,α′‐dimethyl‐α″‐acetic acid) trithio‐carbonate functionalized Ada with tert‐butyl acrylate, followed by functional modification. Additionally, two Ada groups capped triblock copolymer F127 were obtained via an esterification reaction. The dynamic light scattering, transmission electron microscope and 1H 2D NOSEY NMR spectroscopy were conducted to characterize the self‐assembly behaviors. With the inclusion complexation of Ada/CD in 1:1 M ratio in water, the spherical micelles were enlarged at 25°C than that of the adamantyl polymer precursors. Due to the PPO segment of Ada‐F127‐Ada, the micelles aggregation showed temperature dependence from 4 to 37°C for precursor and corresponding inclusion complexation; while in Ada‐PAA/P(β‐CD) system, the hydrodynamic diameters decreased with pH decreasing.