The Castillo at Tulum, a Maya trading center on the Caribbean coast. Tulum was occupied around 1200 A.D. and was still inhabited when the Spanish arrived in 1518, but was abandoned by 1600.
The Castillo and Caracol at Chichen Itza. The Caracol was a "proto-observatory" with lines of sight to astronomical events. Chichen Itza was founded between 750-800 A.D. and dominated the Yucatan from about 850-1100 A.D.
Montejo's House on Merida's town square, 1540 A.D. The facade depicts the Spanish conquering the Maya, who are in "pain or terror." The Montejos conquered the western Yucatan in 1542, and founded Merida and Campeche.
The Governer's Palace in Uxmal is "the finest example of Puuc architecture" (9th-10th centuries). From there you can also see the top of the Magician's Pyramid (35 meters high, 6th-10th centuries) above the tree tops.
The Building of the Five Levels at Edzna. Edzna was inhabited in 400 B.C. and abandoned around 1500 A.D., and is famous for its canal system, used for irrigation, drainage, and defense.
The draw bridge in the Spanish fort of San Miguel (1771 A.D.) in Campeche, which overlooks the Gulf of Mexico.