The chain has expanded into Dominican Republic, Panama, St. Thomas, St. Croix, St. Maarten, St. Kitts, St. Lucia, Antigua, Aruba, Trinidad and Tobago, Guyana, Curaçao, Guadeloupe, Guatemala and Bolivia.

[7] In February 2009, Caribbean Cinemas debuted its first digital 3D theater with Jonas Brothers: The 3D Concert Experience at Plaza las Américas.

[11] In February 2016, Caribbean Cinemas announced the arrival of the first IMAX and 4DX theaters to the Montehiedra location, which meant it had to undergo a complete renovation.

Another renovation to the Montehiedra location is the first 4DX theater hall in Puerto Rico with synchronized motion seats, and special effects such as strobe lightning, mists, wind and bubbles.

[15] In May 2023, Caribbean Cinemas announced the opening of a theater hall with enhanced technology similar to 4DX, called 4D E-Motion, in Las Piedras following a renovation.

[20] In June 2022, Caribbean Cinemas opened Cine Kids, a special theater hall designed for children ages 2 to 10 with a play area and a slide, at the Las Catalinas location in Caguas, Puerto Rico as part of a renovation.