Country Weekly's Jon Freeman thought that "Lindy" and "Happy on the Hey Now" were "poignant sketches of people he's encountered over the years", and that some of the songs showed "the motivations behind his relentless career building".

He criticized "Marley" and "It's That Time of Day" for "meander[ing] aimlessly", and thought that "Pirate Flag" did not fit thematically with the album.

"[11] Freeman of Country Weekly called the album "a mixed bag" that the "most exciting moments come when Kenny pushes his limits on something unusual", and found that Chesney "sounds genuinely exhausted, making his need for respite in the islands all the more understandable.

"[16] David Burger of The Salt Lake Tribune called the release "breezy", which he stated that "while the collection doesn’t break any new ground, and isn’t well-suited to blasting on a car stereo, it shows off Chesney’s always-comforting voice and song-writing talents that too rarely emerge.

"[22] At Calgary Herald, Mike Bell affirmed that "it's hard to imagine a more predictable collection of songs than the superstar’s 10-track cabana Life On A Rock.

[24] On February 13, 2017, the album was certified gold by the Recording Industry Association of America (RIAA) for sales of over 500,000 copies in the United States.