"Vacation" was written by Francis, Gary Weston, and Hank Hunter. Hank Hunter had written the previous Connie Francis single "Second Hand Love" and Francis would subsequently chart with the Hunter compositions "I'm Gonna Be Warm This Winter" (1962) and "Drownin' My Sorrows" (1963). "Vacation" became Francis' only hit on which she had writing credits. Francis has stated: "when ["Vacation"] was brought to me, they only had 'V-a-c-a-t-i-o-n in the summer sun.' That's all they wrote. I wrote the rest of the words and didn't even take credit for it." (In reality, Francis has always received songwriting credit on the track.)

The song was originally intended as a B-side but proved more radio friendly than the intended hit, "The Greatest Sin of All." Both sides of the single were recorded at Columbia Recording Studio in Nashville on June 18 1962, with Bill McElhiney of the Nashville Brass performing, arranging, and conducting duties.

"Vacation" entered the Billboard Hot 100 in July 1962 to peak at #9 the first week of September 1962: on the Top 100 Singles chart in Cashbox "Vacation" peaked at #10. "Vacation" debuted in the Top 40 UK singles chart at #40 in the first week of August 1962 and peaked at #10 in the first week of that September. The track became a hit in several territories in the autumn of 1962 reaching #3 in Australia, #2 in Hong Kong, and #5 in Israel. In Japan, where Francis' version was co-ranked with a cover by Michi Aoyama, "Vacation" reached #1 in December 1962.

Enough US radio stations played "The Biggest Sin of All," as well or instead of "Vacation," for "The Biggest Sin of All" to appear on the Cash Box top 100 for one week at #89. The track also appeared on the Bubbling Under Hot 100 Singles chart in Billboard with a #16 peak.

"Vacation" was recorded by Alisa Mizuki for the Mizuki-led film Nurse no Oshigoto: The Movie and released as a single on April 24, 2002, under the name of the main character, Izumi Asakura with Nurse no Oshigoto. Mizuki's "Vacation" is a Japanese-language cover of the 1962 Connie Francis hit of the same name. The Japanese lyrics were written by . The song is included on Mizuki's fourth compilation album History: Alisa Mizuki Complete Single Collection.

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