Recording for the song took place at New York City's Sigma Sound Studios; although Madonna and Benitez did not want the final version to differ too much from the demo, minor alterations were made in the composition, including the addition of a piano solo, which was done by their friend Fred Zarr.

[5] However, she soon realized that there was not enough material for a full length album ― the only songs available were "Everybody", "Burning Up", "Lucky Star", "Think of Me", "I Know It", and one called "Ain't No Big Deal".

[5] Another issue arose when the singer learned Bray had sold "Ain't No Big Deal" to disco act Barracuda, thus rendering it unavailable for her album.

[2] The writers were not given production credits, since it was Benitez who presented the track to Sire Records and Madonna; although they pressed for one, they ultimately let it go since they felt that the song would be their chance to get recognized as efficient songwriters.

[12][13] According to Rikki Rooksby, author of The Complete Guide to the Music of Madonna, the label wanted to release "Lucky Star" as a stand-alone single, but changed their mind after "Holiday" began receiving heavy radio play and reached the first spot of Billboard's Dance Club Songs chart.

[21] On a similar note, it was described as a "festive, infectious anthem [that] caught fire almost immediately [...] in dance clubs all across the country" by J. Randy Taraborrelli, author of Madonna: An Intimate Biography.

[22] Writing on Encyclopedia Madonnica, Matthew Rettenmund referred to "Holiday" as a "prime example of Madonna's reliance on infectious optimism", that has "aged remarkably well".

[7] Adam Sexton, author of Desperately Seeking Madonna: In Search of the Meaning of the World's Most Famous Woman (1992), named it a "loping disco ditty" with an "ineffable charm".

[24] "A song as utterly '80s as Rick Astley or the Pet Shop Boys, 'Holiday' is also surely the most evocative theme tune ever created when it comes to packing a suitcase and jetting off for beach cocktails [...] A feel-good pop giant with an infectious chorus - and the closest thing we have to bottled sunshine".

[26] AllMusic's Stephen Thomas Erlewine singled out "Holiday" as "effervescent", and as one of the "great songs" on his review of the Madonna album;[27] from the same portal, Stewart Mason highlighted its "undeniable electronic groove".

[33] The same opinion was shared by The Quietus' Matthew Lindsay, who also added that it "bubble[s] with joie de vie", and compared it favorably to Kool & the Gang's "Celebration" (1980).

[38] "Holiday" is considered a "serotonin-raising pop classic that will be filling dance floors at gay bars and family gatherings from now unto eternity" by Variety's Mike Was, and the "ultimate feel-good party anthem" by author Marc Andrews.

[20][39] Jude Rogers, from The Guardian, described it as a "blissfully simple" song that has "never lost its freshness or warmth"; she placed it at number 8 of her ranking of Madonna singles.

[46] Finally, The National Student's Emily D'Souza named it one of Madonna's most underrated songs, as it gets "overshadowed by its arguably overrated counterpart 'Like a Virgin'", and "should exceed the pop-prestige it has received".

[54] During a 2005 interview with CBS host Harry Smith, Madonna listed "Holiday" among her favorite top-ten hits, but was corrected and told that it had actually peaked at number 16.

[60] In Australia, "Holiday" entered the Kent Music Report's top 50 in April 1984, eventually peaking at number 4 and spending a total of 16 weeks on the chart.

[66][69][67] In 2012, Pure Energy revealed that the success of "Holiday" had helped them financially, having used the money from royalties to move out of the boarding house they were living in at the time.

On the Virgin Tour (1985), it was the second number: Madonna wore lace leggings and bra, a colorful jacket, crucifixes on her neck and ears, and was joined by two male dancers.

[78] On July 13, 1985, Madonna sang "Holiday" at the Philadelphia Live Aid benefit concert;[79] her outfit consisted of flowery trousers, a cutoff shirt, and long white jacket.

[81] Two years later, it was the final number of the Who's That Girl World Tour; decked out in a red flamenco dress, Madonna would stop the performance halfway through and ask the crowd to throw combs onto the stage, so she could fix her sweaty hair and finish the song.

[85][82] Madonna wore a Jean Paul Gaultier-designed Polka dot ensemble during the song's performance on 1990's Blond Ambition World Tour, which also sampled the Fatback Band's "(Are You Ready) Do the Bus Stop" (1975).

[88] Three different performances can be found in Blond Ambition Japan Tour 90, taped in Yokohama, Blond Ambition World Tour Live, taped in Nice, and in the documentary Madonna: Truth or Dare (1991);[89][90][91] the latter performance was released as music video to promote the documentary and received four nominations at the 1992 MTV Video Music Awards.

[96] "Holiday" was sung on the second promotional concert for Music (2000), which took place on December at London's Brixton Academy; Madonna wore a top imprinted with the names of son Rocco and daughter Lourdes for the performance.

[98] The singer wore a white fur coat, a rhinestone T-shirt with the words "Mother" in the front and "F*cker" in the back, and a burgundy velvet fedora.

[101] For the Re-Invention World Tour three years later, it was reworked as a "tribal drum dance"; the number saw the singer and dancers decked out in kilts, and walk on an elevated V-shaped ramp over the audience.

[110][111] The number also included a tribute to Michael Jackson, who had passed shortly before the tour began;[112] a medley of "Billie Jean" and "Wanna Be Startin' Something" (1983) played as dancer Kento Mori, dressed in Jackson's trademark black and white outfit, with a wide-brimmed hat and white gloves, began performing his most famous moves, including moonwalking across the stage.

[115][116][117] During the final show in Córdoba, Argentina, Madonna did an impromptu rendition of "Holiday" with a megaphone after a broken generator caused a 40-minute power outage.

[125] The performance at the March 19–20, 2016 shows in Sydney's Allphones Arena was recorded and released in Madonna's fifth live album, Rebel Heart Tour (2017).

[129] The performance sees Madonna and her troupe dancing underneath a big disco ball, on top of a circular stage set up to resemble New York's Danceteria and Paradise Garage.

[131][132] The ending showcases "how AIDS permeated joyous queer spaces around the globe in the '80s and '90s", as noted by PinkNews: The dancers slowly drop to the floor, Madonna disappears behind the disco ball as the song's "dying strings echo away like a flashback in a movie", giving way to "Live to Tell" (1986).