Upon its release as the fifth and final single from True Blue on February 25, 1987, "La Isla Bonita" received generally positive reviews from music critics, who praised its Latin-inspired sound.

In the accompanying music video, directed by Mary Lambert, Madonna portrays two opposite characters: A young Catholic woman and a flamenco dancer.

The clip received mixed reviews from authors and contemporary critics; some saw the use of Hispanic imagery as a successful marketing strategy, while others accused the singer of cultural appropriation.

[6] She came up with the title "La Isla Bonita", which roughly translates to "The Beautiful Island", and wrote the lyrics while in Hong Kong filming Shanghai Surprise (1986).

[24] Lyrically, "La Isla Bonita" talks about a "humble observer, captured by the rhythm of an imagined island" named San Pedro, with mentions of "tropical breeze" and "nature wild and free".

[32] Similarly, Daniel Garrán from Spanish radio station Los 40 argued that the lyrics are a "tribute to the Latin community from New York [Madonna] has always been close to", and do not talk about a real place.

[43] William McKeen, author of Rock and Roll is Here to Stay, deemed the song "tranquil", and compared its lyrical theme of an "imaginary escape from the big city" to that of the Drifters' "Up on the Roof" (1962).

[46] Daryl Easlea, author of Madonna: Blond Ambition, wrote that "La Isla Bonita" and the other singles are "so strong that they overshadow the reminder of [True Blue]".

[b] Of the production, Paul Schrodt from Slant Magazine said it "gave a dynanism to [Madonna's] music that finally perished the thoughts, based on her earliest hits, that she was simply a Danceteria pop tart".

[52] By his part, David Browne from Entertainment Weekly added that Leonard and Bray's input turned the song into a "perfectly conceived pop record".

[46] Influence has been perceived in later Latin-tinged songs, such as "Viva Forever" (1998) by Spice Girls, Geri Halliwell's "Mi Chico Latino" (1999), Lady Gaga's "Alejandro" (2010), and "Despacito" (2016) by Luis Fonsi and Daddy Yankee.

[60] Echoes of "La Isla Bonita", "pop up more than once" on J.Lo (2001), the second studio album by American singer Jennifer Lopez, as noted by Natalie Nichols from the Los Angeles Times.

[62] On March 21, 1987, "La Isla Bonita" debuted at number 49 on the Billboard Hot 100, becoming Madonna's eleventh consecutive single to be named the week's top new entry –a streak that began with "Lucky Star" in 1984.

[83] "La Isla Bonita" was Madonna's first number one song in France, where it spent three weeks at the top spot in July 1987, and was certified gold by the Syndicat National de l'Édition Phonographique (SNEP) for shipment of 500,000 copies.

[9] In one scene, she is in a New York City apartment dressed in white, lighting candles at a living room altar, reminiscing about the song's titular island.

He went on to compare it negatively to the previous True Blue videos, further noticing a "pervading sense of humor [that is] not supposed to be there", specifically in the scene when Madonna dances out in the street.

[114] "La Isla Bonita" has been included on eight of Madonna's concert tours: Who's That Girl (1987), the Girlie Show (1993), Drowned World (2001), Confessions (2006), Sticky & Sweet (2008–2009), Rebel Heart (2015–2016), Madame X (2019–2020), and Celebration (2023–2024).

[125] Decked out in black slacks and backless dress, and surrounded by a "gaggle of percussionists and dancers", she played acoustic guitar in an "unplugged flamenco" version of the song.

[126] Reviewing one of the London concerts, NME's Alex Needham pointed out that, "by the time 'La Isla Bonita' rolls around, the relief in the audience is palpable and Madonna also finally seems relaxed".

[129] She wore a white leotard while the backdrop screen showed colored images of a tropical island that mirrored the "voluptuousness of [her] dancing", according to Slant Magazine's Ed Gonzalez.

[133] On July 7, 2007, Madonna and gypsy punk band Gogol Bordello performed a "crazed hoedown" version of "La Isla Bonita" at the London Live Earth concert.

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

[152] On October 9, 2021, Madonna gave an "intimate performance" in the basement of Marcus Samuelsson's Harlem restaurant Red Rooster, and sang lounge renditions of "La Isla Bonita", Madame X album tracks "Dark Ballet" and "Crazy" (2019), and Cape Verdean coladeira song "Sodade".

[159][160] Music & Media magazine gave a positive review of the rendition: "Although the vocals are sometimes too hasty and the sophistication that Madonna puts into this stack is lost, the track is so commercial, one can hardly spoil it".

[164] American rapper Black Rob's song "Spanish Fly", included on his album Life Story (2000), features Jennifer Lopez singing a chorus based on "La Isla Bonita".

[165] In 2004, American actor David Hasselhoff included a rendition of "La Isla Bonita" on his album Sings America, which was criticized for being "decidedly karaoke" by the BBC's Jake Jakeman.

[170][171] On his review of a concert Alizée offered in Mexico City, Arturo Cruz Bárcenas from La Jornada was not impressed with the cover: "[She] dreams of being like Madonna [...] but [her rendition of 'La Isla Bonita'] only shows how far she is from that goal".

[172] In May 2010, American blogger Perez Hilton released "Gagalupe", a parody of "La Isla Bonita" with lyrics that mock Madonna's "New Age beliefs".

[174] Aired on February 7, 2012, the twelfth episode of the third season of American television series Glee, "The Spanish Teacher", had guest star Ricky Martin singing the song with actress Naya Rivera, who played the character Santana Lopez.

[179] "Mamacita", a 2020 song by American group Black Eyed Peas and Puerto Rican singer Ozuna, samples "La Isla Bonita".