In one Spider-Man story, Mysterio's ultimate goal when he takes over the Maggia is to grab as much money as he can, and "buy an island in the tropics where I can sit under palm trees and drink things out of coconuts".
The Batman storyline Heart of Hush ends on this note. Catwoman is relaxing at a resort while recovering from getting her heart ripped out, recording a message for Hush explaining how she got her revenge.
Johnny English has a scene like this, with a twist: earlier in the film, the title character bungles up preventing a robbery, and invents a highly improbable "villain" to cover up his ineptness. The "villain" is shown to be a real person at the end in this scene, but that's pure coincidence - English was purposely trying to make up a person who didn't exist (perhaps to prove how good he was by fighting with him when no one else would be able to find him).
The Silence of the Lambs ends with Hannibal Lecter phoning Clarice from Bimini, where he's having an old friend for dinner.
The Producers plan on having one of these in Rio de Janeiro once their scheme comes to fruition, but it doesn't work out as planned.
xXx ends by Vin Diesel finally travelling to Bora Bora.
In Things to Do in Denver When You're Dead, the criminal group that main characters run in will often say, "Boat drinks," to remind each other of their ultimate dream: retiring to some tropical paradise to sip cocktails on a yacht. In the end, we see all of the main characters doing exactly that, except they're all dead.
Referenced in Out of Sight. Karen (Jennifer Lopez) mockingly asks bank robber Jack (George Clooney) if he imagines he'll retire to some tropical paradise. He counters that he always preferred mountains.
Kathleen Turner's character in Body Heat ends this way, whatever her name may be.
Amusingly subverted with Alec Guinness' character in The Lavender Hill Mob: Holland is relating the story to a fellow Englishman in the comfort of sunny Rio, but the man is revealed to be the police officer extraditing him back to England a year after the events.
At the end of the Boris and Natasha movie, the title characters get warped back in time to the beginning of the movie. They then decide that they really don't want to go through all the grief they experienced throughout the film again, so they decide to quit their jobs and retire to Tahiti.
Subverted in Repo Men, while it does end in a tropical setting, we find out that the entire last half of the movie is really a dream-sequence in the protagonist's mind, so long as his buddy can keep up the payments.
The bank robber in Inside Man brags about this plan (though it's probably misdirection), though the cop he's talking to begs to differ:
Dalton Russell: This time next week I'm going be sucking down pina coladas in a hot tub with a couple of girls named Amber and Tiffani.
Keith Frazier: Next week you're going to be showering with a couple of guys named Jamal and Jesus. And that thing you're sucking on? Not a pina colada.
The bad ending to the first Wayne's World movie has the villain and Wayne's love interest end up in one together (she's wearing a tiny bikini and tells him how great he was in bed last night as she hands him a drink). Then he turns to the camera and mocks the audience for expecting her to end up with a loser like Wayne. Good thing it's not the real ending.
Played with in Matthew Reilly's Ice Station. The fate of a minor character from the backstory is revealed when the epilogue zips to a South American beach, where a scavenger finds debris in the ocean from the character's crashed plane.
In Matilda, Mr. and Mrs. Wormwood move to Guam after Mr. Wormwood's car dealership is under investigation for fraud, and their daughter is legally adopted by Ms. Honey.
At the end of ''Captain Vorpatril's Alliance, after what initially seems to be a case of Reassigned to Antarctica, Ivan manages to alter it to this instead by realising that there's absolutely no reason why their planetary embassy needs to be in the rainswept capital rather than somewhere near the equator.
As perhaps evidenced by the theme song, Red Dwarf's Lister dreams of getting back to Earth and setting up a burger bar on Fiji with his cat. Technically speaking, this is the Series Goal of the whole programme - if only because the main characters are so hopelessly screwed that no-one can come up with a better plan.
In Due South this is a Discussed Trope. The villain, in a standoff with Fraser, brags that he'll soon be in Tahiti living off his spoils.
Jimmy Buffett's song "Banana Republic" is about precisely this sort of person — "expatriated Americans, hoping to find some fun."
Jimmy Buffett in general likes to present himself as such - the fact that he's extremely wealthy means it is some degree of Truth in Television for him.
Subverted in the Zac Brown Band song "Toes", where everything is great for the tourist... until he runs out of money.
The "Quest for Fruit" adventure in GURPSDiscworld Also states that, in accordance with the Theory of Narrative Causality, the Hwondaland trading post must contain at least one white-suited Ankh-Morporkian expat, who can never return for some unspecified reason.
Banjo-Kazooie features an ending sequence with our heroes relaxing on a tropical island somewhere.
If the player amasses a tidy sum as an independent commander in Mech Warrior 2: Mercenaries, they will get this as an ending after the Battle of Tukayyid cutscene.
Suggested by Dr Neo Cortex at the bad ending of Crash Bandicoot 3: Warped as an idea or what to do now that he's been beaten yet again, shortly before his boss, UkaUka reminds him they could still triumph by getting all the gems.
More of a Tropical Prologue, unless you count it for the previous game, but the PC title 7.62: High Calibre begins with your mercenary crew lounging on a beach before getting the call to action.
Rock Band 3 plays this straight after you complete the tour modus. Your band presumably dies in a plane crash while they really just faked their deaths to escape stardom and enjoy their wealth in some tropical paradise.
Bad Mojo ends with the protagonist and his long lost father using a bunch of stolen money to retire to the Carribean.
Discussed between Commander Shepard and Garrus in Mass Effect 3, and Zaeed will ultimately be shown enjoying his retirement as such assuming he survived the events of the game.
Depicting the entire crew in this setting seems to be a pervasive theme for dozens of pieces of fan art in an effort to fix the controversial ending.
In Max Payne 3, the last scene is one of Max, having both successfully kicked his alcoholism and brought down Victor Branco's conspiracy, drinking a soda and watching a Coincidental Broadcast about Victor's death at a beach in Bahia, at peace with himself for the first time in a long time.
If memory serves, once it was Palm Springs, the second time Pismo Beach. Some sort of clam festival was involved at one point.
An episode of Batman: The Animated Series titled "The Worry Men" features the Mad Hatter admitting that he's been thinking of retiring from crime, purchasing an island out in the middle of nowhere, and opening up a sun-bonnet shop.