The Big Bad Jail Scaglietti and four of the Numbers are imprisoned in Orbital Prisons, but they live very comfortably there. Scaglietti even tells that Quattro got a little bit fat, though, the latter claims that she becomes back to normal.
The main antagonist in Zettai Karen Children first appeared in one of these. In his case, it is probably not so much about connections as about having ability to teleport stuff in and out as needed.
In One Piece, Impel Down, the World Government's super-max prison is not only a Hellhole Prison, but one of the worst in fiction. However, there exists a secret enclave in the fifth level called Newkama Land where an inmate lucky enough to find one of the passages to it can gain a reprieve and a small semblance of freedom that is unknown even to the guards. Prior to Luffy's infiltration, it is ruled by Emporio Ivankov, who has the ability to, among other things, gender bend people. With this ability, he offers newcomers to his "New Kama land" the opportunity to be whichever gender they choose. The place has several luxuries like the main room, which is a combination of a sit-down cafe and a discotheque, but Ivankov's guests have to follow a few strict rules that prohibit them from actively interacting with the rest of the prison (so as not to blow their cover), at least not without covert movement. (Otherwise, Ivankov is nonbiased as to who may enter.) As of the Time Skip, Ivankov and the bulk of the prisoners he had recruited have returned to his homeland, and Straw Hats ally Bentham, better known as former Baroque Works agent Mr. 2 Bon Kurei, has taken over.
In Jojos Bizarre Adventure, when Jotaro is arrested at the start of the Stardust Crusaders arc, so many things pop up constantly in his cell that it looks more like someone's bedroom than a prison. He later finds out that all of this is due to Star Platinum's powers, but since he didn't know what a Stand was back then, he just assumed it was some sort of demon doing his bidding.
In part V, the Passione operative Polpo lives in cell filled with luxury paintings and well stocked with food.
A minor character from Alan Moore's Watchmen, the Big Figure, is seen wearing a silk cravat with his prison blues, smoking a big Cuban cigar, and walking freely through the prison accompanied by two henchmen (though it is implied that he's coercing some of the guards for these privileges, as demonstrated when he asks Rorschach's guard about his wife and children and the guard becomes terrified).
A variant in Alan Moore's comic book Albion; psychotic British superhero Captain Hurricane is given a life of luxury in prison because, if he entered one of his "ragin' furies", he could tear the place apart. The warden describes him as "more of a permanent guest than a prisoner"; due to the drugs in his tea he isn't aware he's in prison at all. As you can imagine he's part of the mass breakout in the climax.
In the All-StarSuperman comic book series, Lex Luthor has an underground cavern hideout connected to his maximum-security jail cell, complete with an attractive ferrygirl to navigate the underground river and a baboon in a Superman costume.
When The Joker had his own short-lived series during the 1970s, he somehow had a miniature hide-out constructed beneath his cell in Arkham Asylum.
The alternate continuity Punisher series, published under the Max imprint, subverts this in the storyline ''The Cell'. The five that fired the bullets that killed Frank's family are all in the same large cell in Riker's. It looks like any old regular cell, but the narration reveals that they can get whatever the hell they want (except women) and the guards will look the other way. It's implied they could just outright leave if they wanted to. Frank doesn't let them.
Matt Murdock: Nice setup. You get maid service, too?
In the next story arc, Mr. Fear uses his designer pheromones to make everyone afraid of him. Effectively making him king of prison.
The Fabulous Furry Freak Brothers raid a prison to free their cousin Country Cowfreak. After killing dozens of police they find him, and are shocked to find he doesn't want to leave. He has a cell to himself with everything he could want - waterbed, 8-track stereo, color teevee...and they let him have all the dope he wants. At the end it turns out it was All Just a Dream.
In Astérix and the Laurel Wreath, Asterix and Obelix are enjoying luxury food while waiting to be thrown to the lions. The jailer explains that this is to ensure they taste nice for the lions. If they were to be thrown off the Tarpean Rock, they would get solid, heavy food.
In Harry Potter and the Methods of Rationality, it's mentioned that the reason a holding cell is so comfortable isn't because the suspect is held in especially high esteem or anything like that, it's just that wizards have such a high standard of living that it didn't really occur to anyone not to include a few basic comforts.
A similar situation was displayed in the film Goodfellas when Henry Hill was serving his first prison sentence with Big Paulie and other members of their crew. As the film was based on Henry Hill's memoirs it was exaggerated, but still...
In Cradle 2 the Grave Chi McBride's character had nice rugs, food and a prisoner butler (who was seen preparing food with knives), until they were both killed by the big bad.
Used mildly in The Hurricane. Rubin Carter began with the privilege of wearing prison hospital pajamas rather than standard uniforms and clung to an ironclad determination not to adhere in any way to the normal prison lifestyle. Over the sixteen or so years of his confinement, prison guards allowed him various luxuries in his cell out of a combination of pity, belief in his innocence, and appreciation for not making as much of a nuisance of himself as he could have. Eventually, his cell was filled with various posters of civil rights leaders, pieces of African art, a typewriter on which he writes his memoirs, a small collection of books, and a miniature stove.
In a more subdued example, in The Shawshank Redemption, living conditions in prison improves when Andy helps the Warden with his finances and they turn a blind eye to his contraband. Andy can customize his prison cell with shelves with knick-knacks and posters.
The most famous female prisoners in Chicago manage this, through gifts and money sent to them by the public.
The main premise of Russian comedy film I Want To Go To Jail is how many Western prisons are like this by Russian standards, hence the protagonist's Title Drop.
In Quills the Marquis de Sade initially has a spacious room at Charenton Asylum with books, luxury furnishings, wine and freshly-cooked meals separate from the other inmates. As the film progresses he has these items gradually taken away by the new doctor who runs the institution.
In Office Space, Samir is convinced to participate in the scam by being assured that American prisons are like this. He was assured they would go to "White collar resort" prison, as opposed to "Federal 'Pound me in the ass' prison".
The A-Team: Due to his top-notch people skills and extensive contacts both military and civilian, Lt. Templeton "Faceman" Peck isn't suffering during his incarceration for a crime he didn't commit. His cell looks like a college dormroom, he was allowed knock down walls to expand it, and no one seemed to bat an eye that he's sleeping with the female guards.
Subverted in Law Abiding Citizen. The villain insists a special mattress and a porterhouse steak be placed in his cell in exchange for his confession. The other inmates all shout with rage when they see these items delivered, and the warden pointedly says he'd hate to be the only one who has something in a prison wing full of the Have-Nots.
In the novel L.A. Confidential incarcerated mob king Mickey Cohen is even allowed to keep a dog in his cell.
In Wolves Eat Dogs by Martin Cruz Smith (featuring the cop from Gorky Park) a wealthy Russian crime-boss has bagged the cell that has been fitted out to comply with European human rights laws. Ironically if he didn't do this he'd risk being raped by the hard-core lifers who still control the prison system.
Arkady Renko (the cop in question) even jokes about it with the mob boss. When the mobster talks about going on vacation later on, Renko pointed out that if he wanted luxury quarters, good food, and a staff that catered to his every whim, why not stay in Butyrka Prison?
In Inherit the Wind a jailed schoolteacher jokes that his cell is more comfortable than the rented room he normally lives in. Similar to the Charlie Chaplin example above, this is not meant to imply that he is getting special treatment, rather that his normal quarters just suck.
In Discworld, Lord Vetinari has his dungeons set up like this, for those periodic times when Ankh-Morpork revolts against his rule; he's even convinced the rats to provide room service. Vimes notes that it has been constructed more for keeping the chaos that ensues when Vetinari isn't in power out than keeping a prisoner in. Naturally, Vetinari has installed several secret exits, should he want to leave, but for all intents and purposes, it's the safest place in the city. In fact, all of the locking mechanisms are on the inside, so he can easily prevent anyone unlocking the door from the outside.
Also, Leonard da Quirm's holding "cell." It's in a secret passageway filled with traps that Leonard designed, and he has a spare key for the door. He's quite comfortable, and Vetinari keeps him supplied with all the paint, wood, metal, and paper he needs.
Leonard is an interesting case because he's only imprisoned in the strictest semantical sense of the word. Sure, he's not allowed to leave unsupervised, but as the books note, Leonard is the sort of guy who can't truly be imprisoned unless they find a way to lock up his intellect. What he's got is closer to protective custody; it keeps Leonard's considerable, yet indiscriminate, genius out of the hands of those who would use it for petty, destructive short-term gain, and in the hands of Lord Vetinari, who is occasionally inclined to exploit it for the long-term good of the city, but mostly finds that what the long-term good of the city needs is for no one to actually have access to Leonard's genius.
In Codex Alera, The Alcatraz has one of these set aside for special prisoners who are there mainly for political reasons and they want to keep as comfortable as possible. It was originally built by a previous ruler who imprisoned the wife of a powerful noble lord there for treason against the crown, and went there to personally "interrogate" her three times a week. Considering she actually did commit treason, that was pretty much the only way to keep her around as his mistress.
In the Australian novel Underground, Leo James ends up imprisoned in the abandoned House of Representatives, and despite being periodically tortured by American agents, he finds it quite comfortable: he has the pick of all the furniture to sleep on, access to the member's lounge and toilets, and just about anything the evacuated members left behind.
In the first Inheritance book, Eragon, this befalls Murtagh at the Varden's headquarters once their leader learns who he is—much to his surprise. When Eragon comes to visit him, Murtagh forestalls the inquisition: "You thought I'd be sitting in some rat hole chewing hardtack."
In Philip Pullman's His Dark Materials, this is the fate of Lord Asriel. He was banished to the North for causing political distress, but was allowed to contract the construction of his own cabin including glass windows (which were very expensive at that time). He even managed to continue the experiments that got him banished in the first place by having materials and equipment smuggled in.
It was Fredric Brown who wrote a short story about a tourist arriving on a distant planet who accidentally kills a local. Told that because the locals enjoy a very long lifespan, the penalty for murder, even accidental murder, is death at dawn the next morning, he despairs. Under the law he is to be housed overnight in a magnificent 100 room mansion with all manner of luxuries, food, liquor, and even women provided to meet any imagined need of the condemned man for his last night. Then he asks how long he has to enjoy all this. He is told that a full day on this planet equates to only about 120 earth years so he only has about 60 years to live (Apparently planetary rotation is very slow). As the story ends, he wonders out loud if he'll make it.
The Alatriste books, as carefully-researched Historical Fiction, occasionally mention the possibility of such in 17th Century Spanish prison. Visitors were allowed and prisoners could purchase no end of luxuries so long as they had the coin, or someone on the outside willing to bring it in for them. Captain Alatriste himself is never in so fortunate a state, though, and opens the first book having just endured a short sentence over some unpaid debts. In the fourth book, Alatriste and Iñigo attend a sizable party in prison honoring a man about to go to the gallows the next day.
Harry Grout in Porridge (BBC prison comedy from the 70's). His assigned job is to clean the swimming pool. Slade Prison has exactly 0 swimming pools.
In one episode Grouty asks Fletcher if he follows The Archers. Fletch explains he doesn't, on account of them not being allowed radios in their cells. "Really? No-one ever mentioned it to me."
The Master, during his imprisonment in the Doctor Who episode "The Sea Devils." The Doctor had evidently pleaded that he be made very comfortable in captivity, as he meant for him to be there rather a long time.
In a novel set after his capture, but before he was placed in a prison with hypnotism-resistant guards, the only reason he's hasn't escaped is that he doesn't want to just yet. He's quite put out when his allies "rescue" him, because that wasn't in his plan.
Simon Adebisi from Oz outfits his pod this way after Unit Manager Querns makes him a trustee. A video of Adebisi partying with his prags in this cell later gets Querns sacked.
Also the inmates in the AIDS ward are allowed pretty much what they want, as the guards figure they're dying anyway.
Dale the Whale in Monk has his own personal cell and lives with a certain amount of luxury. This is partly due to his massive wealth and influence and partly due to his massive size - due to which even the door is left wide open, and he's even allowed to order takeout. But when he tried to assassinate the Governor of California as part of a plan to get himself pardoned and to put Adrian Monk in jail, he had all his luxuries taken away.
Seen in Season 2 of The Wire, all of which drug lord Avon Barksdale spends in prison. He manages to maintain control of his business, take over the supply of drugs flowing into the prison, and spend his free time playing video games and eating KFC.
Mayberry Jail in The Andy Griffith Show features Aunt Bee's home cooking, lace doilies on the bedstands and a key left deliberately within reach of the cell so that Otis, the town drunk, can let himself out when he's sobered up.
Subverted in one episode: after arresting some real criminals leaves the prison full, Otis is put in Aunt Bee's custody - the Taylor house quickly gets nicknamed "The Rock".
Khan lives in one in the MacGyver episode "The Escape".
Battlestar Galactica. At the beginning of Season 3, Athena's previously-stark cell is shown to be fitted out with curtains and furniture, indicating her change in status from hated Cylon prisoner to trusted advisor to Admiral Adama. According to the podcast commentary, the "prisoner with privileges" trope was specifically referred to in the script.
It's later revealed that cylons have the ability to image themselves in surroundings that are far more intricate, making all this 'luxury' unnecessary — except as a means of making Athena's jailors think of her as something other than a machine.
Red Dwarf. After being reprogrammed into a ruthless TV executive, Kryten is seen with a cell full of luxuries, with the guards calling him "Sir".
Whether it's the same one isn't mentioned, but Lister says there's a luxury block which prisoners can use as a reward for good behaviour.
Used in several episodes of Leverage. In one, they have a witness who is in jail. They offer to break him out if he helps them. He laughs at them, because he is quite happy in the minimum-security prison. So they frame him as the leader of the Aryan Nation and threaten to send him to a maximum-security prison if he doesn't give them the info they need.
One of the transferred employees from the Stamford branch of Dunder-Mifflin makes his time spent in white collar prison sound so good that the Scranton employees got jealous.
On Parks and Recreation, Leslie gets arrested in Pawnee's upscale rival town Eagleton. Eagleton is so rich that their jail includes guards who act more like waiters and there are prison gift bags.
In The Magnificent Seven TV series, Ezra's Con Artist mother is briefly imprisoned on charges of theft; she promptly arranges to have her cell comfortably appointed with drapes and furniture.
Season 6 of 24 has Charles Logan under house arrest.
In The Beggar's Opera, Captain Macheath pays to make his stay in Newgate Prison considerably more comfortable, with no chains and excellent food.
In William Shakespeare's Henry VI Part 2, Richard of York's son Edward is imprisoned by the Bishop, but apparently so well-treated he is allowed to go out hunting. That's how he escapes.
Pictured above: In Apollo Justice: Ace Attorney, after Kristoph Gavin is convicted of murder and sent to solitary, he still manages to receive presents, which include: a bookshelf full of novels, little artsy knickknacks, a bottle of the best nail polish on the market, and a comfy chair that's at least 10 times as expensive as the other chairs in the prison. Talk about connections.
In the second episode of Gyakuten Kenji 2, assassin Ryouken Houinbou has had his cell converted into an ostentatious Buddhist shrine.
The Special Prison in Ghost Trick seems relatively cozy. The rock star can keep his instruments and Jowd can paint as much as he pleases. He even gets giant roast chicken for dinner... though it's cold and hard by the time it arrives, and it was supposed to be his last meal. This is justified by the sort of prisoners held in there. Though they all committed crimes of various sorts, Cabanella strongly suspected (correctly) that they did so under the influence of a mysterious "manipulator". Since his personal philosophy is to simply throw someone in jail to keep them from getting into trouble until he can legally free them, it's not a stretch that it was arranged for those prisoners to be kept comfortable until they were proven innocent.
The prison cell that holds Lucretia Merces in Suikoden V is like this. She explains that it was originally a cell for incarcerated royalty or nobility, and ended up in it herself due to her services for, well, royals and nobles (the extreme respect that a few of the guards have for her certainly doesn't hurt).
When the protagonists of Shadow Hearts: From the New World bust into Al Capone's prison cell they find that it's well-furnished and quite comfy, as a nod to the Real Life situation mentioned below.
In Remember11, Inubushi Keiko (a mass murderer), lives in relative comfort at the SPHIA facility. Justified in that SPHIA was built as a psychiatric hospital, rather than a prison.
In Dwarf Fortress, this can be an effective way of keeping dwarves sentenced to imprisonment from getting too upset. Keep them chained up with a high-quality Gem-Encrusted golden chain and the prisoner will be too busy admiring the craftsdwarfship of it to get too worked-up about their predicament. Putting stockpiles of good food and drink within their limited reach can also help.
In The Elder Scrolls V: Skyrim, Sibbi Black-briar is given an eight month sentence in a luxurious "cell" — an actual bed, gourmet food, etc. — for committing murder. This is thanks to his mother Maven being one of the most influential and powerful people in Skyrim. And he still has the gall to complain.
It's implied that the reason he's in there at all is not because of any due process of law, but because his mother Maven was sick and tired of his misbehavior and the murder was the last straw.
Madanach, the leader of the Forsworn and a prisoner in Markarth's Cidna Mines, gets his own bed, desk, and bodyguard, along with other luxuries. This doesn't seem like much, but considering the other prisoners have to mine for silver, and don't even have a bedroll to lay on...
During the introduction of Mass Effect 3, Shepard half-jokes that being detained isn't so bad "once you get used to the hot food and soft beds." What little we see of Shepard's cell features floor-to-ceiling windows looking out on the city, and since nobody bats an eyelash at Shepard walking around unrestrained, we can assume s/he's been given freedom to move about.
How Rex Fury did time in Lego City Undercover. Roughly the size of a small apartment, it has a hot tub, a jukebox equipped with classical music, couches, and even what appears to be a Rock Band drum kit in front of his HDTV.
Due to his high-ranking connections in the mafia, Leo Galante has one of these in Mafia II.
In Homestuck, Derse's Very Important Prisoners' block is probably meant to be a torturous Gilded Cage, and Caliborn seemed to think so when he spent time there, but Dad Crocker, being a normal, classy human who loves the luxurious provisions, seems to be spending his time there nicely.
In Megamind, the main villain is in prison so often that he has turned his prison cell into this, complete with pictures, painting on the walls, sinister chair, TV and so forth.
He grew up in that prison. First he just landed there, but then the fucked-up logic of the setting meant that as a three-year-old participating in a prison break, he was sentenced to jail time instead of being put into the foster care system.
Taurus Bulba in the pilot episode of Darkwing Duck, who connives behind the guards' backs instead of bribing them.
Bulba takes this trope Up to Eleven. His cell is capable of transforming into an executive office, complete with secretary and outside phone line. Then later on you find out he's turned the entire prison into his own flying fortress.
Also done in one episode where Darkwing spies on a villain in a minimum security prison. There's literally no fences or walls, only a loudspeaker thanking the prisoners for not leaving.
The super-maximum-security prison that other super-villains are sent to isn't like this, but Quackerjack seems to enjoy being there anyway. As Megavolt remarks to Liquidator and Bushroot when they're all on work duty, "Someone should tell Quackerjack that prison isn't supposed to be fun..."
Ricochet Rabbit had one episode where he has to evict a cowboy prisoner who is quite happy right where he is, in the county prison. "Where else can I get a room and three square meals a day, for free?"
Guitierrez in Freakazoid! gets away with this. Except for his toilet. He bullies the warden into giving him everything he wants, including an internet connection... which is how he escapes prison.
John Corben, before he becomes Metallo, in the DCAUSuperman animated series. He has what he has because he didn't rat out Lex Luthor in the first episode, and Luthor makes sure he's well taken care of... so to speak.
When Superman needed the Parasite's help to find a bomb, the Parasite was offered a TV inside his cell (with cable, including the premium channels) in exchange for his cooperation.
The Ultrahumanite has one of these in Justice League, albeit it's relatively small. Gourmet food, classical music, TV, books, he has to be heavily bribed by Lex to even consider escaping. And then he agrees to betray Lex and go back anyway in return for Batman doubling Luthor's price... in the form of a charitable "generous donation" to his favorite classical music television channel in the Humanite's- name. The channel even thanks him for it on air.
In the Powerpuff Girls episode "Birthday Bash" where Princess Morebucks is seen in prison, her cell not only has all the luxuries of home (her home, which is better than most), but in the next scene, when she and Mojo are watching the heroines' birthday party in the common room, she has the other inmates waiting on her hand and foot.
In The Simpsons, Homer, as a prison snitch, gets things like a plasma TV, a "Snitch Life" bling chain, and even a Segway from his "Mother".
Also in The Simpsons, Mayor Sideshow Bob is sent to Minimum Security Prison for rigging the election. Looks more like a college campus than a prison.
Given that the local prison Harvard rowing team asked him to join up for a match against Princeton, its likely that the place is a prison for "white collar" criminals like corrupt business men or, in Bob's case, a corrupt politician
In another episode, when Kirk Van Houten was arrested, Chief Wiggum told him the cell he's going to wouldn't be so cold and damp as Van Houten's apartment. In fact, a normal prison cell felt like the trope for him.
In Home Movies, Brendon's class is taken on a field trip to a prison as part of a Scare 'Em Straight program. However, they took them to a white collar prison, which the kids considered akin to this trope. Coach McGuirk even remarked that the cells were better than his apartment.
Xanatos himself had a private cell on Riker's Island to plot his next scheme. It was no larger than an ordinary prison cell, but it was very nicely appointed, making it more cozy than confined.
The above quote is from the DuckTales episode "The Status Seekers". Charles Upstart III visits one of these to hire the help of the Beagle Boys who reside in this prison.
Bonaparte Beagle: Oh, guard! Go pack our bags and tell the warden we've escaped for a week or so.
In one episode of Dexter's Laboratory, his Dad wouldn't hire cable TV, which prompted Dex into building a satellite that (illegally) brought extra channels. When the authorities learned about the fact, they blamed and arrested Dad. When Dexter's Mom went to the precinct where Dad was taken to, she was told he could have left hours ago. Dad was then shown enjoying his cell's TV.
Played with in a Looney Tunes parody of Judge Judy, in which Sylvester successfully sues Tweety and the bird gets jail time. The prison? His birdcage.
Tweety: Frankly, I can't tell the difference!
He even gets to pull the switch on Sylvester's electric chair. (That's right, the plaintiff and defendant are both found guilty. Remember: this is Looney Tunes we're talking about.)
In The Legend of Korra, Varrick ends up in one of these after he's caught trying to kidnap the President of Republic City. In his case, the prison was built by his company and he had a custom cell made for him for when he inevitably ends up in jail.
Surprisingly enough Adolf Hitler. After the Beer Hall Putsch he was tried for high treason and sentenced to five years in Festungshaft (literally "fortress confinement"). Festungshaft was a type of jail that excluded forced labor, featured reasonably comfortable cells, and allowed the prisoner to receive visitors almost daily for many hours. It was the customary sentence for people whom the judge believed to have had honourable but misguided motives. While in prison he dictated most of the first volume of Mein Kampf.
Sharashkas, special prisons in the Soviet Union's Gulag System. As seen in The First Circle they were used as an incentive for political prisoners with useful scientific and engineering skills. Do well enough, build a lot of nukes and WMD's, and you'll get released. Do bad, and you get kicked down back to the hellish slave labour camps.
Exile to Siberia in Tsarist Russia wasn't quite prison, but otherwise it tended to fit this trope. Vladimir Lenin actually thought it was one of the best times of his life as the clean Siberian air and country lifestyle left him a lot of spare time for hunting, philosophizing and other activities and he left it healthier than he entered- and by "left" we mean "of his own free will" as the security was so lax than it didn't take a great deal of planning to get out, and most prominent revolutionaries either did so easily or eschewed it for the relatively comfortable life there. The fact that so many revolutionaries were sent into exile meant that they all tended to form their own communities which helped new arrivals to settle in (or get them fake ID's to escape with); ironically, the Tsarists basically helped them to form their own proto-typical Communist societies. Leon Trotsky had a similar if slightly more unpleasant experience, though Josef Stalin- being a known as a violent Diabolical Mastermind and bank robber (how he collected funds for the revolutionaries)- got exiled into deeper Siberia, which was colder and more barren, but still only required time and effort to escape from. At least once he did so just by hopping on the nearest train!
A fair number of nobles ended up imprisoned like this. In the Middle Ages, the noble may be related to his captor, and nobles were held prisoner primarily to obtain a ransom. Besides, you never knew if your prisoner would one day be holding you hostage. Better to treat him well and hope he'd return the favor in the future.
In Real Life most countries operated this as policy (i.e. you had to pay for most things and the more you paid the more you could get) up until round about the 1700 to 1800 period.
This is an example of Truth in Television. In the real world, cocaine king Pablo Escobar's personal quarters were so good that La Catedral, the prison he was held in, was dubbed the Hotel Escobar.
In his memoir Wiseguy (which was adapted into the film Goodfellas), Henry Hill goes into detail about the time he served at Lewisburg Federal Penitentiary, which was nicknamed "Mafia Manor." How comfy was it? Mobsters got their own special dorm, which was described as looking like a Holiday Inn. Mobsters were allowed to cook their own meals made from gourmet foods smuggled in by the guards. Mobsters didn't have to work if they didn't want to; if they did (for the pay), they could get someone else to do it. And mobsters could use the phone whenever they wanted, and one mobster stored the drugs he was selling in the chaplain's safe. The place was so nice, you couldn't even get in unless you greased the palm of the bureaucrat in charge.
Yet another real life example comes from the mid-19th Century. Boss Tweed, an infamously corrupt New York politician was said to have his own cook and could even come and go as he pleased while in prison.
And another real-life example was the system of debtors' prisons in England during the Industrial Revolution. They were notoriously corrupt, and while the truly broke had to beg passersby for food (meals weren't included unless you could pay the guards), wealthy and well-connected inmates had furniture and meals brought in from outside, got drunk, had prostitutes brought in at all hours, and generally enjoyed a standard of living that only the landed gentry could afford.
A caveat noted in Thackeray's historical novel Henry Esmond, is that while the wealthy like the title character could afford a comfortable confinement, it was at a truly exorbitant price. When their money ran out...
This sort of thing is very common in developing countries. Corrupt politicians practically take over the prisons where they're sent.
During the War of 1812, American prisoners of war were held in Halifax and allowed to wander around the city as they pleased during the day so long as they returned to their cells in the evening. Not a single man even attempted to flee, and many of them stayed in Halifax after the war ended.
This was not especially unusual in that era, at least not for officers. An officer who gave his word not to attempt escape might very well be allowed free run of the city he was being held prisoner in. And, being an Officer and a Gentleman, he (usually) wouldn't try to escape.
Taken a step further in the American Civil War. At times when holding or exchanging prisoners of war was unfeasible, captors would often grant prisoners a parole: They would be flat out released and free to go in exchange for signing a paper saying that they will not take up arms against their captors again. Of course, if you got caught violating your parole, then things get ugly.
This system broke down later in the war, once Grant and the Union realized that a manpower shortage was the South's greatest weakness. They held onto their prisoners, the Confederates responded in kind, and by the end of the war POW camps on both sides were some of the nastiest prisons to be seen until the 20th century.
During WWII, Italian prisoners of war kept at a camp in northern New Jersey were frequently given weekend passes to stay with Italian families living in Philadelphia.
More Truth in Television - Minimum security prisons are more comfortable than max-security ones, for obvious reasons. Oh, and there's that Austrian Max-Sec prison that looks like an art college dorm...
Of course, most people who get sent to minimum security are nonviolent and used to a high standard of living on the outside (tax evasion, securities fraud, embezzlement). Simply being deprived of their freedom is a huge blow, not to mention the social stigma. Besides, if they misbehave they can always be sent somewhere worse...
Well-behaved prisoners and convicts of other nonviolent crimes even in medium-security facilities are allowed privileges such as books, art supplies, writing materials, and even non-uniform clothing. However these usually must be earned and can be revoked should they act up.
Martha Stewart was sentenced for misleading federal prosecutors. She spent some of her sentence in a minimum-security prison, and some of it under "house arrest." Bearing in mind that Martha Stewart lives in a very nice town in New England and has built an entire career around telling people how to make their homes elegant and comfortable, it stands to reason that "house arrest" for such a woman would hardly be a punishment, right? Wrong... she said in an interview that house arrest was actually harder than prison time.
And on that note, being under "House Arrest" is pretty much the definition of a Luxury Prison, as you have the same amenities as before - paying for them, however, is a different story.
Norway, with its focus on rehabilitation, is especially famous for its prison-hotels:
Bastøy Prison in Norway is basically an island colony with just over a 100 inmates on it, accessible by ferry. The inmates walk free and spend most of their time working the island farms. Even the ferry is operated by one of the inmates and during the night there are only five guards. While most of the inmates are non-violent, there are some with murder convictions. The most bizarre case is the man who killed another person with a chainsaw. He's the one in charge of all the land clearing on the island, due to his tremendous skill with the chainsaw. If this happened in fiction you'd probably call it Refuge in Audacity.
Halden Prison: A cell includes amenities such as a television, a refrigerator, unbarred vertical windows that let in more light, and designer furniture. Prisoners share kitchens and living rooms every 10–12 cells, jogging trails, and a sound studio. There are cooking and music classes offered. Half the guards are women and guards are typically unarmed because guns "[create] unnecessary intimidation and social distance". Prisoners receive questionnaires that ask how their prison experience can be improved.
That case is somewhat justified in that Norway's experimental rehabilitation centres serve as an incentive and teaching tool for good behaviour (brutal Wretched Hive prisons, with all the gangs and torture and other such horrors, only end up punishing good behaviour and reinforcing a nihilist might-makes-right way of life, which in turn encourages criminal behaviour) and encourages sublimation - basically, when bad impulses are satisfied in a more acceptable way. Clearly, the chainsaw guy mentioned earlier likes to rip things up with a chainsaw; they just have to make sure he rips up the right things. Keep in mind that Norway also has the lowest criminal recidivism rates in the world, which means that it works- or at least make the prisoners too lazy in Bread and Circuses to be interested in crime.
The Tower of London was historically used as one of these.
Napoleon on Elba, where he was made governor and given a 600-strong guard. After Waterloo, the British cut him down a notch and sent him to Saint Helena in the middle of the Atlantic to live in a damp, crumbling manorhouse.
Justified, because the British exiled him not to punish him so much as to just get him out of their hair.
Alternately, for a man used to having half of Europe at his personal beck and call, the very fact that he was isolated on a rock in the middle of nowhere with no way to fulfill his ambitions was punishment enough.
It also makes escape much harder, as anyone who wants to see Napoleon on anything except official business are required to stay on the island until Napoleon's death
Al Capone, finally convicted on tax related charges, began his sentence in a prison where his money and fame brought him all the finer things in life, including the ability to leave if he wanted to. Unfortunately for Al, it all came crashing down when the guards told a visiting official that he was out, but was supposed to return later. Then he was transferred to Alcatraz, had the crap beat out of him by inmates, and eventually lost his mind to dementia caused by syphilis. Which then killed him when he got out. So... crime doesn't pay if you have an undiagnosed case of syphilis.
When she was imprisoned for tax evasion, "Queen of Mean" Leona Helmsley hired and bullied fellow inmates into waiting on her hand and foot, just like when she ran her hotels. One even served as her personal secretary.
Despite of having the reputation of a Tailor-Made Prison, the famous Bastille in the pre-Revolutionary France was actually designed to be a prison made of this trope. It was next to impossible to escape and the inmates' identities were a carefully guarded secret, but most of them were political prisoners and noblemen who had caused embarrassment to someone of higher status, most who could expect to be released when their families paid the right people. Some even rose to high positions in the government after their release, so the wardens were extra careful on how to treat prisoners who could one day become their immediate superiors.
Brazilian former Judge Nicolau dos Santos Neto, who was arrested and convicted for embezzling funds from the building of a courtroom, is occasionally transferred from prison to house arrest on the pretence of treating a depression case.
When Galileo chose to illegally publish his work rather than frame it as a theory (so as not to contradict the Church's official position that the Sun revolved around the Earth), he was put on house arrest. Unfortunately, his line of work didn't require leaving the house at all, and they didn't take away his telescope, so he just went on doing the exact same thing he was doing before. Whoops.