Designed for Frank Sinatra and his first wife, the 1947 Twin Palms Estate not only brags true midcentury desert bones—Sinatra reportedly walked into the office of architect E. Stewart Williams "wearing a sailor's cap and licking and ice cream," and said, simply, "I wanna house."—but also that famous piano-shaped swimming pool. Anyway, the place fell into disrepair after Sinatra owned it, and it was bought in 1997 for just $138K. After a hefty restoration, the house now asks $2,600 a night—a flip story so inspirational it nigh brings a tear to the eye.

Villa Le Torre near the Tuscan town of Talamone was featured in 2008's Quantum of Solace. The rough-hewn seaside villa sleeps eight in four double bedroom suites, and rents for $1,936 a day.

At the beginning of their romance, the Duke and Duchess of Cambridge rented the Bordorgan Home Farm on Wales' Isle of Anglesey. Back then known as the humble Prince William and Kate Middleton, the couple rented it for about $1,200 a month (by today's conversion rates), though now that it's back on the rental market (the pair and baby George are poised to move to their Kensington Palace apartment, after all), it's expected to fetch much, much more.

This August the Clintons rented this wildly expensive Sagaponack, N.Y., estate in the Hamptons from (surprise!) huge Republican donor Michael Saperstein for a rumored $200K a month, which is its current ask. The 3.5-acre property happens to be one of the most expensive rentals in the country right now.

The penthouse at 40 Central Park South recently returned to the rental market asking $22K a month. For a rather humdrum (if gloriously sited and rather expensive) apartment, the unit boasts an impressive celebrity pedigree trifecta, having been home to Lance Armstrong, Liza Minnelli, and Broadway bigwig Michael Bennett.

The Bing Crosby Estate, located in Rancho Mirage, the same Palm Springs, Calif., neighborhood as Frank Sinatra's old place, has gained a reputation as the "Playground of the Presidents," and given that it once played host to—scandale!—Marilyn Monroe and John F. Kennedy, it's not hard to understand why. Naturally, the listing also brags about the decorative White Christmas crooner memorabilia, which, at $3,000 a night, is rather expensive to stare at.

Earlier this year, fashion designer Marc Jacobs looked for a well-heeled New Yorker to lease his condo in Jean Nouvel's 40 Mercer Street building for $37,500 a month. It'ssince been rented but that's not to say it won't be available at some point again: rumor is that Jacobs lived here only until his West Village home could recover from the beating it took during Hurricane Sandy.

Actor and action movie requisite Bruce Willis is one of a handful of celebrities who own vacation rentals at Parrot Cay in the Turks and Caicos Islands. His six-acre oceanfront compound packs in a five-bedroom main house and two three-bedroom guest villas. All this, plus a 70-foot heated negative-edge swimming pool goes for an eye-watering $20,873 a night.

Gore Vidal's estate on the Amalfi Coast, a villa known as The Swallow's Nest sits atop a 1,000-foot hill, and has played host to the likes of Tennessee Williams, Andy Warhol, Greta Garbo, and Mick Jagger. It's been sold to a luxury hotelier, but is, for now, being rented by some private gazillionaire. The ask is hush-hush.

Magician extraordinaire David Copperfield rents out his private island in the Bahamas, which sleeps 24 in an English Colonial-style main house, for heart-thudding $367,500 a day—and that's for the off-season. For Christmas, New Years, and other holidays that price shoots up to $52,500 a day.

Latin pop icon Gloria Estefan is not only renting out her guest house on Miami's Star Island, but also her main manse, which she recently listed for $75K a month. On offer: seven bedrooms, 330 feet of ocean frontage, and a private dock. Oh there's a pool, too, but for a megamanse in Miami that's kind of a given.

Baywatch star Pamela Anderson may have listed, aggressively restaged, and re-listed her Malibu spread, but apparently her cold feet—"I most likely won't sell ... I had too many people interested ... it scared me," she once told the Post—have determined she will try to rent out the place for $27,500 a month. Last time she tried out as a celebrity landlord she asked $50K a month, so we'll see how this goes.

This 2,400-square-foot loft, the former home of jazz great Charles Mingus, recently asked $8,750 a month. If the jazz connection does nothing for you, consider this: it's also where puppeteer Kermit Love set up studio, building prototypes for Big Bird and Snuffleapagus (!) in the master bedroom.

Barack Obama paid $180 a month to live in a crappy apartment on NYC's West 109th Street in his Columbia days. Unit #3E hit the rental market for $2,400 a month last year. It's no longer available, but the current tenant can only hold on to the political connection for so long before tiring of the completely unremarkable apartment.

Shortly after Curbed covered the listing of this hideous L.A. manse ("a booze cruise to nowhere") a little, barely known band known as One Direction rented it out for $27K for seven days. Not too shabby for an insane party palace.

Forget New York lofts or private islands: TV host Merv Griffin's 45-acre country house in Ireland boasts a 12-room guest house. Also on the property: a golf course, "ample mature woodlands for private walks," hunting and fishing, and horseback riding. It's rentable for $36K a week.

On the same strip of Turks and Caicos' Parrot Bay as Bruce Willis' digs is Christie Brinkley's Lucky House, one of 18 luxury properties owned by the supermodel. This particular villa boasts access to a 13,000-square-foot open-air yoga studio, and it's a damn good thing: one will most certainly need a lot of namaste after spending $8,107 a day.

Described as "a raw emerald anchored in a pool of turquoise" and "a vision of Eden" with "tapering sandbars and shallow coves [to] punctuate the shoreline, and flat planes of sugar white sound form an almost unbroken garland of pristine beaches," Richard Branson's private island in the British Virgin Islands—which makes a weird kind of sense considering Branson made his piles of money founding Virgin Group—is available to rent for, um, $408K a week. Interestingly, Branson very recently showed off his newly rebuilt luxury home on Necker Island; after all, the original one burned to the ground two years ago while Kate Winslet was visiting. Embarrassing.

This villa in Oracabessa, Jamaica is the true birthplace of Agent 007. Writer Ian Fleming created James Bond here and wrote many of his 14 Bond novels in this pile at the edge of a cliff overlooking a private beach. But that's not the only name this estate drops: a dozen years after Fleming died, reggae legend Bob Marley moved in. Sean Connery's Dr. No and Roger Moore's Live and Let Die were filmed nearby, too. The estate now asks anywhere between $40K and $77K a week.

Another Rancho Mirage gem sidling up next to Bing Crosby and Frank Sinatra's midcentury pads: the Harpo Marx Estate, designed by architect Wallace Neff in the mid 1950s. The rental website describes the desert homestead as a place "as tranquil and quiet as the superstar himself," with an "abundance of vibrant, picturesque details [to] catch your eye and capture your imagination." Translation: a tennis court, horse shoe pit, two waterfalls, lagoon with cross-bridge, and 27-foot vaulted ceilings. Oh, and because it is a midcentury Neff, there's the requisite walls of glass and a "resort-sized" pool. The ask? $25,990 a month.

In a successful attempt to create buzz around its L.A. offerings, online room-rental hotspot Airbnb recruited James Franco (as well as actress Anjelica Huston and supermodel Molly Sims) to design one of several pop-up suites in the city's notable locales. Franco's "mausoleum" in the Hollywood Forever Cemetery comes with wall-sized paint-by-numbers work and "YOLO" written on the wall. It's, in theory, available for rent, but it seems there's no option on Airbnb, perhaps because it's already booked solid. A shame; it probably would have been the only reasonably affordable rental on this map.

Earlier this summer, newly single actor/pirate/elf Orlando Bloom hulked his scandalous all-black house in L.A.—the one once burgled by the now very famous Bling Ring—on the rental market for $16,500 a month. While still more than likely available as a rental, Bloom more recently placed the "awe inspiring totally private compound" on the market for $4.5M, perhaps because now his separation from model Miranda Kerr has gone public.

This home's list of celebrity tenants is long and storied: Smokey Robinson vacationed here, actress Eva Gabor of Green Acres fame once owned it, The Godfather's Robert Evans honeymooned here, and, of course, business magnate and aviator Howard Hughes. The three-level abode asks about $3,775 a week.

Back in June director Steven Spielberg—Saving Private Ryan, Indiana Jones, Lincoln—nudged his Malibu beach compound on the rental market for a quiet $125K a month. The compound comes with a 7,237-square-foot Craftsman-style main house and accompanying two-bedroom guest house.