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Ahead of the Curve: Posh Lifestyles for Rent

How to live the good life—jets, luxe homes, fancy cars and boats—without owning a thing.



Visiting Naples for the first time can be a bit daunting. The houses are huge, the cars are shiny and the overall lifestyle can seem out of reach. After all, Forbes knows many of its residents by name. A billion here, a billion there ... pretty soon you’re talking real money. But you don’t need to be a captain of industry or born with a silver spoon in your mouth to look like you fit in. You just need to do a little legwork, schedule your visit and then rent everything you need to look like you have been coming here your whole life. It’s fairly strange to think about it, but it really doesn’t need to cost a lot of money to live like you have a lot of money. Why own a home in Old Naples that you’re barely going to use when you can rent? And that Aston Martin? You’re going to take a monster hit on its value as soon as you drive off the dealer’s lot. And don’t even get me started on jet ownership. It’s like throwing cash into a wood chipper.

No, if you’re just looking to fit in and enjoy some time in Naples without committing to the headaches of actual ownership, you can rent everything you need to look like a baller. So even if your IPO ended up as an IOU, you can still come to town and look like you’re living the good life. And you know what? You are. (For as long as the cash holds out.)

It’s a bird! Nope ...

As an order of practicality, you need to get here. And whether you are from Illinois or Ohio or Michigan, traveling in style is the way to kick off this Naples experience, and you can charter a jet that’ll deliver you right to Naples Municipal Airport without those pesky security lines and bomb-sniffing dogs. If you call up EvoJets, for example,  you’ll find that you can rent a midsize jet (Lear 60 or something similar) one-way from Chicago to Naples for just $11,000. Now, you may scoff at $11,000 for a two-and-a-half-hour flight, but even a used Lear 60 for purchase is approximately $1.5 million. So I just saved you $1,478,000. (I assume you’ll also be flying back to Chicago.) evojets.com

A little shack in Old Naples ...

If you have the good sense to show up in Naples via Lear jet with your luggage, you certainly need a nice place to hang your hat. Yes, golf course condos are admirable and will likely help your short game, but you didn’t just fly business class on Delta. You’re looking to make a splash. And that means waterfront. And it’s available. At press time there were four Port Royal homes available to rent on HomeAway.com. I won’t give you their particulars, but one is just under 8,000 square feet and can be yours for $39,000 per month. Another, which sits directly on the Gulf, is just $16,000 per month. (Most of these places have a 30-day minimum stay.) If you’re looking for a shorter stay, other waterfront mansions are available in Aqualane Shores for $779 nightly with a minimum of seven nights. If you want to be closer to downtown but still close to the beach, there is a smaller, three-bedroom, two- bathroom home just two doors from the beach for just $290 nightly with a three- to seven-night minimum, depending on the season. That’s a steal, and no one will know that this isn’t your regular life! Airbnb has plenty of luxe options as well. homeaway.com, airbnb.com

Be sure to valet ...

So you’ve flown here on a private jet and are staying at a killer joint on the water. But how will anyone know that you mean business? Well, you sure as heck can’t rent a Nissan Altima for your stay. Frankly, I’m not even sure they’d let you drive the streets of Port Royal in an Altima. (Altima owners, don’t send letters. I just bought one myself. They’re great for hauling brush.) So, what are your options for wheeling around town? Vast. Hertz offers Porsche 911s and Mercedes-Benz C63 AMGs and some other high-end rides for rent at their Fort Myers and Naples locations. Enterprise offers Range Rovers, Teslas, BMW convertibles and Jaguars, just to name a few. If those are too mundane for you, Top Gear Exotics Rental offers the Mercedes-Benz SLS AMG, Ferrari California, Ferrari F430 Spyder, Lamborghini Gallardo Spyder and Rolls Royce Ghost. Personally, the Rolls feel more like Naples to me, but to each his or her own. Oz Exotics even offers McLarens, Maybachs, Bentleys and the newest Lamborghinis—the Aventador and the Huracan. hertzdreamcars.com, enterprise.com, topgearexoticsrental.com, ozexotics.com

Dressing to impress ...

I’m not going to lie to you—I don’t recommend renting clothing that has been worn by others (and that’s pretty much how rented clothes work). And, if you flew into town on Lear jet, you can’t possibly be considering this. However, let’s say you have tickets to a fancy benefit and you traveled light. A guy can easily rent a tuxedo at any number of places, such as Men’s Palace, Jim’s Formalwear or Black Tie Tuxedos, and look, if not like a million bucks, somewhere in the mid-six figures. For the ladies, renting gowns seems slightly weirder, but who am I to judge? Locally, don’t expect to spend three hours in a couture Marchesa, but you might get a nice quinceanera gown for a reasonable rate. However, if you must have Marchesa (or Monique Lhuillier or Theia), you can always go with Rent the Runway. florsheim.com, jimsformalwear.com, blacktietuxedosfl.com, renttherunway.com

Remember your life preservers ...

The beauty of Southwest Florida is that there are more boats than happy marriages, which may, in fact, be correlative. The point is, you can rent everything from a kayak to a pontoon boat to a 38-foot Sea Ray to a full-on yacht. We discussed this back in our September issue, so we won’t go into too much detail here, but if you can’t figure out how to rent a watercraft while staying in Naples, I have no hope that you’re capable of getting yourself back to the airport. purenaples.com, naplesflboatrentals.com, naplesnantucketyachtcharters.com

Smile though your checkbook is aching ...

And though we’re sad that you’ve chosen merely to rent rather than buy and become a true Neapolitan, you owe it to yourself to document each and every moment you’ve enjoyed here. And the best way to do that—and feel like a movie star—is to rent a paparazzi to follow you around and capture your awesomeness. There are a number of fabulous photographers in Southwest Florida, so I’m disinclined to recommend any individual ones here. But I promise that if you Google “local photographers” you’ll find several willing to shoot you for somewhere between $100 and $300 an hour. And that’s a small price to pay to have proof you once lived the good life.


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