Hamptons a la carte: how to pull off a short-term rental on the East End

By Virginia K. Smith | March 17, 2015 - 8:59AM

Warmer climes bring thoughts of summer getaways, and though Hamptons haters abound, there's no denying the call of the East End. A mere mention of the place can connote Gatsby (or Gossip Girl)-level opulence, but as long as there have been share houses or people willing to sleep four to a bed, the non-millionaires among us have been finding ways to stake out spots in Long Island's most hyped (and expensive) beach towns.

One of the best options for anyone not trying to drop $70K to live in a "quaint" cottage for three months: the short-term rental. This option has seen its popularity skyrocket in the past few years; HomeAway crunched the numbers for us, and found that between their two sites (the company also owns VRBO), traveler demand in the Hamptons spiked 149 percent between 2009 and 2014, while rental inventory increased by 110 percent over the same period. In other words, you'll have lots of options, and lots of competition. Here's how to handle the hunt for a short-term beach house like a seasoned pro:

WHERE TO LOOK:

VRBO and HomeAway are the most popular sites with Hamptons owners listing their places directly, and Airbnb is gaining traction in the area, as well. "Airbnb doesn't have quite as established a reputation [as the other two sites]," says Douglas Elliman Hamptons broker Jordan Daniel. "It's relatively new and not as popular as it is in the city," though he notes that it's more widely used among younger homeowners and renters. Prices on these sites range anywhere from around $200 to a few thousand dollars per night, or between a few thousand dollars and nearly $20K for weekly rates, depending on size, amenities and location. Suffice it to say, you can tailor your search to just about any budget or set of needs.

However, there's one major legal caveat to keep in mind: Technically, rentals of two weeks or under are illegal in most Hamptons hamlets. And in many of these areas, your host also needs a permit for the set-up to be legit. While this rule is difficult to enforce and would primarily cause problems for your landlord, if you're skirting the law, you may well make enemies of the neighbors (particularly if you're just in town for the weekend to throw a raucous party, precisely the kind of thing these laws aim to discourage).

While renters in New York's illegal short-term rental have been known to get booted out in police "raids," a broker who preferred to remain anonymous tells us that they've never seen anything similar happen in the Hamptons, where most of the ire is focused on the wayward landlords. Still, "renters ought to be aware of what the rules are," says Saunders & Associates founder Andrew Saunders. In a statement, HomeAway told us that while "it is the responsibility of the vacation home owner to check with their local municipality on the legality and regulation of home rentals in their area [...] HomeAway requires in our terms and conditions that those advertising on our sites comply with their local regulations." It's also possible to search their listings by minimum stay to ensure that you're complying with the local rules, and if you'd prefer to tread carefully, check into the laws of the specific town you're looking to rent in, and check with your host about their permit status.

PRO TIPS FOR THE SEARCH

While renters in longer-term setups generally do need to schlep out to Long Island to take a look at prospective properties, those needing shorter stints can handle the hunt from their laptops. "If you're just renting for a week I don't think you have to spend a whole day looking at 15 different houses," says Daniel. If you're not familiar with a particular neighborhood, Google Street View is always a handy way of getting a sense of the area when you can't scope things out in person.

It may also pay off to do research on the landlord to find out if they're experienced in the summer rental game or if this is their first time out of the gate. We recently heard a horror story from a renter who unwittingly stumbled into the middle of a dispute between an inexperienced landlord and the neighbors, who weren't too keen on having short-term renters nearby. Said neighbors decided to "handle" the problem by blasting the same Eminem song on repeat until the police had to intervene (seriously).

In a less extreme example, Citi Habitats broker Kimberly Fisher recounted a recent Hamptons rental—found via Airbnb—from a nervous pair of first-time landlords who were "skittish" about the prospect of renters, and initially tried to keep tabs, calling frequently and requesting names and information about every single guest invited to the house.

THE ALL-IMPORTANT BEACH PASS

If you're planning on spending time at the beach, keep in mind that most Hamptons beaches require special parking passes, which cost $375 for the season and tend to sell out long before the summer starts. Day passes are available, but tend to sell out first thing in the morning. Check into your town's beach situation before you head out so you can plan accordingly.

It may be even worth trying to work out a deal with the landlord. For instance, when renting out her East Hampton home to a couple who'd applied too late for a parking pass, Keller Williams broker Adina Azarian included a clause in the arrangement allowing the renters to take her car to and from the beach. As they say, the squeaky wheel gets to the beach.

Failing that—and if you're too far to walk or ride your bike—you can bite the bullet and take cabs to and from the ocean, or opt for a shuttle like The Free Ride, a relatively new option that runs between major neighborhood parking lots and beaches.

For tips on locking down the longer-term houses (and what neighborhoods are the best bargains), we've got a guide for that, too. In the meantime, let's drool over a few rentals:

This East Hampton three-bedroom is available for a two-week stay that'll cost you $14,780.

This 4-bedroom house—with large outdoor pool—in Tuckahoe, south of the highway and near Southampton, will cost $10K for a two week summer stay (and about half that much in the off-season).

For renters who prioritize a good backyard barbecue, this Sag Harbor 4-bedroom (complete with pool, hot tub, and backyard grilling patio) is asking $11,000 for a two-week stay.

This 3-bedroom East Hampton house comes with an in-ground, heated outdoor pool, as well as amenities like cable, wifi, and lawn service included. A two week stay costs between $6,000 and $8,000.

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