Should you rent your vacation house ASAP, or wait till the last minute to score a deal?

By Virginia K. Smith | February 23, 2016 - 8:59AM

Spring is still a month away, but we've already reached the point in the year where seasoned and organized (and, for the most part, moneyed) renters are locking down their summer rentals.

But while tradition holds that savvy vacationers should start looking for a summer setup as soon as we've entered the new year, there's another school of thought to consider: If you wait until the last minute to rent, you'll find motivated landlords, and the potential for significant discounts. "There are going to be renters that do one or the other," says Elliman Hamptons agent James Keogh. "Any landlord is case by case, so if you come early and make a lowball offer, you may have a better chance than if you come late and lowball." And the reverse can also be true.

So, to wait, or not to wait? Below, we weigh the pros and cons of each approach:

THE EARLY BIRD GETS THE POOL

Unsurprisingly, the general consensus seems to be that if you're looking for something highly specific, or generally on the higher end of the market, you shouldn't risk playing the waiting game.

"I think it really comes down to the quality of the house and the amenities," says Jennifer Grimes, founder of upstate brokerage Red Cottage Inc. "Houses with pools, for example, go quickly and go first," she says, adding that her phone "starts ringing at Christmas for the following summer" for houses with desirable amenities, or that cater to large groups planning far in advance (think family reunions and other events that require a long lead time). If you're looking for an especially large group, or generally picky about amenities and exact location (for instance, a Hamptons house right on the beach), you'll want to start your search early. That, and if you're on the hunt for a full-summer rental.

"Most people who rent their homes out for the full summer have decided on this far ahead of time, or are used to offering up their homes every year," explains Compass agent Chad Maltby, meaning that they're therefore are looking to lock down plans as soon as possible.

So how early is "early" here? The answer to that seems to be changing by the year. "I used to go on vacation in January and February, but those are becoming the busiest times of the year," says Elliman Hamptons broker Carol Nobbs; Maltby tells us that even November and December are becoming prime times to look for full-summer rentals on the (relatively) affordable end of the Hamptons spectrum (think $30,000 to $50,000). "That's the market that's so small and in-demand and tends to go quickly," he explains.

And while this might sound a little exhausting, keep in mind that renting early doesn't necessarily mean you'll be shut out of good deals or the potential for negotiating power. "Nobody has a crystal ball, and sometimes renting early doesn't mean you're paying top dollar," explains Corcoran Hamptons broker Arlene Reckson. "Sometimes the homeowner thinks, 'We don't know what the market will bear later in the season, and we have a bird in the hand,' so they may be more negotiable than not."

ROLLING THE DICE—AND SCORING A DEAL

Playing the odds and waiting until late in the game is an option that seems best suited for searching through short-term rental sites like HomeAway and VRBO (as opposed to through traditional brokerages), and for renters who have a healthy sense of managed expectations.

"If you're willing to bargain during the last week of May for a June rental, you can obviously get a great deal," says Maltby. "I'm not saying you're going to get an amazing place, but you will get a deal. In general the rule of thumb is, the more flexibility you want in price, the more flexible you need to be on the product." This often means houses without a coveted pool, that don't have scenic views, and are a bit of a drive from local attractions like the waterfront or hiking trails, depending on the area.

For less dramatic negotiations, whether or not there are deals to be found will depend on the market, as well as the individual homeowners you're dealing with. "It's a crap shoot," says Reckson. "If we have a really good market and you're looking at what's left over, the quality may not be as good as other houses that were asking the same amount, or it could be that they're still on the market because they were asking a lot more than comparable houses."

As for the current state of the Hamptons market, Reckson notes that last year's rental business started out strong and then softened a bit, while this year, "The rental market appears to be very brisk and people are coming out at all price points." Up in the Catskills, Grimes notes that properties her firm works with make a point of not offering discounts or negotiating down the asking price at all.

Still, it could be worth it, especially if you're looking for a quick trip out of town (as opposed to, say, a full month in a Hamptons house). "On my vacation rentals, if the homes have open days a couple of days in advance, for a $1,000-per-weekend rental, I might do $700 or $750 instead," says Cree Quaker of Catskills brokerage The Machree Group, also citing waived cleaning fees or security deposit as potential perks for the last-minute crowd. "Though weekdays are where you find the really good deals," she notes. "I might even offer a single night for $200, which I never would have otherwise."

(NB: This kind of setup is likely more feasible in an area like the Catskills than in the Hamptons, where some areas have made rentals of less than two weeks illegal. As we've written previously, if you're renting in the Hamptons for a shorter time span, it's not a bad idea to research the specific town's rules to make sure you aren't breaking them.)

The key, she says, is knowing your audience when it comes to landlords. If you find a host who runs it as more of a business, says Quaker—as opposed to, say, the nice couple renting out their beloved vacation home for the first time ever—you're more likely to find the opportunity for haggling. "Those hosts are more flexible," she says. "If you're running it as a business [or have a few properties], any day it's vacant, that's lost income."

7 ways to avoid getting scammed on your short-term rental this summer

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

Which town is right for you? A beginner's guide to the Catskills

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