This comes as a shock to some people new to New York City but no one spends the summer actually in the city, especially with more hybrid/remote work. Spend one day in midtown Manhattan in August with the sweat, trash smell and mystery water falling from the sky and you’ll figure it out. A quick tour of the bullpen and you will see “go bags” under everyone’s desk ready to escape for the (long) weekend. Having done this for seven summers now (Manasquan, NJ and Montauk, NY), I can confidently say securing the house and enjoying the summer is no simple task. Nevertheless, here are my guidelines from experience in the places mentioned above but the framework applies to most beach towns in the Northeast.
Timeline
Always start earlier than you think so you have the most options. For Manasquan, some groups would look at houses and sign on Labor Day Weekend for the following summer. That being said, I would lock something up by Thanksgiving. For Montauk, start looking after New Years and sign something by March latest.
Establish the Budget
Using sites like Wood Agencies for Manasquan and Out East for Montauk, NY, you can get a sense for what is out there. Most listings are accurate but if something is too good to be true, it probably is, so don’t base your budget on the one outlier house you find. Manasquan is definitely the cheaper option of the two with full summer (Memorial Day to Labor Day) rentals running at about $2,000 - $4,000 per person. Montauk will run about $3,000 - $5,000 for July (peak rental month) or $7,000 - $10,000 for the full summer.
Lock in the Squad
With a proposed budget per person and a few example houses, start shopping the idea around to friends, friends of friends, the cute girl from Investor Relations etc. The two keys here are 1) getting a good group with some girls in the mix and 2) getting people to put a “down payment” to secure their spot. It’s always good to have some girls in the mix when your going out (girls attract other girls) but the real value-add is that real estate agents and homeowners are more willing to rent to girls than guys (sexist, I know). Some homeowners, especially in the Hamptons, won’t even consider renting to males under the age of 30. Honestly, it makes sense though. In the eyes of the homeowner, girls are generally cleaner, less likely to host parties and overall less destructive. So, when it eventually comes time to work with a real estate agent, have one of the girls in the group pose as your girlfriend. This will help get the real estate agent and ultimately the homeowner on your side. Now for the “down payment.” This can be a touchy subject with people handing you money before a lease is signed and well before the summer (more on timing later), but absolutely crucial. The timeline of finding a house and signing is a slow grind and then happens all at once. (ex. You send requests for 10 houses, don’t hear back for a few weeks, then all of a sudden a homeowner reviews your application and sends you a DocuSign lease that night). It is common to have to send at least half of the rent plus security deposit at the time of signing. If you don’t have the money ready to go, or worse, someone backs out, the homeowner will just move onto the next group. Tough luck. The “down payment” gets people bought in allowing you to pull the trigger on a house in a tight timeframe. Now that the money is secured, get everyone together for a dinner so people get to know the other housemates and build the hype for summer.
Use an Agent
While it is tempting to use services like AirBnb, VRBO and Outeast, it is nearly impossible to lock anything in with them. AirBnb and VRBO have cancellation policies that are incredibly favorable to the homeowner giving them the power to cancel at any time while the only recourse you have is to write a bad review. They might get zero stars but you’ll still be sitting in your 100 square foot room in the city while everyone else is at the beach.
Now that you have the squad together, and hopefully one girl in the group, find an agent. Wood Agency represents most houses in Manasquan. In Montauk, you have more real estate agency options but Town & Country has been the best to work with in my experience. During the initial call, the agent with inevitably ask “Who is in your group?” With the one girl on board, you can confidently say “My girlfriend and [x] other couples.” Obviously this isn’t the case but having the heir of responsibility will make you more attractive to homeowners. After the initial call, your agent will go through their inventory and send you houses that match your criteria. Put applications in for the ones you like and be ready to sign the lease. It sucks paying broker fees but here they actually help you through the process.
Read the Lease
This is super dry but worth doing or have your friend at Holland & Knight read it for you. While you have literally no flexibility in negotiating the lease (re: the homeowner will just go to the next group in line), it is good to know how you can get fucked and then work around it. How many people are actually allowed in the house? What are the parking rules? When does the trash need to get taken out? Who is responsible for mowing the lawn/landscaping? One common thing to look out for is cleaning service. Homeowners will have cleaning service written into the lease and the cleaners are often friendly with the homeowner and report back. This is a section of my lease for the summer.
![](https://substackcdn.com/image/fetch/w_1456,c_limit,f_auto,q_auto:good,fl_progressive:steep/https%3A%2F%2Fsubstack-post-media.s3.amazonaws.com%2Fpublic%2Fimages%2F0d0e56e2-c22a-46eb-98c0-d62eb4c2391b_751x31.png)
The cleaner’s main priority is to make sure there are not 20 people living in the house. I (and virtually all share houses) stretch the rules on how many people are living so just make sure the air mattresses are put away in someone’s car and the house is not in shambles.
Set the Rules Early
When you get a large group of people sharing a house, you need some high-level rules to offset the chaos. These are some I suggest.
No Half Shares, Buying/Selling Weekends
You commit to the full share knowing you will not be there every night/weekend. If you start splitting things up, everyone is incentivized to only pay for the time they are there which will lead to being short on rent. Better to not go down that rabbit hole.
Everyone committed to the group at the outset. Imagine someone wants to sell their weekend to a friend but, unbeknownst to them, their friend and another housemate hate each other (or had an awkward hookup, or any other reason). Now the full-paying housemate’s weekend is ruined. Stick with the core group and this is a lead in for the next rule.
Guest Policy
For starters, every housemate should have to sign off on a guest. They paid the full amount for the summer and should not have to deal with someone they don’t feel comfortable with in the house.
Guests don’t come empty handed. In our Manasquan houses, guests always came with beer, liquor and/or food. In Montauk, we always asked people coming out to bring things from “the main land” because it was so expensive to get in town. Regardless of what you decide, just make sure all the housemates and guests know what the rules are.
I promise you the headache of getting people on board and collecting rent from everyone is worth it. No better time than the summer and I would HATE to be the person stuck in my apartment watching everyone have fun at Parker House or Surf Lodge. If anyone in your crew needs convincing, tell them to call me. Also, I’ll do more specific recommendations for the Jersey Shore and the Hamptons throughout the summer. Happy hunting.