The { Hamptons Life } Your Guide to Summer Rentals

The { Hamptons Life } Your Guide to Summer Rentals

We had to share this wonderful guide to summer rentals in the Hamptons created by our friends at

If you can’t stand the idea of a Fourth of July BBQ at your apartment and are considering a summer rental, now’s the time to act. Although there are lots of vacation destinations within a weekend’s drive from Manhattan, heading to the Hamptons every weekend between MD and LD (that’s Memorial Day to Labor Day in real estate agent-speak) is ingrained in the circadian rhythms of many New Yorkers.

Here’s a roundup of what you need to know about summer rentals in the Hamptons.

When Hamptons rentals are available
By and large, summer rentals in the Hamptons operate on an MD-LD schedule. While you can find properties that rent by the month, the week or the weekend, landlords generally prefer longer leases, that’s why there are more options for full summer and full-month rentals. If you are looking for a full summer lease, locking one in before the end of March is recommended, otherwise you’ll find mostly monthly rentals. If you only want to rent for a week, you have options into April. Singular weekends – especially the holiday weekends – are hard to come by.

How to rent in the Hamptons

Many major brokerages that transact in the city also transact in the Hamptons, including Douglas Elliman, Corcoran, Halstead and Brown Harris Stevens. There are local, Long Island-based brokerages like Saunders and Daniel Gale. These brokerages offer listings in a wide range of Hamptons enclaves and cater to the needs of short-term, summer renters. HREO is another common place people use to begin their search for short-term summer rentals. HREO compiles listings from all the major brokerages in the area and is quite comprehensive in its coverage, but can be a difficult site to navigate and offers no map view or mobile app. You can also use StreetEasy to find short-term rentals for the entire summer or by the month, which offers equally comprehensive coverage as HREO with the additional benefits of our map view and mobile app. Regardless of whether you choose to search on StreetEasy, HREO or go directly to a broker, you will likely have to pay a broker’s fee as there are very few no-fee rentals available. As an alternative, you can use sites like VRBO, HomeAway or Airbnb to find short-term rentals and avoid the broker’s fee. These sites, however, offer fewer options for month-long and summer-long rentals.

How much you’ll pay

Hampton rentals will vary greatly in price depending on where you’re looking and what you want, but some general rules of thumb apply.

Not surprisingly your rental price will go up when you check off beach access or swimming pool on the amenities list. By forgoing a pool or a view of the beach, you could save thousands of dollars.

Also keep in mind that prices vary according to what side of the highway you’re on. Route 27 is the major and much trafficked thoroughfare running east-west through the Hamptons. North of the highway, you’ll be farther from the ocean beaches and find slightly lower prices. Head south of the highway and you’ll find the soil gets a little sandier, the air a little saltier and the summer rents get a little higher. That’s because the south fork is a narrow strip of land where the roads are highly trafficked, which often make driving short distances to the beach quite an ordeal.

You will likely have to put down a security deposit – between 10 percent and 20 percent of the total rental price. If you plan to bring Fido or your cat, expect a higher deposit. Landlords also may request deposits for utilities and maintenance services (landscaping, pool/spa service, and garbage service are all usually paid for by the tenant). If you put down a utilities deposit, the unused portion will be returned at the end of the lease. If the cost of utilities exceeds the deposit amount, the difference will be taken from your security deposit.

Where to stay in the Hamptons

As mentioned before, your summer in the Hamptons will vary greatly depending on where you stay. Here’s a round up of the main destination spots.


East Hampton


East Hampton is the quintessential Hamptons destination. The downtown is filled with historic windmills, grass tennis courts and upscale resort wear boutiques. There’s often traffic on Newtown Lane – downtown’s main drag – but once you get out of the congestion, you’ll find some of the priciest real estate in the area — especially south of the highway. Areas around the bays and springs are more affordable, offering properties that are newer in construction but farther from the oceanfront beach.

  • Median sales price: $1.495M
  • Median rental price (MD-LD): $37,160/month

Your Guide to Summer Rentals in the Hamptons | Street Easy Blog



Amagansett has more of a beach-y feel than other parts of the Hamptons, smaller lot sizes and numerous celebrity residents, including Alec Baldwin and Paul McCartney. Technically, it’s part of the town of East Hampton, but it offers a much more laidback feel in comparison, if equally high property values.

  • Median sales price: $2.8M
  • Median rent (MD-LD): $45,000/monthYour Guide to Summer Rentals in the Hamptons | Street Easy Blog

Find rentals in Amagansett



Southampton is one of the older enclaves in the Hamptons and less of a destination for day-trippers and one-time weekend visitors. The downtown is light on nightlife and features more local boutiques. Homes are slightly smaller, older and closer together in Southampton, but are often on some of the loveliest lanes lined with large hedgerows and old oak trees.

  • Median sales price: $2.29M
  • Median rental price (MD-LD): $55,000/month

Find rentals in Southampton



Bridgehampton is one of the older and more traditional Hamptons enclaves and about a half hour closer to the city (further west) than East Hampton. Slightly more blue blood, Bridgehampton is known for its wineries, horse stables and as the site of the Hamptons Classic, the much feted, annual horse show. Properties tend to be larger and more expensive than other areas.

  • Median sales price: $5.75M
  • Median rental price (MD-LD): $55,000/Month

Find rentals in Bridgehampton

Sag Harbor


Sag Harbor is more laid back and family oriented than the rest of the South Fork, offering lots of options for summer camps and outdoor activities including sailing and fishing. Traditionally an African-American and artist’s community, Sag Harbor is best known for its properties lining the rocky beaches of Sag Harbor Bay.

  • Median sales price: $2.25M
  • Median rental price (MD-LD): $45,000/month

Find rentals in Sag Harbor



Westhampton is the area of the Hamptons closest to the city, which makes a huge difference if you are driving out East every Friday afternoon. If you’re heading to East Hampton and think you’re nearly there when you’ve hit the Shinnecock Canal, you’ll be sorely disappointed by the additional 45 minutes in the car. Instead consider Westhampton. The beaches in Westhampton are more rugged, the homes simpler and the overall vibe less ostentatious. You’ll also find slightly lower property values here.

  • Median sales price: $1.59M
  • Median rental price (MD-LD): $36,000/month

Find rentals in Westhampton



The furthest east of all the Hamptons enclaves (i.e., the longest drive) and relatively undeveloped until recently, Montauk is now increasingly popular among 20-somethings looking for a good beach party and is often considered a more upscale alternative to Fire Island. The beach can be a party scene and the nightlife can get boisterous.

  • Median sales price (MD-LD): $1.567M
  • Median rental price (MD-LD): $35,000/Month

Claudia Saez-Fromm

An entrepreneur, innovator, and singularly successful real estate salesperson, fitness fiend, foodie, mommy, and fashion fan.

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