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Hamptons.com
March 20, 2015

The Who, What, When And Where Of Hamptons Rentals

Sponsored Guest Post by Gary R. DePersiaby Sponsored Guest Post by Gary R. DePersia
in Real Estate
Home Real Estate

Each year, by this time, hundreds of people have been pondering the above questions concerning rentals in the Hamptons. Should they rent? What should they rent? When should they look? And, where should they be looking? Veteran renters wrestle with this quandary every year with some direction gleaned from past seasons of experience while first timers are sometimes overwhelmed with choices and questions. But there are some easy guidelines to help with these decisions.

The Who: If you’re looking for more than a weekend in the Hamptons, then you are probably looking for a home to rent. Unlike most resort areas, the choices of hotels and large condo complex rentals are limited on the East End in comparison to the number of people looking to spend time out here. The rental of a Hamptons home affords the space, privacy, amenities and ambiance not usually found in the limited number of hotels or inns scattered throughout the Hamptons. After all, it’s really inconvenient to go skinny dipping in the pool of a bed and breakfast with your significant other while the rest of the guests look on. Looking to buy? Then taking a test drive in a house or an area for a month or a summer could be the beginning of making that bigger decision.

The What: The larger the house, the more bedrooms, the better the amenities, and the more you are likely to pay. If costs are at all a factor, then it is imperative to figure out what you actually need. If it’s just you, your wife and two children most of the time, then resist looking at houses to accommodate a much larger group just because you are planning a big party one weekend. Don’t play tennis? Then don’t look at houses with tennis courts which will reduce your options and are bound to be much more money. Want waterfront but don’t have a boat? Then why do you need a house with a dock? Figure out what you actually need before embarking on your search. If you’re only going to use the house in July and August, then there is no need to spend the extra money for June when you might be overwhelmed with graduations, weddings or other June related activities. Ever think of an off-season rental? There are many options from mid-September through mid-May that are available at a fraction of the price of the summer season rates.

The When: When to start looking at rentals becomes a fine art for many veteran renters and should be for the “newbies” as well. There are many people who know where they want to rent and when they want to be there. For them, securing just the right house is much more important than saving money later on when landlords are more negotiable as the pool of renters starts to dwindle. Some of these savvy renters will start at the end of the previous summer season or during the fall to secure exactly what they want, knowing they will pay a fuller price. However, if you are flexible in your location, house choices, and amenities, then you might want to wait until later when landlords start to entertain lower offers. In addition, new options will appear on the market for shorter time frames as landlords hope to capture a broader range of people looking for partial season rentals.

The Where: If all of your friends are in East Hampton and your kids go to camp there, don’t look in Southampton which will add an hour of commuting each day and longer drives to see friends at night. If the focus of your weekends is not the beach, then it shouldn’t matter if you’re south of the highway or not. Why pay south of the highway prices if you want to hang out at your pool and tennis court all day with only occasional dips in the ocean?

Note to Landlords: First of all de-clutter. People have their own clutter at home and don’t want to deal with yours. If you have a bedroom that you use as an occasional office or den, return it to a true bedroom, if that’s not too difficult, as you get a larger pool of renters looking for more bedrooms and thus more money than you do for a cute den or office. And people… get rid of those boxy, 1980’s TVs. A good size flat screen in a living room or family room plus one in the master with smaller flat screens in the rest of the bedrooms goes a long way to attracting renters. When was the last time you checked into a decent hotel without one? Exactly!

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Spring Awakening: Toast To The End Of Winter With These Seven Spring-Themed Cocktails

Spring Awakening: Toast To The End Of Winter With These Seven Spring-Themed Cocktails

  • Hosted in the Hamptons at Calissa, Ja Rule showed off his mixology skills, livin’ it up and serving craft cocktails from Amber & Opal as the premium whiskey brand launched in the Hamptons. 

@jarule 
@calissahamptons 
@amberopalspirits 

#jarule #whiskey #hamptons #calissa #hamptonsweekend #hamptonsevents
  • 24 Saddle Lane, East Hampton, NY 11937⁠
Saunders Exclusive: $2,795,000⁠
⁠
@hamptonsrealestate ⁠
@jenniferwilsonhamptons⁠
@edbruehl⁠
@edmondzenuni_⁠
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This stunning contemporary home redefines modern living with its clean lines, dramatic vaulted ceilings, and walls of glass that flood the interior with natural light. ⁠
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Fully renovated in 2016, the open-concept living area seamlessly blends indoor and outdoor spaces, creating an entertainer’s paradise.⁠
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Imagine hosting gatherings on the expansive deck overlooking the heated pool and spa, or enjoying more intimate moments in the screened porch.⁠
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Read the full article at Hamptons.com (Link in Bio)⁠
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#hamptonsrealestate #easthampton #hamptons #realestate⁠
  • Check out the Top Hamptons Events This Weekend!

🎤 Ja Rule Bar Takeover at Calissa
🗓️ Friday, June 13 | 7–9PM
📍 Calissa, Water Mill
Hip-hop icon Ja Rule takes over the bar to celebrate the launch of his new whiskey, Amber & Opal.
📸 Phillip Faraone/Getty Images for AVA Resort
#calissahamptons #jarule #amberandopal

🍷 Mavericks Montauk Winemaker Dinner
🗓️ Friday, June 13 | 6PM
📍 Mavericks, Montauk
Kick off the Summer Winemaker Dinner Series with Christophe Renard of Domaines Ott.
📸 Photo Credit: Michelle McSwain
#mavericksmontauk #domainesott #winemakerdinner

🌸 Hampton Water Rosé Day Tour
🗓️ Saturday, June 14 | 1–7PM
📍 Bounce Beach, Montauk
Show up in pink and celebrate National Rosé Day with tastings, giveaways & more.
#hamptonwater #roséday #montaukevents

🏃 Beacon of Hope 5K Run/Walk
🗓️ Saturday, June 14 | 9AM
📍 Camp Hero to Montauk Lighthouse
Support awareness and hope on this scenic 5K through Camp Hero.
#beaconofhope5k #montauklighthouse

📚 Book Signing with Julianne Moore & Jesse Eisenberg
🗓️ Saturday, June 14 | 3–4PM
📍 Southampton Playhouse
A special family reading and signing with two stars and authors.
#julianneMoore #jesseeisenberg #southamptonny

🐶 ARF’s Rescues & Rosé
🗓️ Saturday, June 14 | 4–7PM
📍 ARF, East Hampton
Rescue dogs + rosé = summer magic.
#arfhamptons #rescuesandrosé #eastenddogs

🎨 Father’s Day Arts & Crafts Fair
🗓️ Saturday, June 14 | 9AM
📍 Marine Park Drive, Sag Harbor
Shop handmade jewelry, furniture, paintings, home goods, and more.
#sagharborarts #hamptonscraftfair

🍋 Lucky One Lemonade Launch w/ Miss Peaches
🗓️ Saturday, June 14 | 2PM
📍 Shark Bar, Montauk
Meet adoptable dogs and sip dog-lover-approved lemonade.
#misspeaches #southamptonanimalshelter #sharkbarmontauk

🛍️ Alice + Olivia Sip & Shop
🗓️ Saturday, June 14 | 4–6PM
📍 68 Main Street, Southampton
Hosted by Sydney Sadick & Sylvia Hemingway to benefit SAC.
#aliceandolivia #sipandshop #southamptonvibes

🩰 Tiler Peck at Guild Hall
🗓️ Saturday, June 14 | 8PM
📍 Guild Hall, East Hampton
An evening of unforgettable performance and movement.
#tilerpeck #guildhall #easthamptonevents

Check out more events at Hamptons.com (Link in Bio)

#hamptonsweekend
  • Sydney Sadick, Founder, Editor-in-Chief, and Publisher of Spotlight Magazine has been a lifetime Hamptons goer who has created a platform centered around the community she knows and loves. Spotlight Magazine has strong roots with the East End and is a fresh product in an ever-changing landscape.⁠
⁠
Sydney is a fashion and lifestyle expert who regularly appears on television. She is the author of the memoir and educational guide Aim High, which has received praise and recognition in the fashion space, encouraging individuals to find their unique style and achieve their goals.⁠
⁠
Sydney discussed her background and why she decided to launch Spotlight, how the magazine has evolved and grown, and some upcoming projects she is excited to be involved in ahead of the 2025 summer season. ⁠
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Read the full interview at Hamptons.com (Link in Bio)⁠
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#sydneysadick #hamptons
  • At 55 Long Lane, East Hampton, Share the Harvest Farm is more than just rows of vibrant vegetables and rich soil, but a deeply rooted reflection of compassion and the strength of community. Founded in 2010 by John Malafronte, Ira Bezoza and Peter Garnham, this nonprofit farm was built on a simple but powerful idea, that everyone deserves access to wholesome,  locally grown food.⁠
⁠
For over 15 years, Share the Harvest has partnered with numerous other non-profit organizations to serve members of their community who may be dealing with food insecurity. In a region often associated with luxury and wealth, the farm sheds light on a quieter truth in which many local residents struggle to put healthy food on the table. At its core, Share the Harvest Farm is a place of purpose where every tomato, carrot, and pepper represents the spirit of neighbors helping neighbors.⁠
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Meredith Arm, the Executive Director, and Matthew Quirk, the Farm Director, shared more about the farm’s mission, the challenges they face, and the deep sense of purpose that drives their work each day.⁠
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Read the full article at Hamptons.com (Link in Bio)⁠
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#sharetheharvest #community #hamptons #local⁠
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  • So many fun events this weekend! ⁠
⁠
Check out the top Hamptons events this weekend!⁠
⁠
🎸 22nd Annual Battle of the Bands⁠
📅 Friday, June 6 | 8PM–11:30PM⁠
📍 Ponquogue Beach, 280 Dune Rd, Hampton Bays⁠
🎶 Five local high school bands compete for great prizes!⁠
📸 Photo: Rob Rich/SocietyAllure.com ©2024⁠
⁠
🛋️ Decorators-Designers-Dealers (D-D-D) Sale & Auction Benefit Gala⁠
📅 Saturday, June 7 | 4PM⁠
📍 36 Barkers Island Rd, Southampton⁠
✨ Silent & wine auctions + high-end home furnishings amid a summer cocktail party.⁠
⁠
🎨 Magical Thinking Exhibition⁠
📅 Saturday, June 7 | 6PM⁠
📍 Keyes Art, 45 Main St, Sag Harbor⁠
🌌 A stunning show exploring the extraordinary through realism.⁠
⁠
🌅 Second Annual Sunset Soirée for Brain Cancer⁠
📅 Saturday, June 7 | 5PM–9PM⁠
📍 Private Estate, East Hampton⁠
💜 Enjoy sunset views and raise awareness for an important cause.⁠
⁠
🐋 Mini-Whale Workshop with UpSculpt⁠
📅 Saturday, June 7 | 12PM–4PM⁠
📍 Bridgehampton Museum, 2539 Montauk Hwy⁠
♻️ Transform marine debris into art while learning about conservation and local history.⁠
⁠
🎧 Amalfi’s Waterfront Party Series⁠
📅 Saturday, June 7 | 3PM–10PM⁠
📍 Amalfi, 32 Lighthouse Rd, Hampton Bays⁠
🍸 Food, cocktails, and DJ sets with a waterfront view.⁠
⁠
🎬 Tony Gilroy In Conversation⁠
📅 Sunday, June 8 | 2PM⁠
📍 Southampton Playhouse, 43 Hill St⁠
🎥 A deep dive into the filmmaker’s suspenseful storytelling—including Andor.⁠
⁠
💃 Gipsy Kings Live at Canoe Place⁠
📅 Sunday, June 8 | 7PM⁠
📍 Canoe Place Inn, 239 E Montauk Hwy, Hampton Bays⁠
🎶 End your weekend with legendary music and energy!⁠
⁠
🌟 Tony Awards Screening & Red Carpet at Guild Hall⁠
📅 Sunday, June 8 | 8PM⁠
📍 Guild Hall, 158 Main St, East Hampton⁠
🎭 Watch the 78th Tony Awards LIVE from Radio City in red carpet style!⁠
⁠
⁠
#hamptonsevents #battleofthebands #tonyawards #eastendart #hamptonssummer2025 #livemusic #artexhibition #fundraiserevent #guildhall #canoeplace #sagharbor #easthampton #southampton #hamptonbays
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