How to Find a Perfect Luxury Rental in the Hamptons 2019

Looking for the perfect home to rent in the Hamptons for summer 2019? Have a look at our 9-step guide to finding the perfect luxury rental. And assess one which of the 7 social groups in the Hamptons suits you best. Then check out some of the specific fun facts and good things to know that we’ve uncovered, as well as some specific properties that are currently for rent that caught our eye. We’ve also noted our favorite hotels and restaurants, should you decide to visit before you make your final rental decision. Summer’s almost here.

the hamptons basics

The iconic Hamptons are comprised of a group of 10 towns on the South Fork that are collectively the summer playground of choice for many players in the global elite. Think bold-faced names in fashion, media, publishing, entertainment and finance.

This scene is not for everyone — it’s basically Manhattan on the Beach, and you need to dress appropriately — but if you’re up for it, there’s no better place to experience summer luxury (at least in the US). With numerous art galleries, museums, charming shops and gorgeous beaches – plus lots of celebrity-spotting and glamorous parties – there’s very little not to like for luxury lovers.

It’s easy to get distracted by the Hamptons infamous opulence. But there is more to a summer in the Hamptons than all the glitz. Captivating, world class beaches of white sand and dramatic dunes await. It’s the epitome of Atlantic coastal beauty, with spectacular light that has inspired painters like Jackson Pollack and Winslow Homer. If you’re lucky enough to rent a home or be invited to one, it will be an experience you won’t soon forget.

specific villages and homes to consider

1. East Hampton.

We love East Hampton because it has stellar beaches (we’re looking at you, Georgica), tons of upscale shopping, a great bookstore, and top-notch restaurants. The ultra-rich love East Hampton because they can get away from the hustle and bustle with stunning private homes along the ocean or behind thick green hedgerows.

Available Rentals. 

If you’re looking for the cream of the crop (or just want to ogle the inside of a spectacular home) check out this magical, ivy covered estate complete with a sports room, sauna and library. We love the serene quality and clean lines of this contemporary 4-bedroom home with a heated Gunite pool. For a family getaway, you’d be hard pressed to find something  better than this well-appointed and cozy 3-bedroom with a 1.5 acres of rolling lawn.


Baker House 1650The MaidstoneThe 1770 HouseEast Hampton House Resort; The Hedges Inn


FresnoNick & Toni’sEast Hampton GrillEMP Summer HouseHighway Restaurant

East Hampton

2. Southampton

puts all other South Fork villages to shame when it comes to shopping, celebrities and real estate; you’ll see more luxury convertibles passing by on the street in 10 minutes than you’ve seen all year. Multi-million dollar mansions by the sea abound, as do popular clubs and restaurants.


Summertime idyll awaits you at this quintessential 4-bedroom Hamptons style home. Perfect for families with a bunk room, pool and kids’ jungle gym. Impeccably styled and secluded with your own private walkway to the beach, this tranquil 5-bedroom estate is awe-inspiring with a price tag to match! This pristine estate has it all and then some: 2 professional kitchens, a massage room, steam room, sauna and 7 beautifully decorated bedrooms. Oh, and did we mention the infinity pool?


Latch Pop Up InnA Butler’s ManorCapri


Silvers; Sant Amboeus; Tutto il GiornoRed Bar;  Jue Lan ClubSouthampton Social Club


3. Sag Harbor 

is one of the prettiest towns on the South Fork. Charming storefronts line Main Street, alongside outstanding restaurants.  Here you’ll find artists, writers, the homes of many of the long-time African-American summer residents of the Hamptons, incredible sunsets, and the popular Long Beach.


We love the sweet, unassuming exterior of this 5-bedroom shingled house that has all the stylish comforts of a luxurious retreat. Check out this modern, waterfront property that offers water views from nearly every room, complete with a private dock for sunset cruises on your boat. If you’d like to follow in the footsteps of past literary giants like Truman Capote and Kurt Vonnegut who retreated to the Hamptons to write, this quaint 1-bedroom offers a home base for work and play.


The American HotelBaron’s Cove


Le Bilboquet; Lulu Kitchen & Bar; The BeaconPage at 63 Main; Wolffer Kitchen; Grindstone Donuts

Sag Harbor

4. Shelter Island.

Just north of most of the action, the aptly-named Shelter Island remains one of the most serene locations in all of the Hamptons. You’ll find lovely beaches, sunsets, restaurants and homes – minus the hustle, bustle and drama. The downside? You have to take a ferry to get there.


Originally built in the 1860s, this classic 4-bedroom Island home has been renovated with all the modern conveniences and tasteful decor. Can someone rent this glamorous 6-bedroom waterfront villa and invite us over for a weekend? Inspired by a nautilus shell, this Frank Lloyd Wright and John Lautner styled 2-bedroom house is incredibly stylish and tranquil, perfect to summer in with another couple.


Sunset BeachThe Chequit


Sunset Beach RestaurantVine Street CafeWhale’s Tale; 18 Bay

5. Montauk.

Furthest east is Montauk, where during the day surfers flock to Ditch Plains Beach for the best waves on Long Island. After dark, the pubs take over with a nightlife scene that draws both hipster and local crowds.  The sunsets and beaches here are unforgettable.


We’d love to relax in this serene and zen-like 3-bedroom house, steps away from the beach. Looking for a summer cottage for you and your significant other? This colorful 1-bedroom retreat with a private staircase to the beach has your names on it. For extended families, this sprawling 5-bedroom home is full of character and designed for entertaining.


Montauk Beach HouseGurney’sHero Beach ClubThe Crow’s Nest; McKinley Bungalow


Ruschmeyer’sDave’s Gone FishingArborFlagshipGrey LadyNavy BeachWestlake Fish House; Inlet Seafood Restaurant; Scarpetta Beach


6. Bridgehampton

is one of the more low-key spots in the Hamptons. Main Street is filled with unique boutiques, art galleries and lovely restaurants. The equestrian crowd will be out in force here for the annual Hampton Classic Horse Show in late August.


For those who really want to indulge, look no further than this magnificent 7-bedroom compound with 30ft tall cathedral ceilings.  This classic coastal 7-bedroom villa is the perfect gathering spot for friends all summer long. We love the funky fun vibes of this 5-bedroom home complete with pool and tennis court.


Bridgehampton InnTopping Rose House; Room at the Beach


Pierre’sAlmondMercado; Elaia Estiatorio

We hope this helps you find your perfect rental home in the Hamptons this summer. Good luck!

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Crediting her training as a cultural anthropologist at Wellesley College, Julie has immersed herself in various industries in the last 15 years including fashion design, event planning, fitness and even investigating police misconduct. Julie lives in NYC where she loves trying every ramen and dumpling restaurant with her husband and three children. She finds joy in bold prints, biographies of fierce women, kickboxing and spending way too long finding the perfect polish color to express her mood.

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