Large Group Rentals in the Hamptons: 4 Homes Built for Groups
Planning a family reunion, a milestone birthday, or a long summer stay with two or three families under one roof? The hardest part of a large group trip to the East End is not the itinerary. It is finding a house where everyone can cook, sleep, swim, and spread out without anyone ending up on an air mattress in the hallway.
After nearly 20 years of managing homes across the Hamptons, we have learned that the best large group rentals share a handful of traits: enough bedrooms that nobody doubles up by default, a kitchen and dining table built for the whole party, and outdoor space where the group naturally gathers at the end of the day. Below are four Southampton homes from our Family Friendly Collection that check those boxes, along with what it actually feels like to stay in each one with a full house.
What Makes a House Work for a Big Group
Bedroom count gets the attention, but bed configuration is what makes or breaks the stay. A home with several king rooms lets couples in a multi-family group share evenly, while a twin room keeps kids together and frees up the larger suites for adults. Look for a layout that separates generations, too. Grandparents who wake at six and teenagers who stay up past midnight are both happier on different floors.
The kitchen matters more for groups than for any other kind of trip, because a big party rarely eats out every night. An island with bar seating, a dining table that seats everyone, and a grill steps from the pool turn dinner into the main event rather than a logistical puzzle. Laundry in the house, a driveway with room for several cars, and somewhere to go on a rainy afternoon round out the list.
Southampton 5BR with Four Kings, Pool, and Private Yard
This is the house we point multi-generational families to first. It sleeps 10 across five bedrooms, four of them kings, with three king rooms on a quiet lower level that opens straight onto the pool deck. Upstairs, a king with a sleeper sofa and a twin room sit next to the main living space, where a dining table seats all 10 under vaulted ceilings and skylights.
The backyard is the reason guests rebook: a large pool framed by mature trees, a covered hot tub, and a stone fire pit tucked into the woods. Add a gas grill, an outdoor shower for after Cooper’s Beach, and parking for four cars, and the whole group is set. Check dates for the Southampton 5BR with pool and private yard.
Southampton 4BR with Pool House and Game Room
For groups where not everyone does stairs, this Shinnecock Hills home keeps every bedroom on a single level, including two rooms with two queen beds each, a primary suite with a soaking tub, and a den with twin beds for the kids. French doors open from the living room onto the pool patio, and an island plus a dining table for eight keep group meals easy.
The standout is the separate pool house, with a wet bar, a full bathroom, and a pool table and ping-pong table for rainy afternoons. The fenced pool sits at the end of a long private driveway, Meschutt Beach is six minutes away, and dogs are welcome with a fee. See availability for the Southampton 4BR with pool house.
Southampton 4BR with Heated Pool and Garden Backyard
This classic Southampton home sleeps 8 in four bedrooms and 3.5 baths, and two of those bedrooms are king suites with their own ensuite bathrooms, an easy win for two couples sharing the house. The main level has an open living and dining area, a kitchen island with bar seating, a formal dining room for eight, and a den with barn doors that closes off for a quiet work call.
Out back, a heated in-ground pool is wrapped in mature hydrangea gardens and privacy hedging, with a bluestone patio, a fire pit with Adirondack seating, and a cedar outdoor shower. There is parking for four cars, and pool heat can be added for a daily fee. Check dates for the Southampton 4BR with heated pool.
Hamptons Water Living, a Waterfront Home with Private Dock
For groups with young kids, this Southampton Cove home is one of the easiest stays in our portfolio. It sleeps 9 across four bedrooms and a sofa bed, and it comes ready for little ones with a pack-n-play, high chair, baby gates, and a low garden fence along the water’s edge. Each of the two floors has its own entrance and living space, including a kitchenette downstairs, so families can share the house and still keep their own rhythm.
The backyard is built for long days outside, with an oversized deck, a fire pit, a hammock, a swing set, and a private dock with a floating launch for kayaks and paddleboards. A professional ping-pong table handles rainy days, the beach is a mile away, and Southampton Village and Sag Harbor are minutes by car. See availability at Hamptons Water Living, or browse more Southampton vacation rentals.
Traveling with More Than 10
If your group is closer to 15 or 20, the smartest move is often two homes rather than one. We manage several properties close to one another in Southampton, so extended families and friend groups can book neighboring houses, keep separate kitchens and bedtimes, and still gather at one pool for dinner. Tell us your headcount when you get in touch and we will suggest pairings that sit within a short drive of each other.
Find the Right House for Your Group
The right house turns a group trip into the one everyone talks about for years: the long dinners at a table that fits everyone, the kids asleep down the hall, the last swim before the fire pit. Browse the full Family Friendly Collection to compare every home that sleeps a crowd, or contact our local team with your dates and headcount. We will match you with the house, or houses, that fit your group best.
Frequently Asked Questions
How many guests can these large group rentals sleep?
The four homes in this guide sleep between 8 and 10 overnight guests. For groups of 12 to 20, we recommend booking two nearby homes, and our team can help you find properties close to each other.
What is the minimum stay for a large group rental in the Hamptons?
In most of the Town of Southampton, the minimum lawful rental is 15 nights. Check each listing for its exact minimum stay and available dates.
Can we bring our dog?
It depends on the home. The Southampton 4BR with pool house welcomes dogs for an additional fee, pets are considered on request at the Southampton 5BR, and the Southampton 4BR with heated pool is pet-free.
Are the pools heated?
The Southampton 4BR with heated pool offers pool heat for a daily fee, while the pool at the Southampton 4BR with pool house is unheated. Outdoor amenities, including pools, furniture, and grills, are generally available from Memorial Day through early fall, so confirm the dates if you are booking in the shoulder season.
Can we host a party or event at the house?
These homes are for registered overnight guests only, and parties or events are not permitted. If you have a special occasion in mind, reach out before booking and we will help you plan within the house rules.
When should we book for next summer?
Large homes are the first to go. For peak summer, reach out as early as possible to lock in your dates, and consider June or September for more availability and a quieter pace.
