Performance indicators for the Southampton short-term rental market based on reliable data.
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The highest-performing listings in Southampton.
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Challenging to Investors
STRs are allowed townwide with a 14‑day minimum and a two‑year permit, but investors must complete inspections, assemble extensive documentation (floor plans, survey/site plan, COs, affidavits, agent designation), and pay moderate fees (standard $300, certified inspection $200, expedited $750). Strict enforcement bans advertising without an active permit and imposes penalties including a two‑year rental ban and a $500 violation fee, and the adjacent Southampton Village bans STRs under 14 days, creating added jurisdictional risk.
Local STR Agent
STR specialist · Southampton, NY
Southampton is a village in the Town of Southampton, located in Suffolk County on the South Fork of Long Island in New York State. The village itself is home to roughly 3,000 year-round residents, though the population swells dramatically during the summer months when seasonal visitors and second-home owners arrive. Long regarded as one of the original and most prestigious resort communities in the Hamptons, Southampton carries a distinctly polished yet relaxed coastal character, blending historic village charm with manicured estates, boutique-lined streets, and some of the most celebrated ocean beaches in the Northeast. It sits approximately 95 miles east of New York City, accessible by the Long Island Rail Road or a roughly two-and-a-half-hour drive depending on traffic, and serves as a gateway to the broader Hamptons region stretching eastward through Water Mill, Bridgehampton, Sagaponack, and East Hampton.
Coopers Beach is widely considered one of the crown jewels of the South Fork, a wide, white-sand stretch along the Atlantic Ocean framed by rolling dunes and historic estates. The beach lies within the Village of Southampton and is just a few minutes' drive from the town center. Known for its soft sand, rolling surf, and elegant atmosphere, it is consistently ranked among the top beaches in the United States and draws visitors from across the region during the warmer months.
The Southampton Historical Museum preserves and interprets the area's long colonial past, including a landmark 1640 settler-era house, a one-room schoolhouse, and the iconic Heckscher Windmill, which stands as one of the most photographed structures in the village. Located just east of Main Street, the museum complex offers a quiet counterpoint to the busier beach and shopping areas, providing visitors with a tangible sense of Southampton's origins as one of the earliest English settlements in New York.
Just a short drive west, Heckscher State Park sprawls across more than 1,600 acres bordering Great South Bay, offering wooded campgrounds, biking paths, picnic areas, and a long bay beach that is especially popular for families and sunsets. It provides a more natural, less crowded alternative to the ocean beaches and is a favorite for kayaking, paddleboarding, and casual boating.
A few minutes to the east in Water Mill, the Parrish Art Museum houses a notable collection of American art with a strong emphasis on the artists of the South Fork, including figures associated with the Abstract Expressionist and Ashcan movements. Set within a striking horizontal building surrounded by farmland, the museum offers both cultural depth and a calm, pastoral setting that complements the surrounding village landscape.
Southampton is a compelling base for short-term rentals thanks to its combination of storied beaches, historic character, and proximity to the wider Hamptons. Guests can spend mornings walking ocean dunes, afternoons exploring small museums and local vineyards, and evenings dining in the village, all while returning to a property that feels removed from the pace of the city yet remains within reach of New York and the rest of Long Island's South Fork.