Southampton: Vacation Rental By Owner

This is an ideal house for entertaining with an open kitchen built for cooking but made for guests. Dining room, which seats 10 and kitchen both open up to front... ...more

As you walk through the front door into the foyer, you will see the beautiful open plan kitchen with island and stove on the centre island wonderful for social... ...more

Your private Southampton retreat awaits at this charming home nestled in a lush, tree-lined garden. This 4-bed, 3-bath vacation rental is well-appointed with... ...more

Gorgeous four large bedrooms, three full-bath home, beautifully appointed, surrounded by woods for total privacy. Available to rent for summer and year round.... ...more

New to market!! Immaculately updated in 2019, this freshly painted and furnished home in Southampton Shores has something for everyone. This centrally located... ...more

Beachy, casual, feel-good house in Southampton is conveniently located at "The Gateway" to Southampton. Lovely water views from main living area & deck, plus a... ...more

Enjoy an exquisite retreat on a secluded five-acre estate surrounded by open farm fields and vineyards. Southampton Supreme offers guests luxury and leisure in... ...more

Get the family together and enjoy a fabulous vacation in Southampton. The Little Plains Cottage is perfect for a family gathering, offering plenty of room and... ...more

Stress, to-do lists, and deadlines don't get an invitation to Wooley Beach House! Sometimes it takes a simple, no-nonsense vacation getaway to put everything back... ...more

Stand on the sun-warmed tiles surrounding the heated backyard pool, the smell of steaks wafting from the stainless-steel grill on the back porch while the kids... ...more

Enjoy tranquility at Tuckahoe Ranch, a craftsman-style red brick and white wood panel ranch house on a tree-lined property. Located 1/2 miles from the Shinnecock... ...more

Palatial glass doors welcome you inside Moses Lane Escape, a charming 1940s home updated with eco-friendly geothermal heat, solar panels, and a striking... ...more

Winter Way Spacious Southampton Escape, Mins. from Town, Private Pool, Sunny and Open Living 5BR/4.5BA, Elegant Design, Chef's Kitchen, Lush Landscaping, Near... ...more

For more than 20 years, visitors to Southampton checked into this well-loved bed & breakfast. Now, you can rent the entire home as a single property for groups of... ...more

With sunshine streaming through numerous windows, a light breeze in the air, and a sense of peace on the bay right outside your back door, you ll feel totally at... ...more

Families on the lookout for a vacation rental catering to kids, while still serving up the perfect respite for adults, look no further. Part playground, part... ...more

Main House: 5 Bedroom, 3 Full Baths - Sleeps 9+ Situated across from picturesque Wooleys Pond in the highly desirable, very private Southampton Shores, on the... ...more

Over-sized, close to Southampton Village very Private property. Cooper's Beach (rated one the World's TOP TEN) is just a short bike or car ride away. This is a... ...more

Gegan Contemporary NEW LISTING: Open-plan raftered home with beautiful outdoor space 3BR/2BA w/ Heated saltwater pool, charcoal grill This beautiful raftered... ...more

Charming on Moses New Listing: Close to Village and Beaches, Recently Renovated, w/ Heated Pool 5BR/3BA Immaculate, Renovated, w/ Heated Pool, Walk to Village or... ...more