luxury houses for rent Sag Harbor, United States (page 2)

An architecturally distinguished modern barn, this three-bedroom residence offers a rare fusion of artistic design, refined finishes, and resort-level privacy. Set behind meticulously curated landscaping, the home presents a sculptural silhouette and interiors defined by soaring volume, gallery-like light, and a sophisticated contemporary palette. The main living spaces flow effortlessly to the outdoors, framing views of the property's lush grounds. A fully finished loft-ideal as a private office, studio, or additional lounge-elevates the home's versatility and provides a serene, sunlit retreat separate from the primary living areas. The backyard functions as a private resort, anchored by a pristine pool surrounded by native plantings that create a sense of seclusion and seasonal beauty. The outdoor living and dining areas offer elegant settings for both intimate relaxation and open-air entertainment. Perfectly positioned between Sag Harbor and East Hampton Village, the property allows equal access to luxury boutiques, acclaimed dining, marinas, and the Hamptons' most coveted ocean beaches. This is modern East End living at its most polished-where architectural artistry, privacy, and premier location converge. [[Rental Registration # 24-1449]] EH RR #: 24-1449 Rental Terms: October: $30,000 Two Weeks: $15,000

Down a long drive, this charming Hamptons classic house is situated on a professionally landscaped acre. Tucked away in a quiet community and only a stone's throw to both Bridgehampton and Sag Harbor villages. This stylish professionally decorated home is fully equipped with 4 bedrooms and 2.5 bathrooms. The first floor boasts a sun-drenched great room with designer furniture and lighting, wide plank floors and a brick fireplace. Additionally, there is a master bedroom with an en suite bathroom. The kitchen is beautifully appointed with a top of the line Lacanche oven, there is also a powder-room, large pantry, laundry and mudroom with access to the pool and back garden. The second floor has three additional guest bedrooms with beautiful views of the grounds, one of the bedrooms has a walk-in closet and on the second floor there is an oversized shared bathroom. Ideal for summer entertaining the back and front gardens offers complete privacy with an expansive wrap around deck, a heated pool, outdoor shower, and a generous fenced in yard. A true gem not to be missed! #RP201221 Exp 2/10/2025 [[Rental Registration # RP250191]] EH RR #: RP250191 Rental Terms: Two Weeks: $20,000 July: $40,000 July - Labor Day: $85,000 August - Labor Day: $50,000

In a prime Bridgehampton North location just minutes from ocean beaches, Bridgehampton Main Street, and Sag Harbor Village, this recently refreshed shingled traditional offers bright, effortless, and stylish summer living. Light updates and new décor give the home a fresh, current feel throughout. The sun-filled living room, with its vaulted, beamed ceiling and fireplace, creates an inviting centerpiece that flows into the country kitchen and cheerful dining area. A classic screened-in porch provides a perfect spot for breezy mornings or relaxed evenings by the pool. The first-floor primary suite is a standout, featuring a vaulted ceiling, beautiful natural light, and an easy, elevated atmosphere. A versatile den that can serve as a fourth bedroom offers added flexibility, while two upstairs bedrooms share a full bath. Light pine floors, abundant sunlight, a generous landscaped acre, ample parking, and a sunny pool area all contribute to the home's relaxed Hamptons appeal. Thoughtful accessibility features-including a first-floor bathroom designed for ease of use and a discreet wheelchair ramp at the front of the home-add convenience without interrupting the home's classic aesthetic. This inviting Bridgehampton retreat blends style, comfort, and practicality, making it an ideal rental for a cheerful and easy summer. [[Rental Registration # (RP251526]] EH RR #: (RP251526 Rental Terms: Two Weeks: $20,000

Experience the ultimate Hamptons summer at this spectacular 7-bedroom luxury estate in the heart of Bridgehampton, surrounded by premier horse country, vineyards, farm stands, and just minutes to world-class beaches, village dining, and shopping. Recently constructed and impeccably furnished, the interiors were custom-designed by acclaimed designer Alicia Murphy, blending elevated coastal sophistication with relaxed summer living. A charming gated courtyard and welcoming front porch set the tone on arrival, while a dramatic double-height entry leads into a sun-filled great room ideal for entertaining or unwinding. Throughout the home, exquisite stonework, bespoke millwork, and designer finishes reflect meticulous craftsmanship-no detail overlooked from architectural plans to final installation. The open flow layout connects beautifully to the outdoors, creating seamless indoor-outdoor living. The property features: 7 Bedrooms & 6 Baths across three finished levels 20x40 heated gunite pool with stone patio Expansive private grounds & lush professional landscaping Al fresco dining & multiple outdoor lounge areas Finished lower level with bedroom suite, family/TV room, wet bar & gym Attached 2-car garage and ample parking This is a rare Bridgehampton summer rental, offering luxury, convenience, and privacy-the perfect Hamptons retreat close to ocean beaches, Bridgehampton Village, Sag Harbor, acclaimed restaurants, equestrian facilities, wineries, and golf. Available in June for two weeks or the full month of August for the discerning tenant seeking the ideal Hamptons summer experience. Rental Terms: August: $175,000 August - Labor Day: $195,000 July - Labor Day: $350,000 Memorial Day - Labor Day: $450,000 June: $100,000 July: $175,000

Designer decorated mint-condition home with private heated pool surrounded by flowering gardens on a charming lane in Sagaponack. Light bright kitchen overlooks seating and dining area, with a stylish living room with fireplace beyond. Roomy primary, two additional guest bedrooms, and two beautifully appointed baths complete this perfect summer getaway. [[Rental Reg # 22-394]] EH RR #: RP241987 Rental Terms: Other / Short Term - Year Round: $130,000 Memorial Day - Labor Day: $90,000 July - Labor Day: $90,000 August - Labor Day: $50,000 July: $45,000

Immaculate traditional in Bridgehampton North. 5 bedrooms, 3.5 baths on just under 2 acres of beautifully landscaped property. Large mahogany deck with outdoor BBQ and heat lamps. Oversized heated saltwater gunite pool overlooking western sunsets. A wonderful Hamptons retreat. [[Rental Registration # RP200229]] EH RR #: RP200229 Rental Terms: June: $40,000 August - Labor Day: $70,000 July: $65,000

Set on 1.2 acres with distant ocean views, this 5 bedroom home was renovated in early 2014 to provide a new kitchen, 7.5 new bathrooms, and a finished basement with a gym and recreation room. The house features high ceilings with light filled rooms. Privacy abounds since the master bedroom and the ensuite bedrooms are located in three distinct areas of the house. The first floor offers an eat-in kitchen, spacious living room and dining area, comfortable family room, and one of the ensuite bedrooms. A separate study with its own private full bath can serve as a 5th bedroom. Outside, ample decking and tables overlook the 54' heated gunite pool and spa. Mature, lush landscaping and an outdoor shower complete the picture. Also available June 2023 for $30K. EH RR #: RP260632 Rental Terms: July: $100,000 August - Labor Day: $125,000 July - Labor Day: $200,000 June/July: $150,000 Memorial Day - Labor Day: $250,000

Beautifully renovated in 2022, this spectacular design brings a touch of European charm to the Northwest Woods. Tasteful amenities of the first floor of this Tuscan-inspired home include exposed wood beams, a double-height foyer highlighted by a grand staircase with iron railings, a large living room with designer furnishings and fireplace, a separate chef's kitchen with high-end appliances, a large island, butler's pantry, and its own wood-burning fireplace, a large dining room, two office/den spaces, and the primary suite with its own full bath. The second floor features three additional guest rooms and en suite baths that are joined by a long landing that overlooks the stately entryway below. A finished lower level houses another guest room with en suite bath, a living/play area, a gym space, a laundry room and a six-seat stadium home theater. The grandness of the house, however, is quite possibly overshadowed by the meticulous beauty of the grounds and backyard. The long driveway is gated and opens to a circular space surrounded by soaring, sculpted pines. The backyard features a large stone patio that is ideal for entertaining, a beautiful free-form heated gunite pool, a spacious lawn, and an outdoor shower. With its close proximity to East Hampton Village, this property maintains a great sense of privacy and is ideally located near fine area shops, local restaurants, and stunning ocean beaches. [[Rental Registration # Pending]] EH RR #: 24-567 Rental Terms: April: $12,500 March: $12,500 January: $12,500 Winter Season: $50,000 Per Month February: $12,500

Set on 1.11 acres of exquisitely landscaped grounds, this sophisticated post-modern retreat offers a seamless blend of contemporary design and Hamptons elegance. Built in 1995, the single-story residence spans approximately 2,800 square feet and is ideally positioned moments from Bridgehampton and just over a mile to pristine ocean beaches. The outdoor setting is a true sanctuary, featuring a heated pool, beautifully appointed pool house, expansive rolling lawn, and a shaded dining pavilion complete with a barbecue, perfect for effortless summer entertaining. Inside, the home is bathed in natural light, with airy interiors defined by crisp white tones, clean architectural lines, and modern finishes. The main living room centers around a striking brick fireplace, while the open-concept dining area flows seamlessly into a fully updated kitchen designed for both everyday living and hosting. The residence offers4 total bedrooms and 4 full baths, including a luxurious primary suite and a junior primary suite with its own fireplace. Each bathroom is fully renovated in marble, delivering spa-like comfort throughout. Additional amenities include central air conditioning and high-end furnishings, with the home elegantly appointed in all-new pieces from Restoration Hardware. A refined Sagaponack escape offering style, comfort, and proximity to the very best of the Hamptons. [[Rental Registration # RP230701]] EH RR #: RP230701 Rental Terms: October: $25,000 Other / Short Term - Year Round: $220,000

Set on nearly three-quarters of an acre in Wainscott, this beautifully appointed five-bedroom, five-and-a-half-bath residence offers an exceptional Hamptons retreat, combining generous living spaces, privacy, and effortless indoor-outdoor entertaining. Spanning approximately 4,000 square feet, the home features five spacious ensuite bedrooms, providing comfort and privacy for family and guests alike. Light-filled interiors and inviting gathering spaces create an ideal setting for both relaxed everyday living and summer entertaining. Outdoors, the beautifully landscaped grounds back onto a peaceful reserve, offering a secluded setting centered around a heated Gunite pool. An additional pool house/studio provides flexible space for recreation, relaxation, or working from home. Conveniently located near Wainscott's ocean beaches and just minutes from the restaurants, boutiques, and attractions of East Hampton Village, this property offers an ideal balance of tranquility, convenience, and classic Hamptons summer living. [[Rental Registration # 25-970]] EH RR #: 25-970 Rental Terms: Other / Short Term - Extended Season: $25,000 July: $55,000 June/July: $75,000 July - Labor Day: $110,000 June: $30,000 Memorial Day - Labor Day: $135,000 August - Labor Day: $65,000 August: $55,000

Experience summer in this elegant 7-bedroom, 9.5-bath estate set behind tall privets in one of Sagaponack North's most desirable neighborhoods. Spanning approximately 11,000 square feet on the largest fully cleared property on the street, this impressive home offers exceptional privacy, scale, and classic Hamptons living. Manicured grounds feature expansive bluestone terraces, an oversized 20x45 heated pool, spa, and sprawling lawn with ample space for recreation. The setting is both refined and bucolic, bordered by open farmland and a nearby 7-acre horse riding facility, with close proximity to Wolffer Estate Vineyard, Sagaponack Farm Distillery, golf courses, farm stands, and garden nurseries. Inside, 11-foot ceilings highlight the first floor, featuring a grand living room and family room, each with a fireplace and views of the sun-filled backyard. A formal dining room, Bakes & Kropp chef's kitchen with butler's pantry, and breakfast room offer seamless entertaining. The first level also includes a secondary primary suite, an additional en-suite guest bedroom or office, mudroom, laundry, pool bath with sauna, and three-car garage. The second floor features a luxurious primary suite with private terrace, sitting room or office, wet bar, walk-in closets, and a marble bath. Four additional en-suite bedrooms, a mahogany deck, and second laundry complete the upper level. The finished lower level offers a theater, 1,400-bottle handcrafted mahogany wine cellar with tasting room, expansive living and entertaining space, full bath, and additional bonus room. Ideally located just minutes to Bridgehampton, Wainscott, Sag Harbor, and ocean beaches, this timeless Sagaponack estate offers every amenity for an exceptional Hamptons summer. [[Rental Registration # Pending]] Rental Terms: Other / Short Term - 8/1/2026 - 8/8/2026: $40,000 August - Labor Day: $190,000

This spectacular Sagaponack estate offers the best of Hamptons luxury lifestyle. Designed by a renowned interior designer, the graciously appointed interior flows easily to an outdoor living/dining patio, heated gunite pool, hot tub, tennis court, and exquisitely landscaped garden and lawn. The main floor has a living room, great room open to eat-in kitchen, formal dining room, butler's pantry, powder room, and en-suite bedroom. Upstairs has an additional primary suite, and three bedrooms ensuite with a sitting room and three bathrooms. The lower level includes a large luxury bedroom with an excavated, landscaped window well, a den/media room/exercise room and a staff bedroom and bathroom. Amenities include a fully enclosed lot with driveway gate, an attached garage, ample outdoor parking, double laundry room, speaker system, Wi-Fi, and security system. [[Rental Registration # 20251042]] EH RR #: 20251042 Rental Terms: Two Weeks: $120,000 June: $135,000 July: $195,000 June/July: $295,000 Other / Short Term - Year Round: $850,000 Memorial Day - Labor Day: $500,000 August - Labor Day: $225,000