luxury houses with pool 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

This bright and spacious home, nestled down a private driveway and adjacent to a scenic reserve, is a hidden gem off Lumber Lane in Bridgehampton. Ideally located between the charming Villages of Bridgehampton and Sag Harbor, and a short distance from both ocean and bay beaches, this delightful 3-bedroom house boasts a second-floor primary bedroom with its own deck. The expansive double-height living room flows seamlessly to the dining area and a well-appointed chef's kitchen. Glass doors open to a generously sized deck, perfect for summer gatherings, overlooking the inviting heated pool. A detached garage, featuring a home office, adds to the appeal. Residents may also enjoy access to nearby tennis courts, enhancing the quintessential Hamptons experience [[Rental Registration # RP201993]] EH RR #: RP252090 Rental Terms: Memorial Day - Labor Day: $95,000 July - Labor Day: $80,000 June: $20,000 August - Labor Day: $42,000 July: $38,000

Get ready for the perfect summer vacation in this newly renovated and fashionably furnished Bridgehampton Estate. Entering into an oversized living room, this home has many gracious living spaces. The first floor has a newly designed master suite, walk-in closet, oversized master bath, with a gracious shower, soaking tub, and a private covered porch, with heat lamps. There are three additional bedrooms that are all beautifully decorated with newly renovated baths. The kitchen is sun-filled with sleek cabinetry, and a built-in stone dining table. The lower level is fully finished and is great for lounging and watching movies, or the perfect place for the little ones to play. The backyard has it all. Enjoy your summer days lounging around the heated pool and grilling on the beautiful deck enjoying spectacular western sunsets. The backyard is very private with tall hedges, beautifully manicured landscaping, and agricultural reserve views. Located on Lumber Lane, this home has the perfect location. You are minutes to Bridgehampton town and a straight shoot to the beach, driving up Ocean Road. You are also super close to Sag Harbor Village, perfect for dinners out with the family, or casual shopping. [[Rental Registration # Pending]] EH RR #: ra241558 Rental Terms: July: $110,000 July - Labor Day: $230,000 August - Labor Day: $125,000 August: $110,000

Beautifully sited on 3 acres in a most desirable area on Bull Path, East Hampton, this stunning 4 bedroom 4 bath traditional offers the absolute in comfort, enjoyment and privacy. From the limestone entry to the honed black granite and cherry kitchen, superb finishes and attention to detail are evident throughout. The well proportioned living room with fireplace has a bank of French doors that open to a very generous screened porch with ample space for both dining and lounging. For something more formal, there's a separate dining room surrounded by windows, just right for sunsets. The den/media room offers a pullout sofa, cushy chairs and all the audio/video equipment. The house is wired for sound, too. The large primary suite features a gas fireplace, private terrace and exquisite marble bath with soaking tub. In the opposite wing, you'll find two comfortably sized guest rooms each with en suite baths. Outside, there's pure pleasure, extensive mahogany decks overlook the heated gunite pool, spa and the wonderfully landscaped grounds featuring stacked stone walls, perennial beds, ornamental grasses, shrubs and lawn. It's your own private paradise, one of our very best rentals and just minutes from East Hampton Village. [[Rental Registration # 26-1169]] EH RR #: 26-1169 Rental Terms: Memorial Day - Labor Day: $150,000 November: $20,000 Other / Short Term - Dec: $15,000 October: $20,000 August: $75,000 July: $65,000 June: $25,000 September: $25,000

A rare Sagaponack compound, offering 7 bedrooms in total, designed by Val Florio on +/-1.6 acres of curated landscaped grounds. Surrounded by open sky and farmland vistas, the main residence offers sun-filled living spaces, elegant detailing with casual beachy interiors and generous proportions throughout. Gathering rooms open to expansive mahogany decking and manicured lawns, creating a natural flow for summer living. The fully equipped guest cottage provides an additional three bedrooms, ideal for hosting extending family, staff, or friends while maintaining privacy and comfort. The homes are connected through a tunnel in the finished lower level. The heated gunite pool is complimented by a stylish pool pavilion and sunken pickle-ball court. Located across from Wolffer Estate Stables, Sagaponack's premier horse farm, around the corner from Wolffer Vineyard, and close to world class Sagg Main Beach. This compound delivers the ultimate Hamptons experience minutes from the best of Bridgehampton and Sag Harbor. Rental Terms: July - Labor Day: $300,000 August - Labor Day: $175,000 July: $150,000 Other / Short Term - 10/1/2026 - 4/30/2027: $55,000 June: $75,000

This beautiful, airy five bedroom home is situated on a quiet road in the Northwest Woods just a few miles from the ocean and a mile from the bay. A guest suite on the ground floor sleeps four and has a perfectly appointed bath. The large living room with a screened-in porch is a perfect spot for entertaining. Upstairs there are three more bedrooms and two baths. The home is filled with natural light and features skylights and a fireplace for cooler nights. There is a washer/dryer, dishwasher, cable TV and wifi. The pool is heated and there is AC throughout the home. [[Rental Registration # Pending]] EH RR #: 24-1190 Rental Terms: July: $30,000 August - Labor Day: $35,000 June/July: $55,000 June: $25,000 July - Labor Day: $60,000 Memorial Day - Labor Day: $75,000

Stylish 5-Bedroom Retreat with Pool and Tennis Court in the Heart of Bridgehampton. Close proximity to town and train. Rental Terms: July: $55,000 February: $8,000 January: $8,000 Memorial Day - Labor Day: $160,000 November: $8,000 March: $8,000 August - Labor Day: $75,000 Other / Short Term - Dec: $8,000 October: $8,000 April: $10,000 June: $30,000

Rental Registry #: 22-1364, Expires 09/02/2024. Also Available: July 15th - July 30th $60k, July 15th - August 15th $130k, August 1st - August 31st $130k Enjoy the smiles on everyone's faces as they arrive for the summer vacation they have been dreaming about. Enter through the gate, down a long driveway to this secluded award winning Bruce Nagel modern 7000+/- sf oasis over three levels providing three seamlessly integrated living spaces that thoroughly delight the senses. The central living area is a balanced medley of light and volume drawing your attention to the refined front garden or the notable outdoor entertaining, pool and garden room environs. This central gathering wing is comprised of the formal living and dining rooms sharing a architecturally significant double sided fireplace, and an informal great room with sensational kitchen, casual dining, and second fireplace. Two sets of sliding French doors meticulously placed, invite you to the outdoor living room. The principal bedroom suite is situated to the right side of the central living area ensuring complete privacy. The spacious sleeping chamber is complete with a writing desk set against stone wall back drop and its own fireplace. The art filled pass through leads to spa-like bath with double vanity, shower and free standing bath. Walls of glass open to a private patio with sitting area and spa. An artfully positioned opening draws you to the pool beyond. A gallery style library connects the main residence with the subtle modern barn elements of the guest wing. Here one finds a first floor guest suite, powder room and guest living area featuring walls of glass anchored by hewn beams and a spectacular two story stone fireplace. Take the staircase to the second level reading loft and three additional guest suites. Break away from everyone and head to the lower level walk out media room, gym, or if you must, the multi-desk professional office area. If in need of rejuvenation, enjoy the sauna and massage room with adjacent bath and close the door for a relaxing rest before preparing for the evening. There is ample parking for everyone, and attached multi-space garage. The amenities of East Hampton and Sag Harbor Villages and the pristine ocean beaches are easily accessible for this exceptional summer offering. [[Rental Registration # 22-1,364]] EH RR #: 22-1,364 Rental Terms: May: $95,000 August: $150,000 July: $150,000 June: $115,000

Rental Reg. # RP220705 exp. 9/1/24 Also Available: August 16 - September 2 for $250,000 This highly designed new construction--a designer's own home--offers every amenity. The magnificent 11,000+/- sq. ft. estate spans 2+/- lush acres, but feels like it sits on 50 acres, with panoramic reserve views to the West. Enjoy spectacular farm vistas and sunsets every day. It is unique--as the largest and closest field-view estate just outside Bridgehampton Village. The property is a 1/2 mile to some of the Hamptons best restaurants (including Topping Rose, Almond and Pierres), boutiques and shopping. The backyard is nothing short of a resort. The home offers a 50' heated gunite pool, hot tub, and sunken all-weather tennis court. The outdoor terrace stretches the entire length of the house with two covered porches, a state-of-the-art outdoor kitchen, firepit and new outdoor furniture ensuring everyone will relax in comfort. As well, you will be amazed by the thoughtfulness of the interior design. It comes lovingly appointed by Katie White Interiors, replete with gorgeous, hand-selected furniture and artwork that offer elegance, yet a comfortable modern and beachy vibe. The open concept living areas include the living room and great room, eat-in kitchen with Subzero/Wolf appliances (2 full fridge/freezers), a breakfast area, and multiple glass doors that open to an expansive stone terrace and covered porches. There is a highly designed formal dining room, One of the two primary suites is on the first floor (or can be furnished as an enormous office). A mudroom, with laundry and full pool bath round out the first floor. An architectural free-floating modern staircase leads upstairs, where a second luxurious primary suite features a generous balcony with outdoor furniture for lounging any time of day. Four additional ensuite bedrooms, two of which share a large balcony, are also on this level, along with a laundry room. The finished lower level provides large media/recreation space, a gym, and two additional bedrooms. The house has a state-of-the-art sound system and comfort controls. [[Rental Registration # RP220705]] EH RR #: RP220705 Rental Terms: July: $350,000 June/July: $500,000 Other / Short Term - Year Round: $1,300,000 July - Labor Day: $700,000 August - Labor Day: $400,000 June: $200,000

147 Wainscott Harbor Road presents a stunning retreat designed by the acclaimed architect Robert A.M. Stern. This renovated home, situated on 2.8+/- acres, spans 3,600 SF+/- and offers five bedrooms, three full bathrooms, and one half bath. Its prime location provides effortless access to Bridgehampton, East Hampton, Sag Harbor Villages, and the area's picturesque ocean beaches. Every detail of the home has been crafted for both comfort and style. The first level features inviting spaces for seamless entertaining, including a gracious dining room and a living room anchored by a cozy fireplace. Both rooms open to an expansive screened-in porch with ample seating for relaxing or gathering with guests. The eat-in kitchen is a chef's dream, outfitted with top-of-the-line Viking appliances, a central island, and a sunny breakfast area. The first-floor primary suite is a serene retreat, bathed in natural light from oversized windows. The spa-like primary bathroom includes dual vanities, a freestanding soaking tub, and a separate glass-enclosed shower. Upstairs, four additional bedrooms, two full baths and a bonus space offer beautifully designed interiors and flexible living options. The sprawling grounds include lush, manicured lawns, a large heated gunite pool and spa and a DecoTurf all-weather tennis court. 147 Wainscott Harbor Road nestled in near Sagaponack North is the epitome of refined Hamptons living, blending thoughtfully designed interiors and exceptional outdoor amenities in a premier location. Rental Terms: Two Weeks: $55,000 October: $30,000 Other / Short Term - 5/22/2026 - 6/15/2026: $40,000 September: $40,000 May: $30,000 Winter Season: $10,000 Per Month