luxury house with pool for rent Wainscott, United States

Overlooking 55+/- acres of west-facing reserve on Erica's Lane deep in Sagaponack South minutes from the ocean, this stylish 4-bedroom shingled traditional features a newly updated kitchen and bathrooms, new heated, gunite pool with gleaming white surround, Har-Tru tennis court, fire pit with Adirondack chairs, and playset. Central A/C, Sonos, cable, Wifi, HDTVs, 3 sets of washer/dryer, 2 additional full-size refrigerators and wine fridge. Rental Terms: August - Labor Day: $160,000 July: $140,000 Memorial Day - Labor Day: $350,000 June/July: $190,000 September: $50,000 June: $50,000 Other / Short Term - 8/1/2027 - 9/30/2027: $200,000 July - Labor Day: $300,000

In a most sought after location only a block from the beach, this 6000+/- sq. ft. exquisite modern beach house with center courtyard offers the best in clean yet sophisticated modern design, and features second level master wing with sitting salon/library giving to panoramic views of the perfectly manicured grounds, 3 en-suite guest bedrooms, open dining room and gourmet kitchen with top-of-the-line appliances, custom cabinetry, and large stainless steel island/bar, den/media room, living room with wood burning fireplace and large theater screen, second level office/den with gas ribbon fireplace, and gym. The home reflects the finest in workmanship, materials and technology throughout including use of glass with floating slatted walls, radiant heated slate floors, wide-plank pine floors, LED lighting, Crestron technology and back-up generator. Pool house with large wood hot tub, shower and bath opens directly to oversized heated gunite pool. Rental Terms: August - Labor Day: $175,000 September: $100,000

Ideally situated just moments from the pristine ocean beaches of Beach Lane, this beautifully renovated five-bedroom, four-bath Hamptons farmhouse offers an exceptional combination of timeless charm, modern comfort, and effortless indoor-outdoor living. Set amid lush, professionally landscaped grounds, the shingle-style residence is distinguished by its inviting interiors, wide-plank hardwood floors, abundant natural light, and unique architectural details, including a beautifully reclaimed barn transformed into a stunning living room with French doors opening to the lawn. Designed for both relaxed summer living and elegant entertaining, the home features a professional-grade kitchen that flows seamlessly into the great room and breakfast area, overlooking the expansive outdoor patio and heated Gunite pool. Generous living and dining spaces extend onto a spacious deck, where covered seating and alfresco dining areas create an idyllic setting for summer gatherings. Vaulted ceilings and exposed wood beams lend warmth and character throughout select rooms, while five well-appointed bedrooms provide comfortable accommodations for family and guests. The beautifully maintained grounds offer exceptional privacy, with mature trees, expansive lawns, and a charming, thoughtfully appointed pool house and outdoor shower completing the outdoor experience. Just moments from Wainscott's beloved farm stand, ocean beaches, and the world-class shopping and dining of East Hampton and Bridgehampton, this exceptional property embodies the relaxed sophistication and timeless appeal of Hamptons living. [[Rental Registration # 24-432]] EH RR #: 24-432 Rental Terms: June/July: $135,000 August: $110,000 July - Labor Day: $200,000 September: $35,000 July: $110,000 May: $30,000 June: $45,000 Memorial Day - Labor Day: $250,000 August - Labor Day: $120,000 Other / Short Term - Year Round: $325,000 April: $15,000 Winter Season: $43,000 Per Month

Available 1st two weeks of July 2026. Renovated to the highest standards this beautiful traditional home is waiting for your summer enjoyment. The house consists of 4 bedrooms, 4.5 baths, living room/dining room, open gourmet kitchen with top-of-the-line appliances, family room and 3 cozy fireplaces. On the main floor the 4th bedroom set up as office with pull-out couch and full bath. Romantic cottage for (legal) sleeping has king bed and full bath. Savant sound system throughout main rooms, outdoors and the primary bedroom which has a fireplace and covered porch with tranquil views of the pool, mature gardens and specimen trees. The heated gunite pool comes equipped with underwater speakers and spa, the patio offers long summer days of sunbathing and dining. Charming stone pump house conceals pool equipment. [[Rental Registration # 25-477]] EH RR #: 25-477 Rental Terms: Two Weeks: $65,000

Discover the quintessential Hamptons lifestyle in this beautiful 3-bedroom, 2-bathroom retreat nestled at 39 Roxbury Lane, Wainscott. Tucked away on a quiet, sun-drenched lot in one of the East End's most coveted hamlets, this turnkey home offers an unparalleled blend of absolute privacy and effortless proximity to everything that makes the Hamptons legendary. Step inside to a dramatic, double-height great room bathed in natural light, featuring soaring ceilings, crisp architectural lines, and a warm wood-burning fireplace. The open-concept layout flows seamlessly into a fully updated chef's kitchen, outfitted with premium stainless steel appliances and a spacious breakfast bar perfect for casual entertaining. Transition upstairs to find a versatile open loft area-ideal as a dedicated home office, a cozy den, or an extra guest nook. Sliding doors create a seamless indoor-outdoor flow out to an expansive deck and a heated pool completely enveloped by mature privacy plantings. Perfectly positioned between East Hampton and Bridgehampton, this home sits just moments from ocean beaches and local farm stands. [[Rental Registration # 26-218]] EH RR #: 26-218 Rental Terms: April: $10,000 July: $40,000 June: $25,000 June/July: $65,000 August: $40,000 August - Labor Day: $50,000 Other / Short Term - Year Round: $130,000 July - Labor Day: $85,000 Winter Season: $20,000 Per Month November: $8,000 Memorial Day - Labor Day: $110,000 May: $15,000

Rental Registration #: 24-114 expires February 2, 2026 Impeccable and private, this home is located South of the Highway down a wooded lane that feels worlds away from the city and town, but is in fact very conveniently located near Wainscott village and East Hampton, and a quick bike ride to the beaches and historic estates around the corner. An open concept in the barn-inspired great room offers plenty of style and serenity, yet there is plenty of fun set aside in the adjoining wing, with a game room/family room and two bedrooms that can act as it's own guest suite or a perfect extension of the home for the kids. Large level yard with pristine pool and covered patio will be your pride and joy for the summer, welcoming family and friends. Another two ensuite bedrooms are on the upper level, allowing for dramatic views of the beamed great room. When you need your retreat within the retreat, enjoy the master suite with beautiful barn door leading to a simply elegant spa style bath. [[Rental Registration # 26-1]] EH RR #: 26-1 Rental Terms: Other / Short Term - 5/25/2026 - 6/30/2026: $60,000 May: $16,000 August - Labor Day: $110,000 November: $16,000 October: $16,000 September: $16,000

Spectacular living awaits in Sagaponack South, this bespoke home offers 10,000 +/- square feet on 1.5 +/- private acres. Custom build in 2013, this chic residence features seven spacious bedrooms and seven+ baths. This modern masterpiece was designed by Francis D'haene of the award winning architectural firm D'apostrophe Design. Enter into breathtaking light-filled living space graced by walls of glass through a dramatic double-height entryway with a travertine floating staircase and solid white oak floors. This home includes an 68' heated gunite infinity pool, pool house, outdoor shower and full outdoor dining/kitchen area. The ultimate setting for entertaining and enjoyment. 183 Daniels Lane makes a grand statement of elegance while affording contemporary comfort. Rental Terms: Two Weeks: $200,000 August: $450,000 Memorial Day - Labor Day: $950,000 August - Labor Day: $500,000 July: $400,000 June: $200,000

Delightful traditional in exceptional condition with 4 bedrooms, 4 1/2 baths, central air, heated pool, beautiful deck and garage. Furnished beautifully inside and has new teak deck furniture for the outdoors. Centrally located and ideal for summer or year-round living. Excellent opportunity. [[Rental Registration # 22-1531]] EH RR #: 24-1328 Rental Terms: July: $55,000 Other / Short Term - Year Round: $155,000

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

Also available August for $150K. Turn South from fabled Parsonage Lane onto a long private driveway that leads to this 1.7 acre property that backs onto 16 acres of agricultural reserve. There are 5 bedrooms and 6.5 baths in this immaculate modern design with plenty of South and West facing patio for outdoor dining and taking in the view of the lawns, gunite pool and pool patio. Just minutes to Town Line ocean beach. Rental Terms: July: $110,000 August - Labor Day: $150,000 July - Labor Day: $250,000 Other / Short Term - August: $125,000

Location! Location! Location! This Modern home is sited on over 1.5 glorious acres south-of-the highway in Sagaponack, and features 6 bedrooms, 7 bathrooms, an open kitchen, dining area and great room with walls of glass allowing for easy access to the backyard. Three car attached garage. Outside, the expansive decks surround the over sized heated gunite pool, and the professionally landscaped property provides the ultimate setting including a fire pit. Located around the corner from the ocean, this home has it all! Rental Terms: Memorial Day - Labor Day: $350,000

Beautifully appointed clean and fresh 4 bedroom 4 bath rental in Wainscott available for seasonal or year round use. Oversized windows offer plenty of light along with stone fireplace and stylish comfortable furnishings in the living room. A chef's kitchen and eat in island provide an ideal area for cooking and entertaining with a dining area for more formal dining. A lovely covered terrace overlooks 2 acres of privacy including heated gunite pool, lounging area and enchanting landscape with raised field stone accents . Spacious and private with easy access to the very best of Hamptons' living. EH RR #: 18-2245 Rental Terms: August - Labor Day: $50,000

This unique property exudes beauty and tranquility in best South of the Highway location. Close to Sagaponack beaches this charming 3 bedroom house has never been offered for rent. Situated on 1.16 acres of beautifully landscaped vistas by renowned landscape designer, Edwina Von Gal, overlooking Sagg Pond. Any 2 weeks from June 15 - July 27, 2026 for $40,000 Any 3 weeks from June 15 - July 27, 2026 for $70,000 3 weeks from August 17 - September 8, 2026 for $90,000 2 weeks from August 24- September 8, 2026 for $70,000 5 weeks from August 3 - September 8, 2026 for $160,000 Rental Terms: Other / Short Term - Short-Term: $160,000

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 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

Nestled within the coveted Georgica Estates enclave of East Hampton and just moments from the iconic sands of Georgica Beach, this five-bedroom, four-bath residence offers an opportunity to experience one of the Hamptons' most treasured settings with remarkable ease. One of East Hampton's original homes, it carries a sense of history and authenticity that feels increasingly rare. Privately positioned among extraordinary neighboring estates, the property is embraced by mature trees, sweeping lawns, and established gardens, creating a tranquil sanctuary in a premier location. The proximity to Georgica Beach allows for effortless daily rituals - early morning shoreline strolls as the light rises over the Atlantic, spontaneous afternoons by the water, and golden sunset returns as the sky softens into evening. The rhythm of the ocean becomes part of everyday life. Inside, the atmosphere is relaxed and quietly elegant. Sunlight fills the interiors, doors open naturally to the outdoors, and coastal breezes drift through the rooms. The aesthetic is collected and organic - inviting, personal, and uncontrived - offering a refreshing sense of ease. This is a home where sandy towels are draped casually, a place to gather, to read late into the afternoon, and to return from the beach with sandy feet and salt in the air. Lovingly maintained and artist-owned, the home carries a soulful presence. Its aesthetic reflects a collected, organic sensibility - layered, personal, and inviting - offering a refreshing alternative to more polished environments. It is a place to exhale, to gather, to read late into the afternoon, and to return from the beach with sandy feet and salt in the air. A true Georgica retreat for those who value privacy, proximity to the ocean, and the quiet luxury of simplicity. Available August through September. Rental Terms: August - Labor Day: $80,000 July: $75,000

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

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

Wainscott Opportunity - Traditional Home with pool on nearly a half-acre in the heart of Wainscott. The home offers an open and inviting layout that is ideal for entertaining. The spacious living areas flow seamlessly, with natural light enhancing the home's warm character. There is a cozy den and bedroom on the main level with a full bath. On the second level, there is an ensuite primary bedroom with two additional bedrooms and a bath. Outdoors, enjoy a private heated pool and outdoor shower, surrounded by mature landscaping that enhances an idyllic summer retreat. Just a short distance to ocean beaches, local farm stands, and Wainscott shopping, offering a very convenient location. . [[Rental Registration # 26-823]] EH RR #: 26-823 Rental Terms: Winter Season: $50,000 Per Month July: $35,000 August - Labor Day: $45,000 July - Labor Day: $80,000 Memorial Day - Labor Day: $95,000 June: $20,000 June/July: $55,000

Spend your summer in style at Georgica Estates, East Hampton's premier condo community where each unit is a freestanding home offering the privacy and comfort of a single-family residence. Only 10 minutes to Sag Harbor Village & Bridgehampton, this light-filled 4-bedroom, 3.5-bath townhouse is set among nearly 8 beautifully landscaped acres and features an open, airy floor plan perfect for summer living. The first-floor primary suite offers convenience and privacy, while the second level provides three spacious guest bedrooms. With high ceilings, large windows, and sun-drenched living spaces, this home feels bright, cheery, and welcoming. Enjoy cooking in a modern open kitchen with quartz countertops, and stainless steel appliances, and entertain on the private wood deck with a large awning, surrounded by lush gardens and greenery. Other features include hardwood and ceramic tile floors, central air, washer/dryer, fireplace, and a 1-car attached garage. Community amenities are top-tier and meticulously maintained, including: A clubhouse Heated pool 2 tennis courts Pickleball Manicured grounds with walking paths Whether you're looking for a full-season rental or a month-by-month stay, this home delivers carefree luxury with every convenience just minutes from East Hampton Village and world-class beaches and restaurants. Sorry, no pets. HOA: Georgica Estates. Rental Terms: Two Weeks: $18,000 August - Labor Day: $45,000 August: $38,000

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

This Bridgehampton South classic country farmhouse nestled far off the road on a deep flag lot a 1/4 of a mile to town. This charming house is surrounded by hydrangea in a very private .53-acre parcel. A heated salt-water Gunite pool with a sunning level provides for luxurious sunbathing and a private back deck is partially shaded for evening grilling, and dining alfresco. The large custom chef's kitchen is a focal point of the home lined with a custom built-in bar, display cabinets and a restaurant-grade professional 6-burner + grill Viking range, Subzero fridge, and wine/beverage fridge. A ground-floor bedroom and full bath complete the first floor. Upstairs are two extra-large bedrooms, with a shared bath. The lower level has an exterior stair up to the garden. Perfect for an au-pair or private guest suite, there is a bedroom, separate living room with kitchenette, and full bath. The house is a quick bike ride from coffee in town or pop to the ocean along farm field lanes. [[Rental Registration # RP240795]] EH RR #: RP240795 Rental Terms: July: $40,000 August: $45,000 July - Labor Day: $75,000 Other / Short Term - 5/22/2026 - 8/31/2026: $90,000 Memorial Day - Labor Day: $100,000 June/July: $60,000 August - Labor Day: $50,000

Originally part of an estate on Lily Pond Lane, this classic Hamptons home was relocated to its current position in Dune Alpin in the early 1990's. The bucolic horse farms and association tennis play host to a summer oasis complete with four bedrooms, three baths, oak plank flooring, renovated kitchen and baths, formal dining and living as well as a bonus second floor media room. The private yard is complete with a bluestone patio and a gunite pool as well as a newly-crafted scenic garden. The quintessential home is ideally located between East Hampton and Wainscott and close to transportation, shops, restaurants, farms and ocean beaches. [[Rental Registration # 22-394]] EH RR #: 25-48 Rental Terms: July - Labor Day: $89,000 July: $39,000 August - Labor Day: $50,000