luxury houses with pool for rent Southampton, United States

Ideally situated in the heart of Southampton Village this 8 bedroom, 7 1/2 bath home has been lovingly restored to its original excellence with modern amenities. The first floor offers an open and bright Living Room, a sunny family room, a guest bedroom with a bath, a very large and open kitchen with walls of windows and glass doors that lead to the large stone patio, a formal dining room, and a game room. The second floor has a large master suite with 2 baths and a private deck, and 3 large guest bedrooms with 2 baths. The charming third floor has 3 additional guest bedrooms and bath. The lower level has a media room, a full bath, and a laundry room. There is a heated gunite pool, a pool house with a bath and outdoor shower, and a detached 2 car garage. Just a short block from Main Street and Jobs Lane and less than a mile to the ocean beach this home exemplifies summer living at its best. Fabulous, luxurious and light filled, it's the perfect summer retreat. Rental Terms: August: $150,000 July: $120,000 August - Labor Day: $160,000 June: $60,000 Memorial Day - Labor Day: $320,000

Conveniently located, winter or summer living will be seamless in this 2 bedroom 2.5 bath townhome. Recently renovated and styled. Open living, eat in kitchen, and back deck area perfect for evening barbecues. Community tennis, pickle ball, putting range, 2 pools and quick access to village shops and ocean beaches! [[Rental Registration # Pending]] EH RR #: condo n/a Rental Terms: July - Labor Day: $40,000 Memorial Day - Labor Day: $50,000

Stylishly renovated and beautifully appointed, this Southampton village home has it all. Spacious gourmet eat-in kitchen, two living rooms, media room, fireplace, sunporch, and finished lower level with gym (including Peloton Bike+ and Hydrow Rower). Four bedrooms and four baths in main house. Multiple seating and dining areas outside amidst the stunning landscape, provide perfect entertaining spaces both under the sun and protected. The newly redone pool house offers sophisticated living space. Heated gunite pool, lovely lounge furniture, market umbrellas, retractable awning, wisteria covered pergola, outdoor shower, customer gas bbq, there's nothing that has been overlooked for those seeking the amenities of a 5 star vacation hideaway just minutes to Main Street. Rental Terms: Memorial Day - Labor Day: $250,000 Other / Short Term - Year Round: $290,000

Recently, Freshly renovated Beach House with new kitchen and new bathrooms. The main house has 4 bedrooms on the second floor with a total of 3 baths in main house. The legal accessory apartment houses the bunk room and full bath. Extensive new mahogany decking and an outdoor shower. Beautiful, private yard with a gunite heated swimming pool and lush lawn areas. In close proximity to ocean beaches and Village amenities. Rental Terms: July - Labor Day: $169,000 June/July: $129,000 September: $50,000 July: $80,000 August - Labor Day: $90,000 June: $50,000 Memorial Day - Labor Day: $185,000 August: $80,000 April: $10,000 Other / Short Term - Year Round: $250,000 May: $20,000

Conveniently located minutes to Southampton Village, with community tennis, playground, and park, this +/-6000sf custom home is now available either July or August 2027. An open floor plan with chef's kitchen, informal dining, two living rooms, and a study. The primary suite is well-appointed on the main floor with two walk-in closets, a luxurious bathroom, and new deck leading to the backyard. Upstairs, there are four additional bedrooms and four bathrooms. Laundry on both the second and first floor(s). The finished lower level affords a designated work-out area and more space to lounge and spread out. Outside is an outdoor kitchen with stainless BBQ, a beverage refrigerator overlooking the heated saltwater gunite pool and spa and a new infrared sauna. [[Rental Registration # RP241064]] EH RR #: RP241064 Rental Terms: August: $90,000 July: $90,000

Perfectly located on a quiet flag lot in Southampton Village, just minutes from Main Street and the world-famous Coopers Beach, this meticulously maintained seven-bedroom, six-full and two-half-bath Hampton classic offers the very best of Village living. Complete with a heated gunite pool, spa, outdoor shower, 2-car garage and beautifully landscaped grounds, this elegant shingled home is designed for effortless summer enjoyment. Bright, airy interiors and seamless access to the expansive rear deck and pool area create an inviting atmosphere. An impressive double-height entry foyer welcomes you to the main level, featuring a spacious living room, formal dining room, gourmet kitchen with a large center island and multiple seating areas, a comfortable tv den, powder room and main floor laundry. Upstairs, the generous primary suite overlooks the pool and includes a luxurious ensuite bath. Four additional guest suites, one of which serves as a home office, complete the second floor. The thoughtfully designed lower level offers a media and television area, an additional guest suite and a guest bedroom. With direct access to the pool area as well as an additional powder room, the lower level is ideal for family and guests alike. Surrounded by mature hedging and lush landscaping, the private backyard is an oasis. With heated gunite pool, spa, outdoor shower, expansive deck, gas grill, vegetable garden and multiple seating areas, this property is the perfect setting for entertaining and relaxed summer living. Enjoy the summer in privacy, comfort, and convenience in one of the Hamptons' most desirable locations. Rental Terms: July: $125,000

This gorgeous newly constructed 3,700 +/- sq. ft. shingled home is the perfect residence for the Summer 2024 rental season, or next Fall and Winter. The property is situated on a quiet lane South of the Highway in the heart of Southampton Village and just over one-half mile to the ocean beaches. This sun-filled custom residence offers an impressive great room with professional kitchen, living room, double-sided fireplace to back patio, large glass enclosed wine closet, and high ceilings, along with a media room, study, and sun room on the first floor. A spacious primary bedroom suite and two bedrooms and bath are located on the second floor, and the top floor offers an ensuite bedroom. The outdoor living space includes a salt-water gunite pool, blue stone patio with fireplace, and sunny lawn. The 500+/- sq. ft. pool house features a room with fireplace, kitchenette, full bath, and den. Substantial wall moldings, customized closets, second floor laundry, Nest thermostats, top of the line security system with remote cameras, Sonos, central vacuum, professional landscaping and extensive irrigation complete this impeccably finished house, which is a short distance to the ocean and to Village shops and restaurants. EH RR #: na Rental Terms: Other / Short Term - Dec: $16,000 August: $100,000 November: $16,000 February: $16,000 June: $50,000 January: $16,000 August - Labor Day: $115,000 March: $16,000

The peacefulness and serenity of a summer on the East End awaits you in this fully renovated Southampton home. Offering breathtaking views of Peconic Bay and Bullhead Beach, this four bedroom home features 3 over-sized bedrooms each with their own private bath, an open concept main floor with a brand new kitchen, dining room, and a massive great room with vaulted ceilings, gas fireplace and wet bar. Outdoor amenities include a 20'x 40' custom inground pool surrounded by an oversized deck with lush landscaping throughout. If golf is your game, this home literally is surrounded by the top three courses on Long Island (Shinnecock Hills, Southampton and National) Luxury shopping and world class dining are both minutes away in the village of Southampton. This home is the perfect escape from hectic city life, yet it is conveniently located for those in need of a quick return to the hustle and bustle of greater New York City. [[Rental Registration # RP260397]] EH RR #: RP260397 Rental Terms: Memorial Day - Labor Day: $110,000 July: $45,000 August: $45,000 July - Labor Day: $90,000 June: $25,000 August - Labor Day: $50,000

Experience the best of Village living in this recently renovated, impeccably maintained estate, ideally located just moments from renowned restaurants, boutique shopping, and ocean beaches. Set behind mature specimen trees and surrounded by lush lawns and vibrant gardens, the property offers exceptional privacy and a true resort-like setting. Designed for both entertaining and comfortable everyday living, the home features a dramatic two-story entry and great room, formal and casual dining areas, and a chef's kitchen with double Sub-Zero refrigerators and a large center island. Additional highlights include two spacious family rooms, seven bedrooms, and seven-and-a-half baths, including separate staff quarters. Enjoy an array of premium amenities, including a fully equipped gym, home office/library, detached two-car garage, and an oversized heated saltwater Gunite pool. Outdoor living is elevated with an expansive slate patio, a new covered poolside lounge complete with a gas fireplace, and an outdoor shower, creating the perfect summer retreat. Rental Terms: July: $145,000 Memorial Day - Labor Day: $375,000 August - Labor Day: $185,000 July - Labor Day: $300,000 Other / Short Term - Year Round: $450,000

Just moments from the iconic Shinnecock Hills Golf Club, this inviting Southampton home offers the perfect Hamptons escape. Featuring 4 bedrooms and 3 baths across approximately 2,200 square feet, the residence is set on a beautifully landscaped property ideal for relaxed indoor-outdoor living. A wonderful opportunity to enjoy classic Southampton charm in a highly sought-after location. Rental Terms: Other / Short Term - Weekly: $20,000 Two Weeks: $30,000 June: $60,000

This newer construction is a rare find. The inside features high-end, custom furnishings rarely available in a rental at this price. Gorgeous architecture, interior design and mature landscaping will impress. The 7 Bedroom home (all with ensuite baths) spans 5800 feet above ground, plus 2550 feet of finished lower level. The First floor features a dramatic 2-story foyer, 2 spacious living rooms, a chef's kitchen, bar area. There is a Junior Primary, and a mudroom with pool bath. The Second Floor features a Primary suite with terrace, fireplace, and luxurious white marble bath. There are 4 additional ensuite bedrooms and a second laundry. The lower level offers expansive entertainment space, including a theater, living room, and playroom with ping pong. There is a 7th ensuite bedroom with 2 queen beds. Outside, a South-facing large terrace with overlooks a beautifully landscaped, 1-acre property, with farm views. The yard is private and includes a 40' pool, new sunken hot tub and generous patio space for entertaining. The house sits in a very quiet cul de sac of newer homes, 2 miles to Southampton Village, with Southampton beaches just beyond. The property is a short bike ride or walk to the Southampton Rec Center (SYS) which offers a fantastic children's camp, tennis, gym, basketball, track, yoga, and pilates. Its also 1.5 miles to Towd Point Beach, one of the Hamptons prettiest bay beaches. [[Rental Registration # RP230864]] EH RR #: RP230864 Rental Terms: April: $15,000 February: $15,000 Other / Short Term - 1/1/2027 - 4/30/2027: $60,000 November: $25,000 September: $45,000 October: $30,000 January: $15,000 March: $15,000 Winter Season: $90,000 Per Month

Experience the best of Southampton Village living from this beautifully renovated Gin Lane estate rental, ideally located south of the highway just one block from the ocean. Set on 4 lush acres at the corner of Little Plains Road and iconic Gin Lane, this private summer retreat offers timeless Hamptons style, expansive entertaining spaces, and exceptional proximity to the beach, village boutiques, and renowned restaurants. Recently renovated in 2020, the 8-bedroom, 6-bath traditional residence spans approximately 5,800 +/- sq. ft. and features a bright open-concept layout designed for effortless summer living. Interior highlights include a spacious living room with fireplace, great room with open dining area, updated chef's kitchen with staff area, den/office, first-floor primary suite, and multiple gathering spaces ideal for entertaining guests or extended stays. Outdoor amenities include a heated 40' x 20' Gunite pool, expansive west-facing patio ideal for outdoor dining and entertaining, covered porch, mature landscaping, attached 2-car garage, and sweeping manicured lawns set across 4 private acres. Offering exceptional privacy in a premier Southampton Village location, the property is moments from ocean beaches, world-class shopping, and acclaimed village restaurants. Perfectly suited for Hamptons summer rentals, extended seasonal stays, or year-round living, this Southampton Village estate combines location, scale, privacy, and classic Hamptons charm in one of the area's most coveted ocean-block settings. Rental Terms: Other / Short Term - Year Round: $500,000

Convenience at its best. Newly constructed and first time available for rent. This pristine traditional home is located in the heart of Southampton village. The main floor has an open layout with lots of natural light. Gourmet kitchen, living room with fireplace, wet bar and dining area. There is a first floor en-suite bedroom. Second level has 2 guest bedrooms with a shared bath, master suite and laundry room. Lower level has a sitting area, bedroom and bathroom. There is a heated gunite pool, out door fireplace, outdoor pool bath and detached one car garage. Rental Terms: August - Labor Day: $135,000 July: $120,000 Memorial Day - Labor Day: $245,000 July - Labor Day: $230,000

Spend the summer on one of the most iconic private streets in Southampton Village. The classic Beach House was completely renovated and brought up to todays high standards. The elegant, sunny house offers eight wonderful bedrooms, some with ocean views, and six baths spread out over three floors. The ground floor features a formal dinning room, eat in kitchen with living space, grand entrance hall, and a living room with French doors that go to a covered outdoor living space. The beautifully manicured yard is the perfect place to spend your summer. The in ground heated pool is already fenced in with a rose covered picket fence. The true highlight of this property is the private beach access. Rental Terms: June: $80,000 July: $180,000

Welcome to this exquisite rental property - a custom-built home boasting six bedrooms and seven and a half baths, infused with a modern flair and adorned with high-quality finishes in the Hampton's Style. Situated on a serene cul-de-sac on half an acre, this residence offers expansive outdoor living spaces including a pool house, a built-in BBQ kitchen area, and meticulously landscaped grounds. The effortless flow from the eat in kitchen to the double high ceiling living room makes this the perfect home for entertaining while still feeling compfortable and intimate. The sleek kitchen is a culinary haven, equipped with two Thermadore ovens, an induction cooktop, a built-in coffee machine, and an informal dining area. A butler's pantry connects the kitchen to the formal dining room, enhancing the ease of entertaining. Adjacent to the kitchen is a cozy den and a convenient laundry room. The luxurious primary suite is on the main level, featuring a spacious walk-in closet, a rejuvenating soaking tub, a steam shower, and direct access to the pool area for ultimate relaxation.The centerpiece of the home, a stunning floating staircase, floods all three levels with natural light, creating an ambiance of elegance and warmth. On the second level, four additional bedrooms await, including a king-size room with a balcony that could easily function as a secondary primary suite.The lower level and discover a bunk room, a media room, a gym, and a wine cellar, offering an array of leisure and entertainment options. Rental Terms: April: $15,000 March: $15,000

Charming Post Modern home offers an open floor plan with 4 bedrooms, 4.5 baths, dining area, living area with french doors leading on the back deck, hardwood flooring throughout, heated pool. Cul de Sac privacy. Perfect for year round living. Rental Terms: Year-Round: $125,000

Set south of the highway on a long private country driveway, this distinctive Southampton retreat offers a rare blend of creativity, privacy, and effortless summer living. A spectacular heated gunite pool, sauna, and fully outfitted tiki hut create an exceptional outdoor setting designed for sun-filled days and relaxed evenings. Upon entry, the home unfolds with a natural entertaining flow-an inviting living room to the left, perfect for pre-dinner cocktails, and a dining room to the right, ideal for long, leisurely dinners. Both spaces are bright and welcoming, and a piano adds a playful, social element-perfect for impromptu sing-alongs and easy summer entertaining. The kitchen features a European-inspired aesthetic with expressive design details and a charming Dutch door opening to the outdoors, allowing for seamless indoor-outdoor living all season long. With four ensuite bedrooms plus a powder room, including a first-floor primary suite with direct garden access, the layout is both comfortable and well-suited for guests. Upstairs, a separate bonus room offers a relaxed retreat for movie nights or additional gathering space. The lower level offers the ultimate workout space with a fitenss center. Outdoor living takes center stage, with multiple areas for dining and lounging-perfect for daytime lunches by the pool, afternoons under the tiki hut, and evening barbecues. The grounds feel private and relaxed, offering a true summer escape. A deeded waterfront parcel on Middle Pond provides direct access for kayaking and paddleboarding, with routes leading out to Shinnecock Bay and beyond. Located just minutes from Southampton Village, ocean beaches, and several of the area's premier golf courses, this property captures the ease and style of a Hamptons summer. Rental Terms: July: $55,000 June: $40,000 July - Labor Day: $115,000 Memorial Day - Labor Day: $130,000 August - Labor Day: $65,000

This beautiful home spans approximately 2,500 sq. ft. and is situated on 0.32 acres of land. It boasts an excellent location, in very close proximity to the Atlantic Ocean and a short distance from Southampton Village Center. The property is surrounded by mature hedges and landscaping, ensuring maximum privacy. This classic home exudes charm and is exquisitely furnished with meticulous attention to detail. The house features a spacious and welcoming living room with a fireplace, a den/4th bedroom, a formal dining room with French doors to the patio and beyond, a sunny kitchen equipped with professional appliances, four bedrooms, three and a half baths, a 1st-floor laundry room, a large flat-screen TV, indoor and outdoor stereo systems, lush flowering gardens, a heated swimming pool, a pool cabana with a bathroom, and an outdoor shower. Looking for a serene getaway? This Southampton Village retreat is just what you need! Rental Terms: Other / Short Term - Year Round: $285,000

Enjoy this tastefully decorated, eight-bedroom, eight-bath Traditional home just around the corner from Gin Lane and the ocean. A wonderful opportunity to spend a summer in a perfect European-styled home in the Southampton Estate Section. The house has an open floor plan on the first floor offering a the state-of-the-art kitchen, breakfast area, formal dinning, wet bar and a downstairs bedroom. The six, wonderfully furnished, additional upstairs bedrooms, each with a bathroom and some with private terraces, are accessable through two different staircases. The basement is setup with a staff area and a brand new, huge media room. There is plenty of outdoor entertaining terraces with fireplace, a beautiful pool and nicely landscaped gardens. Rental Terms: July: $160,000 June: $80,000 Winter Season: $100,000 Per Month September: $50,000

Welcome to your dream rental house located in the heart of Southampton Village. This charming four-bedroom home offers a perfect blend of comfort and style, featuring whitewashed floors and beachy details that create a relaxed, coastal vibe. Step outside to discover a lush backyard oasis with a sparkling pool and a stylish pool house, perfect for entertaining or unwinding. Additionally, a separate one-bedroom cottage provides extra space for guests or a private retreat. Experience the best of Southampton living in this delightful home, where every detail has been thoughtfully designed to provide a serene and inviting atmosphere. Rental Terms: Other / Short Term - Year Round: $230,000

This 2,610+/- sqft traditional home has gone through an extensive gut renovation, and full landscaping overhaul. Located in the Village of Southampton on a quiet street, offering 4 bedrooms including a primary suite on the first floor, three additional large bedrooms on the second floor and four new bathrooms. The expansive open kitchen with cathedral ceilings features a Wolf gas range, two Miele dishwashers, a Subzero refrigerator and a large island with seating for four. Skylights and large windows throughout, the home lets in the perfect amount of sunlight. Relax indoors in the living room or library, or take a dip in the new 10x26 heated gunite pool. This home provides the perfect place to enjoy and entertain, with repeat rental history, while being minutes to famed Ocean beaches. Rental Terms: March: $5,000 January: $5,000 July - Labor Day: $140,000 September: $25,000 February: $5,000 October: $20,000

Exceptional home located in one of the most desirable streets in the Southampton Estate Section. The home just went through an immaculate renovation and the elegant floor plan includes a grand foyer with windows overlooking the grounds, two oversized and separate living rooms, both accessing terraces and areas of the garden, a beautiful den off the pool, an elegant formal dining room, a TV/media room and a new gourmet state-of-the-art kitchen with a large, sunny and inviting informal dining area. There are nine en suite bedrooms. The master suite features a fireplace, private terrace, two baths and two dressing rooms, and a study overlooking the grounds. All principal rooms have access to the stone patio surrounded by beautifully landscaped and private grounds. There is a heated swimming pool, spa and a tennis court. Additional rooms include a professionally equipped gym, play room and virtual golf practice area. The wonderfully landscaped 2 +/- acre property offers plenty of space for elegant entertaining. Beautiful and a truly relaxing environment, this fabulous home will delight even the most discerning tenant. Rental Terms: Two Weeks: $170,000 June: $150,000

Newly renovated and perfectly located. This 6 bedroom home is immaculate in Design, style and finishing's. Entering through an elegant foyer the first floor has a bright open living room with glass doors leading to the outdoor entraining area, a beautiful eat in kitchen equipped with all a professional chef could dream off, and a formal dinning room. The second floor includes a large main bedroom with a Spa like Bathroom and two additional bedrooms, and the charming third floor features two more bedrooms . The lower level is fully equipped with an en suite bedroom, sauna room with ice tank, and state of the art gym including an infra-red wall This home has plenty of nooks and window seats to get comfortable in. The beautiful terraces overlook the heated pool and wonderful landscaped, private gardens. This home is the perfect example of elegance and comfort all within a few minutes of Southampton beautiful village and desirable beaches. Rental Terms: June: $70,000 August - Labor Day: $150,000