luxury houses with pool for rent Southampton, United States

Newly renovated eight-bedroom home located on South Main Street, just a short distance to the village and ocean beaches. The home includes a completely updated eat-in kitchen with top-of-the-line appliances, formal dining room, living room, den, sunroom and a beautiful outdoor living room. All six bedrooms have been renovated and all have their own en suite bathroom. The property, which is nearly an acre +/-, includes a heated gunite pool, large patio area great for entertaining, a large lawn and lovely landscaping. A must-see rental! Rental Terms: February: $20,000 January: $20,000 March: $20,000 May: $25,000 April: $20,000 June: $70,000 June/July: $200,000 July: $180,000

Spend your vacation in this freshly renovated, five-bedroom home close to ocean beaches and moments to the village. The Traditional house was renovated on the highest level possible and tastefully furnished and decorated. Also offers a separate guest house with its own private terrace. The large covered terrace, heated pool and wonderfully landscaped garden make the perfect place to entertain. Rental Terms: June: $70,000 June/July: $160,000 August - Labor Day: $170,000 August: $160,000 May: $40,000 July: $120,000

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

WATERFRONT COMPOUND WITH POOL! Swim, fish, or launch the kayak, paddle board or sunfish sailboat(included) from this waterside haven! Located on Davis Creek, this Towd Point Beach Rental has unobstructed views of the harbor and beyond to Conscience Point National Wildlife Refuge. Featuring a cottage-style main house with three bedrooms and two bathrooms and a modern-barn style pool house that takes full advantage of the stunning views. The two-story pool house has two full bathrooms, a wet bar, an outdoor kitchen, and seating areas on both levels with sliding doors that bring the outside in - it's where you'll be hanging out. The main house also has outdoor dining, incredible views and an outdoor shower. The heated, salt-water gunite pool is NEW FOR SUMMER 2024 and includes an endless swim current for lap swimmers. Moments to the beautiful Towd Point Beach. [[Rental Registration # rp250468]] EH RR #: rp250468 Rental Terms: August: $85,000 August - Labor Day: $90,000 Memorial Day - Labor Day: $220,000 July: $85,000 June: $50,000 October: $30,000 November: $20,000

A very complete offering in the best of locations. Attractively furnished with mature trees and gardens this very comfortable home offers a large Living /entertaining Room, a formal dining room, a panelled library, a gourmet kitchen, 7 bedrooms, 8.5 baths, including a large first floor guest suite. There is a heated pool with a pool house and a tennis court. A top quality house and location! Rental Terms: August - Labor Day: $250,000 Memorial Day - Labor Day: $495,000 July: $225,000 Other / Short Term - 6/1/2027 - 9/7/2027: $495,000

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

Best location. Best house in best condition. Best waterfront views on Lake Agawam, gated, waterside pool, porches, balconies, multiple living parlors. Great kitchen, dining, offering 7 bedrooms, 2-car garage, on 2 beautiful acres. Very private. Rental Terms: Other / Short Term - Year Round: $850,000 July - Labor Day: $600,000 Memorial Day - Labor Day: $700,000

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

Welcome to 50 Rosko Lane in The Fields, Southampton's premier luxury enclave. This west-facing new construction offers abundant natural light, and over 6,000 sq. ft. of beautifully designed living space. With 7 bedrooms, 7 baths, and a finished lower level, the home balances refined Hamptons style with modern comfort. The airy main level showcases soaring ceilings, wide-plank floors, and a chef's kitchen that flows seamlessly to the dining area, accented by a striking built-in wine display. Walls of glass open to a private backyard with a heated gunite pool, bluestone patio, and landscaped grounds. The serene primary suite features a spa-like bath and generous closets, while the lower level adds a media lounge, recreation space, guest suites, and an impressive gaming lounge with four high-end stations, Xbox Series X and PlayStation 5 consoles, and award-winning Secret lab chairs-perfect for entertaining all ages. A two-car garage, proximity to Southampton Village, and world-class beaches complete this exceptional offering-luxury, convenience, and resort living at its finest. [[Rental Registration # RP250841]] EH RR #: RP250841 Rental Terms: August - Labor Day: $125,000 September: $75,000

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

Also available: December $25K This 2-acre Southampton Village Compound has it all. The 6-bedroom main home (each with dedicated bath) features a nicely designed home and magnificent property with 1) Guest House, 2) Gym House, 3) Pool House, 4) 60' Pool and 5) Basketball. It is an amazing offering, newly furnished, painted and designed. The location is incredibly convenient. Its on a quiet street of estate homes, a mile to ocean beaches, restaurants, or shopping. The home is designed with new furniture and art, for the discriminating tenant who appreciates a boutique feeling. The main house offers 6 bedrooms and 3 living rooms to spread out. It offers 2 offices--a 1st floor windowed corner office fit for an executive and a casual 2nd floor office, off the primary. A finished lower level offers a wet bar, pool table, large flat screen TV and a bedroom with its own entrance. Multiple French doors lead to an expansive slate patio with covered al fresco dining porch and built-in grill. Over 3000 feet of patio allow for gracious entertaining. Enjoy 100% privacy, with 25' privacy trees or privet on all sides. Ed Hollander has designed spectacular landscape, with groves of white crepe myrtles, manicured gardens, open lawn, and an English fountain. The yard features a 60-foot heated pool with waterfall spa and a covered outdoor bar with TV and sound system. There is a guest house, with its own windowed gym building, conveniently near the pool, pool house and steam shower...No excuses not to work out. There is also second building--a pool house with living room, kitchenette, covered dining, and a bath with steam shower. Just beyond the pool house, enjoy a basketball court. This home has it all. Rental Terms: February: $30,000 July: $200,000 May: $40,000 June: $100,000 March: $30,000 Winter Season: $220,000 Per Month November: $30,000 July - Labor Day: $400,000 Other / Short Term - Year Round: $750,000 Memorial Day - Labor Day: $500,000 August - Labor Day: $250,000 April: $40,000 January: $30,000

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

Brand new furnishings await the discerning tenant at 18 Spring Pond located in a quiet, private community. The 2 story home offers a heated, gunite swimming pool and community tennis court. The house is freshly painted, updated and boasts brand new furnishings including pool lounges. Great open floor plan from the kitchen to indoor and outdoor entertaining spaces. There is a junior en-suite bedroom on the first floor in addition to a powder room. The second floor holds the private primate suite with floor to ceiling windows overlooking the private property. There is a private balcony, shower bath, walk in closet and an adjacent den that can serve for relaxation, working. There is a third en-suite guest room with two twin beds and the laundry room on the second floor. [[Rental Registration # RP260246]] EH RR #: RP260246 Rental Terms: Other / Short Term - Dec: $15,000 April: $15,000 July: $40,000 September: $18,000 March: $10,000 November: $10,000 June/July: $60,000 May: $15,000 January: $10,000 October: $10,000 February: $10,000 Winter Season: $60,000 Per Month

Custom-built, new home in a Shinnecock bay front community, now offered as a summer rental. This two-story, energy-efficient, open-plan home offers four bedrooms and three bathrooms, of which one bedroom and bathroom are located on the main floor. The covered front deck opens to the foyer and open living featuring the kitchen with quartz counters and high-end Bosch stainless steel appliances. The over-sized living area includes its own south-facing deck. Upstairs, the second floor offers three bedrooms and two baths, one of which is ensuite. At grade, the lower level houses the one-car garage with its own entry. Well-landscaped with retaining walls, the property features an in-ground, heated salt water pool, is just up the street from the bay front, and a short drive to Southampton Village and ocean beaches. An on-point Hamptons escape, this rental property's location is outside of the summer weekend traffic rush. [[Rental Registration # RP260163]] EH RR #: RP260163 Rental Terms: September: $9,000 August - Labor Day: $35,000 Two Weeks: $15,000 October: $6,000 August: $30,000

Secluded, expansive contemporary with double height ceilings, flooded in natural light. This home offers five bedrooms in all with two en-suite, primary bedrooms. The open floor plan offers great flow for entertaining and casual summer enjoyment as it opens up to a sweeping deck overlooking the heated pool and all-weather tennis court. Laundry room on the first floor and attached two-car garage. Very private setting, yet centrally located within an easy drive to Southampton, Water Mill, Bridgehampton, and Sag Harbor as well as bay and stunning ocean beaches. Enjoy your summer in The Hampton's in this chic, stunning home! Rental Reg. # RP230840 Reg. Expires 7/14/2025 EH RR #: RP251295 Rental Terms: July - Labor Day: $120,000 August - Labor Day: $80,000 July: $50,000 Two Weeks: $25,000 June: $50,000

New to the rental market, this recently updated home is on a very desirable street in the village. 4 bed, 4 1/2 baths and a bright finished lower level. There is a new salt water heated pool with underwater speaker. A pool house and finished space above the garage. Extremely convenient to the train, bus and village shops. Other / Short Term - Last two weeks in August: $25,000

Tucked away on one of the most iconic private streets off world-famous Gin Lane, this classic Southampton residence offers timeless charm, privacy, and exclusive beach access. Set on beautifully landscaped grounds, the property is surrounded by lush greenery, creating a serene oasis just moments from the ocean. Inside, the home is filled with natural light, with large windows and French doors that invite the outdoors in. The main house features five bedrooms and six bathrooms across two levels, including a sun-drenched primary suite with dual baths, walk-in closets, and a private terrace. A separate guest wing offers additional space and comfort for visitors. Gracious living and dining rooms, a bright and functional chef's kitchen, and a cozy den all open to the gardens, perfect for relaxed summer living. Outdoors, the covered porches and patios are ideal for entertaining, while a heated gunite pool is nestled among mature landscaping. With private access to one of the most beautiful beaches in the Hamptons, this is a rare opportunity in the heart of Southampton Village. Rental Terms: August - Labor Day: $150,000 July: $140,000

Located in Parrish Pond just outside the Village of Southampton is this 5 bedroom, 4.5 bathroom traditional. Professionally decorated, this home offers a well-appointed first floor master bedroom and attractive entertaining spaces. Outdoor amenities include a heated Gunite pool and spa, a bocce court, a surround sound system and open grounds and mature landscaping. A five-minute drive to the Village of Southampton and its beaches. Available two weeks in August. THIS PROPERTY IS NOT OFFERED ON AIRBNB, VRBO, OR ANY OTHER HOME-SHARING SITE. [[Rental Registration # RP251741]] EH RR #: RP251741 Rental Terms: Two Weeks: $35,000

This exceptional new 7000+/- sq.ft. home, sited on over 3 acres with pool and over-sized pool house/pavilion has several distinct and superbly-designed living spaces that are perfectly suited for gathering and entertaining family and friends. Constructed by a well-known local builder, this custom-designed home offers seven bedrooms, eight full, and two half-baths between the main residence and pool pavilion. A private drive leads to the shingle-sided Hamptons home with circular drive, and separate service drive to the garage bays. The residence opens with an elegant, double-height ceiling off of which is the powder room, and direct view to the comfortable living room with fireplace. The living room is part of the open-plan living/dining/kitchen, all with superb finish and luxe furnishings. The fully-equipped chef's-level kitchen includes a Fisher Paykel refrigerator, beverage cooler, Bertozzi range/oven, microwave/convection oven, and two dishwashers. The separate formal dining room will seat 8-10 persons. French doors line the entire rear of the house, including the first floor junior primary suite with fireplace, off of which are two covered patios, and outdoor fireplace. From the second floor landing, the primary suite occupies one side with French doors out to its private deck. A sitting area and three more bedroom suites complete the second floor. The finished lower level offers a media room, a sixth bedroom suite, a full bathroom, an additional bedroom, the laundry room with double washer/dryers, and access to the over-sized two-car garage. Among the amenities offered: in-home and outdoor surround sound systems; black-out shades; WiFi; four Eisyrood "cruiser" bicycles, and an Addmotor electric tricycle. Lower level storage closets contain a surplus of labeled luxurious linens for the household. A landscaped glade leads up to the pool area, with its in-ground, 20'x40' heated Gunite pool with bluestone surround and six Euro-style lounges and three "Cape" umbrellas. The outdoor entertaining areas offer a "pizza" kitchen with a Green Egg, and an under-pergola dining area that will accommodate a dozen people. Inside the pool house, a large kitchenette, half bath, and separate changing room. This is a property where every day feels like a retreat and every evening is an invitation to unwind. Offered for various time periods this summer and off-season. [[Rental Registration # RP252030]] EH RR #: RP252030 Rental Terms: November: $15,000 Two Weeks: $50,000 October: $15,000 March: $10,000 January: $10,000 February: $10,000 May: $45,000 Other / Short Term - Dec: $10,000 June: $100,000 April: $10,000

Terrific Southampton Estate Section rental property, sited one "country" block to ocean beaches offers gracious living with six bedroom suites, a full house-length patio, heated Gunite pool, pool house, and attached three-car garage. The 1.05-acre property, accessed by two driveways and semi-circular drive presents a classic clapboard, shingle-sided traditional residence, with covered, columned front entrance. The entry reception offers a powder room, and straight-line access to the residence wings on either side. Recently renovated and expanded, the south wing offers the family/game room with fireplace, that steps down to the over-sized, sun-filled living room with fireplace. The formal dining room seats 10+, and a pantry connects to the dine-in kitchen with breakfast nook and all top appliances. Numerous full-height doors open to the swimming pool area and full house-length back patio with fireplace. A second larger pantry connects to the den/office with full bath. The ground floor guest suite, garden room with dishwasher second fridge and freezer, and utility area with laundry room complete the ground floor. Up the main stair, the primary suite occupies one side, and a guest suite is on the other. The upstairs north wing offers three more guest bedroom suites and sitting/hangout space. Immaculate and spacious, this rental property is perfect for any time of the year. Rental Terms: August: $225,000 August - Labor Day: $260,000