luxury houses with pool for rent Southampton, United States (page 2)

Discover the perfect blend of historic charm and modern luxury in the heart of Southampton Village. Originally built in 1882, this meticulously restored 7-bedroom, 6-bathroom home, including an expansive primary suite, offers an unparalleled living experience. Step inside and be greeted by the elegance of original hardwood flooring and intricate banisters, seamlessly paired with contemporary design elements. The gourmet kitchen serves as the heart of the home, featuring state-of-the-art appliances, custom cabinetry, tin ceiling tiles, and a generous island with seating for seven. The adjoining family room, anchored by a grand wood-burning fireplace, creates an inviting space for gatherings. The first floor also offers a formal dining room, living room, powder room, and a convenient laundry area. Set on 0.42 acres, the meticulously landscaped backyard boasts an inground gunite pool, spa, and charming pool house. Designed for both relaxation and entertainment, the outdoor spaces feature ample dining areas, a spacious patio for al fresco meals, and shaded spots under mature trees, all set against a backdrop of serene natural beauty. This Southampton Village gem offers an exceptional opportunity to own a piece of history, thoughtfully reimagined for today's lifestyle. Rental Terms: August: $100,000 Other / Short Term - Year Round: $290,000 Memorial Day - Labor Day: $250,000 August - Labor Day: $120,000

This one has it all! Spectacular Southampton waterfront offers heated pool with spa and rolling manicured lawn leading to large private dock. Situated on 1.2 acres of privacy, home includes 5 bedrooms, 4 baths, living room with amazing view, fireplace and exquisite art work, a true chef's kitchen with top of the line commercial appliances, incredible glass enclosed dining, extensive decking, central air, well equipped gym, gazebo and garage. Primary suite has it all: water views, balcony, additional private gym, sauna, jacuzzi, wet bar, private bath, office and walk-in closet. There's even an electric vehicle (EV) charger in the driveway! Sought after community offers private beach, tennis courts, basketball and baseball diamond. Bring your boat, kayaks are waiting. [[Rental Registration # RP170421]] EH RR #: RP170421 Rental Terms: Other / Short Term - Year Round: $275,000 August - Labor Day: $85,000 July: $85,000 August: $80,000

This fabulous property has just been recently renovated by a leading artist. Overlooking a bucolic horse farm, and just outside Southampton Village, this pristine home offers Hamptons living at its finest. The first floor is flooded with natural light, with plenty of living space for cozy conversation or quiet reflection. Newly installed chef's kitchen with barn doors leading to the large front yard will make any cook smile. EIK and formal dining room look out on the expansive, manicured grounds. Formal Living Room with built in library is perfection and heavenly! French doors lead outside to the fantastic oversized newly built heated gunite lap pool. Revel in the peacefulness of the adjacent farm, with endless views, all so near to Southampton Village and beaches. Truly a unique and gorgeous home. Also available September for $65K. Rental Terms: Memorial Day - Labor Day: $360,000 Other / Short Term - May: $81,000

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 for rent any two week period from 08/08/19 through 09/03/19 - $25,000. Other / Short Term - Any two weeks 08/08/19-09/03/19: $25,000

Escape to this stunning Southampton village rental, where coastal elegance meets modern luxury. This beautifully appointed 3-bedroom, 2.5-bathroom home is your gateway to a serene Hamptons lifestyle. Located just moments from both the world famouse beach and Village, this Southampton gem offers the best of both worlds-seclusion and proximity to the ocean's beauty. Don't miss your chance to experience Hamptons living at its finest. Rental Terms: June/July: $80,000 Memorial Day - Labor Day: $165,000 July: $60,000 July - Labor Day: $130,000 August - Labor Day: $80,000 August: $75,000 June: $35,000

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

Located at the end of a quiet cul-de-sac is this pristine 5470 sq.ft. custom-built traditional on .76 acres that is constructed and finished to the highest standards. Just off the welcoming foyer is an elegant formal dining room and comfortable den. The open plan has a chef's kitchen with custom cabinetry, and high-end appliances, dining and living area with fireplace. Upstairs is a spacious en-suite primary bedroom with attached bonus office and gym. Also on the second floor are three additional bedrooms and bath. The finished lower level has a media room, den, full bath and recreation room with pool table and video games. Great entertaining outdoor space with a 20x40 heated gunite pool and spa, large slate patio with covered dining area. The property borders a preserve and is especially peaceful. The home is minutes away from the Southampton Recreation Center with pickle ball, community tennis, full gym, track, basketball, exercise classes and a day camp. Southampton Village and beaches are an easy drive making this an ideal summer home. Rental Reg. # RP220457 Reg. Expires 5/13/2024 [[Rental Registration # RP220457]] EH RR #: RP220457 Rental Terms: August - Labor Day: $67,000 July - Labor Day: $120,000 Memorial Day - Labor Day: $130,000 July: $59,000 August: $63,000

This chic designer decorated 4BD, 4 1/2 BA with around 3,000 sq ft living space over three floors offers coveted location and stunning features throughout. Located on a charming and quiet one-way street in Southampton Village and just minutes from Main Street, this sophisticated and modern house thrills with millwork that creates an effortless flow throughout. From the moment you enter, you'll be engaged by the bright and light feel and open floor plan, the perfect backdrop for a fabulous summer vacation. The first floor includes a professional kitchen with large island, dining area, butler's pantry, powder room, and generous living room with an inviting gas fireplace, perfect for a cool evening. The second floor includes three beautifully appointed bedrooms, the primary offering an en-suite bathroom and walk-in closet. The second-floor landing provides a bonus, light-filled study/workspace. The tastefully appointed finished lower level provides a generous media/entertainment room, 4th bedroom, full bath and laundry room. Outside, enjoy the perennial gardens and beautiful grounds that provide privacy for the heated gunite pool and pool house. The pool house is complete with a kitchenette, daybed and full bath, as well as an outdoor shower. This spectacular offering truly embodies the perfect Hamptons retreat! Please call with any questions or to set up an appointment to view. No pets sorry. Rental Terms: July: $60,000 Other / Short Term - 6/25/2026 - 7/30/2026: $65,000

Charming Southampton Village home retains many of its original features, built-in 1870, including wood floors along with more recent additions and upgrades completed in 2020. This 4 bedroom, 4.5 bath house is in the most desirable location in the heart of Southampton Village, a few short blocks to all shops and restaurants as well as the beach! Spacious entertaining areas, library and home office with privacy pocket doors, front sitting room with a wood-burning fireplace, formal dining room, and gourmet eat-in Kitchen including new Subzero fridge, Miele Coffee machine, Miele speed oven, wine beverage center and new stove with adjacent family room w/ wood-burning fireplace overlooking the garden. Light and bright this house has it all! The master suite with a sunny outdoor deck overlooking the garden and 3 additional bedrooms with 2 full baths are on the 2nd floor along with a laundry room. Lots of closets! Completing the main floor is a large and cozy 2nd family room with a full bathroom and French doors that open up to the patio. The entire home and backyard are set up with Bluetooth SONOs speakers. In the private backyard, there is a heated and new resurfaced gunite pool, a covered terrace with sofa seating, outdoor dining, and a built-in state of the art BBQ. Deep driveway for ample parking and a one-car garage complete with bicycles and beach chairs. Rental Terms: August - Labor Day: $115,000 August: $110,000 Other / Short Term - Year Round: $250,000

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

This traditional and recently renovated Southampton Village 4 bedroom home, south of Hill Street, is available to rent for 2 week term. Located in the Rosko neighborhood between First Neck Lane and Halsey Neck Lane, enjoy quiet streets, a neighborhood tennis court and playground just 1/2 mile from Town. The first floor offers a light-filled living room, den with large TV, a sunroom with flex dining possibilities and large eat-in kitchen along with a full bathroom plus laundry. The kitchen has double French doors that lead out to the back terrace with grill and outdoor dining, a fenced in pool and large backyard boasting beautiful mature landscaping. On the second floor there is a primary bedroom with large TV and en-suite bathroom in addition to three other guest rooms that share a bathroom. New furnishings, appliances, and central A/C throughout. With a proven rental history in this convenient location close to Town and Ocean beaches, this is an opportunity not to be missed. Rental Terms: Two Weeks: $35,000 July: $35,000

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

Enjoy all the benifits of living heart of Southampton Village while still having privacy, this meticulously updated home offers the perfect blend of elegance, comfort, and modern convenience. The main house features five bedrooms, including one on the first floor, while the remaining four-each with ensuite bathrooms, including a luxurious primary suite-are located upstairs. Natural light fills the home, highlighting the spacious eat-in kitchen, formal dining room, and multiple living areas, each with its own fireplace. A wrap-around deck provides the perfect spot for morning coffee or evening entertaining. The lower level is designed for relaxation, with a cozy living room, laundry area, and a foosball table, making it an ideal space for rainy days. A separate guest house offers a 750-square-foot apartment with two bedrooms, a full kitchen, and a private living area, perfect for guests or extended stays. Outside, the beautifully landscaped backyard is both private and serene, featuring a heated gunite pool surrounded by lush greenery. Located just minutes from the best beaches, shopping, and dining, this home is an exceptional retreat in one of the Hamptons' most sought-after locations. Rental Terms: July: $180,000 June: $80,000

Experience the ultimate Hamptons summer in this exceptional newly constructed luxury rental in Southampton Village, offering resort-style living just moments from ocean beaches, fine dining, boutique shopping, and the best of Southampton Village. Designed for effortless summer living and entertaining, this modern Hamptons rental features three finished levels with custom Ciuffo cabinetry and millwork, expansive open-concept living spaces, and natural gas fireplaces in both the living room and primary suite. The finished lower level is designed for recreation and relaxation with polished concrete floors, a private gym, guest suite, full bath, state-of-the-art Full Swing golf simulator, and temperature-controlled wine and spirits room. Smart home technology is seamlessly integrated throughout with Control4 automation, Cat6 and fiber connectivity, premium audiovisual systems by HTE, and J-Geiger motorized shades. Outdoors, enjoy a heated gunite saltwater pool with auto-cover, Bullfrog M6 spa, sunken firepit lounge, and fully equipped outdoor kitchen with DCS gas grill and Evo Affinity grill, all surrounded by beautifully landscaped grounds and luxury outdoor lighting. A rare Southampton Village summer rental combining new construction, modern luxury, privacy, and premier Hamptons amenities in one of the most sought-after village locations. Rental Terms: July: $150,000 August - Labor Day: $180,000 June: $90,000 Memorial Day - Labor Day: $420,000

Be one of the first to enjoy this beautifully renovated compound set on over half an acre in the heart of Southampton Village, now offered as a rental, with all new furnishings from Home Nature, Serena & Lily and CB2. Just moments from the iconic Gin Lane beaches and charming village shops, the main residence welcomes with a lovely entry foyer featuring a wood-burning fireplace on one side, and the den on the other. The foyer leads to the dining area and then over sized living room with fireplace, dine-in chef's kitchen, and powder room. The family room that has informal dining table as well opens fully onto the outdoor deck. Upstairs, you'll find a spacious primary suite (king bed) with a private office and three additional en-suite bedrooms ( 1 king and 2 queen beds). Downstairs, the French doors to the back deck, making indoor-outdoor living easy, open to lovely views of well-tended gardens and heated Gunite pool. The guesthouse provides exceptional flexibility with its living room, dining area, kitchenette, full bath and laundry, and upstairs two additional bedrooms with full bath. One room has two twins that can become a king, and the other a day bed with an office. The guesthouse back terrace overlooks the expanse of the long rear yard. This offering combines functionality and location, a true "get" in the Hamptons--less than 1/3 mile to Little Plains Beach and 1/2 mile to Southampton's Main Street. [[Rental Registration # N/A]] EH RR #: N/A Rental Terms: July: $135,000

On over half an acre just minutes from Southampton Village and ocean beaches, this turn-key home offers an exceptional combination of style, privacy, and land. 3 bedrooms, 3 bathrooms, an open living and dining area with wood-burning fireplace and abundant natural light define this truly special residence. The grounds include mature hedging, established trees, an in-ground heated pool, and generous deck. Rental Terms: September: $15,000

New to the 2021 rental market: 6 BR, 5 bath modern Hampton home with fabulous pool house and an inground, heated gunite swimming pool. Several outdoor entertaining spaces and in- and outdoor fireplace. This home offers an open concept floor plan with a large gourmet chef's kitchen, dining area that flows effortlessly into the living/family area with fireplace. On the second floor are 5 bedrooms, 3 bathrooms including the sumptuous master suite with soaking tub and rain shower. Only minutes to Village shopping, restaurants and ocean beaches. [[Rental Registration # RP251145]] EH RR #: RP251145 Rental Terms: August - Labor Day: $90,000 September: $25,000 May: $50,000 June: $40,000 Memorial Day - Labor Day: $249,000 Other / Short Term - Year Round: $290,000

Welcome to your own private oasis in the heart of Southampton Village! This stunning 5 bedroom, 6 bath Traditional home is situated on a meticulously landscaped +/- 1.38-acre lot within a beautiful private compound. As you enter the home, you'll be greeted by a spacious foyer with double-height ceilings, leading to a generous family room with a cozy wood-burning fireplace, a traditional living room, and a formal dining room. The gourmet chef's kitchen boasts stainless steel appliances, a large island with seating, a breakfast area, and a substantial junior primary suite. Sliding glass doors lead from the kitchen and family room to a spacious deck and patio surrounding the pool, spa, outdoor shower, and pool house. This property provides ample space for entertaining and relaxation while maintaining complete privacy. The upper level features four bedrooms, three full bathrooms, and an expansive primary suite with a luxurious bathroom fully equipped with two separate vanities, a jacuzzi tub, and a glass-enclosed walk-in shower. The fully finished lower level offers a recreational room with a TV seating area, an air hockey table, one full bath, and a private office. Located just minutes away from shops, restaurants, and ocean beaches, this property offers the luxurious Hamptons lifestyle you've been dreaming of. Don't miss out on this incredible opportunity so close to ocean beaches Rental Terms: July: $90,000 August - Labor Day: $150,000 August: $130,000 July - Labor Day: $200,000 September: $90,000 Memorial Day - Labor Day: $300,000

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

New to the market is this 2018 constructed 6 bedroom all en-suite Traditional home. Stately foyer leads into the great room, open floor plan for easy entertaining overlooking the very spacious back yard. Covered porches overlook the lawn areas and oversized heated swimming pool with build in lap feature. First floor also offers a formal dining and living room. The second floor offers 5 all large, bright en-suite bedrooms including the master suite. The finished lower level houses an additional en-suite bedroom. Also, several entertaining areas from a game room to a state of the art theater. Rental Terms: September: $75,000 October: $40,000 November: $30,000

This beautiful classic white shingled three-story house with six bedrooms,6 bathrooms, two half-baths, gorgeous backyard, heated pool and spa is the perfect summer rental in Southampton Village. Enter the large foyer and experience the spacious nature and high ceilings that exist throughout the house. The main floor offers an elegant and spacious living room that opens onto the patio and gardens, a wonderful bright sunroom, and a den with fireplace that opens onto a west-facing furnished porch to catch the "golden hour". In addition, there is a state of the art eat-in kitchen with marble and stainless steel counters that opens to a covered porch for informal dining, as well as indoor formal dining room and mudroom. Almost every room on the first floor opens to a porch. Up the wide staircase and onto the second floor, you will find the large primary bedroom including two large walk-in closets, two bathrooms and a beautiful covered porch. In addition, there are two guest bedrooms with ensuite bathrooms, an office, and second floor laundry room all accessed from the large landing with sitting area. The third floor has three more large guest bedrooms and two more bathrooms as well as an additional sitting area. The indoor/outdoor living is what makes this house so special with the multiple covered porches, heated Gunite pool, spa, pool house with changing room and bathroom, outdoor shower and three-car garage surrounded by special mature landscaping. All this and just 1.3 miles to Main Street and 1.1 miles to beautiful Old Town and Wyandanch beaches. Rental Terms: Two Weeks: $110,000 August: $180,000 August - Labor Day: $210,000

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

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

Wonderfully decorated, 7,000 +/- square foot, seven-bedroom, eight-bath Gambrel Traditional is located in the world-famous Southampton Estate Section. A well-considered floor plan, superb finishes and all new elegant decor are combined to provide the ultimate in summer comfort and elegance. A lovely paneled entry leads to a living room, den, custom kitchen with a welcoming sitting area, dining room and screened porch. Upstairs, the generous master with double baths and closets is augmented by three additional guest suites. A new added guest wing offers 2 additional bedrooms with ensuite baths, a well equipped gym and a large office/sitting area. Outdoors, the one-acre +/- property offers a large heated gunite pool, stone patios and a spacious lawn. Mere minutes to legendary Southampton Village ocean beaches, chic shops, and fine dining. Rental Terms: June: $85,000 July: $150,000 August: $200,000

Spacious and airy Home in the Estate Section of Southampton Village in desirable South of the Highway location. A long private drive takes you to this charming and stylish home featuring a spacious living room with fireplace and beamed cathedral ceilings, a handsome library/media room, dramatic dining room with curved glass wall overlooking the rolling lawn. There are 5 bedrooms and 4 baths in this beach home as well as a media room, sauna, Jacuzzi, and central air for maximum relaxation and comfort. The Primary Suite, also with cathedral ceilings and fireplace, overlooks the serene, private swimming pool. Patio doors lead the way directly onto the patio pool area. Enjoy the large heated gunite pool for swimming laps or fun in the sun. Additionally, there is a detached tea house and lovely rolling lawn and gardens. There is an additional, separate entertaining space available or a private office space . Privacy Galore in a highly desirable location! Rental Terms: March: $20,000 Memorial Day - Labor Day: $230,000 May: $35,000 Other / Short Term - Year Round: $350,000 November: $15,000 August - Labor Day: $115,000 April: $20,000 June: $50,000 July: $95,000 September: $50,000 October: $20,000 February: $20,000 January: $20,000