luxury real estate for rent Southampton, United States (page 4)

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 traditional and newly 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 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. Special Notice: This property is available for select short-term rental periods, including two-week stays. Pricing and availability shown under June are for reference only and do not guarantee full-month availability. Portions of June may be unavailable at the listed rate. All dates, rates, and availability are subject to change. Please inquire for confirmed pricing and specific rental dates. Rental Terms: Two Weeks: $35,000 June: $35,000

Southampton Village Condo available for rent in the desirable Southampton Meadows Complex. Enjoy the summer in this beautifully renovated end unit decorated in a mid-century modern style. The condo features a sunny and open downstairs layout with a large foyer, hardwood floors, vaulted ceilings, fireplace with tv above, wet bar, open kitchen dining areas, full bathroom plus washer and dryer. The second floor has two sunny bedrooms, ample closet space and a newly renovated bathroom with a large shower and tub. There is a bonus room/ library area perfect for a peaceful retreat. To complete your stay enjoy the spacious private patio area perfect for outdoor entertaining.The community is set on 17 lush acres featuring an oversized heated salt water pool, two newly refurbished tennis courts, and mature landscaping throughout with numerous specimen trees. Conveniently located to the village and ocean beaches. Must see! Rental Terms: July: $22,000 July - Labor Day: $48,000 August: $22,000

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

Renovated 2-bedroom cottage with water views and access to Big Fresh Pond for swimming, kayaking and paddle boarding. A serene location to unwind and enjoy great sunsets. Open concept living area with dining area, eat-in & fully stocked kitchen, and living room - all with water views. Outdoor BBQ grill & outdoor shower. Kayak & bikes available. Bonus: Piano in living room! [[Rental Registration # RP251276]] EH RR #: RP251276 Rental Terms: Memorial Day - Labor Day: $37,500 October: $4,000 September: $6,000 July: $17,000 June: $9,000 August - Labor Day: $19,000

Experience the epitome of coastal living just steps from the serene shores of Towd Point Beach. Featuring newly refinished white oak flooring, farmhouse kitchen, Central A/C, BBQ slate patio & deck, hammock, outdoor shower, large lawn and bloom filled gardens. And of course easy access to the beautiful Towd Point beach for swimming and stunning sunsets. Kayaks included and Pet Friendly too! [[Rental Registration # RP260737]] EH RR #: RP260737 Rental Terms: May: $8,000 Two Weeks: $8,000 June: $12,000 August: $19,000 July: $17,000

This residence truly has it all. Step inside and be greeted by a dramatic double-height foyer that sets the tone for the home's grand yet inviting design. The open, light-filled floor plan flows effortlessly, perfect for both everyday living and entertaining. Ideally situated just moments from Southampton Village and the pristine ocean beaches, this shingled traditional sits on a generous 0.72-acre Village lot. Offering 5,300 square feet of above-ground living space, plus an additional 2,500 square feet on the beautifully finished lower level, the home provides ample room for all occasions. Outdoors, enjoy extensive bluestone patios, lush landscaped gardens, a 45' x 20' gunite pool, and a 10' x 10' spa. A 468-square-foot pool house completes the resort-like setting, featuring a full bath, sitting room, and wet bar. The gourmet kitchen is a chef's dream, anchored by a statuary marble island and outfitted with top-tier appliances including two Sub-Zero refrigerators/freezers, a wine cooler, and double ovens. The first floor also offers a formal dining room, powder room, formal living room, casual living room with fireplace, and a junior primary suite. Expansive glass doors along the south wall open seamlessly to the partially covered patio, pool, and private backyard for effortless indoor-outdoor living. Upstairs, the primary suite impresses with 11' vaulted ceilings, a fireplace, private balcony, spacious walk-in closet, and a spa-like bath with radiant heat, steam shower, and stand-alone tub. Three additional ensuite guest bedrooms and a large laundry room with dual washers and dryers complete the second floor. The lower level is designed for recreation and relaxation, featuring a glass-enclosed gym, state-of-the-art theater, powder room, seating area, space for a wine cellar, and two bright guest bedrooms with an adjoining bath. This is a rare opportunity to enjoy a Southampton Village home that combines timeless style, modern luxury, and a truly exceptional location. Rental Terms: August: $180,000

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: Two Weeks: $70,000 June: $60,000

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: October: $150,000

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

Also available: Two weeks: Jun 1 - Jun 25 $15K, Two weeks: Sep 9 - Sep 30 $20K As featured in Hampton Cottages and Gardens, located on a quiet Village lane, this exquisite three bedroom three bath plus powder room oasis with separate, private cottage, all on one level, provides maximum privacy yet is in close proximity to Village shops, restaurants and famous ocean beaches. From entering the home, the foyer leads into the open light filled living spaces that invite for entertaining and relaxing. The living spaces easily flow from the Chef's kitchen with a large island into the dining room, living room and covered airy porch. The three bedrooms either have an en-suite bathroom or a full bath in close proximity. Also included is the private cottage with its own bathroom. A wonderful, carefree Village home ready to spend memorable summer weeks. Rental Terms: July: $48,000 Other / Short Term - Short-Term: $18,000 Two Weeks: $18,000 June: $38,000 August - Labor Day: $54,000 August: $50,000 June/July: $82,000 Memorial Day - Labor Day: $135,000 July - Labor Day: $98,000

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

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: June: $60,000 August - Labor Day: $160,000 August: $150,000

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

This Southampton beach house blends playful coastal personality with relaxed Hamptons living. Located in Bay View Oaks, a waterfront community with private beach access, deeded rights to Peconic Bay, and a boat launch, the home sits in a quiet setting within Bay View Oaks, just 10 minutes from both Sag Harbor and Southampton Villages. Inside, the home features high ceilings, light-filled rooms, and professionally designed interiors with a cool design sensibility that incorporates open-plan living, retro pop-culture touches, and colorful accents. The layout includes four bedrooms plus a bonus bunk room, 3.5 bathrooms including a primary ensuite, and multiple indoor-outdoor gathering zones that flow naturally for lounging, dining, and entertaining. A gourmet kitchen inside and out, multiple dining areas, and a layout arranged for smooth day-to-day living make the home easy to enjoy. The outdoor spaces offer a range of playful amenities. After the beach, rinse off sandy toes in the outdoor shower, step into the heated pool, basketball hoop, trampoline, fire pit, and several lounge areas suited for relaxing or gathering. A two-car garage and the overall setting bring everything together for a relaxed Hamptons stay. Offered for the early summer, August, extended season, and winter rental periods. [[Rental Registration # RP241487]] EH RR #: RP241487 Rental Terms: July: $50,000 June: $38,000 August: $55,000 October: $12,500 November: $10,000 Winter Season: $50,000 Per Month

Single story waterfront home offering 3 bedrooms, 2 baths & South of 27! [[Rental Registration # 241322]] EH RR #: 241322 Rental Terms: July: $22,000 July - Labor Day: $55,000 Other / Short Term - Year Round: $80,000 Winter Season: $4,100 Per Month

Welcome to 15 Lake View Court in Southampton, a fabulously reimagined pond front home. The vibe is lux organic, the palette soothing. With water-views from every room, it’s easy to embrace the Zen aesthetic. This east-west facing three bedroom, three bath has space to spread out, yet is ideal for gathering together. The upper level features a kitchen, dining, and main living areas, from which you can walk out and enjoy the deck overlooking Little Fresh Pond. This outdoor space is ideal for dining, gathering or relaxing. The lower level enjoys 3 spacious bedrooms with sublime pond views, sumptuous bedding and 2 additional baths. The fully landscaped and irrigated property offers privacy, a path to the water, a private dock, and of course a fire pit. Complete with water toys and fabulous proximity to both Southampton Village and Sag Harbor, this is a sought-after home away from home.

Completely redone, top to bottom, this pretty Southampton Village 3BR, 2.5BA home is available for rent for the first time. Charm, charm, charm of ""Old Southampton"" yet updated with today's amenities. Available monthly, for the Season, post-season, winter and year-round. They don't come nicer than this one. Rental Terms: Other / Short Term - Year Round: $175,000 July - Labor Day: $90,000 Memorial Day - Labor Day: $120,000

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