luxury houses with pool for rent Southampton, United States

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

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: July - Labor Day: $130,000 August: $70,000 July: $60,000 September: $15,000 Memorial Day - Labor Day: $145,000

Enjoy the ease of being only moments away to Southampton Village and Gin Lane Beaches from this charming and chic compound on one of the main streets in Southampton Village. A private and expansive backyard between the two homes provides exquisite outdoor entertainment and al fresco dining along with a heated gunite pool to enjoy the long summer days. A total of 8 bedrooms between the two homes, one can experience either a multi-family situation or simply enjoy the opportunity to have guests in another home that is joined by the gardens. A secluded, home office is available in the loft space above the garage for those who need the space to work in peace and quiet. The main house has 2 guest bedrooms on the main floor and 2 additional guest bedrooms on second floor. On this same floor, a fabulous outdoor deck is set up for lounging, or morning coffee/ afternoon cocktails which overlooks the lush back yard. The 3rd floor is set up as music/gym den (which could be a private office as well) and the newly renovated designers' cottage has 4 bedrooms, (incl staff bedroom on main floor),2 bathrooms, outdoor fireplace, and 2nd chef's kitchen. Garage not included. Dogs are allowed case by case. Rental Terms: July: $100,000

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: September: $40,000 April: $20,000 Other / Short Term - Year Round: $299,000 October: $20,000 January: $20,000 June: $40,000 November: $15,000 February: $20,000 August - Labor Day: $75,000 July: $60,000 Winter Season: $100,000 Per Month March: $20,000

RENTED June 24th- July 31st!! Open, Bright Contemporary Beach House South of the Highway in Water Mill with 6 bedrooms, and 5.5 bathrooms overlooking a large 27+/- acre Ag. Reserve. All situated on a beautifully landscaped 1.3+/- acre parcel. Two master suites (one upstairs with balcony and one downstairs), a large guest suite/work studio separated from the rest of the home, and a downstairs sitting room/6th en suite bedroom. All bedrooms have king beds. [[Rental Registration # RP250736]] EH RR #: RP250736 Rental Terms: Other / Short Term - Weekly: $25,000

Be the first to experience this brand new modern twist to a classic Hamptons home. This high-end construction flawlessly combines modern and sophisticated interior finishes with a classic exterior design. This beautiful 6 bedroom, 8 bathroom home situated on 1.6 =/-acres, features a sunken Tennis court, oversized Gunite Pool and Pool House. All within minutes of stunning Southampton beaches and Southampton, Watermill and Sag Harbor world-class dining making this the perfect Hamptons getaway. Experience elegant European living with cathedral-style ceilings and an open layout throughout the ground level, while the hidden pocket doors still make each room feel private. Each of the living spaces has direct access to the bluestone terrace with a pergola and retractable awning. The first floor also has a primary bedroom suite, den, formal dining room, and large eat-in kitchen. The expansive living room can be admired from the second-floor gallery. The four bedrooms on the second floor are all en-suite with walk-in closets. The lower level has an additional two bedrooms, gym/spa, home theater, wine cellar, Laundry, and ample natural light with a generous walk-out lounge area. [[Rental Registration # RP230526]] EH RR #: RP230526 Rental Terms: July: $190,000 June: $200,000 September: $150,000

Welcome to your dream home in Water Mill! Nestled on almost 2 acres of waterfront property, this stunning traditional home boasts luxurious amenities and exquisite finishes, all situated in the sought-after south-of-the-highway Water Mill estate area. Enter through one of two gated entrances and be greeted by lush, impeccable landscaping that sets the tone for the grandeur that awaits you. The double-height foyer and powder room provide a dramatic welcome to this gracious home. The soaring double-height living room and day room both open up to the expansive decking overlooking the waterfront-facing, heated, 20'x40' Gunite pool. Perfect for entertaining enjoy formal dining in the dining room, evening barbecues pool side or simply relax in style, this home is sure to impress. The professional-grade, eat-in-kitchen is a chef's dream, opening up to the casual dining and sitting area. The first floor also features a junior bedroom suite. Upstairs, the second-floor primary suite offers two full baths, two walk-in closets, and water views from a private deck, while three additional en-suite guest bedrooms provide ample accommodations for family and friends. Step outside and enjoy the sunken, all-weather tennis court and tennis cabana with kitchen, living area, and bath. Above the 3-car garage, there is an additional bed and bath, gym, and media room. The expansive green lawn leads down to a private dock, providing 170 ft. +/- of Burnett Creek waterfront access, and just a mile to ocean beaches. Experience the ultimate luxury lifestyle in this stunning Water Mill home. With its unmatched elegance and unparalleled amenities, this is the perfect enclave for those seeking the ultimate in comfort, privacy, and style. Don't miss your chance to make this exquisite property your own! Avilable for June, the US OPEN, or starting August 16, 2026 thru Labor Day for $100,000. [[Rental Registration # RA250388]] EH RR #: RA250388 Rental Terms: Other / Short Term - 8/24/2026 - 9/7/2026: $100,000

Exquisite renovation, highest standards, this elegant manor offers 6 bedrooms and 7 bathrooms. In the main house, there are 4 bedrooms, 4 bathrooms, including a primary bedroom on the first floor. A spacious foyer leads to the living room with fireplace, dining/den and a great state-of-the-art eat-in Smallbone kitchen. Additional features include TOTO toilets and a whole-house water filtration system that filters all water throughout both the main house and the guest house/cottage, including showers. On the second floor there is ample room with high ceilings, 3 bedrooms and 2 bathrooms. French doors lead to the patio and lovely garden. The equally exquisitely renovated 2-bedroom, 3-bathroom guest house overlooks the heated saltwater gunite pool with new outdoor furniture and is joined by a 1-car garage with EV charging station. [[Rental Registration # Pending]] Rental Terms: August - Labor Day: $250,000

Beautifully built, fresh, sunny and spacious, this shingled traditional is sited on 1 1/2 acres of mature trees and grounds. There is a gracious living with a fireplace and double height ceilings, a library with a fireplace, formal dining area, a professionally equipped kitchen with pantry, and 5 bedrooms with 4.5 baths including a oversized master with a study. This is a very comfortable country retreat includes a heated gunite pool. [[Rental Registration # RP170055]] EH RR #: RP170055 Rental Terms: June/July: $120,000 August - Labor Day: $100,000 Memorial Day - Labor Day: $220,000 June: $50,000 July: $100,000 September: $60,000 October: $60,000 July - Labor Day: $190,000 November: $60,000

This perfect modern beach house with large heated pool on coveted Flying Point Road is available for August through Labor Day 2026. With 360 degree water views, it's light makes this house one of a kind as well as large front yard and location. The sun rises on Mecox Bay and sets on Channel Pond, and the house sited on 2 acres overlooks both as well as the Atlantic Ocean right across the street. There are a total of 6 bedrooms with both first floor and second floor primary bedrooms in addition to a sitting room, TV room, living room and open kitchen/dining room. There is also a walk-out lower level bedroom. There are 3 different outdoor decks on various levels and they face different locations for view/sun optimization. There is even an outdoor fireplace, spa and outdoor shower. Very bright and furnished in easy haute beach style makes 1030 Flying Point, the ideal summer rental. [[Rental Registration # RP240380]] EH RR #: RP240380 Rental Terms: August - Labor Day: $250,000

This very high-end, newer construction home is available for rent from July 1-Aug 15th, for 2-3 weeks or 1 month. Gorgeous architecture, landscaping and stylish designer interiors are hallmarks of this classic estate. The private gated home sits on a full-lawn property on a quiet street, buffered by fields in front and a pretty tree farm in back. The inside features high-end, custom-designed furnishings and art curated by Mabley Handler, one of the Hamptons most sought-after designers. The nearly 9000SF home offers the ultimate backyard--with an oversized pool with overflowing Hot Tub, and thousands of feet of patios and terraces. You have your choice of entertainment areas, including covered porches, pergolas, open terraces, a fireplace area and a pool house area. Nestled in the heart of Water Mill's horse country on a quiet cul-de-sac, this sleek shingle-style transitional home offers the finest in Hampton's living. Beyond the private gated entrance, the 6 Bedroom home (all with ensuite baths) spans 6300 feet above ground, with a 2500 SF, gorgeously finished lower level. The home features a dramatic 2-story paneled foyer that opens to three different living rooms--a great room, living room and TV room. The kitchen is enormous, designed by Bakes & Kropp kitchen, with a large breakfast area overlooking the yard and a butler's pantry that leads to the formal dining room. The second floor features an enormous primary suite with adjoining sitting room/office and a terrace with views. There are 4 additional ensuite designer bedrooms upstairs. The lower level is truly gorgeous and an extension of teh upstairs. If offers an expansive windowed entertainment space, including a living room, new theater, and an additional bedroom with ensuite bath. There is a state-of-the-art gym, spa bath, sauna and steam room. Spend each day relaxing on the expansive, south-facing terrace with all day sun. The pool house--with kitchenette, living room, outdoor shower and laundry--offer every amenity at your fingertips. The house is controlled by a fully integrated Control 4 Smart system. [[Rental Registration # Pending]] Rental Terms: Two Weeks: $95,000 June: $125,000

Summer or Year Round Living Perfectly positioned south of the highway in one of Water Mill's most desirable locations, this beautifully maintained contemporary offers effortless single-level living on a private, beautifully landscaped acre. A gated entrance and mature plantings create a welcoming sense of arrival, while bright, open interiors with soaring ceilings and walls of glass fill the home with natural light. The thoughtfully renovated kitchen flows seamlessly into the spacious living and dining areas, creating an inviting setting for both everyday living and entertaining. The home offers four bedrooms and four full baths, including a gracious primary suite tucked into its own private wing with double walk-in closets, an oversized spa-like bath, and direct access to the outdoor living spaces. Two guest bedrooms also open directly to the rear deck, creating an ideal layout for hosting family and guests, while a separate study provides the perfect home office or quiet retreat. Designed to embrace the Hamptons lifestyle, expansive decking surrounds the sparkling heated pool, where eastern exposure welcomes beautiful morning light throughout the day. Multiple outdoor entertaining areas, cheerful landscaping, and an exceptional stretch of lawn provide plenty of room for everything from summer gatherings to a game of frisbee or Sunday football. A partially finished lower level offers additional overflow living space, a full bath, laundry area, and generous storage, providing flexibility to suit a variety of needs. Offering privacy, style, and an exceptional south of the highway location, this turnkey Water Mill retreat seamlessly blends easy single-level living with outstanding indoor and outdoor entertaining. [[Rental Registration # RP260361]] EH RR #: RP260361 Rental Terms: Other / Short Term - Year Round: $200,000 Memorial Day - Labor Day: $160,000