luxury houses with terrace for rent Sag Harbor, United States

Designer decorated mint-condition home with private heated pool surrounded by flowering gardens on a charming lane in Sagaponack. Light bright kitchen overlooks seating and dining area, with a stylish living room with fireplace beyond. Roomy primary, two additional guest bedrooms, and two beautifully appointed baths complete this perfect summer getaway. [[Rental Reg # 22-394]] EH RR #: RP241987 Rental Terms: Other / Short Term - Year Round: $130,000 Memorial Day - Labor Day: $90,000 July - Labor Day: $90,000 August - Labor Day: $50,000 July: $45,000

Set on 1.11 acres of exquisitely landscaped grounds, this sophisticated post-modern retreat offers a seamless blend of contemporary design and Hamptons elegance. Built in 1995, the single-story residence spans approximately 2,800 square feet and is ideally positioned moments from Bridgehampton and just over a mile to pristine ocean beaches. The outdoor setting is a true sanctuary, featuring a heated pool, beautifully appointed pool house, expansive rolling lawn, and a shaded dining pavilion complete with a barbecue, perfect for effortless summer entertaining. Inside, the home is bathed in natural light, with airy interiors defined by crisp white tones, clean architectural lines, and modern finishes. The main living room centers around a striking brick fireplace, while the open-concept dining area flows seamlessly into a fully updated kitchen designed for both everyday living and hosting. The residence offers4 total bedrooms and 4 full baths, including a luxurious primary suite and a junior primary suite with its own fireplace. Each bathroom is fully renovated in marble, delivering spa-like comfort throughout. Additional amenities include central air conditioning and high-end furnishings, with the home elegantly appointed in all-new pieces from Restoration Hardware. A refined Sagaponack escape offering style, comfort, and proximity to the very best of the Hamptons. [[Rental Registration # RP230701]] EH RR #: RP230701 Rental Terms: October: $25,000 Other / Short Term - Year Round: $220,000

This spectacular Sagaponack estate offers the best of Hamptons luxury lifestyle. Designed by a renowned interior designer, the graciously appointed interior flows easily to an outdoor living/dining patio, heated gunite pool, hot tub, tennis court, and exquisitely landscaped garden and lawn. The main floor has a living room, great room open to eat-in kitchen, formal dining room, butler's pantry, powder room, and en-suite bedroom. Upstairs has an additional primary suite, and three bedrooms ensuite with a sitting room and three bathrooms. The lower level includes a large luxury bedroom with an excavated, landscaped window well, a den/media room/exercise room and a staff bedroom and bathroom. Amenities include a fully enclosed lot with driveway gate, an attached garage, ample outdoor parking, double laundry room, speaker system, Wi-Fi, and security system. [[Rental Registration # 20251042]] EH RR #: 20251042 Rental Terms: Two Weeks: $120,000 June: $135,000 July: $195,000 June/July: $295,000 Other / Short Term - Year Round: $850,000 Memorial Day - Labor Day: $500,000 August - Labor Day: $225,000

A rare Sagaponack compound, offering 7 bedrooms in total, designed by Val Florio on +/-1.6 acres of curated landscaped grounds. Surrounded by open sky and farmland vistas, the main residence offers sun-filled living spaces, elegant detailing with casual beachy interiors and generous proportions throughout. Gathering rooms open to expansive mahogany decking and manicured lawns, creating a natural flow for summer living. The fully equipped guest cottage provides an additional three bedrooms, ideal for hosting extending family, staff, or friends while maintaining privacy and comfort. The homes are connected through a tunnel in the finished lower level. The heated gunite pool is complimented by a stylish pool pavilion and sunken pickle-ball court. Located across from Wolffer Estate Stables, Sagaponack's premier horse farm, around the corner from Wolffer Vineyard, and close to world class Sagg Main Beach. This compound delivers the ultimate Hamptons experience minutes from the best of Bridgehampton and Sag Harbor. Rental Terms: July - Labor Day: $300,000 August - Labor Day: $175,000 July: $150,000 Other / Short Term - 10/1/2026 - 4/30/2027: $55,000 June: $75,000

Rental Reg. # RP220705 exp. 9/1/24 Also Available: August 16 - September 2 for $250,000 This highly designed new construction--a designer's own home--offers every amenity. The magnificent 11,000+/- sq. ft. estate spans 2+/- lush acres, but feels like it sits on 50 acres, with panoramic reserve views to the West. Enjoy spectacular farm vistas and sunsets every day. It is unique--as the largest and closest field-view estate just outside Bridgehampton Village. The property is a 1/2 mile to some of the Hamptons best restaurants (including Topping Rose, Almond and Pierres), boutiques and shopping. The backyard is nothing short of a resort. The home offers a 50' heated gunite pool, hot tub, and sunken all-weather tennis court. The outdoor terrace stretches the entire length of the house with two covered porches, a state-of-the-art outdoor kitchen, firepit and new outdoor furniture ensuring everyone will relax in comfort. As well, you will be amazed by the thoughtfulness of the interior design. It comes lovingly appointed by Katie White Interiors, replete with gorgeous, hand-selected furniture and artwork that offer elegance, yet a comfortable modern and beachy vibe. The open concept living areas include the living room and great room, eat-in kitchen with Subzero/Wolf appliances (2 full fridge/freezers), a breakfast area, and multiple glass doors that open to an expansive stone terrace and covered porches. There is a highly designed formal dining room, One of the two primary suites is on the first floor (or can be furnished as an enormous office). A mudroom, with laundry and full pool bath round out the first floor. An architectural free-floating modern staircase leads upstairs, where a second luxurious primary suite features a generous balcony with outdoor furniture for lounging any time of day. Four additional ensuite bedrooms, two of which share a large balcony, are also on this level, along with a laundry room. The finished lower level provides large media/recreation space, a gym, and two additional bedrooms. The house has a state-of-the-art sound system and comfort controls. [[Rental Registration # RP220705]] EH RR #: RP220705 Rental Terms: August - Labor Day: $400,000 June/July: $500,000 July - Labor Day: $700,000 Other / Short Term - Year Round: $1,300,000 June: $200,000 July: $350,000

Rental Registration # Pending Also available: Aug 1st - 31st '24 $55k, Sept 1st - Sept 30th '24 $20k Located deep at the end of a private driveway on a shy 2 acres holds this beautiful renovated contemporary with extraordinarily unique design features. The open flow interior with dramatic height ceilings and continuous expanses of glass provide fantastic abundant natural light throughout. The gourmet kitchen and dining area glide effortlessly to the spacious sun room oasis. The living room has a gas fireplace and wet bar for entertaining. The separate guest wing, perfectly situated for privacy, holds a second primary bedroom with bath and two additional bedrooms each en-suite with baths. The expansive primary suite occupies the entire second floor with over-sized primary bath and walk in closet. To complete this perfect outdoor lifestyle is expansive mahogany decking, new heated gunite pool, and north south tennis court. In addition, there is a 3 car detached garage. This unique offering is located moments to East Hampton Village and Ocean beaches. Also available 09/06/2022 - 09/30/2022 for $20K. EH RR #: 26-389 Rental Terms: August - Labor Day: $65,000 Memorial Day - Labor Day: $160,000 July: $65,000 June: $35,000 June/July: $95,000 Other / Short Term - Year Round: $220,000 July - Labor Day: $125,000

Traditional Luxury Getaway Minutes from East Hampton Village & Ocean Beaches Welcome to Handsome Hills, your perfect escape in the Hamptons! This stunning 5-bedroom, 4-bath home is designed for comfort, relaxation, and making unforgettable memories. Nestled in a peaceful neighborhood just minutes from East Hampton Village and the area's best ocean beaches, this home is the perfect retreat for families and friends looking to unwind in style. Inside, You'll Love: A spacious and beautifully decorated interior with plenty of room to spread out. A first-floor primary suite with a private bath and direct access to the outdoor hot tub. A custom eat-in kitchen featuring stainless steel appliances, perfect for cooking up delicious meals. A formal dining room for elegant dinners and special gatherings. A cozy den for quiet reading or morning coffee. A grand living room with a floor-to-ceiling fireplace, perfect for gathering and relaxing. A fully finished lower level with a movie screen, comfy lounge, pool table, bar, poker table, and dart board - entertainment for everyone! Outdoor Living at Its Best: A heated pool and hot tub for ultimate relaxation. A spacious deck with a grilling station and outdoor dining table for alfresco meals. A hammock to soak up the sun or enjoy an afternoon nap. 2 Kayaks to enjoy a paddle on nearby Georgica Pond. A private outdoor shower, perfect after a dip in the pool or a day at the beach. A large fenced-in yard in a quiet, bike-friendly neighborhood. More to Love: A large garage to store bikes, surfboards, and beach gear. Pet-friendly-your well-behaved fur babies are considered! Concierge touch-celebrating a special occasion? Send your pre-ordered items ahead, and we'll set them up before your arrival. Whether you're here to relax, explore, or celebrate, let us welcome you to your home away from home. [[Rental Registration # Pending]] EH RR #: 23-1270 Rental Terms: July - Labor Day: $109,000 July: $59,000 June: $25,000 June/July: $75,000 August - Labor Day: $65,000 Other / Short Term - Weekly: $15,000 Memorial Day - Labor Day: $125,000

Welcome to 4 Scrimshaw Drive, located in the sought-after Whalebone Landing community, where summer feels calm, private, and effortlessly beautiful. Enjoy the private bay beach and tennis courts just moments away, and quick access to the boutiques, restaurants, and harbors of both Southampton and Sag Harbor. Designed for luxury summer living, this home features a heated gunite pool, sun-filled interiors, and three levels of finished living space ideal for both relaxation and entertaining. Coastal-inspired details throughout the home create a natural sense of ease and timeless Hamptons elegance. With convenient proximity to the U.S. Open PGA at Shinnecock Hills Golf Club in June 2026, this residence offers a refined retreat for those seeking to experience the very best of the Hamptons with style, privacy, and comfort.

Ideally situated South of the Highway in Bridgehampton, this exceptional rental offers the quintessential Hamptons lifestyle on a beautifully cleared, one-acre parcel. Tucked away on a quiet cul-de-sac, the property offers a rare combination of privacy, tranquility, and convenience, just moments from ocean beaches, horse farms, world-class dining, shopping, and everything the Hamptons has to offer. The light-filled residence is designed for effortless summer living and year-round enjoyment, with generous spaces for relaxing and entertaining. A welcoming living room with fireplace, updated kitchen and dining area, which flows seamlessly to a grand oversized screened-in porch. The first floor also features a comfortable junior primary bedroom, and a dedicated home office area overlooking the pool. Upstairs, the gracious, private primary suite is joined by two additional guest bedrooms, providing comfortable accommodations for family and guests. Outside, a heated gunite pool with fencing takes center stage amid mature landscaping and expansive, fully cleared grounds. There is abundant room to lounge poolside, dine al fresco, entertain, or simply enjoy the serenity of the property. Additional amenities include a two-car garage and generous parking. With its coveted South-of-the-Highway location, peaceful setting, spacious interiors, resort-style pool, and proximity to the ocean, this is a distinctive opportunity to experience Bridgehampton at its best. Available as a summer or year-round rental. [[Rental Registration # RP230864]] EH RR #: RP230864 Rental Terms: Other / Short Term - Year Round: $250,000 June: $35,000 August - Labor Day: $75,000 Memorial Day - Labor Day: $175,000 July: $65,000

Spectacular living awaits in Sagaponack South, this bespoke home offers 10,000 +/- square feet on 1.5 +/- private acres. Custom build in 2013, this chic residence features seven spacious bedrooms and seven+ baths. This modern masterpiece was designed by Francis D'haene of the award winning architectural firm D'apostrophe Design. Enter into breathtaking light-filled living space graced by walls of glass through a dramatic double-height entryway with a travertine floating staircase and solid white oak floors. This home includes an 68' heated gunite infinity pool, pool house, outdoor shower and full outdoor dining/kitchen area. The ultimate setting for entertaining and enjoyment. 183 Daniels Lane makes a grand statement of elegance while affording contemporary comfort. Rental Terms: Two Weeks: $200,000 August: $450,000 Memorial Day - Labor Day: $950,000 August - Labor Day: $500,000 July: $400,000 June: $200,000

Stunning new modern home with an abundance of natural light throughout. 4 bedroom, 3 bath home with plenty of room for your loved ones. Home has a large open living space with oak floors and high ceilings with huge Anderson doors that opens onto extensive covered deck for seamless indoor outdoor entertaining. Two guest bedrooms and a bathroom complete the first floor. The master suite is on the second floor with a balcony to enjoy morning coffee, a walk through closet, and bathroom with free-standing soaking tub and large shower. The lower level has with sealed concrete floors with underfloor heating, a spacious living/ den area, office space, bedroom, bathroom and laundry room and separate entrance. Great yard with mature Japanese maple tree, birches and hedging. Please call with any questions or to set up an appointment to view. [[Rental Registration # 2025-L-0061]] EH RR #: 2025 -L-0061 Rental Terms: August - Labor Day: $30,000 Memorial Day - Labor Day: $62,500 August: $22,500 July - Labor Day: $47,500 July: $22,500

Indulge in the ultimate Hamptons experience at Historic Box Farm, a magnificent 6-bedroom, 6-bath estate meticulously renovated in 2024. Set on rolling manicured lawns framed by mature trees, this property offers an unparalleled blend of timeless elegance and modern comfort. Grand Heated Pool (20' x 40') - the centerpiece for sun-soaked afternoons and moonlit swims Prime Water Mill Location - minutes from pristine ocean beaches and the world-class dining and boutiques of Southampton, Bridgehampton, and Sag Harbor Three king suites, two queen bedrooms, and a full-size guest room for effortless hosting. Pet-Friendly - Discerning owners will consider pets upon request Outdoor Entertaining - Expansive deck with grilling station, perfect for sophisticated soirées and alfresco dining Multiple Indoor & Outdoor Lounges - curated spaces for intimate conversations or lively gatherings Modern Amenities - TVs in every room, premium cable, and high-speed connectivity [[Rental Registration # Pending]] EH RR #: RP170644 Rental Terms: August: $45,000 August - Labor Day: $50,000 July: $45,000 June: $38,000

This charming cottage on East Hampton Village's Osborne Lane is available for rent. Just doors away from Newtown Lane and the heart of village attractions, this lovely home offers a wonderful combination of provincial appeal and local convenience. The recent renovation includes a first floor that features a living room with a wood burning fireplace, a large kitchen, a dining room, a primary bedroom with en suite bath, and a laundry room. The second floor features two guest bedrooms and a full bath with a clawed foot soaking tub. The backyard is very private and has a hot tub, an outdoor shower, and cheery patio furniture shaded by a large tree. This property offers the dual advantage of peace and quiet while remaining close to village shopping, restaurants, transportation and fine ocean beaches. Authentic charm throughout. [[Rental Registration # Pending]] EH RR #: 24-941 Rental Terms: July - Labor Day: $68,000 June: $20,000 Memorial Day - Labor Day: $80,000 July: $35,000 August - Labor Day: $35,000

Perfectly positioned in the heart of Bridgehampton South, this beautifully designed six-bedroom, five-and-a-half-bathroom home embodies effortless Hamptons living in every season. Filled with natural light, the home offers elegant, sun-drenched interiors, sophisticated yet relaxed furnishings, and a seamless flow between indoor and outdoor spaces. Thoughtfully designed for both comfort and style, expansive living and dining areas create the perfect setting for everyday living, entertaining, and weekends with family and friends. Beautifully landscaped grounds offer multiple outdoor seating and dining areas, while a tucked-away fire pit provides an inviting place to gather on crisp fall evenings or cool spring nights. Designed with every member of the family in mind, the property also features a basketball court, trampoline, playground, and garage, offering plenty of space for recreation and relaxation throughout the year. Located moments from Bridgehampton's renowned restaurants, boutiques, farm stands, ocean beaches, and equestrian facilities, the home offers an ideal balance of privacy, comfort, and convenience - from quiet fall weekends and cozy winters to spring on the East End and the arrival of summer. An exceptional opportunity to experience Bridgehampton living through the seasons. [[Rental Registration # Pending]] Rental Terms: January: $15,000 March: $15,000 November: $30,000 February: $15,000 Other / Short Term - 9/12/2026 - 6/30/2027: $195,000 June: $75,000 October: $35,000 May: $40,000 April: $20,000

Set amid the pastoral beauty of Water Mill's horse country, Casa Lana is a charming three-bedroom, two-and-a-half-bath residence surrounded by lush gardens and sweeping views across neighboring farm fields. Named by a previous owner, a noted biographer of Golden Age film star Lana Turner, the approximately 2,000-square-foot home blends relaxed Hamptons living with thoughtful design and a distinctive sense of place. Interiors have been carefully updated, including a renovated kitchen and refreshed primary and guest baths. Shiplap detailing, transom windows and abundant natural light lend warmth and character throughout, while a media den offers an inviting space to unwind. The main-level primary suite provides ease and privacy, while additional bedrooms are located upstairs. A dramatic double-height art studio with cathedral ceilings and skylights adds an unexpected architectural element and an inspiring space for creative pursuits. Outdoors, the property unfolds as a private garden sanctuary. Stone paths and walls wind through mature specimen plantings, including Cryptomeria, Hinoki cypress, Japanese snowbell and umbrella pine. A nine-foot cocktail pool is tucked into the landscape, while a refurbished deck provides an ideal setting for outdoor dining, morning coffee or evenings overlooking the neighboring horse farm and spectacular western sunsets. Central air conditioning on the main level, mini-splits upstairs, updated windows and sliders, and generous lower-level storage complete the home. Peaceful yet distinctly Hamptons, Casa Lana offers an intimate Water Mill retreat where gardens, farmland and relaxed indoor-outdoor living come together beautifully. [[Rental Registration # RP261554]] EH RR #: RP261554 Rental Terms: August: $35,000 July: $30,000

This brilliant Water Mill South estate is now offered for summer and off-season time periods. When you think of a luxury Hamptons rental, this offering "ticks all the boxes." Sited on over two acres, this estate offers seven bedrooms, nine full baths, three half baths, the main residence scaling some 13,000 square feet, a pool, pool house, and tennis court. With views of Mecox Bay and the Atlantic Ocean, this property features amenities that create unmatched resort-style living, including the indoor gym, home theater, the 30'x50' heated Gunite pool with spa, and sunken clay tennis court. The property and home feature the highest attention to detail and state-of-the art technologies including Control 4 home automation, Lutron lighting, Sonos audio system, and top appliances by Wolf, Sub-Zero, and Miele. The gated drive leads to the covered front entry that opens to the double-height reception foyer and the light-filled, first floor offering myriad spaces to entertain: The great room, living room, and gourmet eat-in kitchen with breakfast area, all of which open to covered porches and terraces, making indoor-outdoor living and entertaining seamless. A generous ground floor guest suite opens to the back patio and pool area. The attached heated garage offers one space, and opens to the rear service areas and back staircase. The main stair case rises to the second level with the primary suite that occupies the south wing and which includes an office, private deck with glorious views of Mecox Bay and the ocean, and an over-sized, spa-like, marble bathroom. This second level also offers five additional guest suites, two with walk-in closets, and laundry room. The finished lower level features the home theater with seating for ten or more, a recreational hangout with a full bar, and full gym with steam room and sauna. The spacious pool house offers a lounge space, kitchenette, full bathroom, and laundry (summer rentals only). Truly, a spectacular residence and property, ready right now for multiple time periods. [[Rental Registration # RA261802]] EH RR #: RA261802 Rental Terms: June/July: $500,000 Two Weeks: $100,000 March: $100,000 May: $150,000 January: $100,000 February: $100,000 June: $200,000 July: $300,000 Other / Short Term - 5/28/2027 - 7/31/2027: $550,000 April: $100,000

Sited at the end of a quiet cul-de-sac in East Hampton Village Fringe, this stylish two-story home is an ideal oasis for your summer holiday. A covered porch with its own swing welcomes you into the beautiful entry foyer where high ceilings permeate throughout the house, with highlights of the first floor including an open concept design of a generous living room with a wood burning fireplace, a separate chef's kitchen with a large island, high-end appliances, and an adjacent dining area, a bright sun room with windows overlooking the backyard, an en-suite bedroom/office with full bath, and a half bath. A dramatic staircase with glass walls leads to the second floor, which plays host to the substantial primary bedroom with vaulted ceilings and an en-suite bath, three additional guest rooms, each featuring their own en-suite bath, and a large loft space equipped with multiple desks and a window seat to enjoy the view. The lower level offers another entertainment experience, with a chic sectional couch and large screen TV, a gym area, and full walkout access to a private sitting area and outdoor fireplace. A long, gated driveway leads to the front of the home and provide a sense of welcome to the classic cedar shake exterior. The backyard is highlighted by a large, heated saltwater Gunite pool with an attached spa tub, a stylishly furnished pool house complete with a recreation area and full bath, an outdoor shower, and an alfresco kitchen with a built-in barbecue and serving stations. A bluestone patio, sundecks, outdoor furnishings, large lawn, and shaded seating areas complete this spectacular home. This secluded locale offers the dual advantage of privacy while remaining close to Amagansett and East Hampton village restaurants, shops, transportation and beautiful ocean beaches. [[Rental Registration # RR-25-1042]] EH RR #: RR-25-1042 Rental Terms: July: $85,000