luxury houses with terrace for rent Sag Harbor, United States

Freshly reimagined with impeccable style and high-end finishes, this five-bedroom, four-bath retreat delivers the best of summer living in the Hamptons. Completely renovated and fully designer-decorated, every inch of this home reflects a polished, curated aesthetic-where form meets function in all the right ways. Enter into a sleek, sunlit kitchen outfitted with top-of-the-line appliances and striking design elements, opening to a chic dining area and a dramatic double-height living room anchored by a fireplace. All main living spaces flow effortlessly to the expansive deck-perfect for entertaining, lounging, or dining al fresco. The first-floor ensuite primary bedroom (California king) opens directly to the deck and pool area, while a stylish twin guest bedroom and full bath complete the main level. Upstairs, two additional guest rooms (California king and queen) share a well-appointed full bath. The newly finished lower level expands the living space with a cool, casual lounge, wet bar, state-of-the-art media room, fifth bedroom, and full bath-perfect for guests or movie nights. Outside, enjoy a heated in-ground pool, generous lawn, and half basketball court. There is a gym/ workout area in the detached garage for a dedicated, workout experience. Ideally located in Bridgehampton, just minutes from the village and moments from Sag Harbor, this turnkey rental blends sophisticated design with summer-ready amenities in one unforgettable package. [[Rental Registration # RA251101]] EH RR #: RA251101 Rental Terms: Other / Short Term - Year Round: $260,000

Also available: June for $35K; June/July for $125K Enjoy the beauty of this recently renovated five bedroom, five-and-a-half bath traditional in Bridgehampton's horse country. This 4,500+/- square foot home sits on a beautifully manicured full acre with open lawns and a 20' x 40' gunite pool. A large double-height foyer and beautiful staircase greet you as you enter the home while a chef's kitchen and spacious, nicely appointed primary suites on both levels are just some of the other amenities featured in this summer oasis. Close proximity to town, shops, restaurants and beaches complete this spectacular property. Reach out now to secure this wonderful home for summer 2023. Rental Reg #: RP230579 EH RR #: (RP251002) Rental Terms: July: $110,000 June: $50,000 August - Labor Day: $135,000

Discover the perfect island getaway in this spacious 4-bedroom, 2-bathroom home tucked away on a large, serene lot. Surrounded by mature landscaping, the property features a generous front porch overlooking a peaceful pond—an ideal spot for morning coffee or sunset relaxation. Inside, the home offers a bright and inviting layout with a well-appointed kitchen complete with a center island, perfect for entertaining. Additional conveniences include an in-unit laundry room, mudroom, and a flexible bonus space great for a home office or playroom. A two-car garage provides ample storage and parking options. Located just minutes from Route 114 and South Ferry, the home offers easy access to all the island’s main destinations. Wades Beach is only 1.5 miles away, making beach days effortless. Guests also enjoy seasonal access (July 4th–Labor Day) to the Coecles Harbor Marina pool for added summer enjoyment. This peaceful retreat combines comfort, privacy, and convenience—ideal for your next stay on Shelter Island.

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.

Spend your summer in style at Georgica Estates, East Hampton's premier condo community where each unit is a freestanding home offering the privacy and comfort of a single-family residence. Only 10 minutes to Sag Harbor Village & Bridgehampton, this light-filled 4-bedroom, 3.5-bath townhouse is set among nearly 8 beautifully landscaped acres and features an open, airy floor plan perfect for summer living. The first-floor primary suite offers convenience and privacy, while the second level provides three spacious guest bedrooms. With high ceilings, large windows, and sun-drenched living spaces, this home feels bright, cheery, and welcoming. Enjoy cooking in a modern open kitchen with quartz countertops, and stainless steel appliances, and entertain on the private wood deck with a large awning, surrounded by lush gardens and greenery. Other features include hardwood and ceramic tile floors, central air, washer/dryer, fireplace, and a 1-car attached garage. Community amenities are top-tier and meticulously maintained, including: A clubhouse Heated pool 2 tennis courts Pickleball Manicured grounds with walking paths Whether you're looking for a full-season rental or a month-by-month stay, this home delivers carefree luxury with every convenience just minutes from East Hampton Village and world-class beaches and restaurants. Sorry, no pets. HOA: Georgica Estates. Rental Terms: Two Weeks: $18,000 August - Labor Day: $45,000 August: $38,000

Great home for entertaining. Very attractive contemporary in country setting. Five bedroom, four bath home in Water Mill with heated gunite pool plus entertainment room in lower lever. [[Rental Registration # RP201246]] EH RR #: RP250236 Rental Terms: June: $35,000 August - Labor Day: $70,000 July: $60,000 July - Labor Day: $125,000 Memorial Day - Labor Day: $150,000 September: $30,000

Located just 2 blocks from Sammy's Beach, in East Hampton, unwind at this stunning original Mid-Century home. This freshly renovated two story, three bedroom, two bath house was built with oak floors, cedar clad walls and ceiling, and antique details for a luxurious yet charming feel.It features a double height living area with floor to ceiling windows, wood burning stove, and integrated fully equipped kitchen and dining areas. Sliding glass doors lead to the expansive wraparound deck with Barbecue, dining and lounge areas, outdoor shower, and the large yard with seating and a fire-pit. The bedrooms are generously proportioned with 2 king and 1 queen beds, and upstairs there is a dedicated office and work out area with its own walkout balcony.Though quiet and elegant in nature, the home is modern where it counts. It features two large flatscreen TVs, 1 GB wi-fi and unlimited music and sound capabilities in every room. Enjoy long days on the beach, paddle board or kayak in Three Mile Harbor, or hikes through the nearby 116 acre Sammys Beach Nature preserve. Conveniently located 2 blocks from Sammys Beach, 7 minutes to East Hampton Village and only 10 minutes from Sag Harbor, the home is a true East End escape. [[Rental Registration # Pending]] Rental Terms: February: $2,975 July - Labor Day: $39,000 September: $4,500 June: $9,900 April: $2,975 March: $2,975 November: $3,200 Other / Short Term - Dec: $3,200 October: $3,200 August - Labor Day: $22,000 Memorial Day - Labor Day: $49,000 August: $18,000 January: $2,975 July: $18,000 May: $3,975

A stunning architectural jewel in Pandion, this freshly built, never-before-lived-in residence is both design-forward and deeply inspiring. Clad in arctic pine tongue-and-groove and corten steel, its twisted gable form captivates from every angle, while exterior decking invites you to soak in the surrounding natural beauty. The design/build owner's home draws inspiration from exposure to Frank Gehry's artist friends' homes in Venice, California. Founded in 2003 by Alexandra Hayden, Octave Studio is known for creating intuitively designed spaces that balance comfort and creativity, honoring the architecture and natural surroundings while reflecting each client's unique spirit. Curate | Build is Shelter Island's premier general contractor, known for high-end residential construction and renovations that blend timeless design, modern function, and uncompromising craftsmanship. The plywood-finished walls pay homage to Sea Ranch and early Gehry Venice architecture, creating a warm yet modern atmosphere that balances precision with artistry. Inside, radiant Indian black limestone floors anchor the soaring, cathedral-height living space centered around a wood-burning fireplace. The kitchen is as stylish as it is functional, featuring a Wolf range, Thermador under-counter fridge-freezer, and a separate beverage fridge. The primary bedroom includes an ensuite bathroom with Beton Ciré waxed gray walls. A guest bedroom and an additional full bath complete the main floor. Upstairs, a vaulted loft offers a lounge and media area, desk space, and a peekaboo window framing bay views. The lower level features a concrete-floored laundry room with a full-size fridge-freezer. Smart Lutron lighting and shades throughout the home add effortless modern convenience. Set on 1.5 acres moments to Mashomac, a 2600 acre preserve, the property provides a serene natural setting that enhances the home's sculptural presence. Residents enjoy access to a Boat House-exclusive to just three homes within the HOA-complete with a living area, bathrooms, outdoor shower, and dock with a dedicated boat slip accommodating up to a 28-foot powerboat. Please note: beam and draft information must be provided to ensure vessel compatibility. The community also features a deco-turf tennis court with bathroom and locker. [[Rental Registration # RP2025]] EH RR #: RP 2025 Rental Terms: July - Labor Day: $62,500

Newly renovated in 2018, this bright and airy four-bedroom home is set on a full acre bordering a private preserve, offering rare tranquility and uninterrupted natural views in the heart of Water Mill. The home is filled with natural light throughout, featuring an open-concept kitchen and living space designed for easy summer living and seamless entertaining. The primary suite opens directly to the outdoor deck, creating a true indoor-outdoor lifestyle. Outside, enjoy expansive, fully fenced grounds, a sparkling in-ground pool, and the privacy that comes with backing onto preserved land. Privacy with just sun, space, and calm. Ideally located minutes from ocean beaches, Southampton, and Bridgehampton villages, and top restaurants, this home delivers both convenience and escape. A clean, modern Hamptons rental that actually feels like a getaway. Available August through Labor Day. [[Rental Registration # RP260066]] EH RR #: RP260066 Rental Terms: Other / Short Term - Year Round: $125,000 Memorial Day - Labor Day: $85,000

Located on an iconic East Hampton Village lane is this incredible home with 5 en-suite bedrooms, plus 2 half baths. Luxe beach vibe decor surrounds you in comfort and style. Open concept living with first floor living room, dining area, centralized cook's kitchen and an oversized den that leads outdoors to secluded grounds with a heated, gunite pool, large patio and an outdoor shower. Upstairs find a spacious primary bedroom with sitting area and a fireplace plus 3 additional en-suite bedrooms. Want more? Head down to the finished lower level for media, recreation, Peloton, free weights, powder room and another en-suite bedroom. This home has all you could want or need for a perfect summer experience! Rental Terms: Memorial Day - Labor Day: $250,000 June: $55,000 August - Labor Day: $110,000 July: $100,000 July - Labor Day: $200,000 Other / Short Term - Year Round: $300,000

Settle into summer on the North Fork in this beautifully maintained and updated 4 bedroom, 3 full bath home located in the Angel Shores community of Southold. The layout is ideal for entertaining or just enjoying the lazy days of summer. This special home offers a 1st floor bedroom and full bath, along with a 2nd story spacious primary en-suite and 2 additional bedrooms to comfortably accommodate guests. Angel Shores is known for its sandy Peconic Bay beach, just a short stroll down the road, perfect for easy beach days and watching sunsets by the water. The home is also conveniently close to Southold’s wineries, farm stands, and village amenities, putting the best of the North Fork right at your fingertips. 2026 Availability: June 16-June 30th $7,000, July $23,000, August $25,000 August-Labor Day $27,500. Permit # 0956

This picturesque traditional on East Hampton Village's Osborne Lane is now available for two weeks at summer's end. Just doors away from Newtown Lane and the heart of village attractions, this lovely home offers a wonderful combination of summer charm and local convenience. Highlights of the first floor include a large entry foyer, a double-height living room with wood burning fireplace, a spacious chef's kitchen with high-end appliances and center island, a stylish dining room, a separate den, a screened-in porch, a half bath, and the primary bedroom with a gas fireplace, two walk-in closets, and an en suite marble bath. The second floor includes three large guest rooms, each with its own en suite bath. The lower level has been finished and offers another living space with TV, wet bar, and wine refrigerator, a gym outfitted with Peleton, Pilates, and free weight equipment, a bonus room, and additional full bath. The backyard is highlighted by a large gunite pool surrounded by bluestone, an expansive lawn, tall evergreens providing ample privacy, a hot tub, and extra decking and patio space - both ideal for entertaining. This exceptional property affords a wonderful sense of warmth and enjoyment while remaining close to world-class restaurants, shops, transportation, and beautiful ocean beaches. [[Rental Registration # 24-941]] EH RR #: 24-941 Rental Terms: Two Weeks: $75,000

A stone's throw from the heart of East Hampton Village, this fully renovated and thoughtfully designed home offers the perfect Hamptons escape. Privately set behind mature landscaping and a gated entry, this new rental delivers a rare combination of charm, convenience, and turnkey ease. Inside features two well-proportioned bedrooms and two full baths, complemented by a spacious living room and eat-in kitchen. Outdoors, enjoy a private yard ideal for relaxing or entertaining after a day at the beach. Minutes to village shops, dining, and the area's most desirable ocean beaches. [[Rental Registration # RR-26-353]] EH RR #: RR-26-353 Rental Terms: July: $16,000 Winter Season: $21,000 Per Month Other / Short Term - Year Round: $75,000 August - Labor Day: $28,000 Memorial Day - Labor Day: $45,000 July - Labor Day: $38,000 June/July: $25,000

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: Other / Short Term - 9/12/2026 - 6/30/2027: $195,000 February: $15,000 May: $40,000 October: $35,000 November: $20,000 September: $60,000 January: $15,000 April: $20,000 March: $15,000 June: $75,000

This light-filled residence is quietly set on a gated and exceptionally private two-acre property in coveted Water Mill. Recently renovated with a natural, timeless aesthetic, the home features sanded oak floors and a thoughtful layout with five beautifully appointed bedrooms across two distinct wings. A welcoming foyer opens to a spacious living and dining area, highlighted by a wall of sliding glass doors that seamlessly connect to the deck and outdoor living spaces. First-floor guest suite enjoys direct access to the deck and pool. Upstairs, the primary suite and an additional guest ensuite share a balcony, alongside a dedicated workspace ideal for focused productivity. A separate wing offers a media / playroom and two additional bedrooms, including one with bunks, served by a full bath-perfect for guests of all ages. Outdoors, enjoy a heated pool and relaxed al fresco dining surrounded by mature landscaping, hydrangeas and natural tranquility. Ideally located just eight minutes from Southampton Village's renowned restaurants, shops, and ocean beaches, this serene and special property offers privacy, comfort, and effortless Hamptons living. Please call with questions or to make an appointment to view this serene and special property! [[Rental Registration # RA260488]] EH RR #: RA260488 Rental Terms: August - Labor Day: $65,000 August: $55,000

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

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

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

Beautifully and stylishly renovated cape in East Hampton Springs is offered for summer. This sunny and cozy home offers a bedroom on the first floor, two on the second. Great deck with hot tub and a large green lawn. Close to Maidstone Beach, Springs General Store, and restaurants and coffee shops. [[Rental Registration # 25-1018]] EH RR #: 25-1018 Rental Terms: September: $8,000 August - Labor Day: $17,000 Memorial Day - Labor Day: $38,000 July - Labor Day: $30,000 July: $17,000

Enjoy August in this sweet, cozy, updated home with pool. Chef's kitchen, open floorplan with 3 bedrooms, and 2 baths, this home is close to bay beaches. [[Rental Registration # 26-1149]] EH RR #: 26-1149 Rental Terms: Two Weeks: $10,000