luxury houses with pool for rent Sag Harbor, United States

Discover a newly completed 2025 modern residence, quietly set far back from the road for exceptional privacy. Thoughtfully designed, the home features three generously scaled primary suites and a striking great room with balcony, oriented toward serene views of the 100-foot pool, spa, and brick-lined terrace. A covered porch and outdoor dining area invite relaxed gatherings framed by the natural landscape. Inside, a spacious chef's kitchen anchors the main level with Thermador appliances, complemented by a large living room, ensuite guest bedroom. Every space has been crafted for comfort, flow, and effortless living, ensuring an elevated experience throughout your stay. Sustainable features include a greenhouse, garage with electric vehicle charging, and geothermal and solar energy systems. Perfectly positioned for quick access to Bridgehampton's ocean beaches and Sag Harbor's boutiques and restaurants, this modern retreat offers the best of the Hamptons in one tranquil setting. Please call with questions or to make an appointment to view this great property! [[Rental Registration # Pending]] Rental Terms: August - Labor Day: $135,000 Two Weeks: $70,000 August: $110,000 Other / Short Term - 8/1/2026 - 9/30/2026: $165,000 September: $65,000

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

Rebuilt in 2000 and maintained to the highest standards, this exquisite Victorian farmhouse is newly available as a first-time rental. Set along one of Bridgehampton's most sought-after corridors, Ocean Road, the property offers immediate access to the best beaches and village amenities. The main residence features 4 exceptionally laid out bedroom suites, multiple living parlors, and 8 fireplaces. Ample entertaining spaces, includes a chef's eat-in kitchen equipped with premium Viking appliances and custom cabinetry, while several bar and kitchenette areas create effortless flow for hosting. Upstairs, the bedroom suites offer generous proportions, walk-in closets, and spa-style baths, with select rooms featuring fireplaces, ceiling fans, and beautiful views of the gardens. Additional living areas include a billiards room, lower-level entertainment room with bar, and wraparound porch. Enter the 1-acre property to beautiful specimen trees, including 5 Japanese Maples. The main house offers outdoor eating area and leads to a stone wall separating it from the heated gunite pool and guest cottage. The fully equipped cottage consists of one bedroom, a separate living room, and outdoor al fresco eating area. Special bonus: one car with beach pass included. Rental Terms: September: $100,000 August: $200,000

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

Also available August for $150K. Turn South from fabled Parsonage Lane onto a long private driveway that leads to this 1.7 acre property that backs onto 16 acres of agricultural reserve. There are 5 bedrooms and 6.5 baths in this immaculate modern design with plenty of South and West facing patio for outdoor dining and taking in the view of the lawns, gunite pool and pool patio. Just minutes to Town Line ocean beach. Rental Terms: July: $110,000 August - Labor Day: $150,000 July - Labor Day: $250,000 Other / Short Term - August: $125,000

Location! Location! Location! This Modern home is sited on over 1.5 glorious acres south-of-the highway in Sagaponack, and features 6 bedrooms, 7 bathrooms, an open kitchen, dining area and great room with walls of glass allowing for easy access to the backyard. Three car attached garage. Outside, the expansive decks surround the over sized heated gunite pool, and the professionally landscaped property provides the ultimate setting including a fire pit. Located around the corner from the ocean, this home has it all! Rental Terms: Memorial Day - Labor Day: $350,000

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: August - Labor Day: $38,000

Perfectly curated, fully renovated, and designed for effortless summer living, this Hamptons retreat delivers a rare combination of style, comfort, and resort-level amenities. From professionally manicured landscaping to a fully updated, expanded designer interior, the home sets a high standard from the moment you arrive. Inside, an expansive family room anchors the living space with a pool table, fireplace, bar and dedicated TV lounge, flowing seamlessly into another more intimate sitting area with fireplace which leads into the open-concept chef's kitchen featuring high-end appliances, counter seating, and a full dining area-all framed by abundant natural light and views through the oversized picture windows and glass doors. The home offers four en-suite bedrooms. The primary suite is a true retreat, complete with distant water views, a private walk-out balcony, fireplace, and a spa-inspired bath with a generous soaking tub. For added convenience, laundry is located on both the second floor and in the lower level. Outdoors, the property feels like a private resort, featuring a heated saltwater pool, updated decking, and thoughtfully designed dining and lounge areas ideal for entertaining or relaxing in total privacy. A truly special offering designed for elevated Hamptons summer living. [[Rental Registration # RP260341]] EH RR #: RP260341 Rental Terms: Two Weeks: $40,000

**ANY 2 WEEKS THIS SUMMER, AVAILABLE FROM JUNE 1-SEPTEMBER 30 FOR $60,000** This quintessential summer rental has it all! On 3.7 + acres you will find a spacious 7 bedroom, 5 1/2 bathroom bright and sunny main residence with plenty of space to entertain. The Living Room with bar flows into the Media Room. The dining room opens up to a generous outdoor deck and the oversized gourmet kitchen offers a casual eat-in area and also has access to the outside outdoor dining overlooking the pool and Mecox Bay. There are 2 primary suites and 2 guest rooms on the 2nd floor and 3 additional bedrooms and a recreation area on the 3rd floor. The boathouse/guesthouse with dock has another guest bedroom, 2 bathrooms and the coolest pool house - offering more space for lounging and entertaining. An oversized 20 x 50 gunite heated pool and tennis court complete this perfectly located vacation home. This could be the perfect setting for a wedding or other special event. **ANY 2 WEEKS AVAILABLE FOR $60,000** [[Rental Registration # Pending]] Rental Terms: Two Weeks: $60,000

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

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

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 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 # Rentalregistrationrenewalinprocessfor2027.]] EH RR #: Rental registration renew Rental Terms: March: $100,000 Other / Short Term - 5/28/2027 - 7/31/2027: $550,000 February: $100,000 May: $150,000 June/July: $500,000 April: $100,000 January: $100,000 June: $200,000 Two Weeks: $100,000 July: $300,000

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

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