luxury houses with pool for rent New York, United States (page 10)

Also available Year Round and Winter months Rental Reg # 22-834, Exp 5/23/24 [[Rental Registration # 26-664]] EH RR #: 26-664 Rental Terms: Other / Short Term - Year Round: $185,000 August - Labor Day: $50,000

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

Enjoy a luxurious summer in this magnificent Robert A.M. Stern designed Georgica traditional, nestled in the heart of East Hampton's estate area on two gracious, quiet acres with mature plantings. Grand entertaining spaces alternate with cozy private nooks, giving everyone lovely spaces in which to be together or apart. Entertaining options abound with extensive indoor and outdoor venues, while there are plenty of private spots to work from home. Three en-suite guest rooms, a staff room and bath, a Primary Bedroom featuring its own WBFP and private deck sleep 8-10. A finished lower level is fully furnished with a Media Room, Fitness Center, Pool table and Laundry Room, as well as a staff kitchenette and bedroom and full bath with its own entrance. A heated, gated Gunite pool and pool house, security system, recently updated systems, and automated driveway gates make this a stress-free, safe and private oasis in which to spend the summer or the year. Rental Terms: Year-Round: $300,000 July - Labor Day: $175,000

Spend the summer on one of the most iconic private streets in Southampton Village. The classic Beach House was completely renovated and brought up to todays high standards. The elegant, sunny house offers eight wonderful bedrooms, some with ocean views, and six baths spread out over three floors. The ground floor features a formal dinning room, eat in kitchen with living space, grand entrance hall, and a living room with French doors that go to a covered outdoor living space. The beautifully manicured yard is the perfect place to spend your summer. The in ground heated pool is already fenced in with a rose covered picket fence. The true highlight of this property is the private beach access. Rental Terms: June: $70,000

Experience the best of Southampton Village living from this beautifully renovated Gin Lane estate rental, ideally located south of the highway just one block from the ocean. Set on 4 lush acres at the corner of Little Plains Road and iconic Gin Lane, this private summer retreat offers timeless Hamptons style, expansive entertaining spaces, and exceptional proximity to the beach, village boutiques, and renowned restaurants. Recently renovated in 2020, the 8-bedroom, 6-bath traditional residence spans approximately 5,800 +/- sq. ft. and features a bright open-concept layout designed for effortless summer living. Interior highlights include a spacious living room with fireplace, great room with open dining area, updated chef's kitchen with staff area, den/office, first-floor primary suite, and multiple gathering spaces ideal for entertaining guests or extended stays. Outdoor amenities include a heated 40' x 20' Gunite pool, expansive west-facing patio ideal for outdoor dining and entertaining, covered porch, mature landscaping, attached 2-car garage, and sweeping manicured lawns set across 4 private acres. Offering exceptional privacy in a premier Southampton Village location, the property is moments from ocean beaches, world-class shopping, and acclaimed village restaurants. Perfectly suited for Hamptons summer rentals, extended seasonal stays, or year-round living, this Southampton Village estate combines location, scale, privacy, and classic Hamptons charm in one of the area's most coveted ocean-block settings. Rental Terms: Other / Short Term - Year Round: $500,000

Charming Post Modern home offers an open floor plan with 4 bedrooms, 4.5 baths, dining area, living area with french doors leading on the back deck, hardwood flooring throughout, heated pool. Cul de Sac privacy. Perfect for year round living. Rental Terms: Year-Round: $125,000

Discover the perfect Fall getaway in this stunning artist's home in Sag Harbor, now available from Sept 8th - Oct 5th 2026. Ideally situated between Sag Harbor Village and Long Beach, this immaculate 4-bedroom, 3.5-bathroom residence is a true oasis, featuring a well-curated collection of art within a sophisticated monochromatic interior. Built in 2018, this contemporary farmhouse beautifully balances exceptional style and comfort. An open-plan kitchen, dining, and living area seamlessly transitions to the 32' x 16' heated gunite pool, surrounded by a bluestone patio with multiple entertaining and lounging areas. A well-thought-out setting for summer gatherings or long days by the poolside. For the art enthusiast, a well-stocked library of art and design books can be found in the first-floor lounge. On the second floor, you will find four well-appointed bedrooms, including two that feature ensuite bathrooms, as well as an additional full bathroom. To enhance your stay, the dedicated laundry room features two washers and dryers for your convenience after days at the beach. Minutes from both Long Beach and Sag Harbor Village, you can also enjoy fresh, local produce from Serene Green Farm Stand, conveniently located at the end of Parkway Drive. [[Rental Registration # RP230356]] EH RR #: RP230356 Rental Terms: July: $60,000 August - Labor Day: $75,000 July - Labor Day: $135,000

New Kitchen Renovation!! Modern waterfront residence with expansive yard and private dock near Long Beach. Enjoy long summer days sailing, kayaking, swimming or swinging in the yard and followed by family bbqs. Great location with proximity to Sag Harbor village restaurants and shops and private outdoor oasis. Revel in spectacular sunset views from the wrap around deck with comfortable seating that is also perfect for outdoor dining and entertaining. Rental Reg. # RP201766 - Reg. Expires 6/07/2023 EH RR #: RP201766 Rental Terms: Other / Short Term - Year Round: $375,000

Handsome classic estate house with sensational sunset views over Maidstone Club and Hook Pond. Period beams and paneling, large sun room with wet bar. Game room with ping pong, pool table and big TV. Newly renovated kitchen with dining for 8 and a comfortable sitting area with flat screen TV. Great location in East Hampton. The house can accommodate 12 -15. The property is a stone's throw from the ocean. A special place for 2, 3, or 4 weeks vacation. Rental Terms: August - Labor Day: $175,000

Welcome to this exquisite rental property - a custom-built home boasting six bedrooms and seven and a half baths, infused with a modern flair and adorned with high-quality finishes in the Hampton's Style. Situated on a serene cul-de-sac on half an acre, this residence offers expansive outdoor living spaces including a pool house, a built-in BBQ kitchen area, and meticulously landscaped grounds. The effortless flow from the eat in kitchen to the double high ceiling living room makes this the perfect home for entertaining while still feeling compfortable and intimate. The sleek kitchen is a culinary haven, equipped with two Thermadore ovens, an induction cooktop, a built-in coffee machine, and an informal dining area. A butler's pantry connects the kitchen to the formal dining room, enhancing the ease of entertaining. Adjacent to the kitchen is a cozy den and a convenient laundry room. The luxurious primary suite is on the main level, featuring a spacious walk-in closet, a rejuvenating soaking tub, a steam shower, and direct access to the pool area for ultimate relaxation.The centerpiece of the home, a stunning floating staircase, floods all three levels with natural light, creating an ambiance of elegance and warmth. On the second level, four additional bedrooms await, including a king-size room with a balcony that could easily function as a secondary primary suite.The lower level and discover a bunk room, a media room, a gym, and a wine cellar, offering an array of leisure and entertainment options. Rental Terms: April: $15,000 March: $15,000

Also Available May 24 - Jul 31 $235K, Sep 4 - Nov 30 $160K Historic Sag Harbor, brilliantly renovated, offers sophisticated, relaxed stylish living. The 1750 Main house offers delightful, light, entertaining public spaces, luxurious en-suite bedrooms and staff quarters. The Carriage house offers added entertaining space with rare architectural features. This rare, near acre, village compound includes an oversized gunite pool, stone terracing, gracious garden dining and entertaining surrounded by a classic garden featuring historic box hedges, cherry trees and wonderful privacy. Rental Terms: Memorial Day - Labor Day: $425,000 July - Labor Day: $335,000 July: $140,000 August - Labor Day: $195,000 Other / Short Term - May 24 - Jun 30: $95,000

On a private cul-de-sac in Northwest Harbor, this sunny 3BR home is the perfect summer retreat in East Hampton. Primary bedroom on the first floor, 2 additional guest bedrooms upstairs, pool and pool house, and beautiful landscaping throughout the property grounds. [[Rental Registration # 25-168]] EH RR #: 25-168 Rental Terms: September: $10,000

Jeremiah Baker built this house in the 1850s from proceeds gained during the California Gold Rush. He later became an entrepreneur operating the first daily stage coach mail from Sag Harbor to East Hampton. Today the house has been renovated to its original splendor, rightfully reclaiming its position as one of the first and most prominent houses in the history-rich hamlet of Amagansett. Combining historical detail and provenance while maintaining right-sized proportions of house, rooms and garden, this property features modern high end appliances and bathrooms ranges from SubZero, LeFroyBrooks, Jura, Waterworks, Steamster, and Wolf. A heated gunite pool, 4 bedrooms and 3.5 bathrooms allow for an immersion into history without sacrificing comfort and convenience. Walking distance to Atlantic and Indian Wells beaches as well as all village restaurants allow for ease of access without planning. This historic house covering 170 years of Atlantic ocean living embraced by mature trees on 0.83 acres offers sunshine and shade, serenity during lazy afternoons of the East End summer, and the perfect venue for wonderful meals in a surrounding that focuses on the irreducible human values of rich conversation and measured elegant timeless aesthetic. [[Rental Registration # 25-824]] EH RR #: 25-824 Rental Terms: September: $40,000

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

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

Stylish contemporary featuring 3 bedrooms and 2 baths, lovely grounds and heated pool. Located in East Hampton's Clearwater Beach community. Living room is open with double height ceilings and fireplace. Dining is open also. Hardwood floors, plenty of light.Perfect summer living. [[Rental Registration # 24-1402]] EH RR #: 24-1402 Rental Terms: Memorial Day - Labor Day: $55,000 August - Labor Day: $25,000 June: $10,000 July: $20,000 July - Labor Day: $45,000

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

Also Available Dec 2024 for $13,000 Newly upgraded for summer 2024, this offering has its own dock with potential kayak and paddleboard, and is 0.4 miles to Long Beach, a gorgeous 1+ mile stretch of West Facing beach. The chic home is west-facing for sunsets from almost every room--even the walk-out lower level. Brand new Ipe decking, modern wire rails, Gunite pool and deep-water dock make for an amazing waterfront experience. There is a tremendous outdoor entertaining space on two levels. The 4,500+/- sq. ft. home is spacious with open flow. A New two-story living room setup features an stunning Modern window package and brand new furniture, plus a big new TV! The kitchen and dining room also offer walls of windows that drench the home with light and views. This is the perfect house for entertaining with 5 bedrooms (plus a room with a sofa bed), and 5.5 baths. A finished lower level offers a wet bar, pool table, family room and pool bath, with a wall of windows and views out to Long Beach. New spacious Ipe decks with cable rails allow for easy outdoor living and entertaining just above the water. The house is in a quiet neighborhood, 2 minutes to Sag Harbor Village. When all the backyards lose their foliage at other Hamptons properties, this winter rental has its most gorgeous views--open water views from all 3 levels. [[Rental Registration # RP200192]] EH RR #: RP200192 Rental Terms: October: $15,000 April: $10,000 February: $8,000 May: $10,000 September: $30,000 January: $8,000 March: $8,000 November: $10,000 Other / Short Term - Dec: $10,000 August - Labor Day: $87,500 August: $85,000

Timeless East Hampton Estate has been recently renovated with old world charm, style, and a true Hampton flare. The 1st floor of the main house features an open living area with fireplace, media room, library/sitting area, formal dining room with fireplace, country kitchen with breakfast nook, fireplace and seating area. The second floor is highlighted by 6 stylish bedrooms and 4 baths. The 3rd floor offers an additional guest bedroom, private office, and an inviting primary suite with ocean views, a drawing room, and fabulous primary bath. The grounds are accented by wrap around porches, an out door grilling station with outdoor fireplace and dining pavilion. The hedged for privacy pool area offers a 2 bedroom guest house, heated gunite pool, another dining pavilion, and lawn areas perfect for the afternoon soccer match. Your vacation will be magical as ocean breezes relax you. Electric Car ready with a 220 voltage outlet, this home is understated perfection. EH RR #: village Rental Terms: Two Weeks: $125,000 Other / Short Term - Weekly: $62,500

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

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

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

Also Available: June '24 $30k, New Waterfront Modern Barn style home with incredible western facing sunset views across Fort Pond. Offering open floor plan with expansive living room, dining area, and top of the line chef's kitchen with Gaggenau appliances, all with dramatic water views. French doors off the living room open to the patio with retractable awning and infinity edge heated gunite pool. Steps lead down to small dock with easy access to launch a kayak or stand up paddle board for a pond cruise. Rental amenities include sauna, cold plunge, outdoor BBQ, luxury massage chair, LED large screen TV's. Convenient location provides easy access to the beaches, village, and docks. [[Rental Registration # Pending]] Rental Terms: August - Labor Day: $90,750 September: $15,000 June: $33,000 February: $10,000 Memorial Day - Labor Day: $181,500 April: $10,000 Other / Short Term - Year Round: $220,000 March: $10,000 June/July: $90,750 October: $15,000 July: $79,750 January: $10,000 November: $10,000

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

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