luxury houses with pool for rent New York, United States (page 2)

Situated on a spacious 2 acre property just minutes to East Hampton or Amagansett Villages and the ocean, this easy living one level contemporary offers 4 bedrooms, 3 new baths, newly renovated kitchen and a central living and dining area that open onto a spacious covered porch that is a living room unto itself. A large pool with generous decking and a great big yard are the perfect place for everyone to gather and enjoy summer and extend summer activities. [[Rental Registration # Pending]] Rental Terms: July: $28,000 August: $28,000 August - Labor Day: $30,000 July - Labor Day: $58,000

Stylishly renovated and beautifully appointed, this Southampton village home has it all. Spacious gourmet eat-in kitchen, two living rooms, media room, fireplace, sunporch, and finished lower level with gym (including Peloton Bike+ and Hydrow Rower). Four bedrooms and four baths in main house. Multiple seating and dining areas outside amidst the stunning landscape, provide perfect entertaining spaces both under the sun and protected. The newly redone pool house offers sophisticated living space. Heated gunite pool, lovely lounge furniture, market umbrellas, retractable awning, wisteria covered pergola, outdoor shower, customer gas bbq, there's nothing that has been overlooked for those seeking the amenities of a 5 star vacation hideaway just minutes to Main Street. Rental Terms: Memorial Day - Labor Day: $250,000 Other / Short Term - Year Round: $290,000

Situated in a prime south of the highway location in the Amagansett Lanes, this brand new construction house completed in 2019, has 6 bedrooms and 7 baths. Designed by a renowned architect, this 5,500 Sf +/- house has unique sleek modern lines throughout the house. All Four bedrooms on the top floor have ensuite bathrooms with beautiful finishes and custom cement tile floors with radiant heat. There are two additional bedrooms on the main floor in a separate private wing of the house. Multiple living areas offer a seamless blend of privacy and open, light-filled social spaces for family and friends. Large chef's kitchen flows into dining area and the great room with double height ceilings, while the extensive limestone patios surrounding the main residence and the pool house are providing beautiful views of the pool and secluded yard. Finished lower level includes media room, with a wet bar, living area, a ping pong table and a full bathroom. The outside living spaces, provide a one-of-kind experience. The modern outdoor living room area features indoor/outdoor living spaces, dining room, pool house with outdoor living area, all overlooking professionally landscaped grounds, and a saltwater gunite pool. Tastefully appointed with top of the line finishes and understated designer furnishings, the outdoor spaces effortlessly host casual afternoons by the pool. This prime south of the highway location in the Amagansett Lanes and steps to the ocean, offers a luxurious retreat environment with modern interiors and beautifully crafted outdoor living and recreational spaces. Top of the line finishes in and out, this home provides a truly unparalleled experience in this south of the highway location, within walking distance to ocean beaches, Amagansett's restaurants and shops. Rental Terms: June/July: $350,000 July: $225,000 June: $150,000 Memorial Day - Labor Day: $550,000

This barn style house has it all with its open and airy living area. It features wooded floors throughout and two fireplaces. It also hosts a European Style kitchen in addition to the open dining, living room and pool table playing area. There is a den leading out to an enclosed screened-in porch, and outdoor decking featuring a swimming pool and outdoor shower. This terrific house is a great hide-a-way for the summer season and close to all in Amagansett. [[Rental Registration # 25-27]] EH RR #: 25-27 Rental Terms: August: $40,000 July: $35,000 August - Labor Day: $47,000

Convenience at its best. Newly constructed and first time available for rent. This pristine traditional home is located in the heart of Southampton village. The main floor has an open layout with lots of natural light. Gourmet kitchen, living room with fireplace, wet bar and dining area. There is a first floor en-suite bedroom. Second level has 2 guest bedrooms with a shared bath, master suite and laundry room. Lower level has a sitting area, bedroom and bathroom. There is a heated gunite pool, out door fireplace, outdoor pool bath and detached one car garage. Rental Terms: August - Labor Day: $135,000 July: $120,000 Memorial Day - Labor Day: $245,000 July - Labor Day: $230,000

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

Beautiful Bucolic Waterfront -- Best Sunsets in the Hamptons. Overlooking Noyak Bay, this newly constructed, triple-mint, modern manor boasts breathtaking water views and stunning sunsets. The soaring floor to ceiling windows, expansive decking, heated gunite waterside pool, plush outdoor furniture, cozy fire pit, outdoor shower and Lynx professional grill, adorn the water side veranda, creating a grand and sumptuous Hamptons experience. So, too, this property has a rare and coveted private deep water dock for backyard paddle boarding, kayaking or...bring your own boat. Ideal for entertaining, this home is appointed with an Il Forno pizza oven, sous vide technology, an outdoor herb garden and an enviable array of Japanese chef's knives, surely to fascinate the boldest of home chef's. With rich oak, warm walnut and modern steel finishes this property exudes serenity and grace and is sure to impress. Impeccably decorated and beautifully appointed, this modern retreat is mired among majestic marine sea grasses which, like a metronome, sway in time to the warm coastal breezes. Conveniently located in the up and coming beach community of Pine Neck. Minutes from ocean beaches, a stone's throw from historic downtown Sag Harbor and a short drive from Bridgehampton, this 5200 square foot, 5 bed room, 6 bath jewel is not to be missed. [[Rental Registration # RP220659]] EH RR #: RP220659 Rental Terms: Two Weeks: $140,000 August: $250,000 August - Labor Day: $275,000 Other / Short Term - Weekly: $70,000 Memorial Day - Labor Day: $550,000 July: $250,000

This beautiful home spans approximately 2,500 sq. ft. and is situated on 0.32 acres of land. It boasts an excellent location, in very close proximity to the Atlantic Ocean and a short distance from Southampton Village Center. The property is surrounded by mature hedges and landscaping, ensuring maximum privacy. This classic home exudes charm and is exquisitely furnished with meticulous attention to detail. The house features a spacious and welcoming living room with a fireplace, a den/4th bedroom, a formal dining room with French doors to the patio and beyond, a sunny kitchen equipped with professional appliances, four bedrooms, three and a half baths, a 1st-floor laundry room, a large flat-screen TV, indoor and outdoor stereo systems, lush flowering gardens, a heated swimming pool, a pool cabana with a bathroom, and an outdoor shower. Looking for a serene getaway? This Southampton Village retreat is just what you need! Rental Terms: Other / Short Term - Year Round: $285,000

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

Savor every ray of sunshine at this elegant and sprawling Amagansett stunner! Perched on top of a rise overlooking a 17-acre preserve, with second story views of the ocean, this gated five-bedroom home is built on a grand scale with abundant room for extended family or friends. An oversized heated pool and plenty of entertaining and lounging space both indoors and out make this an ideal perch from which to enjoy spectacular sunsets and the shops, farm stands, restaurants, and beaches of Amagansett, all literally two minutes away by car. [[Rental Registration # 26-263]] EH RR #: 26-263 Rental Terms: Two Weeks: $75,000

Peaceful Summer Getaway Amazing summer rental opportunity! Spectacular 3 Bedroom, 3.5 Bath contemporary Hamptons home with perfect indoor/outdoor entertaining spaces. Lush 1.6+/- private acres with an extremely private & fenced rear yard. Private sleeping quarters with 2 Main Bedrooms, one upstairs and one downstairs both with en suite baths. The third bedroom located on the main floor also has a full bathroom. Wake up and have breakfast in the sunroom or use the Peloton that is available. Enjoy the heated pool or relax on the deck that is equipped with Sonos sounds system. Want to go out? This home is conveniently located between East Hampton and Sag Harbor just minutes from all the shopping, restaurants, and best beaches the South Fork has to offer. Coming back from exploring and need to recharge? Make use of the Tesla car charger available in the oversized driveway outside the garage. End the evening relaxing in your 2nd floor fully enclosed sunroom, enjoying the peace and tranquility this home has to offer. Your perfect summer awaits! [[Rental Registration # Pending]] EH RR #: 24-284 Rental Terms: Memorial Day - Labor Day: $97,000

Just over three miles from East Hampton Village and less than a mile from the harbor entrance, this newly renovated four-bedroom, four-bathroom residence is set on two beautifully landscaped acres, offering the perfect blend of privacy, luxury, and convenience. Thoughtfully redesigned from top to bottom, the home features an effortless flow throughout. A welcoming living room with a fireplace opens seamlessly to the light-filled kitchen and dining area, where expansive views overlook the lush grounds beyond. The first floor also includes a dedicated guest wing with two spacious bedrooms and a full bath, providing comfort and privacy for family and visitors alike. Occupying the entire second level are two generously sized primary suites, each with its own beautifully appointed en-suite bathroom, creating a peaceful retreat for guests. The finished lower level, complete with a separate entrance, offers additional space for relaxation and entertainment. Featuring a spacious lounge area with a foosball table, bar, dining area, full bathroom, and laundry facilities, it is perfectly suited for casual gatherings and extended stays. Outdoors, multiple areas for lounging, dining, and entertaining invite you to enjoy the property's tranquil setting. From the expansive deck to the bluestone patio surrounding the oversized heated gunite pool, every detail has been designed for effortless indoor-outdoor living. Private and serene, yet moments from the beaches, marinas, fine dining, and cultural attractions that make East Hampton one of the most sought-after destinations in the Hamptons, this exceptional property is the ideal summer escape. [[Rental Registration # 26-1039]] EH RR #: 26-1039 Rental Terms: August - Labor Day: $40,000 Other / Short Term - Year Round: $135,000

Tucked away behind beautiful mature landscaping, this fully updated 6-bedroom, 4.5-bathroom home is the perfect summer escape. Open, airy, and filled with natural light, the spacious living areas flow seamlessly into a stunning chef’s kitchen with high-end appliances, custom cabinetry, and a large center island — ideal for relaxed summer living and entertaining. The flexible layout offers both first-floor and second-floor primary suites, providing privacy and comfort for you and your guests. The finished lower level adds even more living space along with a full laundry area. Step outside to your private backyard retreat, where a gunite pool, a private tennis court, outdoor shower, gas grill, and multiple lounge and dining areas await — all surrounded by lush, mature landscaping for a true sense of seclusion. Home is also equipped with a Tesla EV charger. Located just minutes from Quogue Village and pristine beaches, this is a rare opportunity to spend August in one of the Hamptons' most charming communities.

Welcome to your own private oasis in the heart of Southampton Village! This stunning 5 bedroom, 6 bath Traditional home is situated on a meticulously landscaped +/- 1.38-acre lot within a beautiful private compound. As you enter the home, you'll be greeted by a spacious foyer with double-height ceilings, leading to a generous family room with a cozy wood-burning fireplace, a traditional living room, and a formal dining room. The gourmet chef's kitchen boasts stainless steel appliances, a large island with seating, a breakfast area, and a substantial junior primary suite. Sliding glass doors lead from the kitchen and family room to a spacious deck and patio surrounding the pool, spa, outdoor shower, and pool house. This property provides ample space for entertaining and relaxation while maintaining complete privacy. The upper level features four bedrooms, three full bathrooms, and an expansive primary suite with a luxurious bathroom fully equipped with two separate vanities, a jacuzzi tub, and a glass-enclosed walk-in shower. The fully finished lower level offers a recreational room with a TV seating area, an air hockey table, one full bath, and a private office. Located just minutes away from shops, restaurants, and ocean beaches, this property offers the luxurious Hamptons lifestyle you've been dreaming of. Don't miss out on this incredible opportunity so close to ocean beaches Rental Terms: September: $90,000

Built circa 1750, the historic Tobias Wynkoop House stands as a quiet testament to the early heritage of the Hudson Valley. Constructed in the region's traditional Dutch stone style, the residence reflects the enduring craftsmanship and architectural character of the area's earliest settlements. The property rests upon seven acres across the alluvial fields of the great Kaaterskill Basin, at the foot of Kaaterskill Clove--a dramatic glacier-carved gorge within the eastern Catskill Mountains. Celebrated for its sublime scenery, this remarkable valley inspired many of the Hudson River School painters, including Thomas Cole, whose landscapes first introduced the grandeur of the Catskills to a wider audience. Today the residence has been thoughtfully restored with careful respect for its historic character. Wide kingboard plank floors, recessed windows set within thick stone walls, and generous ceiling heights on the upper levels remain hallmarks of the home's early construction. A Vermont wood-burning stove lends warmth and atmosphere, while the kitchen and bathrooms have been tastefully renovated to balance historic integrity with modern comfort. Across the interiors, curated furnishings create an atmosphere of privacy, calm, and understated elegance--an ideal setting for extended stays in the Hudson Valley countryside. The grounds reveal the property's most enchanting qualities. Rolling meadow, mature trees, and seasonal mountain views surround the residence, while a private in-ground pool, fire-pit gathering area, and open lawn invite long summer afternoons outdoors. A rare historic residence offering pastoral beauty, architectural heritage, and refined country living in the heart of the Hudson Valley. Monthly seasonal rental available 6/1/26.

Enjoy sweeping ocean views from this modern, architect-designed home. Built in 2015, the house has clean lines and beautiful new finishes throughout. On the main level there is an open layout that flows from the spacious kitchen with Carrara marble countertops and professional-grade stainless steel appliances to the open living room with a stone fireplace. A wall of windows and glass sliding doors lead to an expansive terrace again with ocean views. An ensuite primary bedroom has a private ocean facing terrace and a luxurious bathroom with a steam shower. On the lower level there are three ensuite guest bedrooms plus surround-sound media family room with Sonos speakers throughout the home. Outdoors, there is a gunite pool and a beautifully designed lawn and garden landscaped by Ground Works. Sited on a shy acre across the street from ocean beaches and in close proximity of town, this is one of the largest parcels on Surfside Avenue. The absolute best that Montauk has to offer for the ultimate summer getaway. Flexible summer rental dates/minimum two weeks. [[Rental Registration # 22-764]] EH RR #: RR26-636 Rental Terms: August: $95,000 June: $55,000 July - Labor Day: $210,000 July: $95,000 August - Labor Day: $115,000 June/July: $150,000 Memorial Day - Labor Day: $250,000

Welcome to 54 Bay View Drive East, Sag Harbor, where modern luxury meets waterfront living. This stunning, award-winning modern estate is a boater's paradise, boasting a deep water dock and breathtaking sunset views over Sag Harbor Cove. With 4 bedrooms, 4.5 modern baths, and 3100 square feet of sleek living space, this home offers the epitome of waterfront elegance. A primary suite on the first floor and an additional secondary primary bedroom suite on the second floor with endless water views complement this unique offering. Enjoy the convenience of a water view Chef's kitchen, multi-level decks, and a heated Gunite infinity pool. The property features geothermal heating and cooling, ensuring comfort with minimal environmental impact. Custom fixtures from Italy and an outdoor wood-burning pizza oven add distinctive charm. Located near Sag Harbor's amenities, a 10 min walk to Long Beach, and the Shelter Island Ferry, this home offers a unique summer retreat. Don't miss the opportunity to experience waterfront luxury at its finest. [[Rental Registration # 251021]] EH RR #: 251021 Rental Terms: July: $185,000 July - Labor Day: $400,000 August: $185,000 August - Labor Day: $225,000

This bright sun filled Contemporary home has it all with lots of "smart" features, including Nest/Doorbird for the privacy gate and outdoor lighting. Tablets throughout the house connect to Pandora, Spotify and lots of other apps. Situated on a quiet cul-de-sac in Watermill with beautiful scenic views, it includes 8 bedrooms and 8.5 bathrooms. An open, spacious living room, eat-in gourmet kitchen, formal dining room and enclosed sunroom are complimented by tasteful modern furniture and artwork. A media area with wet bar services the main level. The lower level has a gym, kitchenette and laundry, in addition to three bedrooms with en-suite bathrooms. Beautiful French doors lead to heated, gunite pool and tennis court. Close to ocean and both Southampton Village and Bridgehampton, it's ideal for all the shopping & restaurants. A new white Italian tile deck was added in late 2022 with a 9 person hydro-pool hot tub with all the bells and whistles. Additionally, a new generator was also installed. A great spot for fun,filled vacation! [[Rental Registration # RP260204]] EH RR #: RP260204 Rental Terms: July - Labor Day: $275,000 Memorial Day - Labor Day: $375,000 July: $125,000 August - Labor Day: $150,000 June: $80,000

Immaculate traditional in Bridgehampton North. 5 bedrooms, 3.5 baths on just under 2 acres of beautifully landscaped property. Large mahogany deck with outdoor BBQ and heat lamps. Oversized heated saltwater gunite pool overlooking western sunsets. A wonderful Hamptons retreat. [[Rental Registration # RP200229]] EH RR #: RP200229 Rental Terms: June: $40,000 August - Labor Day: $70,000 July: $65,000

Located in a desirable "South of the Highway" Water Mill location, this architecturally significant shingle-style farmhouse offers a blend of historical elegance and modern luxury on an incredibly rare 3 +/- acres. Originally dating to 1785 and thoughtfully renovated and expanded, 265 Mecox Road is designer-decorated and one of the most unique rental offerings in all of the Hamptons. The main house is complemented by a gunite pool, a pool house, a Har-Tru tennis court, an elegant reflecting pond, all surrounded by mature gardens and ancient Linden trees, and behind mature privet hedges for privacy. The main home is designed in a nautical-inspired blue and white palette that enhances its understated sense of style. The 5 bedrooms and 4.5 bathrooms are in an ideal floor plan configuration, offering privacy from one another. The chef's kitchen is well-equipped with commercial-grade appliances by Thermador and Sub-Zero with an oversized center island. Modern conveniences are seamlessly integrated, including Sonos audio throughout the property. Outside, the living experience is enhanced by a classic bluestone patio, an oversized outdoor pavilion with a fireplace capable of accommodating over 20 guests, and an outdoor kitchen with built-in Wolf grill under a pergola of ivy, perfect for summer entertaining. The pool house also offers a kitchenette, full bathroom and covered dining area. Positioned just minutes from the famed Mecox Beach and perfectly situated between the villages of Southampton and Bridgehampton with their many dining, retail and cultural offerings, 265 Mecox Road offers a summer holiday of unparalleled privacy and seclusion for which the Hamptons is known. [[Rental Registration # Pending]] Rental Terms: August - Labor Day: $165,000 July - Labor Day: $330,000 July: $165,000

This beautiful, airy five bedroom home is situated on a quiet road in the Northwest Woods just a few miles from the ocean and a mile from the bay. A guest suite on the ground floor sleeps four and has a perfectly appointed bath. The large living room with a screened-in porch is a perfect spot for entertaining. Upstairs there are three more bedrooms and two baths. The home is filled with natural light and features skylights and a fireplace for cooler nights. There is a washer/dryer, dishwasher, cable TV and wifi. The pool is heated and there is AC throughout the home. [[Rental Registration # Pending]] EH RR #: 24-1190 Rental Terms: July: $30,000 August - Labor Day: $35,000 June/July: $55,000 June: $25,000 July - Labor Day: $60,000 Memorial Day - Labor Day: $75,000

Welcome to this one of a kind, completely renovated, estate in Matinecock with inground heated pool on a park like property. The main house features a large living room with fireplace, formal dining room with fireplace and a sun room open to the garden and patios. The brand new EIK is perfect for family and entertaining. Upstairs is a large primary with fireplace and new primary bath featuring double sinks, bath and shower. There are two additional bedrooms and a new hall bath. The third floor offers a bonus room and the basement is finished. Through a breezeway you access the 1 bedroom cottage that has a kitchen and full bath. The heated free form pool has its own outdoor shower and toilet. The perfect retreat in the country!, Additional information: Appearance:Mint,Interior Features:Guest Quarters

Best location. Best house in best condition. Best waterfront views on Lake Agawam, gated, waterside pool, porches, balconies, multiple living parlors. Great kitchen, dining, offering 7 bedrooms, 2-car garage, on 2 beautiful acres. Very private. Rental Terms: Other / Short Term - Year Round: $850,000 July - Labor Day: $600,000 Memorial Day - Labor Day: $700,000

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: June: $50,000

Hidden on 6 ultra-private rolling landscaped acres, charming European-style retreat that feels like you're in the South of France. Double-height great room within a 200 year old barn with polished concrete floors and French doors to shaded pergola overlooking pool, oversized fireplace, well-equipped chef's kitchen. Primary suite with vaulted ceiling, fireplace, and private access to the pool. Second bedroom suite with multiple windows and skylight. Enchanting romantic cottage only minutes from Bridgehampton Village, Sag Harbor, and ocean beaches available to rent for the first time. Offered Co-Exclusively Vanessa Moore and Beate V. Moore [[Rental Registration # RP251348]] EH RR #: RP251348 Rental Terms: Two Weeks: $60,000 August - Labor Day: $95,000