luxury houses with pool for rent New York, United States

Open, Bright Contemporary Beach House South of the Highway in Water Mill with 6 bedrooms, and 5.5 bathrooms overlooking a large 27+/- acre Ag. Reserve. All situated on a beautifully landscaped 1.3+/- acre parcel. Two master suites (one upstairs with balcony and one downstairs), a large guest suite/work studio separated from the rest of the home, and a downstairs sitting room/6th en suite bedroom. All bedrooms have king beds. [[Rental Registration # RP250736]] EH RR #: RP250736 Rental Terms: August - Labor Day: $125,000 August: $115,000

This elegant and stylish new home has every prerequisite to spend a luxurious summer in the Hampton's. With 7 bedrooms, 8 baths, designer kitchen with marble quarried in Italy, top of the line appliances, formal dining room, beautiful living room and inviting outdoor patio for entertaining. Magnificent finishes throughout, exquisite attention to detail plus a movie theatre, gunite pool, and tennis, all on a beautiful 3 acre lot. [[Rental Registration # RP200840]] EH RR #: RP261401 Rental Terms: Two Weeks: $85,000

Perched at the top of a private drive on a .93+/- acre lot, this stunning traditional offers sweeping panoramic views of Lake Montauk. This 5-bedroom, 7.5-bathroom home is thoughtfully designed for both comfort and elevated summer living. The second floor features a spacious open-concept living room and a gourmet chef's kitchen, seamlessly flowing onto an expansive balcony with dedicated seating and dining areas-perfect for sunbathing or simply taking in the breathtaking lake views. A third-floor retreat provides additional vantage points and serves as an ideal media room or home office. The primary suite is a true sanctuary, complete with a luxurious bathroom featuring top-of-the-line fixtures and a soaking tub overlooking the water. Each bedroom is generously sized and outfitted with newly updated ensuite bathrooms. Outdoors, the property is designed for entertaining, featuring a large heated pool, spa, two outdoor showers, all surrounded by an oversized deck that provides ample space to relax and host. Additional features include a finished lower level with a gym and full bathroom. Located just moments from Montauk's renowned restaurants, village shopping, and ocean beaches, this home is the ultimate summer getaway. [[Rental Registration # 26-299]] EH RR #: 26-299 Rental Terms: Memorial Day - Labor Day: $175,000 August - Labor Day: $86,000 July: $82,000 June: $47,000

A very complete offering in the best of locations. Attractively furnished with mature trees and gardens this very comfortable home offers a large Living /entertaining Room, a formal dining room, a panelled library, a gourmet kitchen, 7 bedrooms, 8.5 baths, including a large first floor guest suite. There is a heated pool with a pool house and a tennis court. A top quality house and location! Rental Terms: August - Labor Day: $250,000 Memorial Day - Labor Day: $495,000 July: $225,000 Other / Short Term - 6/1/2027 - 9/7/2027: $495,000

Rental Registry #: 22-1364, Expires 09/02/2024. Also Available: July 15th - July 30th $60k, July 15th - August 15th $130k, August 1st - August 31st $130k Enjoy the smiles on everyone's faces as they arrive for the summer vacation they have been dreaming about. Enter through the gate, down a long driveway to this secluded award winning Bruce Nagel modern 7000+/- sf oasis over three levels providing three seamlessly integrated living spaces that thoroughly delight the senses. The central living area is a balanced medley of light and volume drawing your attention to the refined front garden or the notable outdoor entertaining, pool and garden room environs. This central gathering wing is comprised of the formal living and dining rooms sharing a architecturally significant double sided fireplace, and an informal great room with sensational kitchen, casual dining, and second fireplace. Two sets of sliding French doors meticulously placed, invite you to the outdoor living room. The principal bedroom suite is situated to the right side of the central living area ensuring complete privacy. The spacious sleeping chamber is complete with a writing desk set against stone wall back drop and its own fireplace. The art filled pass through leads to spa-like bath with double vanity, shower and free standing bath. Walls of glass open to a private patio with sitting area and spa. An artfully positioned opening draws you to the pool beyond. A gallery style library connects the main residence with the subtle modern barn elements of the guest wing. Here one finds a first floor guest suite, powder room and guest living area featuring walls of glass anchored by hewn beams and a spectacular two story stone fireplace. Take the staircase to the second level reading loft and three additional guest suites. Break away from everyone and head to the lower level walk out media room, gym, or if you must, the multi-desk professional office area. If in need of rejuvenation, enjoy the sauna and massage room with adjacent bath and close the door for a relaxing rest before preparing for the evening. There is ample parking for everyone, and attached multi-space garage. The amenities of East Hampton and Sag Harbor Villages and the pristine ocean beaches are easily accessible for this exceptional summer offering. [[Rental Registration # 22-1,364]] EH RR #: 22-1,364 Rental Terms: May: $95,000 August: $150,000 July: $150,000 June: $115,000

Enjoy summer in Westhampton Beach Village at 55 White Oak Lane, a spacious three-bedroom, three-bath rental with inviting indoor and outdoor living spaces. A beautiful inground pool anchors the outdoor setting, offering a refreshing retreat for leisurely summer days. The screened-in porch provides a welcoming space for morning coffee, relaxed dining, and unwinding in the evening. With generous interiors offering the possibility of additional sleeping space and room to spread out, this private Westhampton Beach summer rental offers a comfortable home base for enjoying the Hamptons throughout the season.

Set on 1.2 acres with distant ocean views, this 5 bedroom home was renovated in early 2014 to provide a new kitchen, 7.5 new bathrooms, and a finished basement with a gym and recreation room. The house features high ceilings with light filled rooms. Privacy abounds since the master bedroom and the ensuite bedrooms are located in three distinct areas of the house. The first floor offers an eat-in kitchen, spacious living room and dining area, comfortable family room, and one of the ensuite bedrooms. A separate study with its own private full bath can serve as a 5th bedroom. Outside, ample decking and tables overlook the 54' heated gunite pool and spa. Mature, lush landscaping and an outdoor shower complete the picture. Also available June 2023 for $30K. EH RR #: RP260632 Rental Terms: July: $100,000 August - Labor Day: $125,000 July - Labor Day: $200,000 June/July: $150,000 Memorial Day - Labor Day: $250,000

Located south-of-the-highway at the end of a 160 ft. gated driveway on a secluded 1 acre oasis is this stylish beach house with sophisticated indoor/outdoor living. Recently renovated and re-designed, the house offers 3,100 sq. ft. of pristine living space across three levels finished to the highest standard. The first floor is comprised of spacious open floor plan with eat-in chefs' kitchen, dining and living area, media room, and first floor bedroom. The second story is made up of a primary bedroom with walk-in closet and ensuite bathroom, plus two additional guest bedrooms with vaulted ceilings and a shared full bathroom. The lower level is perfectly finished with playroom, two additional guest bedrooms, a full bathroom, and laundry. Accordion doors off the living room open 40 ft. wide seamlessly connecting indoor environs to expansive outdoor mahogany decking with gas fireplace, heated pool, outdoor shower, and barbecue area. Rolling green lawn leads down to 250 sq. ft. pool house cabana with half bathroom outdoor shower, and connected two car garage. The manicured grounds are surrounded by specimen trees and mature plantings for ultimate privacy. Only a short distance to Georgica Beach and East Hampton Village restaurants and shopping. Rental Terms: August - Labor Day: $80,000 July: $65,000 Two Weeks: $40,000 Memorial Day - Labor Day: $160,000 June: $30,000 June/July: $85,000 July - Labor Day: $145,000

Now booking Summer 2027!! Stunning Westhampton Beach home located a short distance to fabulous restaurants and shops on Main Street in Westhampton Beach. Newly renovated and expanded, this open concept home boasts a resort-like backyard including oversized, heated swimming pool, expansive bluestone patio and gazebo with fire pit. Open concept chef's kitchen & Living room with gas fireplace. Four well-appointed bedrooms including a main floor primary suite. Make summer memories here! Available July 1-August 29, 2027.

Set in the coveted enclave of Wainscott South, moments from the ocean beaches of Beach Lane, this exquisitely renovated Traditional offers a refined interpretation of Hamptons living. Thoughtfully redesigned with an emphasis on timeless elegance, modern comfort, and effortless sophistication, the residence presents an exceptional opportunity to enjoy one of the East End's most desirable coastal settings. Bathed in natural light, the interiors reveal a harmonious balance of classic architecture and contemporary finishes. An open, graciously proportioned layout creates an inviting atmosphere for both intimate gatherings and larger-scale entertaining. The beautifully appointed chef's kitchen, complete with premium appliances and a charming breakfast nook, serves as the heart of the home. Four beautifully appointed bedrooms and five bathrooms include two primary suites upstairs and and a two first floor en-suite guest bedrooms, providing an ideal balance of privacy and comfort. Outdoors, manicured gardens frame a secluded retreat featuring a heated swimming pool and pool house, creating a serene setting for leisurely afternoons and alfresco entertaining. Impeccably updated and ideally positioned near the ocean, this distinguished Wainscott South residence offers an understated yet elevated Hamptons lifestyle, equally suited to year-round enjoyment and seasonal escapes. [[Rental Registration # 26-215]] EH RR #: 26-215 Rental Terms: June: $50,000 July: $110,000 Memorial Day - Labor Day: $275,000 July - Labor Day: $220,000 May: $30,000 Other / Short Term - Year Round: $325,000 August: $110,000 November: $12,000 April: $15,000 Winter Season: $30,000 Per Month August - Labor Day: $120,000 June/July: $135,000

Down a long drive, this charming Hamptons classic house is situated on a professionally landscaped acre. Tucked away in a quiet community and only a stone's throw to both Bridgehampton and Sag Harbor villages. This stylish professionally decorated home is fully equipped with 4 bedrooms and 2.5 bathrooms. The first floor boasts a sun-drenched great room with designer furniture and lighting, wide plank floors and a brick fireplace. Additionally, there is a master bedroom with an en suite bathroom. The kitchen is beautifully appointed with a top of the line Lacanche oven, there is also a powder-room, large pantry, laundry and mudroom with access to the pool and back garden. The second floor has three additional guest bedrooms with beautiful views of the grounds, one of the bedrooms has a walk-in closet and on the second floor there is an oversized shared bathroom. Ideal for summer entertaining the back and front gardens offers complete privacy with an expansive wrap around deck, a heated pool, outdoor shower, and a generous fenced in yard. A true gem not to be missed! #RP201221 Exp 2/10/2025 [[Rental Registration # RP250191]] EH RR #: RP250191 Rental Terms: Two Weeks: $20,000 July: $40,000 July - Labor Day: $85,000 August - Labor Day: $50,000

Enjoy the best of Montauk from this beautifully renovated four-bedroom, four-bathroom waterfront home on Fort Pond. Set on a private half-acre with over 79 feet of water frontage, the west-facing property offers sweeping water views, spectacular sunsets, and a peaceful waterfront setting just minutes from town. Recently renovated with a brand-new custom kitchen featuring luxury Thermador appliances, updated bathrooms, and an expansive new outdoor patio with a six-person spa overlooking the water, the home is designed for relaxed summer living and entertaining. Water views can be enjoyed from nearly every room, including the first-floor primary suite and two bedrooms that open onto a waterfront balcony. The property also features a spacious finished lower level with a private sauna, dedicated workout space, private dock with kayaks, outdoor dining and fire-pit area, Weber grill, and two-car garage. The private dock provides direct access to Fort Pond, with the opportunity to kayak toward The Surf Lodge. Ideally located just moments to the best that Montauk has to offer, with easy access to town, restaurants, shops, and beautiful ocean beaches. [[Rental Registration # 25-446]] EH RR #: 25-446 Rental Terms: August - Labor Day: $75,000 August: $70,000 July: $65,000 June/July: $90,000 July - Labor Day: $135,000 Memorial Day - Labor Day: $155,000

Discover the quintessential Hamptons lifestyle in this beautiful 3-bedroom, 2-bathroom retreat nestled at 39 Roxbury Lane, Wainscott. Tucked away on a quiet, sun-drenched lot in one of the East End's most coveted hamlets, this turnkey home offers an unparalleled blend of absolute privacy and effortless proximity to everything that makes the Hamptons legendary. Step inside to a dramatic, double-height great room bathed in natural light, featuring soaring ceilings, crisp architectural lines, and a warm wood-burning fireplace. The open-concept layout flows seamlessly into a fully updated chef's kitchen, outfitted with premium stainless steel appliances and a spacious breakfast bar perfect for casual entertaining. Transition upstairs to find a versatile open loft area-ideal as a dedicated home office, a cozy den, or an extra guest nook. Sliding doors create a seamless indoor-outdoor flow out to an expansive deck and a heated pool completely enveloped by mature privacy plantings. Perfectly positioned between East Hampton and Bridgehampton, this home sits just moments from ocean beaches and local farm stands. [[Rental Registration # 26-218]] EH RR #: 26-218 Rental Terms: April: $10,000 July: $40,000 June: $25,000 June/July: $65,000 August: $40,000 August - Labor Day: $50,000 Other / Short Term - Year Round: $130,000 July - Labor Day: $85,000 Winter Season: $20,000 Per Month November: $8,000 Memorial Day - Labor Day: $110,000 May: $15,000

Crafted and constructed to meet the highest contemporary standards, this remarkable residence spans over 7,000 square feet, providing the perfect setting for an exceptional summer experience. The airy and luminous open floor plan encompasses a chef's kitchen, living area, dining space, den, home office, four fireplaces, and six en-suite bedrooms. The lower level boasts a gym with a Finnleo indoor sauna, a spacious media room, a wine cellar, and a guest suite. Adding to the convenience is the detached garage equipped with a Tesla charging station. Step outside to a heated, saltwater gunite pool and spa, an outdoor shower, three patios, and two upper decks, creating an ideal outdoor entertainment space. Located within 2 miles of ocean beaches and East Hampton Village, revel in breathtaking sunrises and sunsets while surrounded by 9 acres of protected reserve. This property offers the epitome of modern luxury living. [[Rental Registration # 22-1029]] EH RR #: 26-1073 Rental Terms: October: $50,000 June: $100,000 May: $75,000 Other / Short Term - Dec: $50,000 September: $75,000 November: $50,000 July: $225,000

Recently, Freshly renovated Beach House with new kitchen and new bathrooms. The main house has 4 bedrooms on the second floor with a total of 3 baths in main house. The legal accessory apartment houses the bunk room and full bath. Extensive new mahogany decking and an outdoor shower. Beautiful, private yard with a gunite heated swimming pool and lush lawn areas. In close proximity to ocean beaches and Village amenities. Rental Terms: July - Labor Day: $169,000 June/July: $129,000 September: $50,000 July: $80,000 August - Labor Day: $90,000 June: $50,000 Memorial Day - Labor Day: $185,000 August: $80,000 April: $10,000 Other / Short Term - Year Round: $250,000 May: $20,000

Experience exceptional waterfront living in this stunning modern newly built home, featuring breathtaking views of Montauk's Fort Pond, the ocean, and the bay. It's focus on elegant simple form and honest treatment of materials references Japanese Minimalist Modern Architecture. Situated on a picturesque .54 +/- acre lot with 75 ft. of water frontage, this luxurious home boasts 7 spacious bedrooms, 9 full baths, and a total of 7,141+/- square feet across three levels. As you enter through the large, raw iron hidden door and follow the Zen covered walkway, you'll be greeted by a grand entry foyer with double height ceilings, skylights, and exquisite masonry finishes. The fully equipped chef's kitchen seamlessly flows into the spacious dining area and living room, complete with a wall of sliding doors that open to the outdoor living area. On the first floor, you'll discover three guest bedrooms with en-suite bathrooms and hidden garden patios, perfect for relaxing and enjoying the tranquil surroundings. The second floor is dedicated to the primary bedroom, featuring an en-suite bathroom, walk-in closet, and an expansive balcony with a pergola, outdoor shower, fire pit, and stunning direct water views. The walk-out lower level with stone inspired walls boasts two additional guest bedrooms, a large fitness multi-media room, sauna, hot and cold plunge, and laundry. Outside, the large gunite pool with vanishing edge and ample patio space provide the perfect setting for soaking up the sun and entertaining guests. The relationship between nature and architecture blends effortlessly. Located just moments from Montauk Village, Harbor, and Ocean Beaches, this property offers the ultimate in luxurious waterfront living. [[Rental Registration # Pending]] Rental Terms: February: $10,000 November: $10,000 April: $10,000 July: $79,750 Other / Short Term - Year Round: $220,000 June/July: $90,750 March: $10,000 June: $33,000 Memorial Day - Labor Day: $181,500

72 Talmage Farm Lane - Springs Summer Rental | June, July, August, September - or Any Combination Spend the season in the heart of Springs in this beautiful, modern retreat designed for effortless indoor-outdoor living. This thoughtfully designed home features a stunning chef's kitchen and beautifully appointed bathrooms, blending clean contemporary style with comfort and ease. The open living spaces flow seamlessly to multiple outdoor lounging and dining areas, creating the perfect setting for entertaining or quiet relaxation. The heated gunite pool is surrounded by generous decking and landscaped grounds, offering privacy and sun throughout the day. The ground-floor primary suite provides convenience and comfort, while the finished lower level adds exceptional bonus space, including a game room, gym, and TV lounge - ideal for guests and extended stays. Located in one of the most desirable pockets of Springs, just moments from bay beaches, waterfront dining, and the artistic charm that defines the area. Available for June, July, August, September - or any combination. [[Rental Registration # RR-26-139]] EH RR #: RR-26-139 Rental Terms: July: $85,000 August - Labor Day: $100,000 Two Weeks: $20,000 Memorial Day - Labor Day: $160,000 August: $90,000

Set on nearly three-quarters of an acre in Wainscott, this beautifully appointed five-bedroom, five-and-a-half-bath residence offers an exceptional Hamptons retreat, combining generous living spaces, privacy, and effortless indoor-outdoor entertaining. Spanning approximately 4,000 square feet, the home features five spacious ensuite bedrooms, providing comfort and privacy for family and guests alike. Light-filled interiors and inviting gathering spaces create an ideal setting for both relaxed everyday living and summer entertaining. Outdoors, the beautifully landscaped grounds back onto a peaceful reserve, offering a secluded setting centered around a heated Gunite pool. An additional pool house/studio provides flexible space for recreation, relaxation, or working from home. Conveniently located near Wainscott's ocean beaches and just minutes from the restaurants, boutiques, and attractions of East Hampton Village, this property offers an ideal balance of tranquility, convenience, and classic Hamptons summer living. [[Rental Registration # 25-970]] EH RR #: 25-970 Rental Terms: Other / Short Term - Extended Season: $25,000 July: $55,000 June/July: $75,000 July - Labor Day: $110,000 June: $30,000 Memorial Day - Labor Day: $135,000 August - Labor Day: $65,000 August: $55,000

Get ready for the perfect summer vacation in this newly renovated and fashionably furnished Bridgehampton Estate. Entering into an oversized living room, this home has many gracious living spaces. The first floor has a newly designed master suite, walk-in closet, oversized master bath, with a gracious shower, soaking tub, and a private covered porch, with heat lamps. There are three additional bedrooms that are all beautifully decorated with newly renovated baths. The kitchen is sun-filled with sleek cabinetry, and a built-in stone dining table. The lower level is fully finished and is great for lounging and watching movies, or the perfect place for the little ones to play. The backyard has it all. Enjoy your summer days lounging around the heated pool and grilling on the beautiful deck enjoying spectacular western sunsets. The backyard is very private with tall hedges, beautifully manicured landscaping, and agricultural reserve views. Located on Lumber Lane, this home has the perfect location. You are minutes to Bridgehampton town and a straight shoot to the beach, driving up Ocean Road. You are also super close to Sag Harbor Village, perfect for dinners out with the family, or casual shopping. [[Rental Registration # Pending]] EH RR #: ra241558 Rental Terms: July: $110,000 July - Labor Day: $230,000 August - Labor Day: $125,000 August: $110,000

New to the rental market, this four bedroom, 3 1/2 bath retreat has been freshly decorated and beautifully finished. Tasteful amenities include central air, hardwood floors, renovated kitchen, formal dining room, large living area with fireplace and renovated baths. An expansive wraparound porch highlights the sun-filled backyard that comes complete with a heated pool and blue stone patio. Beautiful specimen trees and perennial gardens complete this special home that is close to many Springs and town attractions. [[Rental Registration # 23-1344]] EH RR #: 23-1344 Rental Terms: August - Labor Day: $35,000

Ideally situated just moments from the pristine ocean beaches of Beach Lane, this beautifully renovated five-bedroom, four-bath Hamptons farmhouse offers an exceptional combination of timeless charm, modern comfort, and effortless indoor-outdoor living. Set amid lush, professionally landscaped grounds, the shingle-style residence is distinguished by its inviting interiors, wide-plank hardwood floors, abundant natural light, and unique architectural details, including a beautifully reclaimed barn transformed into a stunning living room with French doors opening to the lawn. Designed for both relaxed summer living and elegant entertaining, the home features a professional-grade kitchen that flows seamlessly into the great room and breakfast area, overlooking the expansive outdoor patio and heated Gunite pool. Generous living and dining spaces extend onto a spacious deck, where covered seating and alfresco dining areas create an idyllic setting for summer gatherings. Vaulted ceilings and exposed wood beams lend warmth and character throughout select rooms, while five well-appointed bedrooms provide comfortable accommodations for family and guests. The beautifully maintained grounds offer exceptional privacy, with mature trees, expansive lawns, and a charming, thoughtfully appointed pool house and outdoor shower completing the outdoor experience. Just moments from Wainscott's beloved farm stand, ocean beaches, and the world-class shopping and dining of East Hampton and Bridgehampton, this exceptional property embodies the relaxed sophistication and timeless appeal of Hamptons living. [[Rental Registration # 24-432]] EH RR #: 24-432 Rental Terms: June/July: $135,000 August: $110,000 July - Labor Day: $200,000 September: $35,000 July: $110,000 May: $30,000 June: $45,000 Memorial Day - Labor Day: $250,000 August - Labor Day: $120,000 Other / Short Term - Year Round: $325,000 April: $15,000 Winter Season: $43,000 Per Month

Originally part of an estate on Lily Pond Lane, this classic Hamptons home was relocated to its current position in Dune Alpin in the early 1990's. The bucolic horse farms and association tennis play host to a summer oasis complete with four bedrooms, three baths, oak plank flooring, renovated kitchen and baths, formal dining and living as well as a bonus second floor media room. The private yard is complete with a bluestone patio and a gunite pool as well as a newly-crafted scenic garden. The quintessential home is ideally located between East Hampton and Wainscott and close to transportation, shops, restaurants, farms and ocean beaches. [[Rental Registration # 22-394]] EH RR #: 25-48 Rental Terms: July - Labor Day: $89,000 July: $39,000 August - Labor Day: $50,000

Private and tasteful, this extremely comfortable home in the Northwest Woods section of East Hampton is an ideal vacation retreat. Attractively furnished with an open living plan and beautiful pool area, this home has all the elements to create a wonderful getaway experience . All well appointed, this home includes an airy living room with fireplace, dining area, fabulous kitchen, den and lovely bedrooms. Generous decking and lounging areas near the heated pool and outdoor shower add to the vacation feel of the property. Beautiful and comfortable, this is an outstanding option for your summer vacation. May also be available for an extended season. [[Rental Registration # RR-25-1158]] EH RR #: RR-25-1158 Rental Terms: July: $30,000 August - Labor Day: $35,000 July - Labor Day: $60,000

Tucked away down a long, private driveway is this spectacular cottage in Bridgehampton South. Conveniently located just behind the village, this one-story home has been recently renovated and refreshed with crisp new furniture. A cozy front porch and stunning cherry blossom tree welcome you, while interior highlights include an open concept living and dining room highlighted with a wood-burning fireplace and lovely reading nook illuminated with Venetian lanterns. A new backsplash adorns the separate kitchen that opens via a pass-way into the dining area. The primary bedroom has sliding glass doors and a newly renovated en-suite bath with beautiful tile and separate shower. Two additional guest rooms and another renovated bathroom complete the interior space of this finely decorated home. The backyard is tastefully landscaped and adorned with bamboo and tall specimen trees, including a spectacular weeping willow, to help ensure privacy. A large heated pool is flanked by a sunny patio and added decking for great entertaining, all with easy proximity to Bridgehampton shops, restaurants, transportation and ocean beaches. [[Rental Registration # RP220699]] EH RR #: RP261324 Rental Terms: July: $45,000 August - Labor Day: $55,000

Sunny, bright, and tastefully furnished, this designer’s Victorian offers five bedrooms and two updated full baths, with a seamless flow between the main living spaces. The professionally landscaped front and rear gardens include a heated saltwater pool, dining and barbecue patios at both the front and poolside, three hammocks, and an outdoor shower. Nassau Point Beach is at the end of the road, and a marina is nearby. Every detail has been considered to make relaxing and entertaining easy. Offered for August at $40,000. Permit #1501.