luxury house with pool for rent Cutchogue, United States

Available 2025: April: $12,000, May: $17,500, June: $22,500, July: $35,000. Vacation at this spectacular, completely renovated 4 en suite bedroom home this summer located in the desirable Fleet's Neck neighborhood with 2 gorgeous beaches moments away! Entertain in the open concept living area featuring a large island overlooking the family and dining area, perfect for large gatherings. The first floor features 2 bedrooms with 2 full baths with glass sliders leading out to the deck. Downstairs has 2 more ensuite bedrooms with glass sliders leading out to a patio. Soak up the sun and relax by the saltwater pool, rinse of the sand with the spacious outside shower or enjoy the patio where there is plenty of room to entertain throughout any time of the day.

2026 Rates: NO AVAILABILITY New Modern Farmhouse Completed in 2021 and located in the heart Hog's Neck in Southold Hamlet. This home features an impressive 20 x 50 heated pool with electric cover, out door shower and sprawling paver patio. The interior is open and airy with Chef's Kitchen outfitted with Thermador appliances, large living room with built in shelving, gas fireplace and formal dining room. All four bedrooms are located on the second level: 1 Primary En-suite, 1 Junior Suite, 2 Guest Bedrooms and Full Hallway Bathroom. You will enjoy being within close proximity to Goose Creek, South Harbor Park Beach and Southold's vibrant business district!

Impressive Goose Creek home with water views and large heated in-ground pool! This four bedroom, three bath house features a first floor primary bedroom with en-suite, a gourmet kitchen and open living space. The newly designed landscape with outdoor kitchen (not pictured) is ideal for entertaining or relaxing. Enjoy its large fire pit and BBQ grill after an afternoon of Kayaking. Close to Southold town and Corey Creek Beach. 2026 Pricing: July $30K | Aug-LD $35K

2026 Rates: September $7500; October $10,000: Discover your perfect getaway in this expansive and meticulously updated ranch home, designed for relaxation and rejuvenation. Experience a resort-like atmosphere with the stunning gunite, heated saltwater pool, complemented by a beautiful stone surround and convenient outdoor shower. Step inside to find high vaulted ceilings that create an airy ambiance and an abundance of natural light. The home boasts stunning hardwood floors and is elegantly appointed with multiple living areas that provide the perfect balance of open space and private retreats. Ideally situated within walking distance of Kenney’s Beach, you’ll find yourself just moments away from charming local cafes, unique boutiques, renowned wineries, and exceptional dining options. This North Fork gem is truly the ultimate summer haven. Don’t miss your chance to experience the perfect blend of comfort and convenience!

Escape to the heart of the North Fork in this beautiful, spacious four-bedroom home, perfectly designed for entertaining and hosting. Inside, you'll find ample living space complemented by a fully finished basement—ideal for extra lounging or movie nights—while the private backyard oasis features a sparkling heated pool for endless summer fun. Centrally located just one mile from Breakwater Beach, this home offers unbeatable access to the very best of the region, putting you just minutes away from the charming shops on Love Lane, premier local vineyards, and acclaimed farm-to-table restaurants. Book your stay today and secure the perfect central base for your ultimate retreat!

This Southampton beach house blends playful coastal personality with relaxed Hamptons living. Located in Bay View Oaks, a waterfront community with private beach access, deeded rights to Peconic Bay, and a boat launch, the home sits in a quiet setting within Bay View Oaks, just 10 minutes from both Sag Harbor and Southampton Villages. Inside, the home features high ceilings, light-filled rooms, and professionally designed interiors with a cool design sensibility that incorporates open-plan living, retro pop-culture touches, and colorful accents. The layout includes four bedrooms plus a bonus bunk room, 3.5 bathrooms including a primary ensuite, and multiple indoor-outdoor gathering zones that flow naturally for lounging, dining, and entertaining. A gourmet kitchen inside and out, multiple dining areas, and a layout arranged for smooth day-to-day living make the home easy to enjoy. The outdoor spaces offer a range of playful amenities. After the beach, rinse off sandy toes in the outdoor shower, step into the heated pool, basketball hoop, trampoline, fire pit, and several lounge areas suited for relaxing or gathering. A two-car garage and the overall setting bring everything together for a relaxed Hamptons stay. Offered for the early summer, August, extended season, and winter rental periods. [[Rental Registration # RP241487]] EH RR #: RP241487 Rental Terms: July: $50,000 June: $38,000 August: $55,000 October: $12,500 November: $10,000 Winter Season: $50,000 Per Month

Welcome to 4 Scrimshaw Drive, located in the sought-after Whalebone Landing community, where summer feels calm, private, and effortlessly beautiful. Enjoy the private bay beach and tennis courts just moments away, and quick access to the boutiques, restaurants, and harbors of both Southampton and Sag Harbor. Designed for luxury summer living, this home features a heated gunite pool, sun-filled interiors, and three levels of finished living space ideal for both relaxation and entertaining. Coastal-inspired details throughout the home create a natural sense of ease and timeless Hamptons elegance. With convenient proximity to the U.S. Open PGA at Shinnecock Hills Golf Club in June 2026, this residence offers a refined retreat for those seeking to experience the very best of the Hamptons with style, privacy, and comfort.

Tucked away in the sought-after Northside Hills community, this beautifully appointed five-bedroom rental blends classic Hamptons charm with modern comforts. Ideally located just minutes from Sag Harbor Village, bay beaches, and golf courses, it offers a perfect balance of tranquility and convenience. The spacious living room with a cozy fireplace and formal dining room create an inviting setting for entertaining. A chef's kitchen is outfitted with stainless steel appliances, quartz countertops, a breakfast bar, and a sunny eat-in nook-thoughtfully designed for both style and function. On the main floor, a versatile office/den can easily convert to bonus bedroom with pull-out couch. Upstairs, the designer primary suite features an en-suite bath, joined by four additional guest bedrooms and two separate full baths. One of the bedrooms includes an adjacent bonus living area with television and Peloton, ideal for relaxing or keeping active. Outdoors, enjoy a spacious backyard and deck for al fresco dining, plus a heated pool for leisurely afternoons. This is the perfect summer rental for relaxation and refined Hamptons living. #RP260016 [[Rental Registration # RP260016]] EH RR #: RP260016 Rental Terms: Two Weeks: $25,000

Available for rent, this newly renovated Sag Harbor estate blends modern sophistication with laid-back coastal charm-perfect for a luxurious Hamptons escape. Fully gut-renovated and thoughtfully expanded, the 2,680 sq. ft. home features brand-new hardwood oak floors, Restoration Hardware finishes, a built-in sound system, and an abundance of natural light. The main living room boasts soaring ceilings, a custom bar, and seamless flow into the open-concept kitchen outfitted with top-of-the-line WOLF, Sub-Zero, and Miele appliances. With five bedrooms and four-and-a-half spa-like baths, the home comfortably accommodates guests, including two separate master suites with ensuite baths, soaking tubs, and walk-in showers. A flexible nursery space can serve as an office or dressing room, and a second private office at the entrance is ideal for remote work. Outside, enjoy a south-facing 0.58-acre property with a heated gunite pool, sun-drenched deck, lounge and dining areas, and lush landscaping. The home also includes solar panels, an electric car charger, a full laundry room, and deeded beach rights-perfect for launching kayaks or paddleboards. Just a mile from Long Beach and moments from Morton Wildlife Refuge and Noyac Golf Course, this rental offers the ultimate in Hamptons living. [[Rental Registration # RP251335]] EH RR #: RP251335 Rental Terms: September: $35,000 October: $20,000 November: $15,000 Two Weeks: $17,000 Other / Short Term - Dec: $15,000

Privately situated on one +/- acre in Northside Hills, this newly renovated, designer's own home boast every amenity. The chef's kitchen includes all stainless steel appliances, custom cabinetry, stone back splash, granite counter tops, and center island with built in wine cooler. Graciously opening up to dining room, great room with fireplace and living room makes for seamless entertaining. The first floor also includes a large guest suite with private bath. Second level features three bedrooms; two master suites, both with walk in closets, extra large spa baths & fireplace. Enjoy summers with free form, infinity edge heated gunite pool or lounge outside on your mahogany wraparound porch for quiet enjoyment. The finished lower level serves as a game room and tv room with plenty of extra storage. This beautiful homes is minutes from three great villages: Sag Harbor, Bridgehampton & Southampton making it an ideal rental! Dec - April $6,800 per month [[Rental Registration # waitingforrp]] EH RR #: waiting for rp Rental Terms: July - Labor Day: $155,000 May: $28,000 June: $35,000 October: $16,000 September: $30,000 Other / Short Term - Year Round: $280,000 August - Labor Day: $78,000 Memorial Day - Labor Day: $180,000 July: $78,000

Nestled on a quiet cul-de-sac among expansive three-acre estates, this beautifully landscaped Hamptons retreat offers the perfect blend of privacy, recreation, and convenience. Backing directly to Noyac Golf Club and surrounded by more than 135 acres of scenic hiking and jogging trails, the property is an ideal escape for summer living. Designed for effortless indoor-outdoor entertaining, the home features a dramatic double-height living room, a newly renovated kitchen, and a spacious dining room with seating for 12. A wall of sliding glass doors fills the home with natural light and opens to the expansive patio, heated gunite pool, and Har-Tru tennis court. The thoughtfully designed layout includes six bedrooms and six bathrooms, all above ground, with two en-suite guest bedrooms conveniently located on the first floor and a spacious primary suite upstairs, along with three additional guest bedrooms. Furnished with two king beds and five queen beds, the home comfortably accommodates up to 14 guests. Ideally situated just minutes from Towd Point Beach, Long Beach, marinas, and several popular waterfront restaurants, and only 12 minutes from the villages of Southampton, Bridgehampton, and Sag Harbor, this exceptional property offers easy access to the very best of the Hamptons while providing a peaceful country setting. Rental Registration #RP160829. [[Rental Registration # RP160829]] EH RR #: RP160829 Rental Terms: July: $70,000 August - Labor Day: $70,000 July - Labor Day: $140,000

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

This recently renovated and professionally decorated cottage features 3 bedrooms on 0.40+/- acres. The immaculate interior is welcoming and chic, while maintaining the desirable comfort of a beachy summer home. Minutes to both Sag Harbor Village and Southampton, this retreat features new appliances, fresh and stylish furnishings, and interior rooms bathed in natural light. Bar-B-Que on the back deck, swim in the heated pool or in the bay just a short distance away. As part of the Southampton Shores community, the house enjoys access to The Colony Club's private bay beach, pavilion, community tennis and basketball courts. Entertain and enjoy your summer months amidst the private grounds of this attractive Hamptons home. [[Rental Registration # RP260131]] EH RR #: RP260131 Rental Terms: Memorial Day - Labor Day: $65,000 June: $15,000 August - Labor Day: $25,000

Hampton Traditional. Nestled down a private cul-de-sac on 1.2 +/- acres in Southampton North's desirable estate section, Farrel lbuilt home, approximately 6,500 sf, multiple living areas, 5 plus bedrooms, 6.5 marble baths, and a heated Gunite pool. The first floor features a double-height foyer, great room with fireplace and wet bar, living room with fireplace, gourmet kitchen with breakfast area, formal dining room, and a junior primary suite. The second floor offers 5 ensuite bedrooms, including the primary with its own fireplace, laundry, and a bonus room. Additional amenities include coffered ceilings, French doors, top-of-the-line appliances, sound system, 2-bay attached garage, patio, covered porch, over-sized backyard. Beautifully decorated and perfect for summer fun! [[Rental Registration # 230144]] EH RR #: RP250229 Rental Terms: Two Weeks: $60,000 July: $90,000 June: $70,000

Located in a Southampton-North waterfront community, this recently redecorated shingle-style traditional home has been refreshed and decorated with light and bright furnishings, offering comfort and ease in every room. Set on almost a half-acre with in-ground heated pool, the covered front deck opens to an open floor plan starting with the living room with large flat screen TV, and doors out to the large deck. The fully-modern kitchen with stainless steel appliances and stone counters opens to the dining area, and includes a pantry. A separate laundry room, office area, and full bath complete the ground floor. Upstairs, the master bedroom features a flat screen TV, fireplace, and oversized bath. Three more comfortably-appointed bedrooms and full bath finish the second floor. A green yard and attached one-car garage complete the property, and a community gazebo and waterfront area are part of this community. [[Rental Registration # RP261254]] EH RR #: RP261254 Rental Terms: August - Labor Day: $40,000 July - Labor Day: $75,000 July: $35,000

Privately elevated at the end of a long driveway sits a stunning modern home, Clearhouse. With timeless architectural planning by SP design the home is dramatically raised on a central plinth and cantilevers horizontally with floor to ceiling windows and sliding glass doors to create the ultimate indoor/ outdoor modern luxury living. Clearhouse offers one of the single greatest vistas on the east end of Long Island. The house has 360-degree views - 180 degrees being Peconic Bay, The North Fork, The Long Island Sound, and Connecticut - the south view is indigenous manicured forest with undulating elevations. On the first floor you will enjoy a full-width travertine terrace and private office. The upper floor is equipped with a gourmet kitchen with signature appliances, dining area with a wall of glass that opens to let the outdoors in, sitting area and large primary bedroom with views from every angle. The primary bedroom is comprised of 3 sides of glass - the width of the room opens completely to the elements like a modern treehouse. The lower guest level, with equally incredible vast views has a perfectly positioned media den and 2 ensuite guest bedrooms with sweeping bay views. The rooms reveal themselves in a horizontal band with architectural floor to ceiling windows. The interior synthesis of stone and dark rosewood reclaimed from a Manhattan bank and leather details create a warmth and glow that envelop the senses. A level of luxury permeates. Eye catching details such as a suspended black fireplace and world class art and furniture create a dreamy ambience. The home offers a dock with a 6,800 lb. boat lift, including additional room for a 55' boat and a 30' boat. Unparalleled sunset views every evening and ever changing light throughout the day. EH RR #: 2024-L-0045 Rental Terms: June/July: $110,000 Memorial Day - Labor Day: $200,000 July: $85,000 August: $85,000 July - Labor Day: $175,000 August - Labor Day: $105,000

This gated, 10,000 square foot on 5 park-like acres is the perfect Southampton retreat. The home feels like a true "estate," completely secluded on a private cul-de-sac of high-end homes, well off the main road. The recently refreshed interior is grand, with 5500 square feet of 2-story living space, all on one level, plus an additional 4500 square feet of finished lower level with every amenity. The spacious home offers a 2-story foyer and 2-story living room, with a 20' wall of glass as your first impression. There is plenty of room to spread out. A large eat-in kitchen overlooks the enormous yard. There is dining overlooking the yard, formal dining, and enormous great room with fireplace. A grand primary suite and 3 additional ensuite bedrooms (one can have a queen bed or be a second den with a sofabed) round out the first floor. Given the enormous footprint above, the downstairs affords tremendous living as well. There are two additional guest bedrooms, 2 full baths, theater, game/recreation room and gym area. The gated grounds are simply magnificent--gorgeously manicured, with expansive lawn. The focal point is a 60 x 30 show-stopper pool, surrounded by massive patio and gardens on all sides. An outdoor kitchen with barstools is perfect for entertaining. There is ample outdoor furniture for lounging and dining. The location is convenient, only 1.4 miles to perhaps the Hamptons' prettiest sandy bay beach, Towd Point, 4 miles to Southampton or Water Mill Villages, and 5.5 miles to a dozen ocean beaches. [[Rental Registration # RP250976]] EH RR #: RP250976 Rental Terms: July: $75,000 October: $15,000 February: $15,000 May: $15,000 August - Labor Day: $85,000 Other / Short Term - Year Round: $240,000 April/May: $30,000 April: $15,000 November: $15,000 August: $80,000 January: $15,000 September/October: $35,000 June: $40,000 September: $25,000 March: $15,000 Memorial Day - Labor Day: $185,000

This modern and chic four bedroom, four bath home has a gourmet kitchen with Miele appliances. The first floor primary suite opens onto the pool terrace. There is also a den on the main floor with ""en suite"" bathroom. Three bedrooms and two baths upstairs. Heated gunite pool surrounded by beautiful manicured gardens. Located by beautiful Conscience Point and bay beaches. All you need for a perfect summer. [[Rental Registration # RP240339]] EH RR #: RP240339 Rental Terms: August - Labor Day: $41,000

This newer construction is a rare find. The inside features high-end, custom furnishings rarely available in a rental at this price. Gorgeous architecture, interior design and mature landscaping will impress. The 7 Bedroom home (all with ensuite baths) spans 5800 feet above ground, plus 2550 feet of finished lower level. The First floor features a dramatic 2-story foyer, 2 spacious living rooms, a chef's kitchen, bar area. There is a Junior Primary, and a mudroom with pool bath. The Second Floor features a Primary suite with terrace, fireplace, and luxurious white marble bath. There are 4 additional ensuite bedrooms and a second laundry. The lower level offers expansive entertainment space, including a theater, living room, and playroom with ping pong. There is a 7th ensuite bedroom with 2 queen beds. Outside, a South-facing large terrace with overlooks a beautifully landscaped, 1-acre property, with farm views. The yard is private and includes a 40' pool, new sunken hot tub and generous patio space for entertaining. The house sits in a very quiet cul de sac of newer homes, 2 miles to Southampton Village, with Southampton beaches just beyond. The property is a short bike ride or walk to the Southampton Rec Center (SYS) which offers a fantastic children's camp, tennis, gym, basketball, track, yoga, and pilates. Its also 1.5 miles to Towd Point Beach, one of the Hamptons prettiest bay beaches. [[Rental Registration # RP230864]] EH RR #: RP230864 Rental Terms: April: $15,000 February: $15,000 Other / Short Term - 1/1/2027 - 4/30/2027: $60,000 November: $25,000 September: $45,000 October: $30,000 January: $15,000 March: $15,000 Winter Season: $90,000 Per Month

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

Secluded, expansive contemporary with double height ceilings, flooded in natural light. This home offers five bedrooms in all with two en-suite, primary bedrooms. The open floor plan offers great flow for entertaining and casual summer enjoyment as it opens up to a sweeping deck overlooking the heated pool and all-weather tennis court. Laundry room on the first floor and attached two-car garage. Very private setting, yet centrally located within an easy drive to Southampton, Water Mill, Bridgehampton, and Sag Harbor as well as bay and stunning ocean beaches. Enjoy your summer in The Hampton's in this chic, stunning home! Rental Reg. # RP230840 Reg. Expires 7/14/2025 EH RR #: RP251295 Rental Terms: July - Labor Day: $120,000 August - Labor Day: $80,000 July: $50,000 Two Weeks: $25,000 June: $50,000

Minutes to ocean and bay beaches, farmstands, and the best that Water Mill and Bridgehampton have to offer, this one-of-a-kind gated estate delivers an unparalleled blend of Hamptons luxury and Western character. Surrounded by 50+/- acres of reserve, the 18-acre property offers total privacy with equestrian amenities, including paddocks, two stalls, and a professional Grand Prix riding arena. Featured on the cover of Architectural Digest's "Country" issue, this is a stay you won't find elsewhere. The custom Montana-built log home boasts four bedrooms, five full and two half bathrooms, designer furnishings across two levels, four fireplaces, a full movie theater, and a dedicated gym. Outdoors, enjoy a heated pool; outdoor dining, bar, and grilling areas; expansive grounds; and direct access to nature. Full-time groundskeeper/barn manager on-site. [[Rental Registration # RP251906]] EH RR #: RP251906 Rental Terms: Other / Short Term - Dec: $40,000 November: $40,000 Memorial Day - Labor Day: $295,000

This recently renovated and impeccably maintained Water Mill residence with five bedrooms and four-and-a-half baths, located on a quiet cul-de-sac, offers the ideal setting for entertaining and relaxing. Sited on over an acre, the property features a beautifully landscaped, private rear yard with a heated, lighted 20' x 40' Gunite pool surrounded by a heat-resistant patio, with an outdoor kitchen featuring fridges, Lynx Infrared searing barbeque for summer grilling, expansive rolling lawn, and two firepits perfect for star-filled evenings with a Sonos sound system inside and outside. The main level includes a welcoming den with a gas fireplace, a comfortable living room, a gourmet kitchen outfitted with Viking professional appliances, dual dishwashers, wine fridge, ice maker, water cooler, and a generous center island, along with a spacious dining area for hosting family and friends. Upstairs, the serene primary suite offers a king-sized bed, Peloton, and a luxurious bath complete with a soaking tub, Toto Washlet, and double vanities. The second floor also includes an ensuite guest room, two additional bedrooms sharing a hall bath, and a convenient laundry room. The finished lower level with 10-foot ceilings includes a second laundry area, fridge, microwave and sink. It also provides a fifth bedroom, full bathroom, recreation room with pool table, ping pong, and an extensive game system, as well as a gym with a treadmill, free weights, incumbent bike and TV. Located moments from farm stands, world-class ocean beaches, transportation, and the vibrant communities of Southampton Village, Bridgehampton, and Sag Harbor - known for their marinas, dining, cultural venues and shopping - this Water Mill retreat delivers the very best of Hamptons vacation living. Rental Terms: Two Weeks: $25,000 Other / Short Term - 5/22/2026 - 6/26/2026: $50,000

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