luxury house with pool for rent Jamesport, United States

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 impeccably renovated and newly furnished Hamptons retreat offers a rare blend of total privacy, resort-style living, and effortless access to the best of the East End. Set on a shy acre bordering the scenic Red Creek Park trail system, the property feels like a private estate while placing you steps from premier recreational amenities, including newly built pickleball and tennis courts, basketball and baseball fields, volleyball courts, a skate park, and miles of wooded walking trails. Spanning over 4600 sq. ft. of thoughtfully designed living space the residence is ideal for extended summer stays and elevated entertaining. The home offers 6 bedrooms, 3.5 bathrooms, and plenty of room to spread out across two finished levels. A grand, double-height marble foyer sets the tone, flowing into expansive living and entertaining spaces anchored by a sun-filled living room, a cozy den with gas fireplace, and a generous upstairs lounge. The custom eat-in kitchen is designed for gathering with a center island and breakfast area that connects seamlessly to formal dining. Two bedrooms and 1.5 bathrooms round out the first level. Upstairs the primary suite is a true private sanctuary, complete with a balcony overlooking the wooded grounds, a custom walk-in closet, and a spa-inspired bath with radiant heated floors and a jetted soaking tub - offering a true resort-level experience at home. An additional 3 bedrooms and bathroom are on the second level. Outside, the deck and patio features room for dining, conversation and lounging. The mature specimen landscaping frames the 20' x 40' heated saltwater pool with waterfall feature - creating an elevated private resort atmosphere. With effortless access to the highway - marinas, dining, shopping, and beaches across the Hamptons and North Fork are all within an easy drive. This property delivers the ultimate East End rental experience: private, polished, and designed for elevated coastal living. [[Rental Registration # Pending]] EH RR #: RA260624 Rental Terms: July: $45,000 August: $45,000 August - Labor Day: $55,000

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.

A sleek Mid-Century home...Escape to this stunning 3-bedroom, 2-bathroom beach house located in the peaceful Shinnecock Hills area of Southampton. With a private setting on a quiet cul de sac, this professionally designed home offers a seamless blend of indoor and outdoor living, ideal for relaxation and entertainment. Property Highlights: 3 Bedrooms, 2 Bathrooms - Comfortably sleeps 6 Heated Pool & Hot Tub - Relax poolside or unwind in the hot tub after a day at the beach Spacious Outdoor Living - Enjoy sunny days on the large deck, perfect for entertaining or simply relaxing Large Outdoor Shower - Refresh after a swim in the pool or a day at the beach Beautiful Gardens - Professionally landscaped for a serene, private environment Interior Features: Primary bedroom with King bed and ensuite bathroom Two guest rooms with Queen beds, shared bathroom with tub & shower Cable TV & WIFI - Stay connected during your vacation Open Concept Living Areas - Bright and airy spaces, perfect for family gatherings Location & Convenience: Walk to the Shinnecock Bay Beach - Enjoy peaceful days by the water, just a short stroll away Minutes from Southampton Village & Hampton Bays - Only 10 minutes to charming shops, restaurants, galleries and attractions Close to Iconic Beaches - A short 10-minute drive to the beautiful beaches of Southampton and Hampton Bays Wine Country - Located near both the South Fork and North Fork of Long Island's famous wine regions Family Fun Nearby - Take the kids to the Riverhead Aquarium or enjoy a shopping spree at Tanger Outlets, just 20 minutes away. This beach house offers the best of both worlds - a private retreat with all the amenities you need, yet minutes from the vibrant action of Southampton and the natural beauty of the Hamptons. Perfect for those looking for a tranquil getaway with easy access to everything the area has to offer, including boating & water sports. Minutes to the Shinnecock Canal, which offers marinas, many waterside restaurants and a world class spa at the Five Star Canoe Place Inn & Restaurant. Don't miss out on this rare opportunity to stay in one of Southampton's most desirable areas. Book your stay today! [[Rental Registration # RP170644]] EH RR #: RP170644 Rental Terms: June: $25,000 Two Weeks: $18,000 August - Labor Day: $39,000

Welcome to 60 Lynncliff, a chic Hamptons home with every amenity. This three bedroom two bath recently renovated gorgeous enclave is private, comfortable and full of natural light. Enjoy morning coffee on the deck, back yard bbqs, soaking in your hot tub or swimming in the gorgeous in-ground pool. This home is an exceptional option as a Hamptons home base during the US Open in June, being held at Shinnecock Hills. With close proximity to the golf course, enjoy all of the excitement of tournament week! Spend your summer among beautiful Hamptons beaches, shopping and dining. Available June-27k, July-29k and Aug-29k

Custom-built, new home in a Shinnecock bay front community, now offered as a summer rental. This two-story, energy-efficient, open-plan home offers four bedrooms and three bathrooms, of which one bedroom and bathroom are located on the main floor. The covered front deck opens to the foyer and open living featuring the kitchen with quartz counters and high-end Bosch stainless steel appliances. The over-sized living area includes its own south-facing deck. Upstairs, the second floor offers three bedrooms and two baths, one of which is ensuite. At grade, the lower level houses the one-car garage with its own entry. Well-landscaped with retaining walls, the property features an in-ground, heated salt water pool, is just up the street from the bay front, and a short drive to Southampton Village and ocean beaches. An on-point Hamptons escape, this rental property's location is outside of the summer weekend traffic rush. [[Rental Registration # RP260163]] EH RR #: RP260163 Rental Terms: September: $9,000 August - Labor Day: $35,000 Two Weeks: $15,000 October: $6,000 August: $30,000

So bright, sunny and cheerful with all of the amenities to make this home feel like you have arrived home. Perfect retreat designed for solitude as well as entertaining ease. Living room with fireplace, high ceilings overlooking grand deck, heated pool and tennis court. Dining, open islanded kitchen and primary bedroom share the same views as well. Four separated bedrooms allow for nice privacy, Centrally located. Near it all. Wow factor! Come see! *Some images virtually staged. [[Rental Registration # RP260847]] EH RR #: RP260847 Rental Terms: Two Weeks: $16,000

Brand new furnishings await the discerning tenant at 18 Spring Pond located in a quiet, private community. The 2 story home offers a heated, gunite swimming pool and community tennis court. The house is freshly painted, updated and boasts brand new furnishings including pool lounges. Great open floor plan from the kitchen to indoor and outdoor entertaining spaces. There is a junior en-suite bedroom on the first floor in addition to a powder room. The second floor holds the private primate suite with floor to ceiling windows overlooking the private property. There is a private balcony, shower bath, walk in closet and an adjacent den that can serve for relaxation, working. There is a third en-suite guest room with two twin beds and the laundry room on the second floor. [[Rental Registration # RP260246]] EH RR #: RP260246 Rental Terms: Other / Short Term - Dec: $15,000 April: $15,000 July: $40,000 September: $18,000 March: $10,000 November: $10,000 June/July: $60,000 May: $15,000 January: $10,000 October: $10,000 February: $10,000 Winter Season: $60,000 Per Month

The 2020 completed, as good as new construction home has all the bells and whistle of luxurious, modern living at its best. Open public spaces flow from one room to the next into the gourmet chef's kitchen with island seating, breakfast area. Sliding glass doors open to the vast property with lawn areas and a proper patio and in-ground, gunite swimming pool. The home offers 7 bedrooms including the oversized primary bedroom with walk-in closet. The finished lower level offers a media room, exercise room with sauna and storage. A must see and experience! [[Rental Registration # RP250582]] EH RR #: RP250582 Rental Terms: June: $65,000 November: $30,000 Other / Short Term - Year Round: $295,000 August - Labor Day: $105,000 July: $100,000 October: $30,000 Memorial Day - Labor Day: $260,000 April: $20,000 July - Labor Day: $200,000 May: $40,000

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 2027 for $40,000. Permit #1501.

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

Set south of the highway on a long private country driveway, this distinctive Southampton retreat offers a rare blend of creativity, privacy, and effortless summer living. A spectacular heated gunite pool, sauna, and fully outfitted tiki hut create an exceptional outdoor setting designed for sun-filled days and relaxed evenings. Upon entry, the home unfolds with a natural entertaining flow-an inviting living room to the left, perfect for pre-dinner cocktails, and a dining room to the right, ideal for long, leisurely dinners. Both spaces are bright and welcoming, and a piano adds a playful, social element-perfect for impromptu sing-alongs and easy summer entertaining. The kitchen features a European-inspired aesthetic with expressive design details and a charming Dutch door opening to the outdoors, allowing for seamless indoor-outdoor living all season long. With four ensuite bedrooms plus a powder room, including a first-floor primary suite with direct garden access, the layout is both comfortable and well-suited for guests. Upstairs, a separate bonus room offers a relaxed retreat for movie nights or additional gathering space. The lower level offers the ultimate workout space with a fitenss center. Outdoor living takes center stage, with multiple areas for dining and lounging-perfect for daytime lunches by the pool, afternoons under the tiki hut, and evening barbecues. The grounds feel private and relaxed, offering a true summer escape. A deeded waterfront parcel on Middle Pond provides direct access for kayaking and paddleboarding, with routes leading out to Shinnecock Bay and beyond. Located just minutes from Southampton Village, ocean beaches, and several of the area's premier golf courses, this property captures the ease and style of a Hamptons summer. Rental Terms: July: $55,000 June: $40,000 July - Labor Day: $115,000 Memorial Day - Labor Day: $130,000 August - Labor Day: $65,000

The peacefulness and serenity of a summer on the East End awaits you in this fully renovated Southampton home. Offering breathtaking views of Peconic Bay and Bullhead Beach, this four bedroom home features 3 over-sized bedrooms each with their own private bath, an open concept main floor with a brand new kitchen, dining room, and a massive great room with vaulted ceilings, gas fireplace and wet bar. Outdoor amenities include a 20'x 40' custom inground pool surrounded by an oversized deck with lush landscaping throughout. If golf is your game, this home literally is surrounded by the top three courses on Long Island (Shinnecock Hills, Southampton and National) Luxury shopping and world class dining are both minutes away in the village of Southampton. This home is the perfect escape from hectic city life, yet it is conveniently located for those in need of a quick return to the hustle and bustle of greater New York City. [[Rental Registration # RP260397]] EH RR #: RP260397 Rental Terms: Memorial Day - Labor Day: $110,000 July: $45,000 August: $45,000 July - Labor Day: $90,000 June: $25,000 August - Labor Day: $50,000

WATERFRONT COMPOUND WITH POOL! Swim, fish, or launch the kayak, paddle board or sunfish sailboat(included) from this waterside haven! Located on Davis Creek, this Towd Point Beach Rental has unobstructed views of the harbor and beyond to Conscience Point National Wildlife Refuge. Featuring a cottage-style main house with three bedrooms and two bathrooms and a modern-barn style pool house that takes full advantage of the stunning views. The two-story pool house has two full bathrooms, a wet bar, an outdoor kitchen, and seating areas on both levels with sliding doors that bring the outside in - it's where you'll be hanging out. The main house also has outdoor dining, incredible views and an outdoor shower. The heated, salt-water gunite pool is NEW FOR SUMMER 2024 and includes an endless swim current for lap swimmers. Moments to the beautiful Towd Point Beach. [[Rental Registration # rp250468]] EH RR #: rp250468 Rental Terms: August: $85,000 August - Labor Day: $90,000 Memorial Day - Labor Day: $220,000 July: $85,000 June: $50,000 October: $30,000 November: $20,000

Located in Parrish Pond just outside the Village of Southampton is this 5 bedroom, 4.5 bathroom traditional. Professionally decorated, this home offers a well-appointed first floor master bedroom and attractive entertaining spaces. Outdoor amenities include a heated Gunite pool and spa, a bocce court, a surround sound system and open grounds and mature landscaping. A five-minute drive to the Village of Southampton and its beaches. Available two weeks in August. THIS PROPERTY IS NOT OFFERED ON AIRBNB, VRBO, OR ANY OTHER HOME-SHARING SITE. [[Rental Registration # RP251741]] EH RR #: RP251741 Rental Terms: Two Weeks: $35,000

Just moments from the iconic Shinnecock Hills Golf Club, this inviting Southampton home offers the perfect Hamptons escape. Featuring 4 bedrooms and 3 baths across approximately 2,200 square feet, the residence is set on a beautifully landscaped property ideal for relaxed indoor-outdoor living. A wonderful opportunity to enjoy classic Southampton charm in a highly sought-after location. Rental Terms: Other / Short Term - Weekly: $20,000 Two Weeks: $30,000 June: $60,000

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

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

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

Conveniently located, winter or summer living will be seamless in this 2 bedroom 2.5 bath townhome. Recently renovated and styled. Open living, eat in kitchen, and back deck area perfect for evening barbecues. Community tennis, pickle ball, putting range, 2 pools and quick access to village shops and ocean beaches! [[Rental Registration # Pending]] EH RR #: condo n/a Rental Terms: July - Labor Day: $40,000 Memorial Day - Labor Day: $50,000

Welcome to 50 Rosko Lane in The Fields, Southampton's premier luxury enclave. This west-facing new construction offers abundant natural light, and over 6,000 sq. ft. of beautifully designed living space. With 7 bedrooms, 7 baths, and a finished lower level, the home balances refined Hamptons style with modern comfort. The airy main level showcases soaring ceilings, wide-plank floors, and a chef's kitchen that flows seamlessly to the dining area, accented by a striking built-in wine display. Walls of glass open to a private backyard with a heated gunite pool, bluestone patio, and landscaped grounds. The serene primary suite features a spa-like bath and generous closets, while the lower level adds a media lounge, recreation space, guest suites, and an impressive gaming lounge with four high-end stations, Xbox Series X and PlayStation 5 consoles, and award-winning Secret lab chairs-perfect for entertaining all ages. A two-car garage, proximity to Southampton Village, and world-class beaches complete this exceptional offering-luxury, convenience, and resort living at its finest. [[Rental Registration # RP250841]] EH RR #: RP250841 Rental Terms: August - Labor Day: $125,000 September: $75,000

Spend your summer in the heart of Westhampton Beach at 9 Ocame Avenue — a chic, four-bedroom, three-bath retreat designed for effortless coastal living. This bright and stylish home offers the perfect blend of charm, comfort and Hamptons convenience, all moments from Main Street, world-class beaches, boutiques and dining. Step inside to sun-filled living spaces, a well-appointed kitchen, and comfortable bedrooms ideal for hosting gatherings. Outdoors, enjoy everything that makes summer special: a welcoming front porch, patio for dining and lounging, sparkling pool, pool house and a refreshing outdoor shower for after beach. Available September 2026 through April 2027 for $10K a month, this home is an exceptional option providing the perfect Hamptons home base.

New to the 2021 rental market: 6 BR, 5 bath modern Hampton home with fabulous pool house and an inground, heated gunite swimming pool. Several outdoor entertaining spaces and in- and outdoor fireplace. This home offers an open concept floor plan with a large gourmet chef's kitchen, dining area that flows effortlessly into the living/family area with fireplace. On the second floor are 5 bedrooms, 3 bathrooms including the sumptuous master suite with soaking tub and rain shower. Only minutes to Village shopping, restaurants and ocean beaches. [[Rental Registration # RP251145]] EH RR #: RP251145 Rental Terms: August - Labor Day: $90,000 September: $25,000 May: $50,000 June: $40,000 Memorial Day - Labor Day: $249,000 Other / Short Term - Year Round: $290,000

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