luxury furnished house for rent Jamesport, United States

Tucked away on a quiet and private block in Shinnecock Hills, this serene two-bedroom, two-and-a-half-bath bayfront retreat offers a truly special summer escape. Overlooking Shinnecock Bay with open views stretching to the Atlantic Ocean beyond, the home captures some of the most beautiful water vistas in the area. Set within a peaceful enclave along the bulkheaded shoreline, this original Sears Craftsman cottage has been lovingly maintained and offers a rare opportunity to enjoy classic Hamptons waterfront living. The inviting open floor plan allows natural light and bay views to fill the living spaces, creating a calm and relaxed atmosphere throughout. The home features two comfortable bedrooms, two and a half baths, central air, and a welcoming three-season porch-an ideal spot to take in the ever-changing light over the water. Outdoors, enjoy the fresh bay breeze from the porch, dine al fresco using the gas grill, or rinse off after a day by the water in the outdoor shower. A wood-burning fireplace adds warmth and ambiance for cooler evenings. With a 75-foot bulkhead along Shinnecock Bay and unobstructed views to the ocean beyond, the setting is both peaceful and inspiring. Perfect for couples, friends, or a small family seeking a quiet waterfront getaway, this special home offers the kind of restorative Hamptons summer experience that is increasingly hard to find. [[Rental Registration # (RP260026)]] EH RR #: (RP260026) Rental Terms: August - Labor Day: $30,000 July - Labor Day: $55,000 July: $25,000

Renovated 2-bedroom cottage with water views and access to Big Fresh Pond for swimming, kayaking and paddle boarding. A serene location to unwind and enjoy great sunsets. Open concept living area with dining area, eat-in & fully stocked kitchen, and living room - all with water views. Outdoor BBQ grill & outdoor shower. Kayak & bikes available. Bonus: Piano in living room! [[Rental Registration # RP251276]] EH RR #: RP251276 Rental Terms: Memorial Day - Labor Day: $37,500 October: $4,000 September: $6,000 July: $17,000 June: $9,000 August - Labor Day: $19,000

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

This handsome residence is situated on a well-landscaped acre. A bright living room with fireplace and double-height ceiling, dining area, eat-in kitchen, four bedrooms with primary on first floor and three baths provide good living space. Central air-conditioning, two-car garage, outdoor deck, and heated pool complement this home. Located minutes from the Village of Southampton, this property is close to all beaches, shopping and restaurants. [[Rental Registration # RP240739]] EH RR #: RP240739 Rental Terms: June: $18,000 July: $30,000 August - Labor Day: $35,000 September: $15,000 Memorial Day - Labor Day: $65,000 July - Labor Day: $60,000

Simply spectacular, this recently-built Village home in Southampton blends traditional luxury with chic contemporary interior design - extremely convenient to ocean beaches, restaurants and shopping. On 2.5+/- perfectly-landscaped acres, the property includes a two-story residence with eight bedrooms, ten baths, seven fireplaces, chef's dine-in kitchen with four dishwashers and two pantries, double-height living room with fireplace, formal dining room, family room, numerous terraces and balconies, and more. Outside, the generously-sized 50'x20' heated Gunite pool and tennis court will make for an exquisite summer in this extraordinary location. Rental Terms: September: $200,000 August - Labor Day: $500,000

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!

Summer is here, and this home has vacation written all over it. Enjoy spectacular sunset water views of the Long Island Sound from the spacious wrap-around deck or from the bright, open-concept living spaces inside. Perfect for entertaining, the layout features 4 bedrooms and 2 full bathrooms, offering a beautiful oasis for relaxation and togetherness. The lifestyle here is effortless: Kenny's Beach access is just steps away (.02 miles) for swimming in the Sound, complemented by a refreshing outdoor shower back at the house. Plus, you can leave the car behind and stroll down the road (.03 miles) to grab lunch or dinner at the hot new local restaurant, Little Fish. Let's get you set up in the perfect summer getaway—inquire today! Availability: June 15-June 30th $10K | July $35K | August $30K

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

Ideally situated in the heart of Southampton Village this 8 bedroom, 7 1/2 bath home has been lovingly restored to its original excellence with modern amenities. The first floor offers an open and bright Living Room, a sunny family room, a guest bedroom with a bath, a very large and open kitchen with walls of windows and glass doors that lead to the large stone patio, a formal dining room, and a game room. The second floor has a large master suite with 2 baths and a private deck, and 3 large guest bedrooms with 2 baths. The charming third floor has 3 additional guest bedrooms and bath. The lower level has a media room, a full bath, and a laundry room. There is a heated gunite pool, a pool house with a bath and outdoor shower, and a detached 2 car garage. Just a short block from Main Street and Jobs Lane and less than a mile to the ocean beach this home exemplifies summer living at its best. Fabulous, luxurious and light filled, it's the perfect summer retreat. Rental Terms: June: $60,000 August - Labor Day: $160,000 August: $150,000

Enjoy this tastefully decorated, eight-bedroom, eight-bath Traditional home just around the corner from Gin Lane and the ocean. A wonderful opportunity to spend a summer in a perfect European-styled home in the Southampton Estate Section. The house has an open floor plan on the first floor offering a the state-of-the-art kitchen, breakfast area, formal dinning, wet bar and a downstairs bedroom. The six, wonderfully furnished, additional upstairs bedrooms, each with a bathroom and some with private terraces, are accessable through two different staircases. The basement is setup with a staff area and a brand new, huge media room. There is plenty of outdoor entertaining terraces with fireplace, a beautiful pool and nicely landscaped gardens. Rental Terms: July: $160,000 June: $80,000 Winter Season: $100,000 Per Month September: $50,000

On a tranquil street, less than a half mile from the Atlantic Ocean and near the center of the village, this updated Southampton classic offers 5 bedrooms, 5 and a half baths, CAC and heated pool all on 1 private acre. Find a combination of classic Hamptons charm with bright contemporary accents & amenities. Also available Thanksgiving and Christmas weeks for $25K Weekly Rental Terms: September: $35,000 October: $35,000

Newly renovated in 2018, this bright and airy four-bedroom home is set on a full acre bordering a private preserve, offering rare tranquility and uninterrupted natural views in the heart of Water Mill. The home is filled with natural light throughout, featuring an open-concept kitchen and living space designed for easy summer living and seamless entertaining. The primary suite opens directly to the outdoor deck, creating a true indoor-outdoor lifestyle. Outside, enjoy expansive, fully fenced grounds, a sparkling in-ground pool, and the privacy that comes with backing onto preserved land. Privacy with just sun, space, and calm. Ideally located minutes from ocean beaches, Southampton, and Bridgehampton villages, and top restaurants, this home delivers both convenience and escape. A clean, modern Hamptons rental that actually feels like a getaway. Available August through Labor Day. [[Rental Registration # RP260066]] EH RR #: RP260066 Rental Terms: Other / Short Term - Year Round: $125,000 Memorial Day - Labor Day: $85,000

This light-filled residence is quietly set on a gated and exceptionally private two-acre property in coveted Water Mill. Recently renovated with a natural, timeless aesthetic, the home features sanded oak floors and a thoughtful layout with five beautifully appointed bedrooms across two distinct wings. A welcoming foyer opens to a spacious living and dining area, highlighted by a wall of sliding glass doors that seamlessly connect to the deck and outdoor living spaces. First-floor guest suite enjoys direct access to the deck and pool. Upstairs, the primary suite and an additional guest ensuite share a balcony, alongside a dedicated workspace ideal for focused productivity. A separate wing offers a media / playroom and two additional bedrooms, including one with bunks, served by a full bath-perfect for guests of all ages. Outdoors, enjoy a heated pool and relaxed al fresco dining surrounded by mature landscaping, hydrangeas and natural tranquility. Ideally located just eight minutes from Southampton Village's renowned restaurants, shops, and ocean beaches, this serene and special property offers privacy, comfort, and effortless Hamptons living. Please call with questions or to make an appointment to view this serene and special property! [[Rental Registration # RA260488]] EH RR #: RA260488 Rental Terms: August - Labor Day: $65,000 August: $55,000

Summer or Year Round Living Perfectly positioned south of the highway in one of Water Mill's most desirable locations, this beautifully maintained contemporary offers effortless single-level living on a private, beautifully landscaped acre. A gated entrance and mature plantings create a welcoming sense of arrival, while bright, open interiors with soaring ceilings and walls of glass fill the home with natural light. The thoughtfully renovated kitchen flows seamlessly into the spacious living and dining areas, creating an inviting setting for both everyday living and entertaining. The home offers four bedrooms and four full baths, including a gracious primary suite tucked into its own private wing with double walk-in closets, an oversized spa-like bath, and direct access to the outdoor living spaces. Two guest bedrooms also open directly to the rear deck, creating an ideal layout for hosting family and guests, while a separate study provides the perfect home office or quiet retreat. Designed to embrace the Hamptons lifestyle, expansive decking surrounds the sparkling heated pool, where eastern exposure welcomes beautiful morning light throughout the day. Multiple outdoor entertaining areas, cheerful landscaping, and an exceptional stretch of lawn provide plenty of room for everything from summer gatherings to a game of frisbee or Sunday football. A partially finished lower level offers additional overflow living space, a full bath, laundry area, and generous storage, providing flexibility to suit a variety of needs. Offering privacy, style, and an exceptional south of the highway location, this turnkey Water Mill retreat seamlessly blends easy single-level living with outstanding indoor and outdoor entertaining. [[Rental Registration # RP260361]] EH RR #: RP260361 Rental Terms: Other / Short Term - Year Round: $200,000 Memorial Day - Labor Day: $160,000

Discover the perfect Fall getaway in this stunning artist's home in Sag Harbor, now available from Sept 8th - Oct 5th 2026. Ideally situated between Sag Harbor Village and Long Beach, this immaculate 4-bedroom, 3.5-bathroom residence is a true oasis, featuring a well-curated collection of art within a sophisticated monochromatic interior. Built in 2018, this contemporary farmhouse beautifully balances exceptional style and comfort. An open-plan kitchen, dining, and living area seamlessly transitions to the 32' x 16' heated gunite pool, surrounded by a bluestone patio with multiple entertaining and lounging areas. A well-thought-out setting for summer gatherings or long days by the poolside. For the art enthusiast, a well-stocked library of art and design books can be found in the first-floor lounge. On the second floor, you will find four well-appointed bedrooms, including two that feature ensuite bathrooms, as well as an additional full bathroom. To enhance your stay, the dedicated laundry room features two washers and dryers for your convenience after days at the beach. Minutes from both Long Beach and Sag Harbor Village, you can also enjoy fresh, local produce from Serene Green Farm Stand, conveniently located at the end of Parkway Drive. [[Rental Registration # RP230356]] EH RR #: RP230356 Rental Terms: October: $18,000 July: $60,000 July - Labor Day: $135,000 Other / Short Term - 12/23/2026 - 1/31/2027: $30,000 September: $12,000 August - Labor Day: $75,000

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: July: $110,000 June: $50,000 August - Labor Day: $135,000

Perfectly positioned in the heart of Bridgehampton South, this beautifully designed six-bedroom, five-and-a-half-bathroom home embodies effortless Hamptons living in every season. Filled with natural light, the home offers elegant, sun-drenched interiors, sophisticated yet relaxed furnishings, and a seamless flow between indoor and outdoor spaces. Thoughtfully designed for both comfort and style, expansive living and dining areas create the perfect setting for everyday living, entertaining, and weekends with family and friends. Beautifully landscaped grounds offer multiple outdoor seating and dining areas, while a tucked-away fire pit provides an inviting place to gather on crisp fall evenings or cool spring nights. Designed with every member of the family in mind, the property also features a basketball court, trampoline, playground, and garage, offering plenty of space for recreation and relaxation throughout the year. Located moments from Bridgehampton's renowned restaurants, boutiques, farm stands, ocean beaches, and equestrian facilities, the home offers an ideal balance of privacy, comfort, and convenience - from quiet fall weekends and cozy winters to spring on the East End and the arrival of summer. An exceptional opportunity to experience Bridgehampton living through the seasons. [[Rental Registration # Pending]] Rental Terms: Other / Short Term - 9/12/2026 - 6/30/2027: $195,000 February: $15,000 May: $40,000 October: $35,000 November: $20,000 September: $60,000 January: $15,000 April: $20,000 March: $15,000 June: $75,000

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

Discover the perfect island getaway in this spacious 4-bedroom, 2-bathroom home tucked away on a large, serene lot. Surrounded by mature landscaping, the property features a generous front porch overlooking a peaceful pond—an ideal spot for morning coffee or sunset relaxation. Inside, the home offers a bright and inviting layout with a well-appointed kitchen complete with a center island, perfect for entertaining. Additional conveniences include an in-unit laundry room, mudroom, and a flexible bonus space great for a home office or playroom. A two-car garage provides ample storage and parking options. Located just minutes from Route 114 and South Ferry, the home offers easy access to all the island’s main destinations. Wades Beach is only 1.5 miles away, making beach days effortless. Guests also enjoy seasonal access (July 4th–Labor Day) to the Coecles Harbor Marina pool for added summer enjoyment. This peaceful retreat combines comfort, privacy, and convenience—ideal for your next stay on Shelter Island.

Situated on one of the largest lot in Sag Harbor Village at 2 builders acres, this furnished 3,000 sq. ft. Colonial offers 5 bedrooms or converted home office, 2.5 baths, outdoor shower, CAC, finished basement with play room, gym, large heated gunite pool, hot tub, all on a manicured property with organic garden, fire pit, and lovely outdoor dining. Within a short distance to the village center and its restaurants, shopping and entertainment. Store your catamaran, paddle boards and kayak at Havens Beach, or enjoy sailing at the Breakwater Yacht Club.ond largest lot in Sag Harbor Village at 2 builders acres, this furnished 3,000 sq. ft. Colonial offers 5 bedrooms or converted home office, 2.5 baths, outdoor shower, CAC, finished basement with play room, gym, large heated gunite pool, hot tub, all on a manicured property with organic garden, fire pit, and lovely outdoor dining. Within a short distance to the village center and its restaurants, shopping and entertainment. Store your catamaran, paddle boards and kayak at Havens Beach, or enjoy sailing at the Breakwater Yacht Club. Rental Terms: May: $20,000 September: $38,000

Offered July $35,000; Aug $35,000; Sept $25,000; Oct $20,000. Elegantly renovated and exceptionally spacious, this contemporary retreat is nestled within a parklike setting of sweeping lawns, lush gardens, and mature landscaping that affords remarkable privacy. Refined outdoor amenities include a heated gunite pool, outdoor shower, firepit, and walking path to abutting Island’s End Golf & Country Club. The main house and annex are filled with natural light, featuring soaring ceilings, oversized windows, and glass doors that open seamlessly to two expansive decks for effortless indoor-outdoor living. A generous poolside patio offers additional space for lounging and entertaining, while the decks provide inviting areas for alfresco dining, grilling, and relaxation. Bedrooms are thoughtfully positioned to ensure comfort and privacy for guests. Peaceful and secluded, yet just moments from Greenport Village, Seps Farm Stand, and sound and bay beaches, this home is impeccably suited for gracious North Fork entertaining.

Not available for year round rent at this time. Newly renovated three bedroom, two bath bungalow just outside of popular Greenport Village. This house provides a sense of privacy and relaxation close to the beach. Located less than one mile away, the captivating Rocky Point Beach is a picturesque retreat for everyone to enjoy. Additionally, there is the exquisite Truman's Beach nearby, which provides a stunning view of Connecticut. Lavender Bay and Sep's Farm are conveniently located only 0.4 miles away. The exterior of the property is designed for entertainment, featuring a spacious patio, barbecue area, fire pit, and even an outdoor shower to refresh after a dip in the nearby beaches. Seasonal Rates: June $6,000 | July $8,000 | Aug-LD $10,000