luxury house with pool for rent Orient, United States

2026 Rates: June $8,500/week; July and August $10,000/week (Two Week Minimum For All Rentals). Spend your summer in style at this exquisite brand-new modern farmhouse, offering the perfect blend of luxury, comfort, and North Fork charm. Located just minutes from Greenport Village, local farmstands, renowned wineries, and pristine beaches, this home is the ideal summer retreat. Set on a full 1-acre lot, this spacious and sun-filled residence features an open-concept layout with elegant hardwood floors throughout. The heart of the home is a high-end chef’s kitchen, fully equipped for entertaining and flowing seamlessly into a stylish living area complete with a gas fireplace—perfect for unwinding after a day on the Sound. The first-floor primary ensuite bedroom offers a serene private escape, while the second floor includes a junior ensuite and two additional guest bedrooms with a shared full bath—providing ample space and comfort for family and friends. Step outside to your own private oasis featuring a 20x40 heated in-ground pool, surrounded by lush landscaping and plenty of space for outdoor dining and lounging. Whether you’re sipping wine under the stars, enjoying a day at the beach, or exploring nearby Greenport’s vibrant shops and restaurants, this stunning farmhouse offers the ultimate summer experience.

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.

2026 Rates: May $26,000; June $29,000; July $36,000; September $27,000; October $24,000. Experience North Fork summer living in this newly constructed gem! Nestled in the sought-after Stirling Eastern Shores community, this impeccably designed modern farmhouse offers exclusive access to a private Long Island Sound beach, just a five minute walk from the property. Step inside to discover a light-filled and meticulously styled interior adorned with contemporary finishes and furnishings. The heart of the home is the chef's kitchen seamlessly integrated into the Great Room and anchored by a cozy gas fireplace. On the first floor, you'll find a convenient half bath, a junior en-suite bedroom, a spacious mudroom, and a sizeable 2-car garage. Ascend to the second level to encounter two additional guest bedrooms sharing a full bathroom, along with a stunning primary en-suite bedroom. The primary bath boasts a luxurious double vanity, a walk-in shower, a soaking tub, and an expansive walk-in closet for added convenience and indulgence. Outside, the property showcases a captivating landscape featuring a sprawling stone patio enveloping a 20x40 heated salt-water pool, complemented by an outdoor shower - an ideal setting for hosting gatherings and enjoying the summer sun.

2026 Rates: April $7,500; May $12K; June $15K; July $25K; A1-LD $27,500; Sept $12,500; October $10K: This beautifully curated home away from home, blends modern design with warmth and style. Experience elegant comfort in your private retreat with natural light, modern decor and thoughtful touches throughout. Nestled on a quiet, tree lined street, this special haven features a front porch, fully equipped open kitchen, and spacious backyard with a pool and fire pit. Enjoy all season living in this home away from home just a 10 minute walk to The LIRR station, Hampton Jitney, and The North Ferry.

2026 Rates: August 1-15 $20,000, September $25,000, October $20,000: Escape to this exceptional seasonal rental, perfectly situated on the shores of the Long Island Sound. This beautifully appointed waterfront home offers the ultimate coastal living experience, featuring private stairs leading directly to the beach, an in-ground heated gunite pool, and panoramic water views from nearly every room. With 4 spacious bedrooms—including a luxurious primary en-suite—and 3 full bathrooms, there’s plenty of room for family and guests to unwind in comfort. The heart of the home is a dramatic post and beam Great Room, designed for both relaxing and entertaining, with soaring ceilings and expansive windows that flood the space with natural light. Step out onto the large balcony to take in sweeping views of the Sound, enjoy morning coffee as the sun rises over the water, or end the day with a spectacular sunset. Additional amenities include a 1-car garage, central air, and thoughtfully landscaped grounds that ensure privacy and tranquility. Whether you’re lounging poolside, walking along the shoreline, or enjoying evening breezes from the balcony, this home offers an unforgettable seasonal escape.

Experience the private island ambience from this three story modern design by renowned architectural award recipient. Perfectly sited for panoramic waterfront views and stunning direct sunsets, it has a private path for spontaneous access to a secluded meandering beach. The open interior hold five bedrooms including two primary suites, seven bathrooms, a waterside enclosed porch, media room, gym, sauna, cold plunge ice bath and massage room. Walls of glass exhibit continuous water views throughout while inviting in soothing coastal air. The water view salt water pool has multiple surrounding decks, covered porches and pool house with bath. Various additional gathering areas include a fire pit with seating quietly nestled in a dune by the Bay. A private marina, waterfront restaurants and the charm of East Hampton Village are moments away. A magical setting, this is waterfront living at its finest. [[Rental Registration # 24-1446]] EH RR #: 24-1446 Rental Terms: September: $60,000 October: $50,000 November: $50,000 Other / Short Term - Dec: $50,000

Available, year-round! Flex start date of Sept 15,2026 or Oct 1, 2026. Nestled in the hamlet of North Haven, just minutes from the heart of Sag Harbor Village, this exceptional Hamptons retreat embodies refined luxury and timeless design. Thoughtfully crafted with bespoke finishes throughout, the residence offers four bedrooms and five baths, including two first-floor ensuite guest rooms. The elegant interior features a chef's kitchen with generous dining space, a dramatic great room and four tranquil bedrooms (all en-suite) designed for comfort and privacy. Outdoors, an expansive bluestone terrace provides the perfect setting for entertaining, overlooking a serene gunite pool surrounded by beautifully curated gardens. A sweeping circular driveway and lush landscaping create a sense of seclusion, while the property's prime location places you moments from Sag Harbor's renowned beaches, acclaimed restaurants, and charming boutiques. [[Rental Registration # RP#R-2024-0011]] EH RR #: RP# R-2024-0011 Rental Terms: Other / Short Term - Year Round: $215,000

Enjoy August in this sweet, cozy, updated home with pool. Chef's kitchen, open floorplan with 3 bedrooms, and 2 baths, this home is close to bay beaches. [[Rental Registration # 26-1149]] EH RR #: 26-1149 Rental Terms: Two Weeks: $10,000

No expense was spared on this Brand-New, 10,000+/- sq. ft. gated, Custom Construction. Available for the first time for June/July, 2024. This is perhaps the nicest estate rental offering available just outside Sag Harbor Village, only a 1/2 mile to Long Beach. The home itself is magnificent, custom designed, with no detail overlooked. It has every amenity--7 ensuite bedrooms, elevator, magnificent custom-designed Kitchen, glass Breakfast Room, oversized Great Room and Living Room with Wet-bar. The first floor also features a luxurious Bar Room/Butler's Pantry and a large 1st-floor Office with TV. The lower level offers a Gym, Game Room, and Hotel-like Spa, with Steam Shower, Soaking Tub, Shower, and Sauna. The majestic property offers 1.5+/- acres of full lawn--gated and fully enclosed. It includes a Pickleball Court, Basketball, 45' Pool, Hot Tub, Outdoor Living Room, and Outdoor Kitchen/Bar. The property is perfect for family outdoor living and entertaining. And for local daily activities, the offering is also only moments to Community Tennis, two gorgeous Beaches, Sag Harbor Marinas and the Shelter Island Ferry. Rental Terms: November: $30,000 Other / Short Term - Year Round: $650,000 Winter Season: $135,000 Per Month

Also Available: Two Weeks between Aug 1 - Aug 31 28K This very private and dreamy Alfred Scheffer restored home and cottage circa 1967 is surrounded by reserve and views of Accabonac Harbor. Exposed wood beams and an expansive back yard create an atmosphere and environment that set the tone of this great scenic property. It is living with nature at its best. The Barn inspired main house is sited to take advantage of the forever field views and is filled with light. There is a 1st floor ensuite primary bedroom, a kitchen meant for cooking and a barn chic great room. What's special about the living arrangement is the guest cottage creating a true compound and privacy with 2 bedrooms and 2 full baths in addition to a high ceiling studio or gathering spot. The outdoor spaces on 2 acres include a pool, fire pit area, sweeping pastoral vistas and a lovely patio for entertaining off the main house. EH RR #: 25-34 Rental Terms: August: $50,000 Two Weeks: $28,000 August - Labor Day: $55,000

Also available: July $40k, Aug $45k, Sept $12k Beautifully renovated 4 bedroom, 3.5 bath contemporary with bay views from second floor living room. Open floor plan, with professional kitchen, marble counter tops, and stainless steel appliances. Additional office space with futon. Bathrooms are also all recently renovated. Short distance to Long Beach and minutes from Sag Harbor Village. RP # 200736 exp. 6/18/24 EH RR #: rp241233 Rental Terms: August - Labor Day: $50,000 May: $10,000 July: $45,000 Memorial Day - Labor Day: $110,000 Winter Season: $30,000 Per Month Other / Short Term - Year Round: $145,000 June: $20,000

Spend the summer in Sag Harbor-arguably the Hamptons' most vibrant and sought-after destination. Set on half an acre just moments from the village, this five-bedroom home is being offered as a rental for the first time, presenting a rare opportunity to experience Sag Harbor living at its best. With effortless access to the village's renowned restaurants, shops, and marinas, the home offers the ideal balance of privacy and convenience, complemented by stunning views over the bay. Designed for summer living, the open-concept main level flows seamlessly from kitchen to dining to outdoor entertaining, with multiple sets of glass doors opening to the grounds. A separate living room with fireplace provides a quiet counterpoint to the home's airy, social spaces. Upstairs, the primary suite offers a private retreat with its own deck overlooking the property and capturing beautiful water views, while additional bedrooms are thoughtfully arranged across two wings for comfort and flexibility. Outside, a heated gunite pool anchors the grounds-perfect for long afternoons, casual gatherings, and easy evenings under the stars. Ideally positioned for both relaxation and access, this is a turnkey Sag Harbor rental designed to capture the very best of the Hamptons summer. Rental Terms: Other / Short Term - 5/28/2027 - 6/30/2027: $50,000 June: $45,000 Two Weeks: $48,000 November: $12,000

Very stylish, renovated beach-style residence in Bay Point, with water views from almost every window and outdoor decking, offers four bedrooms, three baths, and a new heated salt-water pool. The open floor plan main level includes a new gourmet-style dine-in kitchen, open dining, and living room with fireplace that opens onto a deck. The master suite includes a luxurious new bath and its own deck. An additional guest bed/den and laundry are located on this main level also. The finished at-grade level with its own living room and kitchenette includes two guest bedrooms, and a spa-bath. An outdoor shower and fire pit join the pool in the private backyard. The attached one-car garage adjoins a covered car port. Mooring rights now available. [[Rental Registration # RP250380]] EH RR #: RP250380 Rental Terms: Other / Short Term - Year Round: $180,000

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

Totally renovated with the finest historic details, offering spacious, light-filled double parlors, a grand chef's entertaining kitchen fully opens to an expansive porch with built in heating for chilly nights, a private dining patio, gunite pool, spa, poolhouse bar, powder room & outdoor grotto shower. Three floors offer 5+ bedrooms, 7 baths, luxe library, butler's pantry, 7 fireplaces, viewing balcony decks on the 2nd floor. Perfect entertaining home in the heart of Sag Harbor village, close to theater, restaurants and marina. [[Rental Registration # landlordrequested]] EH RR #: landlord requested Rental Terms: Other / Short Term - Year Round: $550,000 Winter Season: $270,000 Per Month Memorial Day - Labor Day: $325,000

Also Available Dec 2024 for $13,000 Newly upgraded for summer 2024, this offering has its own dock with potential kayak and paddleboard, and is 0.4 miles to Long Beach, a gorgeous 1+ mile stretch of West Facing beach. The chic home is west-facing for sunsets from almost every room--even the walk-out lower level. Brand new Ipe decking, modern wire rails, Gunite pool and deep-water dock make for an amazing waterfront experience. There is a tremendous outdoor entertaining space on two levels. The 4,500+/- sq. ft. home is spacious with open flow. A New two-story living room setup features an stunning Modern window package and brand new furniture, plus a big new TV! The kitchen and dining room also offer walls of windows that drench the home with light and views. This is the perfect house for entertaining with 5 bedrooms (plus a room with a sofa bed), and 5.5 baths. A finished lower level offers a wet bar, pool table, family room and pool bath, with a wall of windows and views out to Long Beach. New spacious Ipe decks with cable rails allow for easy outdoor living and entertaining just above the water. The house is in a quiet neighborhood, 2 minutes to Sag Harbor Village. When all the backyards lose their foliage at other Hamptons properties, this winter rental has its most gorgeous views--open water views from all 3 levels. [[Rental Registration # RP200192]] EH RR #: RP200192 Rental Terms: October: $15,000 April: $10,000 February: $8,000 May: $10,000 September: $30,000 January: $8,000 March: $8,000 November: $10,000 Other / Short Term - Dec: $10,000 August - Labor Day: $87,500 August: $85,000

A private oasis in the heart of Sag Harbor. Located on a beautifully landscaped shy acre in the heart of Sag Harbor's historic district, this Federal-style house dates back to 1780 and has been beautifully restored and updated with every modern amenity. Featured in Elle Décor and The New York Times, this peaceful and private retreat, only a short stroll from Sag Harbor's wonderful shops and restaurants, boasts century old boxwoods, an allée of cherry trees, a gunite pool, bluestone terraces, a Carriage House reimagined as a pool house, and even a Chicken Coop. The principal rooms include a library, living room, mudroom, double height great hall perfect for entertaining, a TV room and office, dining room overlooking the garden and a gourmet chef's kitchen with cathedral ceiling, 2 Bosch dishwashers, a Viking range, a SubZero refrigerator, wine cooler and fireplace. The private rooms include an exquisite primary suite with fireplace, cathedral ceiling and spa bathroom, two en-suite guest bedrooms, staff quarters with separate egress, as well as two additional private guest areas each featuring an en-suite bedroom with living room for a total of six bedrooms, six fireplaces and seven bathrooms. Beautifully designed for gracious living and entertaining, this property is truly the jewel of Sag Harbor. Rental Terms: Other / Short Term - Extended Season: $145,000

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

Moments from the heart of Sag Harbor Village, this exceptional designer residence offers a rare opportunity to experience a seamless blend of modern sophistication and timeless coastal living. Privately sited on a beautifully landscaped 0.47± acre, the property delivers a serene and elevated summer retreat in one of the Hamptons' most desirable locations. Spanning approximately 4,500± square feet, the home is thoughtfully designed with expansive, light-filled interiors and an effortless flow throughout. The main level features a gracious open-concept layout, anchored by a beautifully appointed chef's kitchen with premium appliances and custom finishes. Adjacent living and dining spaces are designed for both relaxed living and refined entertaining, complemented by a separate lounge with fireplace that provides an intimate setting for quieter moments. The second level is highlighted by a well-proportioned primary suite offering a private sitting area and spa-inspired bath, creating a true retreat within the home. Additional guest bedrooms are generously sized and finished with the same attention to detail, offering comfort and flexibility for a variety of living arrangements. The outdoor setting is equally compelling, with meticulously maintained grounds that create a sense of privacy and calm. A heated pool is surrounded by expansive lounging and entertaining areas, ideal for enjoying the full Hamptons lifestyle-from sun-filled afternoons to evening gatherings under the stars. A fully finished lower level enhances the offering, providing additional space for recreation, media, or wellness use-thoughtfully designed to support both relaxation and entertainment. Ideally located just minutes from Sag Harbor Village, the property offers convenient access to renowned dining, boutique shopping, marinas, and local beaches, while maintaining a peaceful residential setting. An exceptional rental offering defined by design, comfort, and location-crafted for a sophisticated Hamptons summer experience. Rental Terms: May: $35,000 June: $40,000 Other / Short Term - Year Round: $265,000 August: $87,500 September: $30,000 July: $85,000

In the Village of Sag Harbor, with a large veranda and a summer porch, a heated gunite saltwater pool with Jacuzzi, surrounded by a private garden, comfy lounge chairs, outdoor dining with Umbrellas and double Barbecue grill, and an entertaining barn to hang out and play ping pong in. Inside the furnishings are magazine wonderful. There is an open dining room that flows into a living room with an overstuffed white couch and chairs, which opens into a den/TV room/ library with a fireplace. Light-filled and spacious, the brand-new country kitchen is a great hangout, featuring a Sub-Zero Fridge, a Viking Stove, a farm sink, a pantry, and a new washer and dryer. The new oversized Primary Bedroom addition is gorgeous, featuring a new bath with a separate tub, shower, and double sinks. There is an extra full bath downstairs with a tub. Upstairs are 3 spacious bedrooms and another full bath. Central AC, this house has all the perks and tons of charm. The gardens have exploding flowers, a lush green yard, old-world trees, and a fenced saltwater heated pool. On a quiet street, but close to everything, parks, Main St., dining, and bay beaches. Featured in design publications, this is the perfect essential retreat. Comes with bikes too. Please feel free to contact me for a video tour. Rental Permit R-25-0058 expires 06/14/2027 Rental Terms: August - Labor Day: $58,000 August: $55,000

Discover refined Hamptons living in this beautifully designer-finished Sag Harbor Village retreat, just moments from shops, dining, and the waterfront. This 5-bedroom, 4.5-bath home features an open, light-filled layout where a sophisticated living and dining area flows effortlessly into a well-appointed kitchen with a large center island and counter seating, perfect for casual entertaining. Two ensuite bedrooms are conveniently located on the first floor, ideal for guests, while the second level hosts three additional bedrooms, including a spacious primary suite with a private deck overlooking the serene backyard. The finished lower level adds versatile space with a media and entertainment area, as well as a dedicated home office. Outdoors, enjoy a private oasis with a heated gunite pool, a stylish cabana with lounge seating and television, and a separate dining area for eight-perfect for effortless summer entertaining. With its prime village location, elevated designer style, this Sag Harbor home is an ideal Hamptons getaway-offering both tranquility and access to all the excitement of Sag Harbor Village. Rental Terms: Other / Short Term - 8/24/2026 - 9/7/2026: $50,000 June: $50,000

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

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

Rental Registration # Pending Also available: Aug 1st - 31st '24 $55k, Sept 1st - Sept 30th '24 $20k Located deep at the end of a private driveway on a shy 2 acres holds this beautiful renovated contemporary with extraordinarily unique design features. The open flow interior with dramatic height ceilings and continuous expanses of glass provide fantastic abundant natural light throughout. The gourmet kitchen and dining area glide effortlessly to the spacious sun room oasis. The living room has a gas fireplace and wet bar for entertaining. The separate guest wing, perfectly situated for privacy, holds a second primary bedroom with bath and two additional bedrooms each en-suite with baths. The expansive primary suite occupies the entire second floor with over-sized primary bath and walk in closet. To complete this perfect outdoor lifestyle is expansive mahogany decking, new heated gunite pool, and north south tennis court. In addition, there is a 3 car detached garage. This unique offering is located moments to East Hampton Village and Ocean beaches. Also available 09/06/2022 - 09/30/2022 for $20K. EH RR #: 26-389 Rental Terms: August - Labor Day: $65,000 Memorial Day - Labor Day: $160,000 July: $65,000 June: $35,000 June/July: $95,000 Other / Short Term - Year Round: $220,000 July - Labor Day: $125,000