luxury house with pool for rent Orient, United States

Stunning waterfront shingle style home overlooking Long Island Sound with private beach access. Waterview, heated pool. Wrap-around porch. Original beach stone fireplace, vintage beadboard walls, large, updated gourmet kitchen, open common area, 5 bedrooms, 3 bathrooms, large master ensuite with private screen water view balcony. Beautiful interior furnishings, with teak rocking chairs, chaise lounges and picnic table on porch and pool area for entertaining. Close to Orient Village amenities, marinas, Country store, Yacht Club, and bay beaches. Offered June 3-27 $28,000; Sept 2-16 $14,000. Permit# 1108.

Experience breathtaking views of Long Island Sound and Orient Point County Park from this spacious open-concept home. Beautifully updated 4-bed, 4-bath home offers private 20x40 heated saltwater pool and serene backyard. Host memorable gatherings in the spacious kitchen, perfect for indoor & outdoor dining. The expansive master suite boasts breathtaking views, king-size bed, office nook, dressing area, full bath, and private balcony. The lower level features a cozy sitting and entertainment room, an exercise room, a full bathroom, laundry facilities, a 2-car garage, and direct access to the pool and backyard. Enjoy easy access to the pristine sound beach, hiking trails, Orient State Park, and Duryeas restaurant. Located at the tip of Long Island, this exceptional home is perfect for anyone seeking coastal living with ample entertainment and relaxation space. Offered Apr $11,000; May $20,000; June $25,000; July $35,000 (RENTED); July 31-Aug14 $20,000; Aug15-Sept 8 (RENTED); Sept 10-30 $20,000; Oct $20,000; Nov $15,000. Permit# 0234.

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.

Bright and spacious Contemporary summer rental on the North Fork. Featuring floor to ceiling windows, great room, 6 bedrooms, 3.5 bathrooms, eat-in kitchen, recreation room. Private back yard with 40x20 salt water heated pool. Offered June $25,000; July 1-23 $27,000 (RENTED); Aug 1-15 $20,000; Sept 9-30 $18,000. Permit #1230.

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.

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

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!

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

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!

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 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

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

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

Privacy and charm pervade this lovely one-story ranch located at the end of a secluded cul-de-sac in the Springs. Tasteful amenities of this pristine home include three bedrooms, two baths, open concept living-dining areas with cathedral ceilings, and a wood-burning fireplace. The private yard features a large heated pool, grassy lawn, gas barbecue, and mature trees. Enjoy your private oasis while remaining close to East Hampton shops, restaurants and ocean beaches. [[Rental Registration # 22-1479]] EH RR #: 24-1377 Rental Terms: September: $15,000

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

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

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

This pristine newly renovated traditional sits high on a hilltop in Wainscott, which is one of the many stunning features of this incredible rental property. Two-story, shingle style traditional home with 5,000 +/- square feet of living space offers top quality finishes throughout and offers five bedrooms, five and one-half baths, a professional kitchen with a breakfast bar, a family room, a formal dining room, a living room and two fireplaces. Sun or clouds, the entire home is filled with light enhanced by high ceilings throughout most rooms. Outdoors enjoy the new heated pool with retractable cover, a hot tub and spa, 1,800 +/- square feet of new decking and beautiful new landscaping, along with a three-car garage. [[Rental Registration # 23-1305]] EH RR #: 23-1305 Rental Terms: August - Labor Day: $115,000 July - Labor Day: $200,000 Memorial Day - Labor Day: $245,000 September: $18,000 July: $110,000 October: $18,000

This modern Bayfront masterpiece designed by renowned architect Robert Barnes, perfectly situated on a Dune for panoramic water and meadow views, instantly captivates. The dramatic walls of glass invite in continuous water views throughout with stunning exterior environs. On 1.16+/- acres of complete privacy, it is enveloped by 10+/- acres of pastoral meadows with spectacular evening sunsets and sunrises. The terraced structure holds a dramatic floating second story creating a bridged covered patio with flowing natural light overlooking a 50' saltwater pool. The huge stone outdoor fireplace and pool house complete a perfect setting for memorable gatherings. Exquisitely landscaped grounds abound in the tranquility of nature. Designed by Thomas Balsley, delight in the splendor of a stone pond, exquisite gardens, specimen plantings and native grasses. The interior separation of space was well planned for privacy with various wings. The primary bedroom suite and water view balcony are located on a private level with four guest bedrooms on separate wings. A custom chef's dream kitchen with Subzero and Wolf appliances has a curvature design featuring oversized windows to maximize the extraordinary surrounding views. Additionally, there is a library and media room. The 500+/- square foot waterside deck extends from kitchen along entire length of the living room to primary suite. Immediate beach access provides a meandering sandy shore for therapeutic waters of iconic Gardiner's Bay. Experience inspiring waterfront living at its very finest. EH RR #: 25-831 Rental Terms: July - Labor Day: $270,000 August: $135,000 July: $135,000 June: $85,000

Discover a newly completed 2025 modern residence, quietly set far back from the road for exceptional privacy. Thoughtfully designed, the home features three generously scaled primary suites and a striking great room with balcony, oriented toward serene views of the 100-foot pool, spa, and brick-lined terrace. A covered porch and outdoor dining area invite relaxed gatherings framed by the natural landscape. Inside, a spacious chef's kitchen anchors the main level with Thermador appliances, complemented by a large living room, ensuite guest bedroom. Every space has been crafted for comfort, flow, and effortless living, ensuring an elevated experience throughout your stay. Sustainable features include a greenhouse, garage with electric vehicle charging, and geothermal and solar energy systems. Perfectly positioned for quick access to Bridgehampton's ocean beaches and Sag Harbor's boutiques and restaurants, this modern retreat offers the best of the Hamptons in one tranquil setting. Please call with questions or to make an appointment to view this great property! [[Rental Registration # Pending]] Rental Terms: August - Labor Day: $135,000 Two Weeks: $70,000 August: $110,000 Other / Short Term - 8/1/2026 - 9/30/2026: $165,000 September: $65,000