luxury houses with pool for rent Greenport, United States

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.

Refreshed log cabin on a large and private piece of property abutting a reserve. This rental is close to Greenport village, and also all the amazing vineyards and farm stands that the north fork is known for. This great house has three bedrooms, and two baths, foosball, air hockey, an outdoor hot tub, and brand new pool in 2025. Updated kitchen and baths, ready for enjoyment. [[Rental Registration # 0952]] EH RR #: 0952 Rental Terms: Winter Season: $35,000 Per Month July: $27,000 September: $22,000 August - Labor Day: $27,000 June: $22,000 Other / Short Term - Year Round: $70,000 May: $20,000 October: $20,000

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

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.

Beautifully renovated and furnished and now ready for its first tenants. This lovely two story home is your perfect retreat. A wonderful location close to Wades Beach, The South Ferry, and the 2,350 acre Mashomack Park and Preserve. The house sits on a 1.13 landscaped acre property complete with a heated gunite pool, pool house, outdoor shower, and spacious entertainment patio. The tranquil elegance of this home is visible everywhere, from the welcoming entry foyer to the living room and formal dining room. Enjoy the bright well appointed kitchen with access to the outdoor patio and a comfortable lounge area. Upstairs there are three guest bedrooms, a full bath and a spacious ensuite principle bedroom. This property is the newest project of Eldon Wong, a respected designer who has reinvented houses throughout the Hamptons area. His talent is showcased in this property. A great combination of comfort and high design. [[Rental Registration # 2025-L-0135]] EH RR #: 2025-L-0135 Rental Terms: June: $15,000 Memorial Day - Labor Day: $70,000 July: $25,000 August - Labor Day: $40,000

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!

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!

Enjoy a beautiful airy and bright mint condition Bay Front Orient Contemporary home, perfect for relaxing and entertaining. This 4-bedroom 4.5 bath home has gourmet kitchen, fireplace, open common space for easy entertaining. First floor has access to bay side screened porch from living room and den (or 4th bedroom with full bath). Second floor master bedroom and a guest bedroom open onto upper bay side deck, a third bedroom with full bath completes the layout. Private stairs to the beach and deeded beach rights to association Bay beach just a short walk from the house. Property is close to all village amenities: Country Store, Post Office, Marinas, Bay and Sound beaches. Available Apr $10,000; May $12,000; Sept $20,000; Oct $15,000; Nov $10,000; Dec $10,000. Permit# 1020.

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

Experience luxury living in this newly constructed North Haven modern estate, set on 3.25 acres with breathtaking harbor views. Interior design by the renowned Melanie Roy, this estate offers a state-of-the-art chef's kitchen with a dining area overlooking the water, two stunning living rooms, and a second primary bedroom on the main level. The grand entrance is spectacular, featuring a floating staircase and an elevator. Outside, enjoy a 20x50 waterside saltwater heated gunite pool and jet spa, a spacious lounge area with magnificent views, and a path leading to the water for paddle boarding and kayaking. The property also includes a detached studio/office/yoga room with a full bath and an electric screened-in porch with panoramic waterfront views. The second level boasts four spacious ensuite bedrooms, including a grand primary suite, all with terraces and beautiful vistas. The lower level is perfect for entertainment with a large flatscreen TV, sound system, a game room with a pool table, an additional full bedroom with bath, a gym, and a 5-person sauna. With a 3-car garage and ample parking in the front courtyard, North Haven Manor also offers resident pathways to the beach and open water. Boat mooring is available, also great for kayaking and paddle boarding. Located just minutes from the village of Sag Harbor, this premier rental listing is available for THE US OPEN in JUNE, offered exclusively through Sotheby's International Realty. [[Rental Registration # R-2025-0006]] EH RR #: R-2025-0006 Rental Terms: June: $150,000 July: $375,000

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: 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

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.

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

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

Nestled in the quiet community of Bay Point, this 3-bedroom, 3-bath summer residence offers a refined coastal experience near Long Beach-the best bay beach in the Hamptons! The front door is centered by a classic rose trellis, and the lushly landscaped grounds feature a 16x38 heated gunite saltwater pool, a 900 sq ft Bluestone patio and convenient outdoor shower. While the grounds are intimate, they are meticulously planted to ensure a secluded and luxurious atmosphere. Upstairs, the primary bedroom and ensuite guest bedroom give everybody privacy, while the main level offers room to spread out with plenty of access to the pool area and backyard. Order grocery delivery, and you'll never have to leave! [[Rental Registration # Pending]] Rental Terms: July - Labor Day: $120,000

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: July: $45,000 Other / Short Term - Dec: $15,000 October: $20,000 August - Labor Day: $60,000 August: $55,000 November: $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: July: $60,000 August - Labor Day: $75,000 July - Labor Day: $135,000

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

Built in 1830 and painstakingly restored/renovated in 2013, this 3,000 sf, 4 bedroom, 3 bath home in the heart of Sag Harbor Village offers a beautiful living room, formal dining room and wonderful, fully-equipped chef's kitchen. French doors from the kitchen lead to the elegant and expansive gardens and landscape designed by a renown architect, heated salt water pool and pool house to lounge in with a pull out sofa, TV & full bath. This historic home is perfection, as is the location...2 minutes to Main Street! Rental Terms: July - Labor Day: $175,000 July: $85,000 August - Labor Day: $95,000

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.