luxury house with pool for rent Shelter Island, United States

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 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.

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

Private and tasteful, this extremely comfortable home in the Northwest Woods section of East Hampton is an ideal vacation retreat. Attractively furnished with an open living plan and beautiful pool area, this home has all the elements to create a wonderful getaway experience . All well appointed, this home includes an airy living room with fireplace, dining area, fabulous kitchen, den and lovely bedrooms. Generous decking and lounging areas near the heated pool and outdoor shower add to the vacation feel of the property. Beautiful and comfortable, this is an outstanding option for your summer vacation. May also be available for an extended season. [[Rental Registration # RR-25-1158]] EH RR #: RR-25-1158 Rental Terms: July: $30,000 August - Labor Day: $35,000 July - Labor Day: $60,000

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

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

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

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: 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.

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

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

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

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 July - Labor Day: $285,000 Winter Season: $270,000 Per Month Memorial Day - Labor Day: $325,000

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

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

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

This beautiful, airy five bedroom home is situated on a quiet road in the Northwest Woods just a few miles from the ocean and a mile from the bay. A guest suite on the ground floor sleeps four and has a perfectly appointed bath. The large living room with a screened-in porch is a perfect spot for entertaining. Upstairs there are three more bedrooms and two baths. The home is filled with natural light and features skylights and a fireplace for cooler nights. There is a washer/dryer, dishwasher, cable TV and wifi. The pool is heated and there is AC throughout the home. [[Rental Registration # Pending]] EH RR #: 24-1190 Rental Terms: July: $30,000 August - Labor Day: $35,000 June/July: $55,000 June: $25,000 July - Labor Day: $60,000 Memorial Day - Labor Day: $75,000

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

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.

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

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

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.

Set on a substantial .35-acre lot, the fully- fenced backyard features a gunite pool, pool shed, and patio that is perfect for outdoor dining and entertaining. Inside offers tremendous versatility. The first floor has an open floorplan with renovated kitchen and bathrooms. There is a first floor bedroom plus 2 bedrooms upstairs. The location offers a fantastic lifestyle, 0.7 Miles to Main Street, with a couple dozen high-end restaurants and bars, boutique shops, and renowned Bay Street Theater and Sag Harbor Cinema. The homes upgraded amenities include Central A/C and Central Vac. Rental Terms: Other / Short Term - Year Round: $78,000 Winter Season: $25,000 Per Month Memorial Day - Labor Day: $50,000