luxury houses with terrace for rent Shelter Island Heights, United States

Stunning new modern home with an abundance of natural light throughout. 4 bedroom, 3 bath home with plenty of room for your loved ones. Home has a large open living space with oak floors and high ceilings with huge Anderson doors that opens onto extensive covered deck for seamless indoor outdoor entertaining. Two guest bedrooms and a bathroom complete the first floor. The master suite is on the second floor with a balcony to enjoy morning coffee, a walk through closet, and bathroom with free-standing soaking tub and large shower. The lower level has with sealed concrete floors with underfloor heating, a spacious living/ den area, office space, bedroom, bathroom and laundry room and separate entrance. Great yard with mature Japanese maple tree, birches and hedging. Please call with any questions or to set up an appointment to view. [[Rental Registration # 2025-L-0061]] EH RR #: 2025 -L-0061 Rental Terms: August - Labor Day: $30,000 Memorial Day - Labor Day: $62,500 August: $22,500 July - Labor Day: $47,500 July: $22,500

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

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

Escape to Sag Harbor for the month of August and take in sweeping water views and unforgettable sunsets from this 3-bedroom, 2-bath Cape perched above Noyack Bay. Located in peaceful Bay Point, this home offers a private path to Long Beach and an effortless balance of quiet beachfront living with easy access to Sag Harbor Village's dining, shopping, and entertainment. [[Rental Registration # Pending]] Rental Terms: August - Labor Day: $30,000 August: $28,000

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

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

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 July: $185,000 July - Labor Day: $400,000

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

Step into the season with a top-to-bottom Spring refresh-brand new mattresses, crisp bedding and towels, a sparkling new kitchen stove, a sizzling barbecue, and a fresh coat of paint. Watch the sunsets dance across the water and feel the cool breezes that make every evening unforgettable. With a sandy entrance to Sag Harbor Cove for a refreshing dip and an outdoor shower to rinse off, it's the perfect blend of charm and modern comfort. This gem is priced right and ready for your best summer yet-just unpack and start making memories! [[Rental Registration # RA240090]] EH RR #: RA240090 Rental Terms: September: $10,000

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

This Sag Harbor home offers a unique opportunity to be able to vacation in a beautifully renovated and tastefully decorated home in the middle of all the action - boating, dining, theater, shopping, swimming. This three-level home takes full advantage of the water views with a living area and wet bar on the third floor. The chef's kitchen flows seamlessly into both indoor & outdoor dining options - great for entertaining. All of the bedrooms have access to a private bathroom - two bedrooms are en-suite. The fourth bedroom is being used as a third-floor lounge area and has a pull out couch for guests. The lower level is fully finished and offers a cozy space for rainy days and functions well as a home office with natural light and walk-out access to the backyard garden. There is a full bathroom and laundry on the lower level as well. Rental Terms: September: $40,000

Convenient to town and bay beaches, this recently renovated home is picture perfect. Features 3 bedrooms, 2 baths, living area, current kitchen, and a crisp decor. Outside entertaining under a pergola. A great Hampton's vacation home. Available year round for $110,000. [[Rental Registration # Rp250475]] EH RR #: Rp250475 Rental Terms: Other / Short Term - Year Round: $115,000 July: $30,000 August - Labor Day: $35,000 June/July: $45,000 Memorial Day - Labor Day: $75,000 July - Labor Day: $65,000 June: $15,000

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

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

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

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

Charming Sag Harbor Village Cottage with inviting garden, dining pergola, entertaining deck & outdoor shower. A dream setting, just a short stroll to village shops, restaurants and harbor Rental Terms: Other / Short Term - 08/23/2021 - 09/30/2021: $11,500

This lovely three bedroom cottage offers light filled interiors on a quiet street located in the heart of the Historic District of Sag Harbor Village. A private backyard with patio, outdoor dining and outdoor shower, along with a private driveway for two cars make this a special home in a great location. The main floor offers - living room with fireplace, dining room, family room with french doors out to the back patio, a galley kitchen with all of the modern appliances, laundry, half bath, and a main floor ensuite primary bedroom and bathroom. Upstairs you will find two guest bedrooms each with their own bath. Enjoy your summer in the heart of the best village in the Hamptons and all it has to offer. Rental Terms: November: $7,000 October: $8,500 September: $12,000

A stylish, gorgeous construction designed by award-winning architect James Merril. Set on an acre, this 5- 5-bedroom home has every desirable amenity. The primary bedroom has a terrace and a beautiful bathroom with a shower and a separate bathtub. The 4 guest rooms are all spacious and light-filled. Downstairs, there is an open living room and a den/ 5th bedroom with a full bath. An exquisite gourmet kitchen has all the bells and whistles, from a 6-burner Viking with a grill to a double Sub-Zero Fridge, wine fridge, double sinks, and dishwashers; it also has its own breakfast area. There is a formal dining area with a fireplace that is magnificent. The sunny Living Room shares the same dual-sided open fireplace. A lower-level gym. Many French doors open to the deck that has a gorgeous outdoor dining area- and a shaded lounge area with a 32' by 15' ft. heated pool. A path to the dock on the bay, which is a divine protected sanctuary, that accesses the big open bay. There is a lower basement level with a 2-car garage. The front of the house has a great veranda, all set on a quiet and charming high-end street in the Village of Sag Harbor. Rental Terms: Other / Short Term - Year Round: $450,000 Memorial Day - Labor Day: $375,000 September: $25,000 July - Labor Day: $300,000 October: $25,000 November: $20,000 June: $60,000

SAG HARBOR VILLAGE WOW HOUSE! This lovely 1840's Village home was recently purchased and designed to create an open floor plan with high-end details. All brand new furnishings, fantastic art, beautiful light: it has a wonderful flow for easy living. There is an outdoor deck with a new grill and a dining table. The yard is serene with chairs around a fire pit. All new systems have been installed, including Central Air, an updated kitchen with glazed Moroccan white tiles, a Viking stove and hood, and 2-inch thick marble countertops. There are two new full baths, one upstairs with a tub and one downstairs with a shower. There are 3 bedrooms upstairs, with laundry. The spacious open living area flows into a dining area that's off the enclosed kitchen. There is a separate Den/TV room with a full bath on the main floor. A deck that overlooks a newly landscaped, hedged, and fenced-in lush garden with irrigation. Featuring a Barn/Storage. There is also a full lower level of clean space. New hedges have been installed at the front of the home for privacy with a new gated-entry portico. The rear yard is serene with plantings and is seemingly quiet. There is a two-car individual parking area to the side of the house, and the yard is gated and fenced with English-style gardens. This home is move-in ready and is surrounded by the choicest homes in the Village, while the designer's taste warrants savvy appreciation. This home is minutes to the village, dining, shopping, and transportation, with the Harbor Market just around the corner for morning coffee and croissants. Here you have a quiet residence in the heart of Sag Harbor Village, with quick access to Main Street, Shopping, Dining, and Beaches. Newly listed for the first time! [[Rental Registration # R-26-0002]] EH RR #: R-26-0002 Rental Terms: September: $31,500 August - Labor Day: $50,000 August: $25,000

Nestled on a quiet cul-de-sac among expansive three-acre estates, this beautifully landscaped Hamptons retreat offers the perfect blend of privacy, recreation, and convenience. Backing directly to Noyac Golf Club and surrounded by more than 135 acres of scenic hiking and jogging trails, the property is an ideal escape for summer living. Designed for effortless indoor-outdoor entertaining, the home features a dramatic double-height living room, a newly renovated kitchen, and a spacious dining room with seating for 12. A wall of sliding glass doors fills the home with natural light and opens to the expansive patio, heated gunite pool, and Har-Tru tennis court. The thoughtfully designed layout includes six bedrooms and six bathrooms, all above ground, with two en-suite guest bedrooms conveniently located on the first floor and a spacious primary suite upstairs, along with three additional guest bedrooms. Furnished with two king beds and five queen beds, the home comfortably accommodates up to 14 guests. Ideally situated just minutes from Towd Point Beach, Long Beach, marinas, and several popular waterfront restaurants, and only 12 minutes from the villages of Southampton, Bridgehampton, and Sag Harbor, this exceptional property offers easy access to the very best of the Hamptons while providing a peaceful country setting. Rental Registration #RP160829. [[Rental Registration # RP160829]] EH RR #: RP160829 Rental Terms: July: $70,000 August - Labor Day: $70,000 July - Labor Day: $140,000