luxury furnished house for rent Shelter Island, United States

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

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 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

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

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: June: $85,000 Other / Short Term - Extended Season: $145,000 July - Labor Day: $365,000 August - Labor Day: $200,000 July: $175,000 Memorial Day - Labor Day: $450,000 June/July: $250,000

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

5BR/ 6.5 BA w/ Tennis on 5 + acres with Pool, Hot Tub, Sauna & Basket Ball Court! Open plan living / dining room / Kitchen and so much more! Escape Out East to Sag Harbor! Live the good life on this remarkable, 5.4 acre gated compound. There's no doubt you'll fall in love with the Hamptons, as you enjoy a peaceful stay at this private retreat! This stunning contemporary home sleeps 12, with five en-suite bedrooms, including three primary suites, one on the first level with a sauna and a private deck. The sun-filled open concept living room features a cathedral ceiling, skylights, a gas-burning fireplace, and an open dining room with French doors leading to a covered porch. The spectacular state of the art kitchen features Subzero and Wolf appliances as well as a miele and nespresso machines. Additional highlights include a fully finished lower level with ping pong and pool tables, tennis ball machine office set up and an additional queen pull out bed. You and your guests will love the convenience of the 7 smart TVs, 5 separate Sonos zones inside and a 6th outside, the Mesh wifi system (gigabyte internet) by Optimum, and the Samsung dryer and washer. In the sun-filled study guests will find a fully functioning office setup complete with a laser printer and IMac computer. Additional features include top of the line mattresses on each of the beds, a peloton bike and brand new furniture throughout. The north wing master suite features a wood burning fireplace, a private study, a jacuzzi tub and a double shower. In the south wing primary suite, you will find 20 foot ceilings, a surround sound system, an additional gas burning fireplace, soaking tub and a double rain head shower. Step outside for some fresh air and enjoy beautiful views of the large grounds featuring a heated gunite pool plus a 10 seat hot tub, a new secluded and lighted tennis court, with separate covered entertaining space as well as a fire pit area. Guests can enjoy the use of adult and children's bicycles, beach chairs, a paddleboard and even a kayak. The home is surrounded by miles of nature preserve trail systems and private ponds to discover. Prepare to fall in love with the Hamptons lifestyle, as you experience it at its very best! This property is a 5 minute drive to Sag Harbor's Main Street and 7 minutes to East Hampton. [[Rental Registration # RR-25-1159]] EH RR #: RR-25-1159 Rental Terms: Other / Short Term - Year Round: $500,000 Memorial Day - Labor Day: $295,000 July - Labor Day: $225,000 July: $125,000 June: $85,000 August - Labor Day: $135,000

Designer decorated mint-condition home with private heated pool surrounded by flowering gardens on a charming lane in Sagaponack. Light bright kitchen overlooks seating and dining area, with a stylish living room with fireplace beyond. Roomy primary, two additional guest bedrooms, and two beautifully appointed baths complete this perfect summer getaway. [[Rental Reg # 22-394]] EH RR #: RP241987 Rental Terms: Other / Short Term - Year Round: $130,000 Memorial Day - Labor Day: $90,000 July - Labor Day: $90,000 August - Labor Day: $50,000 July: $45,000

Set on 1.11 acres of exquisitely landscaped grounds, this sophisticated post-modern retreat offers a seamless blend of contemporary design and Hamptons elegance. Built in 1995, the single-story residence spans approximately 2,800 square feet and is ideally positioned moments from Bridgehampton and just over a mile to pristine ocean beaches. The outdoor setting is a true sanctuary, featuring a heated pool, beautifully appointed pool house, expansive rolling lawn, and a shaded dining pavilion complete with a barbecue, perfect for effortless summer entertaining. Inside, the home is bathed in natural light, with airy interiors defined by crisp white tones, clean architectural lines, and modern finishes. The main living room centers around a striking brick fireplace, while the open-concept dining area flows seamlessly into a fully updated kitchen designed for both everyday living and hosting. The residence offers4 total bedrooms and 4 full baths, including a luxurious primary suite and a junior primary suite with its own fireplace. Each bathroom is fully renovated in marble, delivering spa-like comfort throughout. Additional amenities include central air conditioning and high-end furnishings, with the home elegantly appointed in all-new pieces from Restoration Hardware. A refined Sagaponack escape offering style, comfort, and proximity to the very best of the Hamptons. [[Rental Registration # RP230701]] EH RR #: RP230701 Rental Terms: October: $25,000 Other / Short Term - Year Round: $220,000

Located in a Southampton-North waterfront community, this recently redecorated shingle-style traditional home has been refreshed and decorated with light and bright furnishings, offering comfort and ease in every room. Set on almost a half-acre with in-ground heated pool, the covered front deck opens to an open floor plan starting with the living room with large flat screen TV, and doors out to the large deck. The fully-modern kitchen with stainless steel appliances and stone counters opens to the dining area, and includes a pantry. A separate laundry room, office area, and full bath complete the ground floor. Upstairs, the master bedroom features a flat screen TV, fireplace, and oversized bath. Three more comfortably-appointed bedrooms and full bath finish the second floor. A green yard and attached one-car garage complete the property, and a community gazebo and waterfront area are part of this community. [[Rental Registration # RP261254]] EH RR #: RP261254 Rental Terms: August - Labor Day: $40,000 July - Labor Day: $75,000 July: $35,000

Beautifully sited on 3 acres in a most desirable area on Bull Path, East Hampton, this stunning 4 bedroom 4 bath traditional offers the absolute in comfort, enjoyment and privacy. From the limestone entry to the honed black granite and cherry kitchen, superb finishes and attention to detail are evident throughout. The well proportioned living room with fireplace has a bank of French doors that open to a very generous screened porch with ample space for both dining and lounging. For something more formal, there's a separate dining room surrounded by windows, just right for sunsets. The den/media room offers a pullout sofa, cushy chairs and all the audio/video equipment. The house is wired for sound, too. The large primary suite features a gas fireplace, private terrace and exquisite marble bath with soaking tub. In the opposite wing, you'll find two comfortably sized guest rooms each with en suite baths. Outside, there's pure pleasure, extensive mahogany decks overlook the heated gunite pool, spa and the wonderfully landscaped grounds featuring stacked stone walls, perennial beds, ornamental grasses, shrubs and lawn. It's your own private paradise, one of our very best rentals and just minutes from East Hampton Village. [[Rental Registration # 26-1169]] EH RR #: 26-1169 Rental Terms: Memorial Day - Labor Day: $150,000 November: $20,000 Other / Short Term - Dec: $15,000 October: $20,000 August: $75,000 July: $65,000 June: $25,000 September: $25,000

A rare Sagaponack compound, offering 7 bedrooms in total, designed by Val Florio on +/-1.6 acres of curated landscaped grounds. Surrounded by open sky and farmland vistas, the main residence offers sun-filled living spaces, elegant detailing with casual beachy interiors and generous proportions throughout. Gathering rooms open to expansive mahogany decking and manicured lawns, creating a natural flow for summer living. The fully equipped guest cottage provides an additional three bedrooms, ideal for hosting extending family, staff, or friends while maintaining privacy and comfort. The homes are connected through a tunnel in the finished lower level. The heated gunite pool is complimented by a stylish pool pavilion and sunken pickle-ball court. Located across from Wolffer Estate Stables, Sagaponack's premier horse farm, around the corner from Wolffer Vineyard, and close to world class Sagg Main Beach. This compound delivers the ultimate Hamptons experience minutes from the best of Bridgehampton and Sag Harbor. Rental Terms: July - Labor Day: $300,000 August - Labor Day: $175,000 July: $150,000 Other / Short Term - 10/1/2026 - 4/30/2027: $55,000 June: $75,000

This newer construction is a rare find. The inside features high-end, custom furnishings rarely available in a rental at this price. Gorgeous architecture, interior design and mature landscaping will impress. The 7 Bedroom home (all with ensuite baths) spans 5800 feet above ground, plus 2550 feet of finished lower level. The First floor features a dramatic 2-story foyer, 2 spacious living rooms, a chef's kitchen, bar area. There is a Junior Primary, and a mudroom with pool bath. The Second Floor features a Primary suite with terrace, fireplace, and luxurious white marble bath. There are 4 additional ensuite bedrooms and a second laundry. The lower level offers expansive entertainment space, including a theater, living room, and playroom with ping pong. There is a 7th ensuite bedroom with 2 queen beds. Outside, a South-facing large terrace with overlooks a beautifully landscaped, 1-acre property, with farm views. The yard is private and includes a 40' pool, new sunken hot tub and generous patio space for entertaining. The house sits in a very quiet cul de sac of newer homes, 2 miles to Southampton Village, with Southampton beaches just beyond. The property is a short bike ride or walk to the Southampton Rec Center (SYS) which offers a fantastic children's camp, tennis, gym, basketball, track, yoga, and pilates. Its also 1.5 miles to Towd Point Beach, one of the Hamptons prettiest bay beaches. [[Rental Registration # RP230864]] EH RR #: RP230864 Rental Terms: April: $15,000 February: $15,000 Other / Short Term - 1/1/2027 - 4/30/2027: $60,000 November: $25,000 September: $45,000 October: $30,000 January: $15,000 March: $15,000 Winter Season: $90,000 Per Month

This sun-filled 5 bedroom newer construction home is the perfect rental. Just purchased, the home features new designer-picked furniture...a rare find at this price. The home offers a chef's kitchen with Calcutta counters and Viking appliances, and large formal living and dining rooms with cathedral ceilings. A gracious family room with French doors accesses a large private back yard, with an attached blue stone terrace for entertaining and 40' heated gunite pool. A king-sized master bedroom features high ceilings and includes a dressing area (or home office) and master bath with Jacuzzi. There are 4 additional bedrooms on the top two floors. The location is the best of both worlds, only 2 miles north of Southampton village, but on a quiet cul-de-sac of newer homes, backing to farm. Just a half mile away, the Southampton Recreation Center offers tennis, yoga, pilates, basketball, track and a full gym. [[Rental Registration # RP220522]] Rental Terms: July: $50,000 August - Labor Day: $65,000 July - Labor Day: $115,000 Other / Short Term - Jun 1 - Jun 30: $30,000 Memorial Day - Labor Day: $160,000

Indulge in the ultimate Hamptons experience at Historic Box Farm, a magnificent 6-bedroom, 6-bath estate meticulously renovated in 2024. Set on rolling manicured lawns framed by mature trees, this property offers an unparalleled blend of timeless elegance and modern comfort. Grand Heated Pool (20' x 40') - the centerpiece for sun-soaked afternoons and moonlit swims Prime Water Mill Location - minutes from pristine ocean beaches and the world-class dining and boutiques of Southampton, Bridgehampton, and Sag Harbor Three king suites, two queen bedrooms, and a full-size guest room for effortless hosting. Pet-Friendly - Discerning owners will consider pets upon request Outdoor Entertaining - Expansive deck with grilling station, perfect for sophisticated soirées and alfresco dining Multiple Indoor & Outdoor Lounges - curated spaces for intimate conversations or lively gatherings Modern Amenities - TVs in every room, premium cable, and high-speed connectivity [[Rental Registration # Pending]] EH RR #: RP170644 Rental Terms: August: $45,000 August - Labor Day: $50,000 July: $45,000 June: $38,000

This modern and chic four bedroom, four bath home has a gourmet kitchen with Miele appliances. The first floor primary suite opens onto the pool terrace. There is also a den on the main floor with ""en suite"" bathroom. Three bedrooms and two baths upstairs. Heated gunite pool surrounded by beautiful manicured gardens. Located by beautiful Conscience Point and bay beaches. All you need for a perfect summer. [[Rental Registration # RP240339]] EH RR #: RP240339 Rental Terms: August - Labor Day: $41,000

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

PLEASE NOTE: This property is available for US Open dates June 15th- June 22nd. Beautifully renovated Gambrel on 1.17 acres +/- bordering two reserves. This custom classic includes 3 Master suites, one downstairs and 2 upstairs master suites up. Main floor has a living room with vaulted ceiling, dining room, library/office, open kitchen to lounge / dining area and many possibilities for outdoor dining accessed from kitchen and living room. Upstairs there is a large secondary gathering room, outdoor lounging and dining on deck and 5 guest rooms.The lower level has a separate staff room,full bathroom and super-sized playroom with wet bar, bathroom, rock climbing wall, gym and more bunk beds.. A new heated salt water gunite pool is surrounded by beautifully landscaped grounds, built in BBQ, many outdoor decks and a putting green. Private flag lot with farm field views and 3 fireplaces. Stunning!!! [[Rental Registration # RP260815]] EH RR #: RP260815 Rental Terms: August: $225,000 July: $225,000 Other / Short Term - 7/1/2027 - 8/31/2026: $450,000

Summer or Year Round Living Perfectly positioned south of the highway in one of Water Mill's most desirable locations, this beautifully maintained contemporary offers effortless single-level living on a private, beautifully landscaped acre. A gated entrance and mature plantings create a welcoming sense of arrival, while bright, open interiors with soaring ceilings and walls of glass fill the home with natural light. The thoughtfully renovated kitchen flows seamlessly into the spacious living and dining areas, creating an inviting setting for both everyday living and entertaining. The home offers four bedrooms and four full baths, including a gracious primary suite tucked into its own private wing with double walk-in closets, an oversized spa-like bath, and direct access to the outdoor living spaces. Two guest bedrooms also open directly to the rear deck, creating an ideal layout for hosting family and guests, while a separate study provides the perfect home office or quiet retreat. Designed to embrace the Hamptons lifestyle, expansive decking surrounds the sparkling heated pool, where eastern exposure welcomes beautiful morning light throughout the day. Multiple outdoor entertaining areas, cheerful landscaping, and an exceptional stretch of lawn provide plenty of room for everything from summer gatherings to a game of frisbee or Sunday football. A partially finished lower level offers additional overflow living space, a full bath, laundry area, and generous storage, providing flexibility to suit a variety of needs. Offering privacy, style, and an exceptional south of the highway location, this turnkey Water Mill retreat seamlessly blends easy single-level living with outstanding indoor and outdoor entertaining. [[Rental Registration # RP260361]] EH RR #: RP260361 Rental Terms: Other / Short Term - Year Round: $200,000 Memorial Day - Labor Day: $160,000

Modern beach cottage on three acres with beautiful ocean views and pathway to the beach. 3 bedrooms, 2.5 baths and expansive decks, from which to enjoy the ocean breezes. Available May 27th - Jul 19th 2021- $55,000 August-LD: Jul 30th - Sep 6th 2021- $55,000 Rental Terms: August - Labor Day: $55,000 Other / Short Term - June/July: $55,000

Southampton home centrally located yet convenient to ocean beaches along with a private setting backing a peaceful reserve. The inviting open & bright floor plan consists of a cooks kitchen, sunroom/playroom, stylish living room & dining room with multiple sliding glass doors leading to the pool and generous poolside deck with new patio furniture perfect for outdoor entertaining. Particulars include: CAC, 4 bedrooms & 4 baths.. Flexible on dates, also available short term off season. [[Rental Registration # RP250807]] EH RR #: RP250807 Rental Terms: August - Labor Day: $60,000 March: $15,000 November: $10,000 September: $15,000 June: $35,000 April: $15,000 October: $15,000 Memorial Day - Labor Day: $125,000

A perfect village summer retreat awaits at this new 3 bedroom, 2.5 bath home right in the heart of East Hampton's village. High end kitchen, sophisticated and well appointed baths, plus three well proportioned bedrooms. There is also a large upstairs den that can double as a bedroom. Gorgeous yard and winning location make this one a real delight. Rental Terms: July: $32,000 Other / Short Term - June: $15,000 August - Labor Day: $35,000 Memorial Day - Labor Day: $80,000

Located on an iconic East Hampton Village lane is this incredible home with 5 en-suite bedrooms, plus 2 half baths. Luxe beach vibe decor surrounds you in comfort and style. Open concept living with first floor living room, dining area, centralized cook's kitchen and an oversized den that leads outdoors to secluded grounds with a heated, gunite pool, large patio and an outdoor shower. Upstairs find a spacious primary bedroom with sitting area and a fireplace plus 3 additional en-suite bedrooms. Want more? Head down to the finished lower level for media, recreation, Peloton, free weights, powder room and another en-suite bedroom. This home has all you could want or need for a perfect summer experience! Rental Terms: Memorial Day - Labor Day: $250,000 June: $55,000 August - Labor Day: $110,000 July: $100,000 July - Labor Day: $200,000 Other / Short Term - Year Round: $300,000