luxury furnished houses for rent Shelter Island, United States

Authentic 1770 Cottage in the heart of Orient Village. Lovingly restored & maintained Village home on beautifully landscaped lot, offering private grounds & distant views of sunsets over the bay. Furnished in period antiques, screened-in porch off kitchen, first floor bedroom. Walk to amenities, bay beach, Yacht Club, marina, farm stand & Jitney. Offered Sept 3-Oct 3 for $8,000. Permit #0091.

Located just 2 blocks from Sammy's Beach, in East Hampton, unwind at this stunning original Mid-Century home. This freshly renovated two story, three bedroom, two bath house was built with oak floors, cedar clad walls and ceiling, and antique details for a luxurious yet charming feel.It features a double height living area with floor to ceiling windows, wood burning stove, and integrated fully equipped kitchen and dining areas. Sliding glass doors lead to the expansive wraparound deck with Barbecue, dining and lounge areas, outdoor shower, and the large yard with seating and a fire-pit. The bedrooms are generously proportioned with 2 king and 1 queen beds, and upstairs there is a dedicated office and work out area with its own walkout balcony.Though quiet and elegant in nature, the home is modern where it counts. It features two large flatscreen TVs, 1 GB wi-fi and unlimited music and sound capabilities in every room. Enjoy long days on the beach, paddle board or kayak in Three Mile Harbor, or hikes through the nearby 116 acre Sammys Beach Nature preserve. Conveniently located 2 blocks from Sammys Beach, 7 minutes to East Hampton Village and only 10 minutes from Sag Harbor, the home is a true East End escape. [[Rental Registration # Pending]] Rental Terms: February: $2,975 July - Labor Day: $39,000 September: $4,500 June: $9,900 April: $2,975 March: $2,975 November: $3,200 Other / Short Term - Dec: $3,200 October: $3,200 August - Labor Day: $22,000 Memorial Day - Labor Day: $49,000 August: $18,000 January: $2,975 July: $18,000 May: $3,975

Offered July $35,000; Aug $35,000; Sept $25,000; Oct $20,000. Elegantly renovated and exceptionally spacious, this contemporary retreat is nestled within a parklike setting of sweeping lawns, lush gardens, and mature landscaping that affords remarkable privacy. Refined outdoor amenities include a heated gunite pool, outdoor shower, firepit, and walking path to abutting Island’s End Golf & Country Club. The main house and annex are filled with natural light, featuring soaring ceilings, oversized windows, and glass doors that open seamlessly to two expansive decks for effortless indoor-outdoor living. A generous poolside patio offers additional space for lounging and entertaining, while the decks provide inviting areas for alfresco dining, grilling, and relaxation. Bedrooms are thoughtfully positioned to ensure comfort and privacy for guests. Peaceful and secluded, yet just moments from Greenport Village, Seps Farm Stand, and sound and bay beaches, this home is impeccably suited for gracious North Fork entertaining.

Not available for year round rent at this time. Newly renovated three bedroom, two bath bungalow just outside of popular Greenport Village. This house provides a sense of privacy and relaxation close to the beach. Located less than one mile away, the captivating Rocky Point Beach is a picturesque retreat for everyone to enjoy. Additionally, there is the exquisite Truman's Beach nearby, which provides a stunning view of Connecticut. Lavender Bay and Sep's Farm are conveniently located only 0.4 miles away. The exterior of the property is designed for entertainment, featuring a spacious patio, barbecue area, fire pit, and even an outdoor shower to refresh after a dip in the nearby beaches. Seasonal Rates: June $6,000 | July $8,000 | Aug-LD $10,000

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

Situated on one of the largest lot in Sag Harbor Village at 2 builders acres, this furnished 3,000 sq. ft. Colonial offers 5 bedrooms or converted home office, 2.5 baths, outdoor shower, CAC, finished basement with play room, gym, large heated gunite pool, hot tub, all on a manicured property with organic garden, fire pit, and lovely outdoor dining. Within a short distance to the village center and its restaurants, shopping and entertainment. Store your catamaran, paddle boards and kayak at Havens Beach, or enjoy sailing at the Breakwater Yacht Club.ond largest lot in Sag Harbor Village at 2 builders acres, this furnished 3,000 sq. ft. Colonial offers 5 bedrooms or converted home office, 2.5 baths, outdoor shower, CAC, finished basement with play room, gym, large heated gunite pool, hot tub, all on a manicured property with organic garden, fire pit, and lovely outdoor dining. Within a short distance to the village center and its restaurants, shopping and entertainment. Store your catamaran, paddle boards and kayak at Havens Beach, or enjoy sailing at the Breakwater Yacht Club. Rental Terms: May: $20,000 September: $38,000

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

With direct views of the water and access to Gardiners Bay, this newly refreshed beach cottage exudes a chic and pared-down simplicity, making it the perfect waterfront retreat for relaxing days that feel like a true getaway from it all. Nestled in the serene natural surroundings of Gerard Drive in East Hampton Springs, this light-filled two-bedroom, two-bathroom cottage features central air conditioning and an abundance of outdoor activities, and the beach right on your doorstep. An outdoor shower provides a convenient way to rinse off after swimming or kayaking in the Bay or hanging out at the beach on Gerard Drive. Additionally, there's a fire pit with beach chairs on the bulkhead, offering a cozy spot to unwind at the end of a perfect day in the Hamptons. Please inquire about custom off-season dates . [[Rental Registration # RR-25-785]] EH RR #: RR-25-785 Rental Terms: August: $36,000 Other / Short Term - 11/1/2026 - 4/30/2027: $30,000 September: $20,000 October: $10,000

A modern retreat, cradled in a park-like oasis, where privacy and style intertwine in effortless harmony. Originally crafted in 1966 and thoughtfully renovated, this hidden gem awaits those who seek beauty and tranquility. Nestled along a storybook street and moments from the breathtaking shores of Louse Point, the home invites nature to dance within. Wide wraparound decking blurs the line between indoors and out, while golden light spills through every space, illuminating vaulted cottage-style ceilings that seem to breathe with the breeze. With two serene bedrooms, two spa-like baths, and a whimsical loft accessed by a library-style ladder, the home is both intimate and enchanting. Meandering pathways wind through the lush grounds, leading to a glistening pond, secluded seating nooks, and a fire pit encircled by Adirondack chairs-each moment here designed for quiet wonder. An automated driveway gate ensures a sanctuary of privacy. A place where time slows, light lingers, and every corner whispers serenity. Simply perfect. [[Rental Registration # 26-368]] EH RR #: 26-368 Rental Terms: July - Labor Day: $64,500 August - Labor Day: $33,500

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!

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

A stone's throw from the heart of East Hampton Village, this fully renovated and thoughtfully designed home offers the perfect Hamptons escape. Privately set behind mature landscaping and a gated entry, this new rental delivers a rare combination of charm, convenience, and turnkey ease. Inside features two well-proportioned bedrooms and two full baths, complemented by a spacious living room and eat-in kitchen. Outdoors, enjoy a private yard ideal for relaxing or entertaining after a day at the beach. Minutes to village shops, dining, and the area's most desirable ocean beaches. [[Rental Registration # RR-26-353]] EH RR #: RR-26-353 Rental Terms: July: $16,000 Winter Season: $21,000 Per Month Other / Short Term - Year Round: $75,000 August - Labor Day: $28,000 Memorial Day - Labor Day: $45,000 July - Labor Day: $38,000 June/July: $25,000

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

Also available: June for $35K; June/July for $125K Enjoy the beauty of this recently renovated five bedroom, five-and-a-half bath traditional in Bridgehampton's horse country. This 4,500+/- square foot home sits on a beautifully manicured full acre with open lawns and a 20' x 40' gunite pool. A large double-height foyer and beautiful staircase greet you as you enter the home while a chef's kitchen and spacious, nicely appointed primary suites on both levels are just some of the other amenities featured in this summer oasis. Close proximity to town, shops, restaurants and beaches complete this spectacular property. Reach out now to secure this wonderful home for summer 2023. Rental Reg #: RP230579 EH RR #: (RP251002) Rental Terms: July: $110,000 June: $50,000 August - Labor Day: $135,000

Summer is here, and this home has vacation written all over it. Enjoy spectacular sunset water views of the Long Island Sound from the spacious wrap-around deck or from the bright, open-concept living spaces inside. Perfect for entertaining, the layout features 4 bedrooms and 2 full bathrooms, offering a beautiful oasis for relaxation and togetherness. The lifestyle here is effortless: Kenny's Beach access is just steps away (.02 miles) for swimming in the Sound, complemented by a refreshing outdoor shower back at the house. Plus, you can leave the car behind and stroll down the road (.03 miles) to grab lunch or dinner at the hot new local restaurant, Little Fish. Let's get you set up in the perfect summer getaway—inquire today! Availability: June 15-June 30th $10K | July $35K | August $30K

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

Jeremiah Baker built this house in the 1850s from proceeds gained during the California Gold Rush. He later became an entrepreneur operating the first daily stage coach mail from Sag Harbor to East Hampton. Today the house has been renovated to its original splendor, rightfully reclaiming its position as one of the first and most prominent houses in the history-rich hamlet of Amagansett. Combining historical detail and provenance while maintaining right-sized proportions of house, rooms and garden, this property features modern high end appliances and bathrooms ranges from SubZero, LeFroyBrooks, Jura, Waterworks, Steamster, and Wolf. A heated gunite pool, 4 bedrooms and 3.5 bathrooms allow for an immersion into history without sacrificing comfort and convenience. Walking distance to Atlantic and Indian Wells beaches as well as all village restaurants allow for ease of access without planning. This historic house covering 170 years of Atlantic ocean living embraced by mature trees on 0.83 acres offers sunshine and shade, serenity during lazy afternoons of the East End summer, and the perfect venue for wonderful meals in a surrounding that focuses on the irreducible human values of rich conversation and measured elegant timeless aesthetic. [[Rental Registration # 25-824]] EH RR #: 25-824 Rental Terms: September: $40,000

Situated in a prime south of the highway location in the Amagansett Lanes, this brand new construction house completed in 2019, has 6 bedrooms and 7 baths. Designed by a renowned architect, this 5,500 Sf +/- house has unique sleek modern lines throughout the house. All Four bedrooms on the top floor have ensuite bathrooms with beautiful finishes and custom cement tile floors with radiant heat. There are two additional bedrooms on the main floor in a separate private wing of the house. Multiple living areas offer a seamless blend of privacy and open, light-filled social spaces for family and friends. Large chef's kitchen flows into dining area and the great room with double height ceilings, while the extensive limestone patios surrounding the main residence and the pool house are providing beautiful views of the pool and secluded yard. Finished lower level includes media room, with a wet bar, living area, a ping pong table and a full bathroom. The outside living spaces, provide a one-of-kind experience. The modern outdoor living room area features indoor/outdoor living spaces, dining room, pool house with outdoor living area, all overlooking professionally landscaped grounds, and a saltwater gunite pool. Tastefully appointed with top of the line finishes and understated designer furnishings, the outdoor spaces effortlessly host casual afternoons by the pool. This prime south of the highway location in the Amagansett Lanes and steps to the ocean, offers a luxurious retreat environment with modern interiors and beautifully crafted outdoor living and recreational spaces. Top of the line finishes in and out, this home provides a truly unparalleled experience in this south of the highway location, within walking distance to ocean beaches, Amagansett's restaurants and shops. [[Rental Registration # Pending]] Rental Terms: September: $120,000

Newly renovated in 2018, this bright and airy four-bedroom home is set on a full acre bordering a private preserve, offering rare tranquility and uninterrupted natural views in the heart of Water Mill. The home is filled with natural light throughout, featuring an open-concept kitchen and living space designed for easy summer living and seamless entertaining. The primary suite opens directly to the outdoor deck, creating a true indoor-outdoor lifestyle. Outside, enjoy expansive, fully fenced grounds, a sparkling in-ground pool, and the privacy that comes with backing onto preserved land. Privacy with just sun, space, and calm. Ideally located minutes from ocean beaches, Southampton, and Bridgehampton villages, and top restaurants, this home delivers both convenience and escape. A clean, modern Hamptons rental that actually feels like a getaway. Available August through Labor Day. [[Rental Registration # RP260066]] EH RR #: RP260066 Rental Terms: Other / Short Term - Year Round: $125,000 Memorial Day - Labor Day: $85,000

CHIC AMAGANSETT SURFER COTTAGE Turn key, fully renovated Amagansett Dunes, stylish, very comfortable cottage with reclaimed oak flooring, recessed lighting, and luxe bathrooms complete with beautiful kitchen with Viking appliances. Minutes to town. Great outdoor space with dining pergola, fire pit and outdoor shower. Direct ocean beach access. It does not get better. [[Rental Registration # 25-1161]] EH RR #: 25-1161 Rental Terms: August - Labor Day: $55,000 September: $25,000 August: $50,000

Discover this modern gem of a beach house on 3 private acres with 355 feet of water frontage on Gardiner's Bay. The private path over a dune leads to an oasis of wide sandy beach perfectly situated for sensational direct evening sunsets. The open interior has walls of glass for continuous water views and to invite in warm coastal breezes throughout. There are 5 bedrooms, 6 baths, den and separate studio. The waterside heated pool and hot tub are surrounded by expansive decking. Architect designer Joe D'Urso worked on the design of the compound which consists of the main house, an art studio, guest house and pool. The house was designed "upside down" by having the bedrooms on the first floor and the living room, dining room and kitchen on the second floor. [[Rental Registration # 24-1298]] EH RR #: 24-1298 Rental Terms: August - Labor Day: $100,000 Two Weeks: $55,000

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

This light-filled residence is quietly set on a gated and exceptionally private two-acre property in coveted Water Mill. Recently renovated with a natural, timeless aesthetic, the home features sanded oak floors and a thoughtful layout with five beautifully appointed bedrooms across two distinct wings. A welcoming foyer opens to a spacious living and dining area, highlighted by a wall of sliding glass doors that seamlessly connect to the deck and outdoor living spaces. First-floor guest suite enjoys direct access to the deck and pool. Upstairs, the primary suite and an additional guest ensuite share a balcony, alongside a dedicated workspace ideal for focused productivity. A separate wing offers a media / playroom and two additional bedrooms, including one with bunks, served by a full bath-perfect for guests of all ages. Outdoors, enjoy a heated pool and relaxed al fresco dining surrounded by mature landscaping, hydrangeas and natural tranquility. Ideally located just eight minutes from Southampton Village's renowned restaurants, shops, and ocean beaches, this serene and special property offers privacy, comfort, and effortless Hamptons living. Please call with questions or to make an appointment to view this serene and special property! [[Rental Registration # RA260488]] EH RR #: RA260488 Rental Terms: August - Labor Day: $65,000 August: $55,000

Perfectly positioned in the heart of Bridgehampton South, this beautifully designed six-bedroom, five-and-a-half-bathroom home embodies effortless Hamptons living in every season. Filled with natural light, the home offers elegant, sun-drenched interiors, sophisticated yet relaxed furnishings, and a seamless flow between indoor and outdoor spaces. Thoughtfully designed for both comfort and style, expansive living and dining areas create the perfect setting for everyday living, entertaining, and weekends with family and friends. Beautifully landscaped grounds offer multiple outdoor seating and dining areas, while a tucked-away fire pit provides an inviting place to gather on crisp fall evenings or cool spring nights. Designed with every member of the family in mind, the property also features a basketball court, trampoline, playground, and garage, offering plenty of space for recreation and relaxation throughout the year. Located moments from Bridgehampton's renowned restaurants, boutiques, farm stands, ocean beaches, and equestrian facilities, the home offers an ideal balance of privacy, comfort, and convenience - from quiet fall weekends and cozy winters to spring on the East End and the arrival of summer. An exceptional opportunity to experience Bridgehampton living through the seasons. [[Rental Registration # Pending]] Rental Terms: Other / Short Term - 9/12/2026 - 6/30/2027: $195,000 February: $15,000 May: $40,000 October: $35,000 November: $20,000 September: $60,000 January: $15,000 April: $20,000 March: $15,000 June: $75,000