luxury houses for rent Amagansett, United States

This bright, inviting home is located 350' off the southside of Amagansett Main Street, down a long driveway, thereby affording privacy at home, while having easy access to local shops, restaurants, and beautiful ocean beaches. The front foyer opens onto the living room with built-in bookshelves and a welcoming fireplace. At the rear of the living room area are a large dining table, the chef's kitchen, and the spacious sunroom/den with sliding glass doors leading to decks and overlooking the heated pool and ample lawn. There are four ensuite bedrooms: a junior primary ensuite bedroom on the first floor, and two guest ensuite bedrooms and the primary ensuite bedroom on the second floor. This home offers "easy-living" in one of the best locations in the Hamptons - Amagansett! [[Rental Registration # 25-274]] EH RR #: 25-274 Rental Terms: July: $50,000

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

Set deep within a private, wooded enclave of Amagansett, 41 Deep Wood Lane offers a rare opportunity to experience one of the East End's most cherished natural settings with remarkable tranquility. Approached by a long, secluded drive and enveloped by mature trees and lush plantings, the property feels deeply peaceful, yet remains moments from Amagansett's beloved farm stands and its world-class ocean and bay beaches-pristine, sought-after stretches of shoreline that define the area's enduring allure. Inside, the home carries an atmosphere of relaxed refinement. Sunlight pours through magnificent windows, illuminating interiors layered with soft tones and natural textures. The aesthetic is collected and organic, inviting, unforced, and quietly elegant. Multiple living spaces offer room to gather or retreat, each shaped by the surrounding landscape. The home features six generously sized bedrooms and five-and-a-half bathrooms, including a main primary suite privately positioned upstairs, a serene sanctuary among the treetops, and a second primary suite on the main level offering its own sense of ease and comfort. A dedicated gym, indoor sauna, and a second prep kitchen on the lower level further enhance the home's thoughtful, restorative nature. Outdoors, the property unfolds into a series of beautifully considered spaces, each deserving its own attention. A stunning gunite, pool with a bluestone surround anchors the grounds, framed by generous seating and lounging areas that invite long, unhurried afternoons. A separate firepit area, complete with its own seating, creates a natural gathering place as the day softens into evening. A large, private outdoor shower offers a refreshing post-beach ritual, while a wisteria-draped pergola provides a shaded, romantic setting for outdoor dining. An outdoor grilling area completes the experience. Everywhere, mature trees and dense greenery create a sense of privacy and immersion in nature. This is a home that feels deeply connected to its surroundings-soulful, secluded, and effortlessly livable. A true Amagansett retreat for those who value quiet luxury, natural beauty, and proximity to some of the most pristine beaches on the East End. [[Rental Registration # RR-26-242]] EH RR #: RR-26-242 Rental Terms: August - Labor Day: $120,000 August: $110,000

Available for the first time, this charming 3-bedroom, 2-bathroom home presents a rare opportunity just moments from East Hampton Village. Ideally located only one mile from the village center, 1.9 miles from pristine ocean beaches, and 2.5 miles from Amagansett Village, the property offers the perfect balance of convenience and coastal living. Sunlight pours into the home, enhancing its fresh, airy interiors and relaxed beachside aesthetic. The thoughtfully designed single-level layout provides effortless flow throughout, with sliding glass doors from the living room opening onto a spacious new deck-ideal for indoor-outdoor living and entertaining. The outdoor space is equally inviting, complete with an outdoor shower-perfect for rinsing off after a day at the beach. Enjoy easy access to world-class dining, boutique shopping, and the natural beauty that defines the Hamptons lifestyle. OWNER WILL REPLACE TWIN BEDS WITH FULL/QUEEN UPON REQUEST. [[Rental Registration # 26-395]] EH RR #: 26-395 Rental Terms: July: $15,000 August - Labor Day: $19,000

Handsome classic estate house with sensational sunset views over Maidstone Club and Hook Pond. Period beams and paneling, large sun room with wet bar. Game room with ping pong, pool table and big TV. Newly renovated kitchen with dining for 8 and a comfortable sitting area with flat screen TV. Great location in East Hampton. The house can accommodate 12 -15. The property is a stone's throw from the ocean. A special place for 2, 3, or 4 weeks vacation. Rental Terms: August - Labor Day: $175,000

This East Hampton charmer is moments away from Main Street East Hampton and ocean beaches. It has four bedrooms and two full baths, beautiful open kitchen and dining overlooking the beautiful backyard. Convenient location, moments to town where you will find great restaurants, shopping to explore, close to ocean beaches and transportation via The Jitney and Long Island Railroad. [[Rental Registration # 24-864]] EH RR #: 24-864 Rental Terms: August: $30,000 Other / Short Term - Year Round: $120,000 July: $30,000 August - Labor Day: $40,000

This picturesque traditional on East Hampton Village's Osborne Lane is now available for two weeks at summer's end. Just doors away from Newtown Lane and the heart of village attractions, this lovely home offers a wonderful combination of summer charm and local convenience. Highlights of the first floor include a large entry foyer, a double-height living room with wood burning fireplace, a spacious chef's kitchen with high-end appliances and center island, a stylish dining room, a separate den, a screened-in porch, a half bath, and the primary bedroom with a gas fireplace, two walk-in closets, and an en suite marble bath. The second floor includes three large guest rooms, each with its own en suite bath. The lower level has been finished and offers another living space with TV, wet bar, and wine refrigerator, a gym outfitted with Peleton, Pilates, and free weight equipment, a bonus room, and additional full bath. The backyard is highlighted by a large gunite pool surrounded by bluestone, an expansive lawn, tall evergreens providing ample privacy, a hot tub, and extra decking and patio space - both ideal for entertaining. This exceptional property affords a wonderful sense of warmth and enjoyment while remaining close to world-class restaurants, shops, transportation, and beautiful ocean beaches. [[Rental Registration # 24-941]] EH RR #: 24-941 Rental Terms: Two Weeks: $75,000

Rental Reg #: 22-1105, Expires 06/29/2024. Chic modern 4 bedroom, 4 bath plus den/office on beautiful 2.4+/- acres located at the edge of East Hampton Village. Enter the double height living room with walls of glass overlooking the patio and child-secure heated gunite pool and spa. The living room kitchen-dining area, principal bedroom and one guest room open to the patio. A fourth bedroom not shown can be set up as guest bedroom. The den/office is set aside for privacy at the front corner of the house. The rolling and expansive lawns are bordered by mature trees and plantings for exceptional privacy. EH RR #: 22-1105 Rental Terms: Other / Short Term - 7/17/23-7/31/23: $36,000

Located within a few blocks of the village, this well maintained farmhouse offers comfortable living. The main floor is open and bright with living, dining and kitchen. Dining area opens to an outdoor patio. The upper floor has 2- ensuite bedrooms. Nicely furnished and uncluttered. The 1.2 acre property is private and set at the end of a cul-de-sac. [[Rental Registration # RentalRegistry26-24]] EH RR #: Rental Registry 26-24 Rental Terms: Other / Short Term - Year Round: $6,350

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

Lovely cape located on a quiet street, convenient to all the wonderful things East Hampton village has to offer. Tastefully decorated living room and formal dining room, fully equipped kitchen with adjacent breakfast area, 4 bedrooms and 2.5 baths. The property offers plenty of room for fun and entertaining. Rental Terms: September: $25,000 June: $35,000

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

Privacy and charm pervade this lovely one-story ranch located at the end of a secluded cul-de-sac in the Springs. Tasteful amenities of this pristine home include three bedrooms, two baths, open concept living-dining areas with cathedral ceilings, and a wood-burning fireplace. The private yard features a large heated pool, grassy lawn, gas barbecue, and mature trees. Enjoy your private oasis while remaining close to East Hampton shops, restaurants and ocean beaches. [[Rental Registration # 22-1479]] EH RR #: 24-1377 Rental Terms: September: $15,000

Set South of the Highway in East Hampton, this pristine traditional offers an idyllic Hamptons retreat just moments from Main Beach and East Hampton Village. Beautifully maintained throughout, the home features four generously sized bedrooms, an inviting open living room with fireplace and built-in library, and an eat-in kitchen that flows seamlessly into a cozy sitting area. A formal dining area with sliding glass doors creates an effortless connection to the outdoors and an ideal setting for entertaining. Just off the primary suite, a private study offers flexibility as a home office or fifth bedroom. Set on 1.2 acres of lush, rolling lawn framed by mature specimen trees, the property offers exceptional privacy and a peaceful setting in one of East Hampton's most desirable locations. Rental Terms: July: $40,000 Memorial Day - Labor Day: $125,000 July - Labor Day: $85,000 June/July: $50,000 August - Labor Day: $50,000

Timeless East Hampton Estate has been recently renovated with old world charm, style, and a true Hampton flare. The 1st floor of the main house features an open living area with fireplace, media room, library/sitting area, formal dining room with fireplace, country kitchen with breakfast nook, fireplace and seating area. The second floor is highlighted by 6 stylish bedrooms and 4 baths. The 3rd floor offers an additional guest bedroom, private office, and an inviting primary suite with ocean views, a drawing room, and fabulous primary bath. The grounds are accented by wrap around porches, an out door grilling station with outdoor fireplace and dining pavilion. The hedged for privacy pool area offers a 2 bedroom guest house, heated gunite pool, another dining pavilion, and lawn areas perfect for the afternoon soccer match. Your vacation will be magical as ocean breezes relax you. Electric Car ready with a 220 voltage outlet, this home is understated perfection. EH RR #: village Rental Terms: Two Weeks: $125,000 Other / Short Term - Weekly: $62,500

Beautifully and stylishly renovated cape in East Hampton Springs is offered for summer. This sunny and cozy home offers a bedroom on the first floor, two on the second. Great deck with hot tub and a large green lawn. Close to Maidstone Beach, Springs General Store, and restaurants and coffee shops. [[Rental Registration # 25-1018]] EH RR #: 25-1018 Rental Terms: September: $8,000 August - Labor Day: $17,000 Memorial Day - Labor Day: $38,000 July - Labor Day: $30,000 July: $17,000

Also Available: Two Weeks between Aug 1 - Aug 31 28K This very private and dreamy Alfred Scheffer restored home and cottage circa 1967 is surrounded by reserve and views of Accabonac Harbor. Exposed wood beams and an expansive back yard create an atmosphere and environment that set the tone of this great scenic property. It is living with nature at its best. The Barn inspired main house is sited to take advantage of the forever field views and is filled with light. There is a 1st floor ensuite primary bedroom, a kitchen meant for cooking and a barn chic great room. What's special about the living arrangement is the guest cottage creating a true compound and privacy with 2 bedrooms and 2 full baths in addition to a high ceiling studio or gathering spot. The outdoor spaces on 2 acres include a pool, fire pit area, sweeping pastoral vistas and a lovely patio for entertaining off the main house. EH RR #: 25-34 Rental Terms: August: $50,000 Two Weeks: $28,000 August - Labor Day: $55,000

Just over three miles from East Hampton Village and less than a mile from the harbor entrance, this newly renovated four-bedroom, four-bathroom residence is set on two beautifully landscaped acres, offering the perfect blend of privacy, luxury, and convenience. Thoughtfully redesigned from top to bottom, the home features an effortless flow throughout. A welcoming living room with a fireplace opens seamlessly to the light-filled kitchen and dining area, where expansive views overlook the lush grounds beyond. The first floor also includes a dedicated guest wing with two spacious bedrooms and a full bath, providing comfort and privacy for family and visitors alike. Occupying the entire second level are two generously sized primary suites, each with its own beautifully appointed en-suite bathroom, creating a peaceful retreat for guests. The finished lower level, complete with a separate entrance, offers additional space for relaxation and entertainment. Featuring a spacious lounge area with a foosball table, bar, dining area, full bathroom, and laundry facilities, it is perfectly suited for casual gatherings and extended stays. Outdoors, multiple areas for lounging, dining, and entertaining invite you to enjoy the property's tranquil setting. From the expansive deck to the bluestone patio surrounding the oversized heated gunite pool, every detail has been designed for effortless indoor-outdoor living. Private and serene, yet moments from the beaches, marinas, fine dining, and cultural attractions that make East Hampton one of the most sought-after destinations in the Hamptons, this exceptional property is the ideal summer escape. [[Rental Registration # 26-1039]] EH RR #: 26-1039 Rental Terms: August - Labor Day: $40,000 Other / Short Term - Year Round: $135,000

Nestled within the coveted Georgica Estates enclave of East Hampton and just moments from the iconic sands of Georgica Beach, this five-bedroom, four-bath residence offers an opportunity to experience one of the Hamptons' most treasured settings with remarkable ease. One of East Hampton's original homes, it carries a sense of history and authenticity that feels increasingly rare. Privately positioned among extraordinary neighboring estates, the property is embraced by mature trees, sweeping lawns, and established gardens, creating a tranquil sanctuary in a premier location. The proximity to Georgica Beach allows for effortless daily rituals - early morning shoreline strolls as the light rises over the Atlantic, spontaneous afternoons by the water, and golden sunset returns as the sky softens into evening. The rhythm of the ocean becomes part of everyday life. Inside, the atmosphere is relaxed and quietly elegant. Sunlight fills the interiors, doors open naturally to the outdoors, and coastal breezes drift through the rooms. The aesthetic is collected and organic - inviting, personal, and uncontrived - offering a refreshing sense of ease. This is a home where sandy towels are draped casually, a place to gather, to read late into the afternoon, and to return from the beach with sandy feet and salt in the air. Lovingly maintained and artist-owned, the home carries a soulful presence. Its aesthetic reflects a collected, organic sensibility - layered, personal, and inviting - offering a refreshing alternative to more polished environments. It is a place to exhale, to gather, to read late into the afternoon, and to return from the beach with sandy feet and salt in the air. A true Georgica retreat for those who value privacy, proximity to the ocean, and the quiet luxury of simplicity. Available August through September. Rental Terms: August - Labor Day: $80,000 July: $75,000