luxury houses with pool for rent East Hampton, 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

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

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

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

Peaceful Summer Getaway Amazing summer rental opportunity! Spectacular 3 Bedroom, 3.5 Bath contemporary Hamptons home with perfect indoor/outdoor entertaining spaces. Lush 1.6+/- private acres with an extremely private & fenced rear yard. Private sleeping quarters with 2 Main Bedrooms, one upstairs and one downstairs both with en suite baths. The third bedroom located on the main floor also has a full bathroom. Wake up and have breakfast in the sunroom or use the Peloton that is available. Enjoy the heated pool or relax on the deck that is equipped with Sonos sounds system. Want to go out? This home is conveniently located between East Hampton and Sag Harbor just minutes from all the shopping, restaurants, and best beaches the South Fork has to offer. Coming back from exploring and need to recharge? Make use of the Tesla car charger available in the oversized driveway outside the garage. End the evening relaxing in your 2nd floor fully enclosed sunroom, enjoying the peace and tranquility this home has to offer. Your perfect summer awaits! [[Rental Registration # Pending]] EH RR #: 24-284 Rental Terms: Memorial Day - Labor Day: $97,000

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

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

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

Experience the private island ambience from this three story modern design by renowned architectural award recipient. Perfectly sited for panoramic waterfront views and stunning direct sunsets, it has a private path for spontaneous access to a secluded meandering beach. The open interior hold five bedrooms including two primary suites, seven bathrooms, a waterside enclosed porch, media room, gym, sauna, cold plunge ice bath and massage room. Walls of glass exhibit continuous water views throughout while inviting in soothing coastal air. The water view salt water pool has multiple surrounding decks, covered porches and pool house with bath. Various additional gathering areas include a fire pit with seating quietly nestled in a dune by the Bay. A private marina, waterfront restaurants and the charm of East Hampton Village are moments away. A magical setting, this is waterfront living at its finest. [[Rental Registration # 24-1446]] EH RR #: 24-1446 Rental Terms: Other / Short Term - Short-Term: $125,000 November: $50,000 September: $60,000 October: $50,000

Stylish contemporary featuring 3 bedrooms and 2 baths, lovely grounds and heated pool. Located in East Hampton's Clearwater Beach community. Living room is open with double height ceilings and fireplace. Dining is open also. Hardwood floors, plenty of light.Perfect summer living. [[Rental Registration # 24-1402]] EH RR #: 24-1402 Rental Terms: Memorial Day - Labor Day: $55,000 August - Labor Day: $25,000 June: $10,000 July: $20,000 July - Labor Day: $45,000

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

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

Sensational, grand and elegant 5,000 sq. ft. shingled home. Open concept living/ dining/ kitchen, with soaring ceilings, works well for entertaining. There are two first floor guest bedrooms which share a full bath, and beautiful den/office with its own full bath. Second floor has three bedrooms, two of which are primary bedrooms ensuite. There is a full unfinished basement, two car garage, heated gunite pool set in expansive lawn surrounded by exquisite landscaping. Secluded area only 5 minutes to East Hampton Village and close to Sag Harbor as well. Owner is open to other periods. [[Rental Registration # 25-132]] EH RR #: 25-132 Rental Terms: Two Weeks: $30,000 July - Labor Day: $160,000 Memorial Day - Labor Day: $200,000

Now available for a few 2 week periods! This spacious and pristine traditional home boasts over 3900+/- square feet of living space that includes 4 bedrooms, 4.5 bathrooms, formal dining room, an intimate study with large flat screen TV, and an impressive, light-filled two-story great room with fireplace and glass doors that open to the deck. The first floor primary suite with fireplace also opens to the deck area. There's a large, open kitchen with countertop seating and a window lined breakfast room. Everything you need for that perfect entertaining. There's also a first floor living space with an office/ den, and additional ensuite bedroom. Upstairs on the second level you'll find 3 guest rooms and a comfortable media room. The half-acre property has been beautifully landscaped with seclusion in mind and boasts a heated pool, a new, spacious mahogany deck with outdoor shower and new hot tub. A convenient location not far from East Hampton Village and ocean beaches complete the picture. A summer home to enjoy! [[Rental Registration # 24-1422]] EH RR #: 24-1422 Rental Terms: June: $35,000

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

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