luxury houses with pool for rent Montauk, United States

A striking custom-built modern retreat in Amagansett, this home embodies refined architecture where nature and minimalist interiors meet in light-filled harmony. Expansive windows and a retractable sliding glass wall provide a seamless mix of privacy and openness, while custom woodworking and high-end finishes elevate every detail. Enter through a floor-to-ceiling teak door into a zen-like oasis. The main living area, with its 5' Ortal gas fireplace, opens to two outdoor spaces, including a 40' deck with built-in seating, a gas grill, an outdoor shower, and a heated gunite pool. Floor-to-ceiling windows connect the living room to the dining area, a minimalist bedroom, and a private reading nook, emphasizing the modern, airy feel. The kitchen features European appliances, an MSG Italian faucet, and a Pitt cooking system, offering style and functionality. In the spa-like bathroom, Cocoon Waterworks fixtures, a rain shower, and an open-air teak bath pad create a serene retreat. The finished lower level is a special setting with a dreamy bedroom and full bath and lounging area. Located close to Gardiner's Bay, with private bay access at the end of the lane, this home offers breathtaking sunsets and is just minutes from Amagansett Main Street and Montauk. For those seeking serenity and modern luxury in the Hamptons, this hidden gem is the perfect retreat. [[Rental Registration # 26-928]] EH RR #: 26-928 Rental Terms: March: $8,500 April: $8,500 Other / Short Term - Dec: $8,500 June/July: $70,000 January: $8,500 July - Labor Day: $125,000 July: $60,000 February: $8,500 Memorial Day - Labor Day: $135,000 August - Labor Day: $65,000

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

Located in the desirable Amagansett Dunes, this impeccable modern beach house designed by the renowned architectural team from Stelle, Lomont, Rouhani, is just a moments to the ocean beach. The main floor features a spectacular kitchen with a center island and top-of-the-line appliances, seamlessly flowing into the dining area and living room, complete with a cozy fireplace. Floor-to-ceiling windows and sliders flood the space with natural light while offering stunning views of the dunes. Completing the first floor is a private junior master suite with an ensuite bathroom, perfect for guests or family. A striking floating staircase leads to the second level, where you'll find the primary bedroom wing along with two additional ensuite bedrooms, each with access to a deck overlooking the backyard. Outdoors, enjoy a heated gunite pool surrounded by a spacious deck, a fire pit area, a barrel sauna, and an outdoor shower. With community tennis and a beach path at the end of the road, this is the ultimate beach retreat! [[Rental Registration # 25-714]] EH RR #: 25-714 Rental Terms: July - Labor Day: $225,000 Other / Short Term - 6/15/2027 - 9/6/2027: $250,000 August - Labor Day: $130,000 July: $120,000

Savor every ray of sunshine at this elegant and sprawling Amagansett stunner! Perched on top of a rise overlooking a 17-acre preserve, with second story views of the ocean, this gated five-bedroom home is built on a grand scale with abundant room for extended family or friends. An oversized heated pool and plenty of entertaining and lounging space both indoors and out make this an ideal perch from which to enjoy spectacular sunsets and the shops, farm stands, restaurants, and beaches of Amagansett, all literally two minutes away by car. [[Rental Registration # 26-263]] EH RR #: 26-263 Rental Terms: Two Weeks: $75,000

Rental Reg 24-740 expires 5/10/2026. Totally renovated top to bottom and ready for a fabulous summer in Amagansett. We present this amazing 4 bedroom beach house complete with heated gunite pool and brand new poolside cabana. The 3/4 acre grounds are open and spacious with plenty of room to play, entertain, or just relax in the sun. The ocean beaches and Village of Amagansett are just a short distance away, close enough to grab your beach gear and go! How about a great meal in one of the East End's favorite restaurants or a stop in Amagansett Square for a bit of shopping. The house boasts a finished lower level, a designer open kitchen, a bright separate dining area with glass sliders to the brick patios, and two and a half crisp new bathrooms. It's the perfect Amagansett Beach House! [[Rental Registration # 24-740]] EH RR #: 24-740 Rental Terms: June: $25,000 September: $21,000 Other / Short Term - Year Round: $190,000

Simply beyond compare, it will be love at first sight with this awe-inspiring 8,000 SF custom oceanfront mansion retreat on two magnificent acres with 200 feet of private oceanfront. An artistic masterpiece of modern architecture, combined with a world-class private beach, breathtaking ocean views, and cool Atlantic breezes provides the ultimate setting for luxurious living, relaxation, inspiration, and unmatched privacy. Located off an exclusive private cul-de-sac lane, down a 400 foot-secluded drive, you are greeted with a contemporary masterwork of three extraordinary stories. majestically facing the Big Blue. You will be dazzled by the soaring 11 foot ceilings and floor-to-ceiling walls of glass throughout, affording amazing ocean panoramas. Surrounding the home is gorgeous landscaping with lush gardens, shrubbery and privacy trees creating a Zen setting. Not to mention over 4,000 square feet of spectacular new decking and exquisite glass railings. Inside, you will fall in love with the unparalleled new renovation and designer furniture. Each room in this grand home provides the ultimate private beach refuge including 7 enormous bedrooms, 9 new bathrooms, 2 tremendous living rooms, 2 unparalleled new kitchens, and 2 spectacular fireplaces. There is an astounding brand new, drop-dead gorgeous state-of-the-art kitchen facing the ocean that seats 18 -- perfect for grand-scale entertaining! This chef's dream includes a gigantic Sub Zero refrigerator and freezer, Wolf stove and microwave, Miele dishwasher, and Zip Water filtration system. Relax in the incredible media room or workout in the amazing gym, while your children can play in the large playroom or fantastic new outdoor private swing set/play system with awesome playhouse. The luxurious two-car garage has a car charger, and there is a tremendous heated gunite ionized-water "healthy" pool with a dazzling large jacuzzi. You will love having two outdoor showers, an all-weather tennis court, huge-wrap-around new decks on all three levels, two new built-in outdoor gas grills, skylights, a tandem Kayak that is awesome for fishing or just paddling (seats one or two), and so much more. A private walkway to your magical backyard beach makes this the ultimate getaway of your dreams. The upper floor features a dazzling living room facing the ocean with a gorgeous working fireplace and large skylights. Also, conveniently located on this level is the luxuriously large master suite that includes a gigantic marble master bathroom with Jacuzzi tub facing the ocean, two-person shower, sauna, and huge walk-in closet. The glassed-in new designer kitchen and dining room are simply outstanding, and there is also a fantastic media room. Children or guests will love the large guest bedroom that feels like a second master suite on the upper level, with new marble en-suite bathroom featuring double sinks. The middle level includes a family room of grand proportion with a 75" TV and working fireplace right off the outstanding oceanfront pool with enormous deck and second glamorous new kitchen for entertaining by the pool along, in addition to a new powder room. There are four huge bedrooms on the floor, each with a stunning new marble en-suite bathroom and luxury fixtures. Your guests will feel pampered! The first level features a fantastic gym, another large guest bedroom with new-en suite marble bathroom, a terrific playroom, and two-car garage with Electric Vehicle Car Charger. This Rockstar custom home was designed and built by award-winning architect Bill Hayes. With three levels of glamorous, huge living and entertaining space, you will have your dream oceanfront oasis for your family and friends, offering the ultimate paradise of privacy and security. Perfectly positioned on one of the most coveted and private beaches in the world in beautiful Amagansett, between the sophisticated town of East Hampton and the gorgeous natural environs of Montauk...your modernistic oceanfron

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

Conveniently located near Amagansett Village and Ocean Beaches, 6 Katie Lane is a meticulously crafted 7,000 square foot transitional residence that sits on 1.4 private acres. Composing the interior main floor is a first floor junior primary bedroom with outdoor access to the covered porch. Living room with a wood burning fireplace, an open kitchen and dining area, a separate den/TV room, powder room, laundry room with double washer dyer units, and built in cabinetry within the side entry hall. The covered porch is designed for casual entertaining including several outdoor heaters making it a perfect place to cozy up in the winter which is easily accessible from the dining, living and bedroom spaces. On the second level, you will find an open landing area designed for casual sitting. 3 guest bedrooms which are all en-suite, plus the en-suite upper principal bedroom with a private entry and oversized bathroom. The lower level has an open entertaining space with pool table, separate gym area, private office, and the 6th bedroom complete with two queen beds perfect for overflow guests. There is a double car detached garage, outdoor living features with heated 18'x42' gunite pool and spa, along with cedar pergola covering an outdoor fireplace, grill, and entertainment center, on the side you will find oversized outdoor shower. Among the private and beautifully hedged backyard you will find an outdoor dining area highlighted by London Plane trees. This peaceful oasis is waiting for you! [[Rental Registration # 22-345]] EH RR #: 22-345 Rental Terms: Two Weeks: $80,000 July: $160,000

This spectacular home in Amagansett is located at the end of a cul-de-sac and has been tastefully renovated with many modern conveniences. Highlights of the first floor include a sunken living room with fireplace and double-height ceiling, a chef's eat-in kitchen with high-end appliances and large island, a separate dining room, a large first floor primary suite, a separate office, two enclosed patios with seating, and a half bath. The second floor features the second primary bedroom with vaulted ceilings and a remodeled en suite bath. Two additional guest rooms are located across the hall, as is a seating area loft and a large guest bath. The allure of the interiors, however, is quite possibly overshadowed by the meticulous beauty of the grounds and backyard. The long driveway leads to the back of the property, which features a large gunite pool and separate spa surrounded by a bluestone patio and coping. Lush lawn, perennial trees and an outdoor shower help to complete the outdoor experience. With its close proximity to Amagansett Village, this property maintains a great sense of privacy while remaining close to fine area shops, local restaurants, and stunning ocean beaches. [[Rental Registration # RR-25-914]] EH RR #: RR-25-914 Rental Terms: September: $25,000 Two Weeks: $50,000 August - Labor Day: $90,000

Rental Registry #: 21-252, Expires 07/20/2023. Located in the coveted Amagansett Dunes, minutes to the ocean and village shopping, is this stylish four bedroom two bathroom contemporary in a private setting. First floor open flow layout offers fully equipped kitchen, formal dining, spacious living room, master bedroom with ensuite bath, and media room. Sprawling deck with outdoor dining area overlooks reserve and leads down to heated pool surrounded by lush landscaping. EH RR #: 21-252 Rental Terms: Other / Short Term - 08/25/2022 - 09/01/2022: $35,000

Rental Reg# 22-1532 expires 11/10/24 Also available August $70K Superb, new 5 bedroom, 4.5 bath traditional prominently sited on 1.5 acres in Amagansett's Bell Estate, convenient to town, ocean and bay beaches. Custom architectural features enhance the 4,400 sq.ft. interior flooded with natural light. Impressive 60' Salt Water pool and home stereo wired throughout including outside. Extended season - upon request. EH RR #: 24-1381 Rental Terms: August: $75,000 August - Labor Day: $80,000 Memorial Day - Labor Day: $180,000 July: $70,000 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

Rental Reg# 22-396 expires 4/4/24 Also available Aug $40K Stately 5,800 square foot, 5 bedroom, 5.5 bath home on 2 acres surrounded by lush old growth beech forest. House is centered on an expansive and open floor plan perfect for gathering and entertaining and featuring large living and dining rooms, chefs kitchen, and sunny den. Large primary bedrooms on ground level and second floor. Multi-level exterior features deck off living area, overlooking extremely private and beautifully landscaped heated pool and patio. Perfect for an after-beach swim and barbecue. Less than 10 minutes from the center of Amagansett Village, shops, restaurants and ocean beaches. EH RR #: 22-396 Rental Terms: July: $52,500 Other / Short Term - July 15 - Sep 4: $77,000 July - Labor Day: $118,000 August - Labor Day: $54,000

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

Discover the charm of Amagansett at this stunning Bluff Road Beach House, available for summer and fall 2025. Located in one of the area’s most sought-after spots, this historic 5+ bedroom home offers spectacular views of the dunes and ocean, with a perfect mix of vintage character and modern comfort. Built in 1911 and recently renovated, the home features a sun-soaked interior, full of natural light and cozy charm. Whether you're lounging in the spacious living areas, enjoying a morning coffee on the front porch, or entertaining in the expansive backyard, this property is designed for ultimate relaxation and enjoyment. The home boasts: 5+ spacious bedrooms, ideal for family or guest stays, a newly furnished, open and inviting floor plan, a large backyard with a private pool, perfect for lounging and summer fun Proximity to shopping, dining, beaches, and transportation (no car needed!) Whether you're looking to unwind with a peaceful ocean breeze, entertain in style, or take in the surrounding beauty, this Bluff Road Beach House offers the perfect setting for a memorable vacation. Book your stay for 2025 and experience the best of Amagansett living! [[Rental Registration # 22-905]] EH RR #: 22-905 Rental Terms: Winter Season: $90,000 Per Month

Rental Registry#: 21-875, Expires 06/17/2023. Easy summer living is the benchmark of this lovely one level 4 bedroom, 2 bath home just down the street from the Jitney stop. Spacious backyard featuring ample decking surrounding a heated pool and outdoor shower after the beach or pool. Completely convenient to Amagansett village, and the ocean in addition to its close proximity from transportation. EH RR #: 21-875 Rental Terms: July - Labor Day: $65,000 August - Labor Day: $37,500 July: $30,000

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 Terms: July - Labor Day: $400,000 Memorial Day - Labor Day: $495,000

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

This wonderful 4 bedroom, 3 bathroom home, nestled on a quiet cul de sac in the lanes, provides comfort and convenience at its best. There are two bedrooms located on the first floor, one is ensuite, with two bedrooms on the second floor and 1 full bath. Two comfortable living spaces on the main floor with streaming natural light entering from all angles, the kitchen, with all stainless steel appliances, offers an easy flow to the outside patio and pool area. The yard is magical, in both the front and back, offering generous open space. Enjoy the fire pit or dine by the pool on the back deck. The location is minutes to ocean beaches, shopping, fine dining and moments away from catching a bus or a train. This home provides a charging station for an electric car too! [[Rental Registration # Pending]] EH RR #: 22-1514 Rental Terms: July: $75,000

Enjoy August in this sweet, cozy, updated home with pool. Chef's kitchen, open floorplan with 3 bedrooms, and 2 baths, this home is close to bay beaches. [[Rental Registration # 26-1149]] EH RR #: 26-1149 Rental Terms: Two Weeks: $10,000