luxury houses with pool for rent Montauk, United States

Rental Reg# 23-128 expires 6/15/25 Experience beachside living at this completely renovated Montauk Beach house. Boasting 3 bedrooms and 2 modern bathrooms, this home provides the perfect summer retreat. Step inside to discover a brand new open kitchen, complete with top-of-the-line stainless steel appliances and ample storage space. The light-filled living room features large windows and a cozy gas fireplace, creating an inviting atmosphere for relaxation and entertainment. Outside, you'll find a beautiful bluestone patio with BBQ and plenty of comfortable outdoor furniture, perfect for lounging and soaking up the sun. Take a dip in the heated saltwater pool, or rinse off in the outdoor shower after a day at the beach. Short distance from private access to Culloden beach, as well as shops, restaurants, and marinas. EH RR #: 26-38 Rental Terms: September: $20,000

Located high above Hither Hills with outstanding panoramic ocean views, sits this modern new construction with top of the line finishes. Second story offers Gourmet Chef's Kitchen with stainless steal appliances, great room with fireplace and soaring height ceilings, master suite with master bathroom, all seamlessly incorporating the spectacular ocean views. Sliding doors open to expansive second story decking perfect for outdoor entertaining. First floor is comprised of two guest bedroom suites with ensuite bathrooms, and spacious living room. The property is landscaped for privacy with large heated gunite, outdoor patio, and rolling green lawn. The best Montauk has to offer! [[Rental Registration # 23665]] EH RR #: 23665 Rental Terms: August: $110,000 July - Labor Day: $235,000 September: $49,000 May: $42,000 August - Labor Day: $125,000 Memorial Day - Labor Day: $260,000 October: $17,500 July: $125,000 June: $60,000

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

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

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

Rental Permit # 23-338 Spend the summer in The Lanes of Amagansett . . . Five bedrooms, spacious living room, dining room, and kitchen all opening to a sprawling lawn with refreshing pool and lovely cabana. Oh, and yes! It's located a short distance to the Village. [[Rental Registration # 25-721]] EH RR #: 25-721 Rental Terms: July - Labor Day: $150,000 August - Labor Day: $85,000 Memorial Day - Labor Day: $175,000

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

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 newly renovated modern in the Dunes with a new pool has four bedrooms and 4 bathrooms. The first floor has a bright and open kitchen and living room with a fireplace overlooking a deck with a heated pool, three bedrooms and two bathrooms. The second floor has the master bedroom and bathroom, a loft with two additional trundle beds, and a guest bathroom. There is a beautiful collection of contemporary art work throughout the house. [[Rental Registration # 23-259]] EH RR #: 23-259 Rental Terms: Memorial Day - Labor Day: $170,000 September: $42,500 August - Labor Day: $75,000 July: $65,000 July - Labor Day: $135,000

Renovated both inside and out, this beautiful Amagansett Dunes cottage has it all! Located just around 400 feet to ocean beach walkway, this charming house has just been completely landscaped including a brand new lawn, blue stone patio in back with all new outdoor furniture including dining table and chairs, gas BBQ, and entertaining area with sofa and chairs. The new blue stone walkway leads both around the house and heated pool. Pristine and recently updated, the interior first floor includes living room with fireplace and large screen TV, kitchen and dining area that overlook the back patio, a full bathroom, den/office with sofa sleeper. Separated for privacy, the large primary ensuite bedroom opens to an expansive deck with heated pool, lounge chairs and second entertaining area. The second floor includes two additional guest bedrooms, 1 with Queen bed, the other with twin beds, and a full guest bathroom. [[Rental Registration # 24-1987]] EH RR #: 24-1987 Rental Terms: July - Labor Day: $130,000 August - Labor Day: $70,000 July: $60,000

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: $135,000 July - Labor Day: $270,000 August: $135,000

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

Chic renovated cottage in the heart of the Amagansett Dunes. Located on a prime street minutes to Exclusive Mako Lane beach access, this 4 bedroom, 2 bath charming beach house offers vaulted ceilings and a wood burning stove in the airy living room and a sunny open kitchen with sliders leading outside. An uber-stylish primary bedroom and bath is separated from 3 additional guest rooms providing privacy for all. Expansive decking offers plenty of room for sunning, outdoor dining, relaxing and entertaining. The enclosed outdoor shower is a perfect last stop after a day at the Ocean! Also available: Two Weeks: $35,000 Jun 1st - Jul 11th 2022 Two Weeks: $35,000 Jul 23rd - Sep 5th 2022 EH RR #: to come Rental Terms: Two Weeks: $30,000

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

This barn style house has it all with its open and airy living area. It features wooded floors throughout and two fireplaces. It also hosts a European Style kitchen in addition to the open dining, living room and pool table playing area. There is a den leading out to an enclosed screened-in porch, and outdoor decking featuring a swimming pool and outdoor shower. This terrific house is a great hide-a-way for the summer season and close to all in Amagansett. [[Rental Registration # 25-27]] EH RR #: 25-27 Rental Terms: August: $40,000 July: $35,000 August - Labor Day: $47,000

Wonderfully decorated contemporary home on Neck Path with heated pool and tennis. Convenient to Amagansett and East Hampton yet totally private. 5 bedrooms and 4 baths, open living area and two back decks make this house perfect for all your summer enjoyment. Flat screen TV's throughout and Sonos system. Amazing home, amazing rate, amazing rental. Services included, utilities additional to tenant. [[Rental Registration # 22-904]] EH RR #: 22-904 Rental Terms: August: $80,000 August - Labor Day: $85,000 Memorial Day - Labor Day: $185,000 July - Labor Day: $155,000 June: $50,000