395 Hamptons Rentals

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21 Oak View Road
$125,000

Southampton, NY
Rental
Bedrooms: 8
Bathrooms: 8.5
Web ID: 916927

RA150520 New to market rental, stunning, turnkey and practically new! This elegant home is sited on 1.4+/- cleared acres in Southampton. The estate-like setting is expansive, private, located on a cul-de-sac and only a block to bay beaches. The magnificent property features an immaculate, 7,500 +/- gambrel traditional, heated gunite pool, pergola, mahogany deck, as well as fantastic outdoor dining and entertaining spaces all set among sprawling lawns and a perfectly-manicured landscape. Inside, a total of 8 bedrooms, 8.5 bathrooms spread over an open and well-designed interior with a luxurious primary suite on the second floor with fireplace. Traditional details combined with contemporary design. Six en suite bedrooms are located on the first and second floors while the remaining 2 are found on the finished, 1,711+/- sf lower level which also includes a recreational room, ample storage and could be a perfect space for a movie theater, gym, and...

May Rental: $75,000
July Rental: $125,000
July / Aug Rental: $275,000
August Rental: $150,000
Two Week Rental: $45,000

Craig Beem
(631) 537-4350

139 Herrick Road
$125,000

Village of Southampton, NY
Rental
Bedrooms: 2
Bathrooms: 1.5
Web ID: 910107

Enjoy the perfect location for convenience and coastal living. This charming 2 bedroom and 1.5 half bath home just a few blocks from Main Street's shopping, restaurants and the ocean beaches. Step inside and be greeted by the open plan with wood-burning fireplace, multiple oversized glass doors open to central deck and garden allow for one story living at its best. Designer owner touches throughout create a warm and inviting atmosphere. The recently renovated kitchen and fresh furnishings will make for a great summer experience on one of the most desirable streets in Southampton Village. Listing ID: 910107

Year Round: $125,000

Robert M Lohman
(631) 204-2404

109 Buell Lane
$125,000

Village of East Hampton, NY
Rental
Bedrooms: 5
Bathrooms: 4.5
Web ID: 755079

This ultra-chic new construction is pleasing from every angle. High end finishes, sleek, top of the line everything, in this now 5 bedroom, 4.5 bathroom beach house. The oversized central living space is stunning, with high cathedral ceilings and walls of glass on three sides. Sparkling Sub Zero/Wolf kitchen with wine fridge, natural stone counters, and custom glass backsplash. Added amenities include a screened-in sunroom and a fully equipped gym. All bathrooms feature walk in showers, Grohe fixtures and Toto toilets. Beautifully landscaped grounds host a large stone patio, a heated gunite pool, pool house, and two outdoor showers, one conveniently located next to the Primary Bedroom, the other closer to the pool. Nicely proportioned half-acre lot, with electronic gate and privacy hedges; convenient to all in the heart of East Hampton Village. Listing ID: 755079

July Rental: $125,000
August - LD Rental: $125,000

Timothy R O'Connor
(631) 771-5321

Jeffrey C Carter
(631) 771-5323

East Hampton
$120,000

East Hampton, NY
Rental
Bedrooms: 4
Bathrooms: 4
Web ID: 907655

Rental Registration #: 23-1209 Experience the best of East Hampton living year-round in this exquisite beach house. This beautifully renovated home offers an inviting atmosphere that's perfect for all seasons. As you step inside, you'll be greeted by an open and sunlit first floor featuring an en-suite master bedroom and an additional full bath. The custom high-end eat-in kitchen seamlessly flows into a cozy TV/den area, creating an ideal space for gatherings and relaxation. Venture to the second floor, where you'll find two more bedrooms and another full bath, providing ample room for guests or family. An exciting new addition to this property includes a fourth bedroom and a sleek TV area, adding versatility to your living space. What truly sets this property apart are its remarkable outdoor entertaining spaces. At every turn, you'll discover unique spots for dining or lounging, surrounded by lush, tropical plantings. The heated gunite pool...

Year Round: $120,000

Timothy R O'Connor
(631) 771-5321

Jeffrey C Carter
(631) 771-5323

Amagansett
$120,000

Amagansett, NY
Rental
Bedrooms: 4
Bathrooms: 4
Web ID: 913196

YOUR PRIVATE OCEAN BEACH ACCESS JUST A FEW HUNDRED FEET AWAY! Designed by the renowned architectural firm Stelle, Lomont, Rouhani, this exclusive modern beach home is set against 1.4 acres of rolling sandy dunes. Its dynamic facade combines Zinc and Cedar, showcasing a 4-bedroom, 4-bathroom private retreat. Floor-to-ceiling glass frames picturesque views of the private dunes and adjacent dune reserve. The sleek interiors feature a Poggenpohl kitchen with Quartz countertops, Subzero and Miele appliances, wide-plank White Oak floors, and a Spark modern gas fireplace. A total of 1,000 square feet of exterior decking surrounds the 30-foot infinity edge pool on the first level and serves as a viewing platform from the second floor, creating the perfect outdoor oasis. Situated on the highly coveted and private Mitchell Dunes Lane in Amagansett, this property offers private beach access and resident tennis courts. YOUR DREAM OF THE TRUE HAMPTONS BEACH LIFE IS HERE!

July Rental: $120,000
July / Aug Rental: $240,000
August Rental: $120,000
August - LD Rental: $120,000

Timothy C Burch
(631) 771-5315

Water Mill
$120,000

Water Mill, NY
Rental
Bedrooms: 4
Bathrooms: 4
Web ID: 735953

Rental Reg. # 240587: Beautiful two-story recently updated traditional, with a living room with fireplace, dining room, breakfast room, kitchen, four bedrooms and four baths (including master suite with fireplace and balcony, and guest suite). Additional amenities include sitting room (may serve as fifth bedroom), second-floor laundry room, full basement, central air-conditioning, two-car garage, indoor/outdoor sound system; 1.84+/-acres of landscaped grounds hold a heated Gunite pool and are bordered by two separate agricultural reserves.Listing ID: 735953

July / Aug Rental: $120,000
Year Round: $156,000

Susan L Ratcliffe
(631) 537-4327

Richard Finder
(631) 702-7511

421 Edge Of Woods Road
$120,000

Water Mill, NY
Rental
Bedrooms: 7
Bathrooms: 8.5
Web ID: 737889

RR# RP201387. Down a long driveway, this wonderfully appointed home situated on 2.5+/- acres offers exceptional privacy and seclusion in Water Mill. The compound features a beautiful main house, a guest cottage, and a pool house, this newly-updated traditional offers 7 bedrooms and 8.5 baths. The main house features an oversized gourmet kitchen with stainless steel appliances with an open floor plan to the spacious living room with a fireplace. The dining area features several French doors leading to the deck, which overlooks the pool area. Additionally, the main floor features a den with a fireplace, powder room, and a full bath with access to the backyard. The second floor features 2 primary suites. One features a fireplace, access to the balcony, a spa bath with a floating tub, and a 6-foot shower. The other spacious primary suite also features balcony access. Two additional ensuite bedrooms and a laundry...

January Rental: $7,500
February Rental: $7,500
March Rental: $7,500
April Rental: $7,500
May Rental: $7,500
MD - LD Rental: $270,000
June Rental: $40,000
July Rental: $120,000
July / Aug Rental: $240,000
August - LD Rental: $125,000
November Rental: $7,500
December Rental: $14,000

Cristina Matos
(631) 204-2408

561 Wainscott Northwest Road
$115,000

Wainscott, NY
Rental
Bedrooms: 7
Bathrooms: 6.5
Web ID: 910462

Rental Reg. # 24-1034. Privacy abounds in this beautifully renovated Wainscott traditional home. Sited on 5.5 acres with deco turf tennis/basketball. This 4500 Sq ft with 2500 sq ft lower level, 7 bedroom, 6.5 bath home is the perfect summer rental. As you enter the grand open living areas, you are greeted with tons of natural light from a wall of French doors that open to expansive outdoor deck area. The living room flows into dining area and huge eat in renovated chef's kitchen with island seating, marble counter tops, stainless steel appliances, and breakfast area with window seating. Bedrooms and baths consist of a first floor primary suite with vaulted ceilings, access to the backyard and a renovated expansive en -suite bathroom. There is another main floor bedroom as well. The second floor boast an additional primary bedroom with double granite vanity and soaking tub and...

January Rental: $20,000
February Rental: $20,000
March Rental: $20,000
May Rental: $45,000
MD - LD Rental: $295,000
June Rental: $50,000
July Rental: $115,000
July / Aug Rental: $250,000
August - LD Rental: $135,000
November Rental: $20,000
December Rental: $25,000

David Tenenbaum
(631) 771-5322

191 Rose Hill Road
$115,000

Water Mill, NY
Rental
Bedrooms: 5
Bathrooms: 5.5
Web ID: 896064

RR# RP241211. Offering 5 bedrooms and 5.5 baths on a full acre with a private dock on Hayground Cove in the Water Mill estate section, this exquisite slate roof Georgian carriage house built circa 1920 has been extensively renovated with every modern convenience. It features an open floor plan flooded with light from sets of French doors with interiors finished in a casually elegant décor. On the first floor, a welcoming foyer offers views of the circular dining area, which is bookended by a large formal living room (31'6' x 19'9') with a fireplace on one side and a kitchen/dining/common room with 10'11 ceilings on the other. An en suite bedroom, additional full bath, laundry room, and den with patio leading to the heated gunite pool are also provided. The second floor features a primary en suite with double closets, a private balcony, and three additional guest bedrooms, one...

MD - LD Rental: $270,000
June Rental: $45,000
July Rental: $115,000
July / Aug Rental: $230,000
August - LD Rental: $120,000

Cristina Matos
(631) 204-2408

Anna Kahn
(631) 771-5303

Southampton
$110,000

Southampton, NY
Rental
Bedrooms: 3
Bathrooms: 3
Web ID: 736801

RR#:RP160726 Newly renovated 3 bed, 3 bath home. Finished basement with bath. Beautiful heated Gunite pool. New furniture and bedding, and tastefully done. Listing ID:736801

Winter Rental: $5,500
Year Round: $110,000

Richard Finder
(631) 702-7511

Southampton
$110,000

Southampton, NY
Rental
Bedrooms: 6
Bathrooms: 6.5
Web ID: 876834

RR# RP201389. Gorgeous contemporary house offering 6 en-suite bedrooms and 6.5 baths done by world-renowned Italian architect, Leopoldo Rosati. This 5,200 square foot interior offers an abundance light and floor to ceiling walls glass overlooking the Great Peconic Bay. Triple-heighted living room with fireplace, modern kitchen and a large finished basement with a media room, en-suite bedroom and a library. Outside, enjoy the pool house with kitchen and half bath, heated gunite swimming pool and spa on a large deck which overlooks the water. Looking out from the 100' bluff, walk down to the private sandy beach and enjoy your summer with all this gorgeous home has to offer. Listing ID: 876834

June/July Rental: $150,000
August - LD Rental: $110,000

John P Vitello
(631) 204-2407

55 Old Town Crossing
$110,000

Village of Southampton, NY
Rental
Bedrooms: 6
Bathrooms: 4.5
Web ID: 904679

Located in the most desirable location between Wyandanch Lane and Little Plains Road, sits this 6 bedroom, 4.5 bathroom classic home spanning 3,620 s/f over 3 levels. With a luxurious open space interior design boasting an abundance of natural light and furnished with meticulous detail. Featuring a captivating and fully-equipped chef's kitchen with state-of-the-art stainless steel appliances, central air conditioning and a music room with equipment for those that want to entertain and play. Outdoors, the spacious backyard features a patio, perfect for entertaining with ease, a beautiful landscape offering mature estate privet hedges with a manicured garden and a 44 x 20 heated gunite pool with outdoor shower. With only a short distance to world class shopping and world famous ocean beaches, this is an opportunity for living the Hamptons life you won't want to miss. Listing ID: 904679

August - LD Rental: $110,000

John P Vitello
(631) 204-2407

Wainscott
$104,500

Wainscott, NY
Rental
Bedrooms: 6
Bathrooms: 4.5
Web ID: 737760

Rental Registration #: 24-114 (Feb 2, 2026)• Dynamic great room with two story vaulted ceilings • 1st floor master bedroom suite with fireplace • 6 bedrooms • 4 1/2 bathrooms • 3 fireplaces • Cook's kitchen featuring Wolf stove, Subzero refrigerator and wine refrigerator, Bosh dishwasher and Scotsman ice machine • Covered bluestone patio with ceiling fans and dining and seating area for entertaining with fire pit • 2 washing machines and 2 dryers • Indoor/outdoor sound system • Central air conditioning and heating (Nest Thermostat) • Heated 20 X 40 gunite pool (Jandy pool heater with iPhone control) • Beautiful landscaping including extensive privacy screening • Nest locks and thermostat • Housekeeping, handy-person and chef available on request • Town water connection with top-of-the-line water filtration system; garbage disposal • Dogs allowed with owner permission. Listing ID: 737760

MD - LD Rental: $264,000
June Rental: $82,500
July Rental: $104,500
August - LD Rental: $110,000
Year Round: $440,000

David Blumenfeld
(631) 537-4329

Undisclosed Address
$100,000

Sag Harbor, NY
Rental
Bedrooms: 5
Bathrooms: 6
Web ID: 736834

Enjoy this chic and sophisticated property with all it has to offer. The house has 5 very generous bedrooms, new bathrooms and beautiful new kitchen, formal dining room, 2 large main floor common areas with direct access to the heated pool . The second floor features a primary ensuite bedroom with a balcony, as well as 4 guest suites, 3 of which are also ensuite with private balconies. There is also a lovely loft study/office. The 2.43 acres surround the Har-Tru tennis court, extensive decking, swimming pool and pool house, all with great views of Noyac Golf Course. A truly great Hamptons rental in the Sag Harbor area.

July Rental: $100,000
July / Aug Rental: $225,000
August Rental: $125,000
August - LD Rental: $125,000

Andrea L Ackerman
(631) 537-4340

Elizabeth A Phenis
(631) 537-4357

North Haven
$100,000

North Haven, NY
Rental
Bedrooms: 6
Bathrooms: 5.5
Web ID: 754738

Luxury and comfort await you. This six bedroom villa is designed for both indoor and outdoor living and an active waterfront lifestyle. Moor your boat just yards away in the bay, or lounge by the unique, wrap around pool. There's also a full spa with sauna and steam shower, gorgeous chef's kitchen, and intimate covered patios for relaxing and entertaining. The views over the bay at sunset are absolutely breathtaking, and the lush grounds filled with flowering trees and shrubs are reminiscent of the tuscan countryside. A private chef is available for an additional cost. Listing ID: 754738

MD - LD Rental: $275,000
July Rental: $100,000
July / Aug Rental: $250,000
August - LD Rental: $125,000
Year Round: $500,000

Korine M Konzet
(631) 537-4323

Village Of Southampton
$100,000

Village of Southampton, NY
Rental
Bedrooms: 5
Bathrooms: 7.5
Web ID: 735873

Oceanfront property with ocean and bay views. Private master bedroom suite with 2 fireplaces, 2 baths, sauna, sitting room, oceanfront and bayfront balconies with gorgeous views. Guest wing with 4 en-suite bedrooms and an additional sauna. Multiple entertaining spaces. Flat screen TVs throughout. Heated gunite pool and hot tub. Listing ID: 735873

Short Term Weekly: $100,000

John P Vitello
(631) 204-2407

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