398 Hamptons Rentals

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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

10 Bay Woods Drive
$120,000

Hampton Bays, NY
Rental
Bedrooms: 7
Bathrooms: 5
Web ID: 3529787

The open floor plan features a beautifully maintained interior that is awash with natural light and contains a formal dining room, large entertainment spaces, expansive great room, first-floor bedroom, expansive living areas, flow-through living/dining area, generous living spaces, bonus room, home office, separate dining room. Lavish fireplace. Highlights of this house include floor-to-ceiling windows, sweeping staircase to the upper level and vaulted ceilings. User-friendly and spacious, the eat-in kitchen features stainless-steel appliances, gas oven, granite countertops, tile backsplash, large center island, wooden cabinetry, recessed lighting, butler's pantry, over-the-range microwave, gas stove and wine rack. Drift off to sleep each night in the grand master-on-main suite that benefits from a luxury ensuite bathroom and a walk-in closet. Sparkling and airy, the master bathroom includes a walk-in shower, Jacuzzi tub, granite vanity and beautiful flooring. Adding to the home's appeal and Enhancing the home are top-of-the-line oak floors throughout. You'll enjoy...

Constance Porto
(9177314317) ) ) ) ) ) ) ) ) )

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

717 Dune Road
$110,000

Westhampton Beach, NY
Rental
Bedrooms: 3
Bathrooms: 2
Web ID: 3540683

Experience luxury living in this exquisite oceanfront sanctuary nestled along the pristine shores of the Hamptons. Positioned on one of the most coveted roads in the area, this magnificent summer haven offers an unparalleled escape for those craving coastal tranquility. Step inside to discover a meticulously designed interior seamlessly merging contemporary elegance with coastal charm. Expansive living areas flooded with natural light provide the perfect backdrop for relaxation and entertainment, while high-end finishes and designer touches ensure a heightened sense of relaxed sophistication. Enjoying hundreds of feet of uninterrupted sweeping Ocean vistas and breathe in that fresh Atlantic Ocean air. Retreat to your luxurious bedroom sanctuary, where plush furnishings, soothing color palettes, and sumptuous bedding beckon rest and rejuvenation while soaking in the enchanting seaside ambiance. Awaken to the breathtaking sight of the sun rising over the ocean from your sprawling wrap-around deck, setting the tone for another day of...

Albert Bongiorno
(6316177748) ) ) ) ) ) ) ) ) )

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

11 Watersedge Ct
$110,000

Westhampton Beach, NY
Rental
Bedrooms: 5
Bathrooms: 6
Web ID: 3529119

This large modern 5 bedroom / 5 bath home in heart of Westhampton Beach Village is available for rent. Just one block south of Main Street on a quiet cul-de-sac, this one-acre property is lush with beautiful landscaping, a gunite swimming pool, and a large outside deck area perfect for entertaining. The light-filled living room and dining room open to the gourmet kitchen with a large breakfast bar and top-of-the-line appliances. Two of the bedrooms and baths are in a separate guest wing with its own kitchen and entrance. There is also a large media room on the first floor. The home's prime south-of-the-highway location is near every desirable Village amenity and of course, the ocean beaches. $7000/April I August 26th-September 9th $15,000 I September $20,000

Bridget Terry
(6314667118) ) ) ) ) ) ) ) ) )

53 Tanners Neck Lane
$105,000

Westhampton, NY
Rental
Bedrooms: 6
Bathrooms: 8.5
Web ID: 3582560

Discover unmatched luxury in Westhampton at this custom built, gated, new construction, meticulously designed for the ultimate Hamptons experience. This expansive residence is set back from the road and boasts six bedrooms, seven full baths, and two half baths, offering ample space for every occasion. With over 5,600 square feet of main living space, not including a fully finished lower level, the home is perfect for both relaxation and entertainment. The grand double-height entry foyer, and living room provide a breathtaking view of the vast backyard, setting the tone for the elegant living experience within. The fully stocked, gourmet eat-in kitchen features an oversized center island and top-of-the-line Wolf appliances, including a gas range, wall oven, microwave, and a custom coffee bar. Dual dishwashers, sinks, and a wine fridge complete this culinary haven. On the first floor, you'll find a versatile den ideal for a home office or cozy retreat,...

Ashley J Farrell
(6316808001) ) ) ) ) ) ) ) ) )

24 Settlement Ct Ct
$105,000

East Hampton, NY
Rental
Bedrooms: 4
Bathrooms: 4
Web ID: 3577400

Katherine Casey
(9176452696) ) ) ) ) ) ) ) ) )

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

Water Mill
$100,000

Water Mill, NY
Rental
Bedrooms: 5
Bathrooms: 5.5
Web ID: 758247

This 5,000 +/- sf gambrel home on 1+/- acre in the heart of Water Mill is moments away from Bridgehampton Main Street and less than 5 miles away from ocean beaches. This open-concept 5 bedroom, 5.5 bath home is filled with natural light. The first floor features a great room with double-height ceilings, a gourmet eat-in kitchen with stainless steel appliances, a formal dining room, a spacious primary suite, 2 additional bedrooms with a shared bath, and walls of glass leading to the spacious back deck. The second level features 3 ensuites with renovated marble baths. The fully finished basement offers 2 game rooms and ample storage. The grounds feature lush landscaping, a heated pool, and a har-tru tennis court. This exquisite, one-of-a-kind summer rental is not to be missed.

April Rental: $40,000
May Rental: $60,000
MD - LD Rental: $275,000
June Rental: $65,000
July Rental: $100,000
July / Aug Rental: $220,000
August - LD Rental: $120,000
September Rental: $70,000

Christopher J Burnside
(516) 521-6007

Aubri Peele
(631) 252-5434

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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