506 Hamptons Rentals

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East Hampton
$80,000

East Hampton, NY
Rental
Bedrooms: 4
Bathrooms: 3.5
Web ID: 905709

Situated on a sprawling 2.39+/- private acres in East Hampton, this stunning gated property features 4 bedrooms and 3.5 baths with a 20 X 40 heated pool, pool house, basketball and your own private tennis court. A two-story living room with a fireplace, glass sliders, and oversized windows impresses upon entering. The open-concept floor plan flows seamlessly from living room to dining area and into the modern kitchen with professional chefs kitchen with stainless steel appliances. There are two luxurious primary suites one on each floor plus two additional guest bedrooms each with two queen size beds providing ample space, comfort and luxury for family and friends. The first-floor primary suite has a gorgeous marble bath with a spa tub, stream room and glass shower and opens to the pool deck. The second-floor primary bedroom with en-suite bathroom also in marble, features a soaking tub, glass shower, and...

MD - LD Rental: $185,000
June Rental: $50,000
July Rental: $80,000
July / Aug Rental: $160,000
August - LD Rental: $85,000
September Rental: $50,000
Year Round: $250,000

James Blueweiss
(631) 903-6133

Oregon Rd
$80,000

Cutchogue, NY
Rental
Bedrooms: 6
Bathrooms: 8
Web ID: 802499

Don't miss your chance to rent this unparalleled estate, nestled on 5 picturesque acres among the region's most prestigious vineyards.This magnificent home is a perfect blend of elegance and tranquility, ideal for those seeking a refined living experience.Spanning an impressive 7,000 sf, the residence is designed with sharp attention to detail. Floor-to-ceiling windows flood the space with natural light and provide breathtaking views of the surrounding vineyards. Featuring six generously sized bedrooms and six opulent bathrooms, ensuring ample space and privacy for everyone.The expansive roof deck is a standout feature, offering panoramic views that stretch across thevineyards to the Long Island Sound. A beautiful gunite heated pool in the courtyard with firepit and entertainment space. This serene setting is perfect for both entertaining guests and enjoying quiet moments.This is a perfect house to share with friends and family. Two-week availability; monthly availability. $80K per month.

Lisa B. Gillooly
(6312518644) ) ) ) ) ) ) ) ) )

N Quarter Road
$80,000

Westhampton, NY
Rental
Bedrooms: 4
Bathrooms: 3
Web ID: 3592148

Your Hamptons Retreat awaits! Spend Summer 2025 in this chic, contemporary, one level home which enjoys 4 bedrooms & open floor plan across a cozy, sun drenched living space from its western sun exposure. Both primary & junior primary en suite bedrooms are fitted with sliders that lead to the rear yard's outdoor decking. A lower level game room is perfect for any rainy day activities. The remodeled, handsome kitchen and dining rooms flow seamlessly to a grand outdoor space, picture perfect for entertaining, equipped with Sonos Sound System. The expansive deck encompasses an inviting, heated pool (protective fence available) and is enhanced with canopied dining space. An impressive grilling station along with the North\South Har Tru tennis court make for a summer holiday filled with activity and fun! Less than 3 miles to the bustling village of Westhampton Beach, shops and ocean beaches. Available for 2025., Additional information: Appearance:excellent,ExterioFeatures:Tennis

Maria C. Cunneen
(6314457890) ) ) ) ) ) ) ) ) )

Village Of Southampton
$80,000

Village of Southampton, NY
Rental
Bedrooms: 5
Bathrooms: 4
Web ID: 735460

A wonderful south of the highway location in the Village estate area. The immaculate and stylish five-bedroom house features a living room with fireplace and beamed cathedral ceiling, handsome library/media room, dramatic dining room with curved glass wall, four baths and sauna/steam bath. Master suite with cathedral ceiling fireplace and steam bath. Two of the 5 bedrooms are located on the walk-out lower level with media extra sitting room. Central air conditioning and new Sonos sound system. The landscaped one-acre grounds feature rolling lawns and a courtyard with heated swimming pool, Jacuzzi, gazebo and studio above garage. Minutes to Coopers Beach. Listing ID: 735460

MD - LD Rental: $195,000
June Rental: $40,000
June/July Rental: $115,000
July Rental: $80,000
July / Aug Rental: $165,000
August - LD Rental: $90,000
September Rental: $40,000
Winter Rental: $140,000
Year Round: $295,000

Village Of Sag Harbor
$80,000

Village of Sag Harbor, NY
Rental
Bedrooms: 5
Bathrooms: 4
Web ID: 736852

Circa 1830 and completely restored in 2015, this stunning, beautifully appointed home is just a short stroll to Main Street restaurants and shops. The first floor offers the fully outfitted chef's kitchen, a separate formal dining room, a very spacious living room and a quiet office. The laundry is conveniently located off the kitchen in the sun/mud room. Upstairs, you find the primary ensuite bedroom with gas fireplace and two additional bedrooms with a full bathroom. An added bonus is the third floor media and game room. The lushly landscaped garden offers privacy at the heated salt water pool and patio complete with a terrace dining area. A separate, nicely furnished pool cabana with a full bathroom and loft offers additional living space and an oversized outdoor shower. This home is elegant and gracious but at the same time inviting and comfortable. Listing ID: 736852

July Rental: $80,000
July / Aug Rental: $165,000
August - LD Rental: $95,000

Maureen J Geary
(631) 903-6167

Sag Harbor
$80,000

Sag Harbor, NY
Rental
Bedrooms: 5
Bathrooms: 4.5
Web ID: 876286

RR#:201499 Spend summer in the Hamptons at a quiet cul-de-sac in Sag Harbor at this 5-bedroom, 5.5 bathroom countryside estate that enjoys equal amounts of privacy and access to the Hamptons' nearby beaches, golf, dining, and shopping. A thoughtfully decorated, elegant decor blends with rustic accents to create a sophisticated, welcoming atmosphere. The master suite features a marble bath with air jet tub and separate shower. The finished lower level of the home includes a gym, home theatre, jacuzzi bath and steam shower. Outdoors, a sunken 40x18 gunite swimming pool, hot tub, outdoor shower, screened porch, covered dining veranda and vine-covered pergola with fire pit await amid lush landscaping and plenty of room for relaxing and entertaining. So close to reserve, trails to fresh water Trout Pond, marinas, secluded bay inlets and Foster Memorial Long Beach for paddle boarding and kayaking while Sag Harbor Village is...

July Rental: $80,000
July / Aug Rental: $180,000
August - LD Rental: $90,000

Cynthia R Barrett
(631) 537-4322

Bayfield Lane
$80,000

Westhampton Beach, NY
Rental
Bedrooms: 3
Bathrooms: 3
Web ID: 3480408

SOUTH OF HIGHWAY WESTHAMPTON BEACH UPDATED WITH GUNITE POOL. Escape to this cozy one-level home in Westhampton Beach, ideally located just one block from the tranquil waters. This beautifully updated home with generous living space offers a perfect blend of comfort and sophistication. Spacious and airy layout, perfect for relaxation or entertaining. Modern European cabinetry in the kitchen and bathrooms, add a touch of elegance to your daily life. Primary bedroom with a luxurious king-sized bed. Second bedroom featuring a comfortable queen-sized bed. Third bedroom offers the flexibility of a king-sized bed or two twin beds. Stream your favorite shows and movies with our streaming television service on all TVs throughout the house, including all bedrooms. There is a large, state-of-the-art home office for those who work remotely or seek a quiet space. Outside you'll find a heated Gunite swimming pool, perfect for a refreshing dip or poolside relaxation. Attached...

Linda Zelin
(6312886900) ) ) ) ) ) ) ) ) )

38 Three Mile Harbor Drive
$80,000

East Hampton, NY
Rental
Bedrooms: 4
Bathrooms: 4
Web ID: 906085

RR# 22-1583. Enjoy sensational views over Three Mile Harbor and beyond from this dramatic waterfront home set high atop a freshly landscaped shy acre in Settlers Landing. The residence is set back on the property to offer both privacy and an exceptional vantage point for its 180-degree vistas. Recently renovated and professionally designed, the 4,100 sq ft interior features an open concept living and dining room with a soaring double-height wall of windows that create a dramatic theatre for the surrounding natural beauty. Sliders lead to a 1000+ SF furnished deck that extends the dining, lounging and entertainment space to the outdoors. A Sonos indoor/outdoor music system enhances the seamless environment. Three spacious bedrooms and two full bathrooms complete the first level. An expansive ensuite primary bedroom on the second level features a sitting area with fireplace, a private balcony and floor to ceiling windows that...

January Rental: $25,000
February Rental: $25,000
March Rental: $25,000
April Rental: $25,000
May Rental: $30,000
June Rental: $60,000
July Rental: $80,000
August - LD Rental: $80,000

Robert Stearns
(631) 771-5317

John Scott JT Thomas
(631) 771-5327

36 John Street
$80,000

Village of Sag Harbor, NY
Rental
Bedrooms: 3
Bathrooms: 5
Web ID: 913469

Ideally located on the tranquil waters of Upper Sag Harbor Cove with a private dock and waterside pool, this Sag Harbor Village summer house is only one block to the Main St sidewalk for direct access to restaurants, shopping, and Long Wharf. The magic happens outside where sunsets can be enjoyed from the patio furnished with ample seating, umbrellas, and gas grill. This beautiful traditional home is bathed in natural sunlight from an abundance of sliding glass doors on 2 levels. The open floor plan boasts a large kitchen with granite counters, 4 burner Wolf range, rolling butcher block island, wine fridge, and stainless steel appliances. It leads to the living room with a big comfortable sectional sofa and dining for 4. The first level primary suite with tile bathroom and stall shower has views over the pool and the water beyond. A convenient den with ensuite bathroom and access...

August - LD Rental: $80,000

Clare J Tenkarian
(631) 725-5586

25 Pleasant Lane
$80,000

Village of Southampton, NY
Rental
Bedrooms: 4
Bathrooms: 3.5
Web ID: 879602

Be the first to enjoy the immaculate high-end renovation! This pristine house sits on a shy half acre property located on a peaceful Southampton Village street close to the best beaches, renowned restaurants and stores. Enter the home to an inviting entry foyer which flows into a gorgeous new open floor plan with large new windows that invites an abundance of light into its interior and new mahogany floors. The first floor comprises of a formal living room, which opens to an outdoor sitting area for perfect al fresco entertaining, a large scale family room with a wood burning fire-place, a formal dining room and a brand new gourmet kitchen with quartz counter tops, a center island and state-of-the-art appliances: Wolf range, Subzero refrigerator, garbage disposal and a Miele dishwasher. The fully re-designed powder room, laundry and mud room complete the main floor. On the second floor you...

May Rental: $30,000
MD - LD Rental: $200,000
June Rental: $40,000
July Rental: $80,000
August - LD Rental: $90,000
Winter Rental: $60,000
Year Round: $260,000

Lillian A Holtzclaw
(631) 204-2430

127 Seascape Lane
$80,000

Sagaponack, NY
Rental
Bedrooms: 3
Bathrooms: 3.5
Web ID: 754727

Down a flag drive is a magical spot bordering a farm. The property offers sweeping views and sounds of the ocean waves. You are greeted by a stand of hydrangea and flowering trees. This 3 bedroom 3 and 1/2 bath home was designed by a Southampton architect. The open floor plan offers lots of light and French Doors to let the outside inside. The first floor has a living room with an especially tall fireplace and dining area. There is a state of the art kitchen open to a sunroom for dining and relaxing. A pantry, laundry room and half bath are off of the kitchen. There is a library that could work for additional sleeping with a full bathroom. Second floor has master bedroom bathroom suite with a deck that provides magnificent views, two additional bedrooms and hall bathroom, and...

MD - LD Rental: $200,000
June Rental: $45,000
July Rental: $80,000
August - LD Rental: $100,000

Leslie Hillel
(631) 771-5311

Trumans Path
$79,000

East Marion, NY
Rental
Bedrooms: 3
Bathrooms: 3
Web ID: 3471559

Cape-Cod-Style Cedar-Shingle House situated on edge of low bluff. Wooded lot with 2nd-story master bedroom suite/deck. Fantastic 180-degree views of Gardiner's Bay, Bug Lighthouse, Shelter Island, Orient Village and East Hampton with 150-feet of private sandy beach and boat mooring. Permit #0049., Additional information: Appearance:Excellent, Interior Features:Separate Thermostat

Anna Carlino CBR
(6315534174) ) ) ) ) ) ) ) ) )

Water Mill
$78,000

Water Mill, NY
Rental
Bedrooms: 4
Bathrooms: 3
Web ID: 736759

RR# RP231095. Upside down modern totally renovated. This 4 bedrooms 3 baths is beautifully decorated. Enjoy an acre of privacy on a very quiet street. Additional amenities includes pool, top of the line appliances, one car garage and more. Listing ID: 736759

Year Round: $78,000

Amelia M Doggwiler
(631) 204-2426

Newtown Road
$78,000

Hampton Bays, NY
Rental
Bedrooms: 2
Bathrooms: 2
Web ID: 3548155

Year Round Serenity Awaits This private, waterfront property offers expansive views of Squires Pond and the Peconic Bay. Enjoy easy access to Squires Pond where you can Kayak or Canoe. Relax with your morning coffee while watching the swans swim by. Large Patio with Bar Area and Dining Area for outdoor entertaining. Centrally located to ocean beaches, Peconid Bay beach, walking trails, Good Ground Park and the best restaurants and shopping the Hamptons has to offer.

Doranne Telberg
(9145820793) ) ) ) ) ) ) ) ) )

128 Newtown Lane
$77,000

Village of East Hampton, NY
Rental
Bedrooms: 4
Bathrooms: 3.5
Web ID: 869249

This stunning East Hampton Village classic features a large open floor plan with chic living room and cozy den space divided by a double-sided gas fireplace. A sun-filled custom kitchen is outfitted with a social center island and inviting dining spot. Glass sliders open bring you to the back and side yard lounging and dining areas. Meticulously landscaped gardens and lush lawn lead to a glorious heated pool. A gracious junior primary guest room and powder room finish the main floor. The second level contains the primary suite with vaulted beamed ceiling overlooking the backyard as well as two additional guest rooms and a full bath. The lower level entertainment space boasts a large screen TV, relaxing sectional sofa and regulation sized pink pong table. Within a few steps of renowned shopping, restaurants, the East Hampton train station and Hampton Jitney stop, this chic oasis of...

January Rental: $10,000
February Rental: $10,000
March Rental: $15,000
April Rental: $20,000
July Rental: $77,000
August Rental: $77,000
October Rental: $15,000
November Rental: $15,000
December Rental: $15,000

John Scott JT Thomas
(631) 771-5327

Robert Stearns
(631) 771-5317

Sunset Avenue
$75,000

Westhampton Beach, NY
Rental
Bedrooms: 4
Bathrooms: 3
Web ID: 3581865

This beachy chic renovated home is less than one mile to the restaurants and shops of the Village of Westhampton Beach and two miles to Rogers Beach The immaculate home includes an open living area, three bedrooms, two and one-half baths, and a den/office or fourth bedroom with sleeper couch. Outdoors, relax in the fenced in yard with heated pool, outdoor shower, and decking for al fresco dining and barbecues. A perfect Hamptons retreat. *NOTE: min of 3 mos lease for winter; May 1-15 rate-$5500, Additional information: year rent:7500

Geraldine N. Wyman
(6315252227) ) ) ) ) ) ) ) ) )

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