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48 Skinner Street
$20,000

Village of Southampton, NY
Rental
Bedrooms: 3
Bathrooms: 1
Web ID: 907743

In the heart of Southampton Village, on a quiet tree lined street you'll find this crisp fresh 3 bed 1 bath charming cottage with eat in kitchen, living and dining rooms, laundry room with deck for outside dining overlooking a fully cleared side yard. Walk to the Village!.

May Rental: $7,000
MD - LD Rental: $50,000
June Rental: $12,000
July Rental: $20,000
August Rental: $20,000
August - LD Rental: $20,000

Dennis Gallagher
(631) 771-5309

49 Arbutus Road
$50,000

Shinnecock Hills, NY
Rental
Bedrooms: 5
Bathrooms: 4
Web ID: 755073

Rental Reg. # RP201765: Designer modern home set on a private acre in Southampton. This architectural gem features three floors of living space, each floor with additional outdoor terrace/deck areas allowing for seamless enjoyment to the open air. The top floor offers a comfortable den/media/bonus room area with a full bath, a large lounging deck as well as a small balcony. The main floor contains a spectacular chef's kitchen with outdoor dining space, a full bathroom, and large open living/dining area with direct staircase access to the pool area. The lower level offers an ensuite primary suite as well as three additional guest rooms and full bathroom. A large changing/wet area opens directly to the lushly manicured backyard, complete with heated pool and sun-soaked lounging areas. Listing ID 755073.

January Rental: $10,000
February Rental: $10,000
March Rental: $10,000
April Rental: $10,000
May Rental: $15,000
MD - LD Rental: $115,000
June Rental: $20,000
July Rental: $50,000
August - LD Rental: $50,000
September Rental: $20,000
November Rental: $15,000
December Rental: $15,000

John Scott JT Thomas
(631) 771-5327

Robert Stearns
(631) 771-5317

492 East Hampton Sag Harbor Turnpike
$185,000

Wainscott, NY
Rental
Bedrooms: 5
Bathrooms: 5.5
Web ID: 889464

Rental Registry #24-407. Ideally located between the villages of East Hampton and Sag Harbor is the perfect summer getaway for family and friends. Take the 375-foot-long private driveway to this beautiful and secluded 4,800 sq ft home, situated on a quiet 1.5 acres that has so much to offer by way of both luxury and entertainment. As you enter the house there is an expansive great room filled with natural light. The open kitchen was designed with a great open floor plan which is perfect for entertaining. The main floor primary bedroom is en suite with a private deck, walk-in-closet, double sinks and a soaking tub. There are 3 additional en suite guest bedrooms that are all nicely-appointed on the main floor. The finished lower level with full egress is a wonderful bonus. There is an oversized en suite guest bedroom, home theater, office space, wet bar, cedar closet and...

Year Round: $185,000

Michael Petersohn
(631) 771-5336

Cristina Matos
(631) 204-2408

5 Orchard Lane
$96,000

Springs, NY
Rental
Bedrooms: 3
Bathrooms: 2.5
Web ID: 917628

This three bedroom 2 full and 2 half bath rental sits in clear water beach. The houes features a pool, hot tub, expansive deck, garage, finished basement, and spacious living.

Year Round: $96,000

Jared Schiavoni
(631) 537-4337

Mitchel L Natter
(631) 903-6154

5 Anthony Lane
$6,000

Quogue, NY
Rental
Bedrooms: 5
Bathrooms: 4.5
Web ID: 737855

Beautiful Quogue South home on a quiet private lane. The mahogany front porch with tranquil rocking chairs awaits. A refresh of new furniture, rugs, curtains, and paint was recently completed. The first floor is open and light filled and includes a living room with a soaring cathedral ceiling, a great room with chef's eat-in-kitchen and top-of-the line appliances, a dining area, separate office and laundry room. A first floor primary suite with a sitting area completes the lower level. The second floor includes three ensuite bedrooms and a fourth guest bedroom. The backyard hosts a heated gunite pool with blue stone patio and a 100 year old barn that has been restored for your entertainment. The barn includes a pool table and outdoor shower. Close by is the Quogue Village Beach. Listing ID #737855

January Rental: $6,000
February Rental: $6,000
March Rental: $6,000
April Rental: $10,000
November Rental: $10,000
December Rental: $6,000

Lauren A Battista
(631) 288-5534

5 Marlin Drive
$60,000

Amagansett, NY
Rental
Bedrooms: 4
Bathrooms: 2.5
Web ID: 755138

Rental Registration # 23-158. This wonderfully decorated contemporary home, located just two blocks from prime Atlantic Ocean beaches in the Amagansett Dunes, is a super chic 4 bedroom, 2.5 bathroom home. The 2-story home has an upside-down configuration affording wonderful views of the unobstructed natural dunes from the main entertaining areas. The upper level open-style great room is complimented with stylish cathedral beamed ceilings and features a brand-new kitchen, large island, separate dining area, comfortable living room with fireplace and a half bath. An expansive outdoor deck extends the living space beautifully with a large sectional sofa, sunken hot tub, built-in grilling station and outdoor dining table. The upper floor primary bedroom suite, also with high ceilings, contains a large marble bathroom, walk in closet, gas fireplace and private balcony. The main floor opens with a welcoming entry foyer, 3 spacious bedrooms each with sliding doors allowing direct access...

January Rental: $6,000
February Rental: $6,000
March Rental: $6,000
April Rental: $10,000
May Rental: $15,000
MD - LD Rental: $140,000
June Rental: $25,000
July Rental: $60,000
July / Aug Rental: $100,000
August - LD Rental: $60,000
November Rental: $7,000
December Rental: $7,000

John Scott JT Thomas
(631) 771-5327

Robert Stearns
(631) 771-5317

5 Mill Race
$25,000

Hampton Bays, NY
Rental
Bedrooms: 4
Bathrooms: 2.5
Web ID: 755870

Lovely rental in Harbor Colony that offers a private bay beach. This spacious 4 bedroom, 2.5 bath home has a large living area, open eat-in kitchen, den, dining room, and a 2 car attached garage. The large yard has a patio surrounding a heated pool and deck with a natural gas grill. The home has been newly-painted and furnished. Minutes to Ocean beaches, waterfront restaurants and town. Listing ID: 755870

MD - LD Rental: $70,000
June Rental: $20,000
July Rental: $25,000
August Rental: $30,000
August - LD Rental: $32,500

Maritza Jimenez
(631) 204-2411

5 Spinnaker Way
$75,000

Southampton, NY
Rental
Bedrooms: 6
Bathrooms: 6.5
Web ID: 736830

Located on an oversized 2.42+/- acre parcel on a cul-de-sac in the North Sea area of Southampton, this stunning traditional with a lake view and bright, modern interiors is the perfect Hamptons vacation home. It offers proximity to North Sea Beach, Southampton Village, and renowned Atlantic Ocean Beaches. The residence features 6 en suite bedrooms, 6.5 full baths and a chef's kitchen which opens to an exceptional family room with a wood burning fireplace below a 75' wall mounted TV monitor. Proper living and dining rooms are provided for more formal entertaining. The residence has sound throughout and has numerous smart TV's as well as multiple Sub Zero / Wolf appliances integrated within custom kitchen cabinetry. A pristinely finished lower level features a media room with Sonos surround sound, a foosball table and workout equipment as well as a complete, separate bedroom/ensuite bath with private...

July Rental: $75,000
July / Aug Rental: $150,000
August Rental: $80,000

Christopher J Burnside
(516) 521-6007

51 Egypt Close
$300,000

Village of East Hampton, NY
Rental
Bedrooms: 5
Bathrooms: 4
Web ID: 899212

Rare find. Located on coveted quiet lane SOH. Moments to all village amenities, ocean beaches and Maidstone Golf Club. Complete remodel in 2023, interior and exterior, tastefully decorated w/all new furnishings and accessories. Formal living/dining room, eat-in kitchen, gym/yoga room, bar room, Primary, Jr Primary and Guest bedrooms all en-suite on main level, 2 additional bedrooms, fully bath and office located on upper level. Beautifully landscaped with tall mature perimeter privet ensures privacy for expansive front and back lawns. Stone patio with built-in grill, fireplace, 20' x 40' heated gunite pool, spa and enclosed outdoor shower.Listing ID:899212

MD - LD Rental: $300,000
Year Round: $450,000

Dennis Gallagher
(631) 771-5309

51 White Oak Lane
$36,000

Southampton, NY
Rental
Bedrooms: 5
Bathrooms: 3.5
Web ID: 901746

RP# 230300. Welcome to a one-of-a-kind charming home in the Hamptons! This stunning first time rental 3800+/- sf home, boasts a perfect blend of quality and style that will take your breath away. As you step inside, you'll be greeted by a tranquil setting that immediately sets the tone for the upscale lifestyle that awaits. The classic covered front porch and cedar shingled exterior are just the beginning of the architectural beauty you'll find here. Inside, a dramatic 2-story living room, bathed in natural light from its southern exposure, features a wood-burning fireplace that creates an inviting atmosphere perfect for cozy nights in. The eat-in kitchen is a masterpiece of design, featuring marble countertops and top appliances. The first floor also includes a formal dining room, powder room, and a spacious master suite. Upstairs, accessed by front or back stairways, you'll discover four double bedrooms, two full baths, and a...

MD - LD Rental: $85,000
July Rental: $36,000
July / Aug Rental: $65,000
August - LD Rental: $37,000

Cristina Matos
(631) 204-2408

52 Manor Lane South
$30,000

Springs, NY
Rental
Bedrooms: 4
Bathrooms: 3
Web ID: 758200

Rental Registration # 24-17 Expires January 8th, 2026 Charming picturesque country cottage surrounded by mature lush landscaping with specimen plantings and perennials on 1/2 acre. Tastefully decorated throughout. Main level offers living room with fireplace, formal dining room and gourmet kitchen that overlook beautiful backyard gardens and brick patio perfect for alfresco dining and entertaining and a generous Primary Suite with full bath. Upper Level provides privacy for 2 additional bedrooms with shared full bath. Lower Level offers family room, an authentic 'Tavern' bar and a fourth bedroom and full bath. This home is a tranquil experience perfectly situated between the bay and ocean beaches with a Marina, Maidstone Park, Springs dining and markets nearby. Listing ID: 758200

June Rental: $20,000
July Rental: $30,000

Dennis Gallagher
(631) 771-5309

541 Wainscott Northwest Road
$60,000

Wainscott, NY
Rental
Bedrooms: 4
Bathrooms: 4
Web ID: 912584

Rental Reg # 24-1045 Your Summer oasis awaits. Situated minutes away from both Sag harbor and East Hampton Villages and it's beaches, this renovated 4 bedroom and 4 bathroom with Pool and basketball is ready to embrace all the fun that summer has to offer. The gourmet kitchen features Silverstone countertops, a new Viking stove and Bosch dishwasher, and overlooks the dining area large enough to seat family and guests as they enjoy one of the two gas fireplaces. There are two en-suite bedrooms with renovated bathrooms as well as two other bedrooms and a shared bathroom on the main floor. There is also a large living/family room with its own gas fireplace and patio doors that flow seamlessly to the outdoor space. It's all about the outdoor living as this home boasts an expansive resort style covered blue stone patio which features a commercial grade outdoor...

MD - LD Rental: $150,000
June Rental: $35,000
July Rental: $60,000
July / Aug Rental: $120,000
August - LD Rental: $65,000

David Tenenbaum
(631) 771-5322

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

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

57 Sammy S Beach Road
$85,000

East Hampton, NY
Rental
Bedrooms: 4
Bathrooms: 5.5
Web ID: 878838

Rental Reg. # 23-719 Offered for the first time. Stunning new construction directly on Gardiners Bay beach front. Sparkling bright interiors and high end, clean finishes and furnishings throughout. Main level has a large open concept living/ dining and kitchen, office/ den with full bath, another 1/2 bath and laundry and a custom built in bar with wine fridge. Floor to ceiling custom doors open to a massive back deck with Restoration Hardware furniture, gas and charcoal grills and outdoor shower. Step off the deck into the sand and to the path leading to the beach. Upstairs is a huge gallery landing with floor to ceiling doors leading to a large deck on the front overlooking Three Mile Harbor and Sammy's Beach Preserve and an even larger deck on the back looking out to Gardiners Bay, The North Fork, Shelter Island and Gardiners...

June Rental: $75,000
July Rental: $85,000
August Rental: $100,000

Philip Judson
(631) 771-5328

59 North Captains Neck Lane
$60,000

Village of Southampton, NY
Rental
Bedrooms: 4
Bathrooms: 3.5
Web ID: 879997

Estate-like, lush privet hedges surround this immaculate, Traditional situated on a beautiful .46-acre property on a tranquil lane in Southampton Village. Stylish, light-filled rooms, include a spacious living room, a cozy den/family room with fireplace and a separate formal dining room. A recently-renovated open kitchen with new stainless steel appliances, includes a breakfast area with sliding doors leading out to the spacious deck. The home offers 4 bedrooms, 3.5 baths, including an impressive master suite. Amenities include glistening wood floors, central air-conditioning, a full basement and an attached 2 car garage. You can relax outside enjoying the spacious lawn, mature landscaping and gather around the large sun-filled deck overlooking the 20x40 heated pool, just perfect for entertaining, or just sit on the front porch and relax your summer away. Just minutes to Coopers Beach and less than a mile to restaurants, boutiques and all that...

January Rental: $12,000
February Rental: $12,000
March Rental: $12,000
April Rental: $12,000
May Rental: $15,000
MD - LD Rental: $145,000
June Rental: $29,000
July Rental: $60,000
July / Aug Rental: $115,000
August - LD Rental: $65,000
September Rental: $25,000
December Rental: $15,000

Cristina Matos
(631) 204-2408

62 Old Montauk Highway
$25,000

Amagansett, NY
Rental
Bedrooms: 3
Bathrooms: 2
Web ID: 736918

Hamptons Summer Rental Reg. # 24-1058 Charming renovated Hamptons Beach House in prime Amagansett South location! Have it all this summer with the village amenities and wide sandy beach just seconds away. This private hidden gem offers 3 bedrooms, 2 baths, a huge sun porch with pullout for guest overflow, open living room with vaulted ceilings, bright open marble & stainless steel kitchen, a separate formal dining room and lovely landscaping. Central air and an automatic generator too. No need for a car since the side walks lead you to the shops, transportation, restaurants and to the ocean. Beautifully decorated and very private. The most convenient location at a fantastic price.Listing ID: 736918

MD - LD Rental: $75,000
June Rental: $20,000
July Rental: $25,000
August - LD Rental: $35,000

James J MacMillan
(631) 267-7171

64 Moses Lane
$170,000

Village of Southampton, NY
Rental
Bedrooms: 7
Bathrooms: 7.5
Web ID: 874353

The perfect rental home in the Hamptons! Located just north of Hill Street and in close proximity to the estate section of the Village of Southampton is this modern traditional with gunite pool, spa, and pool house built in 2016 by Farrell. It is well sited on a prime rectangular and level .81 acre +/- parcel. The house comprises 7 bedrooms, 7 full and 2 half baths. The generous entry foyer leads to double barn doors opening into a grand open floor plan which includes a spacious living room and family room with fireplace; extra height windows and oversized sliding doors allowing pure natural light via southeastern exposures. The main level includes a large master bedroom w/ ensuite bath. Featured in the gourmet chef's kitchen is a Wolf 8-burner range and Subzero refrigerator, 2 wall ovens, 2 dishwashers, wine fridge and a breakfast area with view to the backyard. The...

Custom Rental: $245,000
Winter Rental: $170,000

Kimberly Kakerbeck
(631) 537-4351

Juliana Frei
(212) 396-5886

640 Orchard Street
$13,000

New Suffolk, NY
Rental
Bedrooms: 3
Bathrooms: 2
Web ID: 860643

This classic updated 19th century home in the heart of historic New Suffolk is just moments to one of the North Fork's best bay beaches, plus two renowned local restaurants. It offers stylish living spaces; living room, den, dining room, eat-in kitchen, 3 bedrooms and 2 baths. Central air conditioning. Many antique details and original wood floors add to the charm. The wrap-around porch invites summer lounging, as does the spacious backyard. Listing ID #860643

May Rental: $6,000
June Rental: $8,000
August - LD Rental: $13,000
September Rental: $8,000
October Rental: $6,000
Winter Rental: $4,500

Marianne Collins
(631) 734-2957

643 Stephen Hands Path
$65,000

East Hampton, NY
Rental
Bedrooms: 4
Bathrooms: 3.5
Web ID: 735901

Rental Registration #: 24-1271 Welcome to Camp Courtside the ultimate compound for summer sun and fun! Just minutes to East Hampton Village and world-class ocean beaches, this bright open immaculate contemporary is a sports lovers paradise. Start your day on your private tennis/pickleball/basketball court and finish lounging on your expansive mahogany deck complete with oversize crystal clear blue pool, 6 person hot tub, outdoor shower and a fire-pit with 4 cozy Adirondack chairs. Inside the brand new chef's kitchen has all the latest appliances and overlooks the living/dining great room with a double-height stone fireplace, skylights that bathe the interior in natural light and multiple glass sliders that open to the pool, lounge space and outdoor dining. There are four bedrooms (3 ensuite) all with cable TV and four new bathrooms. Behind a sliding barn door on the main floor are two well appointed guest rooms that share a hallway...

July Rental: $65,000
August - LD Rental: $70,000

James Blueweiss
(631) 903-6133

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