60 Hamptons Rentals

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Sag Harbor
$70,000

Sag Harbor, NY
Rental
Bedrooms: 4
Bathrooms: 4.5
Web ID: 908778

Moments from all that Sag Harbor Village has to offer, this luxuriously chic home features 4 bedrooms, 4 1/2 bathrooms, an inviting floorplan, heated saltwater gunite pool, and huge, private backyard. The entire home has been newly decorated in a Hamptons chic style. 1500sf of finished lower level space further enhances the enjoyment of the home. The beautifully landscaped and ultra private backyard allows plenty of space for lazing by the pool or entertaining with your outdoor kitchen for a perfect Hamptons summer. . Listing ID:908778

May Rental: $10,000
MD - LD Rental: $190,000
June Rental: $40,000
July Rental: $70,000
August - LD Rental: $80,000
September Rental: $30,000
October Rental: $15,000
November Rental: $10,000
December Rental: $10,000

Jeanne Galante
(631) 903-6184

Village Of Sag Harbor
$70,000

Village of Sag Harbor, NY
Rental
Bedrooms: 4
Bathrooms: 3.5
Web ID: 742725

Rental Reg. # R-24-0004 Designer's own newly renovated home is the perfect blend of village charm and modern amenities. Located equidistant to the beach and the village center, the house has a gracious open floor plan that makes summer entertaining ideal, with an easy flow to back deck and tastefully landscaped backyard. This 4 bedroom, 3 1/2 bath has it all: large spacious and light-filled bedrooms, modern designer bathrooms; fully-loaded gourmet kitchen with top-of-the-line appliances and a large comfortable living room with wood-burning brick fireplace and 40' 3D-HDTV. Master bedroom features en-suite bathroom with oversize glass shower and radiant heat floor as well as Romeo and Juliet balcony overlooking its own peach tree and heated gunite pool.. Additional conveniences include: large mudroom, double W/D, high speed wireless internet broadband, state of the art and super efficient 3-zone AC/heat, instant hot water, central vac, irrigation system, covered porch, garage,quiet street...

Custom Rental: $150,000
August - LD Rental: $70,000
September Rental: $30,000
Winter Rental: $45,000

Mary Ellen McGuire
(631) 537-4324

Timothy R. O'Connor
(631) 771-5321

Village Of Sag Harbor
$67,500

Village of Sag Harbor, NY
Rental
Bedrooms: 6
Bathrooms: 7.5
Web ID: 897595

Close to the Village, within a few blocks to a private community beach, and less than 1.5 +\- miles to Havens Beach in Sag Harbor, this stunning, modern farmhouse features 6 bedrooms and 7- and one-half baths across 3,800+\- sf. Multiples of sleek windows and oversized sliders create walls of glass in the grand, double-height living room with a fireplace that opens to the formal dining room and a designer chef's kitchen with a center island and counter dining. The spectacular primary en suite includes a vaulted-tray ceiling, a gas fireplace with a flat screen, and access to a large mahogany deck overlooking the back grounds. A separate guest wing on the 2nd level is accessed across the gallery bridge. Additional guestrooms and bathrooms are well-appointed with marble and contemporary fixtures. An extensive covered mahogany deck includes lounge and dining space, ceiling fans, an...

June Rental: $67,500

Sharman S. Peddy
(631) 903-6171

Dennis Gallagher
(631) 771-5309

Sag Harbor
$65,000

Sag Harbor, NY
Rental
Bedrooms: 5
Bathrooms: 4.5
Web ID: 736949

This 5BR chic and private Traditional home is stunning and surrounded by lush landscaping and beautiful gardens which backs on an 18 acre reserve. First floor features gourmet kitchen, open concept living space with dining areas with fireplace and bar, en suite guest room, office, play area, powder room and screened in porch. Second floor features master bedroom suite with walk in closet, master bath, and large spacious deck overlooking pool and pavillion and two guest bedrooms with shared bath. Finished lower level Includes large en suite bedroom, brand new gym, and washer/dryer. All bedrooms have tv's, sonos sytemss, Xbox and WiFi. Large covered pavillion features 2 flat screen tv's, large wooden bar, and stone fireplace overlooking heated pool and 7 person, 47 jet hot tub. Lastly, there is a large children's playground in the expansive back yard bordered by reserve.Listing ID: 736949

Custom Rental: $16,000
July Rental: $65,000
August - LD Rental: $70,000
September Rental: $35,000

253 Northside Drive
$65,000

Sag Harbor, NY
Rental
Bedrooms: 5
Bathrooms: 4
Web ID: 738997

Rental Permit# 200858 - Only few miles to the villages of Sag Harbor and Southampton this home is located in the Northside Hills Community. The five bedroom, four bath postmodern home was recently renovated. Its bright open floor plan offers a beautiful kitchen with stainless steel appliances, breakfast nook, dining area, living room with fireplace, and den/TV area with fireplace. The open floor plan allows easy access to a heated pool and har-tru tennis court. The lower level is finished with a rec-area, bedroom, bath, and office space. The gated property and mature plantings offer excellent privacy. This is your perfect Hamptons retreat. Listing ID: 738997

Custom Rental: $65,000
July Rental: $65,000

JB Jose B. DosSantos
(631) 903-6147

11 Sims Drive
$65,000

Sag Harbor, NY
Rental
Bedrooms: 3
Bathrooms: 3.5
Web ID: 736424

New construction. Just completed, this brilliant new dream home has been designed to maximize its beautiful location on Sag Harbor Cove. The bold 2,800 +/- sf interior of sleek living space offers three bedrooms and 3.5 baths. With walls of glass throughout, the light-filled gourmet eat-in kitchen opens to the living room with fireplace. Upstairs, the master suite features a large bathroom with pondviews , walk-in closet, fireplace, and an expansive deck. This level also has a guest bedroom with full bath, and an entertainment area overlooking the water. The third level of this modern masterpiece features a wraparound rooftop terrace, perfect for outdoor lounging.Exterior amenities include a spacious deck with heated gunite spa and outdoor kitchen with stainless built-in barbecue, sink, two burners, and storage cabinets. Deep water dock permits in place

August - LD Rental: $65,000

Christopher J. Burnside
(516) 521-6007

Aubri Peele
(631) 252-5434

5 Scrimshaw Drive
$63,000

Sag Harbor, NY
Rental
Bedrooms: 4
Bathrooms: 4.5
Web ID: 885714

First time available for rent, this pristine 4-5 bedroom with pool and privacy abutting reserve in the premier Whalebone landing waterfront community with community bay beach, cabana pavilion, tennis and beach volleyball. The newly refurbished 4,000sf home has all that you could wish for in a seasonal getaway in the Hamptons with easy access to ocean beaches, golf courses, Elizabeth Morton Wildlife Preserve, Southampton and Sag Harbor's village restaurants and shopping. The light-filled living-room, sitting room and dining room have french doors leading out to a substantial mahogany deck for outdoor entertaining that also extends to the pool area and lawn. Also, on the first floor is an oversized den/office, and a grand master suite with an ensuite newly renovated marble bathroom. The second floor has yet another sitting room for those that want their own privacy or kids space, a second master suite plus 2...

Custom Rental: $120,000
MD - LD Rental: $120,000
July Rental: $63,000
July / Aug Rental: $100,000
August - LD Rental: $65,000

Cynthia R. Barrett
(631) 537-4322

Village Of Sag Harbor
$60,000

Village of Sag Harbor, NY
Rental
Bedrooms: 4
Bathrooms: 3
Web ID: 874749

Recently renovated, architect owned 4 bedroom, 3 bath 1919 Dutch Gambrel reflects the historic Sag Harbor Village neighborhood while the interior has a modern open format with a connection to the garden and landscape. The interior is a wooden jewel box with white oak floors, walls and ceilings throughout the house. Large windows bring in light while connecting the space to the outdoors. On the first floor there is a comfortable living room with fireplace, separate dining room, master suite with spa like bathroom, and modern kitchen with stainless appliances and quartz counters. Off the living room is a large screened porch that transitions the space between indoors and outdoors. On the second floor is an en suite queen guest room and two guest rooms that share a bath, one with twin beds which could also function as an office, and another with a queen bed overlooking the garden. Outside,...

August - LD Rental: $60,000

Clare J. Tenkarian
(631) 725-5586

Village Of Sag Harbor
$60,000

Village of Sag Harbor, NY
Rental
Bedrooms: 3
Bathrooms: 2
Web ID: 875124

Located on a prime Sag Harbor Village street and close to a side walk that leads straight into Main St shopping and restaurants. This clean and bright Traditional home has been thoughtfully furnished throughout. 3 bedrooms and 2 bathrooms including a large master suite with private sitting area. Beautiful kitchen and bathrooms. Wonderful back yard with deck and heated gunite pool. Listing ID: 875124

August - LD Rental: $60,000

Clare J. Tenkarian
(631) 725-5586

28 Deerwood Path
$60,000

Sag Harbor, NY
Rental
Bedrooms: 4
Bathrooms: 4.5
Web ID: 890277

Welcome to a one-of-a-kind property located off Deerfield Road in the desirable private community of Northside Hills, a stone's throw from Water Mill, Sag Harbor and Bridgehampton. Sited on 1.3 acres, this gracious, 5,200+ sf stucco home offers soaring ceilings, wide hallways, and tall windows bathing each room in natural light. The majestic interior space is complimented by hardwood floors, triple crown molding, two stone wood-burning fireplaces and hand-carved wood beams adding warmth, sophistication, and character to this beautiful home. The grand entry foyer opens to a breathtaking living room with an overlooking Juliet balcony, formal dining room, intimate library / office and a large eat-in kitchen and family room. There are two Master Bedroom Suites (1st and 2nd floors), plus two Ensuite Guest Bedrooms, all with large walk-in closets. The large, heated Gunite pool with waterfall is flanked by stone terracing, perfect for entertaining, grilling...

August - LD Rental: $60,000
Two Week Rental: $38,000

Andrea L. Ackerman
(631) 537-4340

Elizabeth A. Phenis
(631) 537-4357

21 Cove Road
$60,000

Village of Sag Harbor, NY
Rental
Bedrooms: 4
Bathrooms: 3.5
Web ID: 736991

Architect's own striking and virtually brand new 4 bedroom 3.5 bath modern interior with a victorian exterior just totally renovated and expanded with harbor views, heated pool, boat mooring availability and water access across the street. Two long blocks to Sag Harbor's Main Street. Fabulous beach house with a wrap around porch, mahogany and stone patios, spectacular kitchen and baths in Sag Harbor Village's Redwood waterfront community with water views. The lower level great room is complete with a lounge area and flat screen for movies or streaming music, gym area and pool/pingpong table. Enjoy your water sports and serene lifestyle while, at the same time, have the convenience of village life. Close to both ocean and bay beaches.

MD - LD Rental: $160,000
July Rental: $60,000
July / Aug Rental: $120,000
August - LD Rental: $65,000

Cynthia R. Barrett
(631) 537-4322

Sag Harbor
$50,000

Sag Harbor, NY
Rental
Bedrooms: 5
Bathrooms: 5
Web ID: 833456

Rental Reg. # RP230862. In Sag Harbor, affectionately known as The Treehouse, this gut-renovated 5 bedroom home is truly an entertainer's paradise. Completely re-imagined inside and out, this getaway has it all. Featuring a grand entertaining floor complete with an open kitchen, a dining room as well as a living room with a fireplace, vaulted ceilings, and an outdoor deck. 5 bedrooms, sun room, and laundry room occupy the remaining floors, each promoting privacy and allowing for maximum natural sunlight throughout the day. Outdoors, a heated pool with pool house/bar awaits, surrounded by lush landscaping, a secondary outdoor dining area, and gas fire pit. Located minutes from Sag Harbor and Bridgehampton. Listing ID #833456

Custom Rental: $15,000
August Rental: $50,000

Sag Harbor
$49,000

Sag Harbor, NY
Rental
Bedrooms: 5
Bathrooms: 3.5
Web ID: 741471

Available summer 2023, extended season and other periods upon request. Sunsets over your own private wooded six+ acres personal sylvan reserve, set back from road and away from any visible neighbors, yet within a few minutes' to Mashashimuet Park/Otter Pond and Sag Harbor Main Street. Winding circular driveway leads to a five-bedroom, three and one half-bath, post-modern and approx. 4000+/- sq.ft. home. Double entrance doors open into a five-columned, spectacular three-story cantilevered ceiling living room with slate fireplace, flat screen mounted above fireplace entertainment center, restored antique mahogany baby-grand piano for sing-along, and two ecru overstuffed queen-size convertible couches and matching chaise lounge. Bricked terrace, newly lined heated pool and newly laid Har-Tru tennis court, all accessed through living room or master suite four French doors. Medieval style wood dining room table from Europe which seats 12, wood paneled grandfather clock and breakfront. Large country kitchen with all new...

MD - LD Rental: $139,000
June Rental: $30,000
June/July Rental: $75,000
July Rental: $49,000
July / Aug Rental: $105,000
August - LD Rental: $58,000
September Rental: $32,500
October Rental: $20,000
December Rental: $15,000
Short Term Weekly: $12,500
Year Round: $157,000

Christopher J. Burnside
(516) 521-6007

Aubri Peele
(631) 252-5434

Village Of Sag Harbor
$45,000

Village of Sag Harbor, NY
Rental
Bedrooms: 4
Bathrooms: 2
Web ID: 754580

Newly renovated - Wonderful Village home, within a short distance to all the shops, restaurants, and Wharf of Sag Harbor. 4 bedrooms, 2 bathrooms, beautifully furnished, well appointed kitchen, and roomy living room. Great deck area with very private and secluded heated pool with a salt water aqua pure cleaning system. Great value. Great location. New BBQ grill and New 50' flat screen TV! Have the summer you always dreamed about! . Listing ID: 754580

July Rental: $45,000
August - LD Rental: $55,000
September Rental: $15,000

Philip Judson
(631) 771-5328

Linley Pennebaker Hagen
(631) 725-5583

Sag Harbor
$45,000

Sag Harbor, NY
Rental
Bedrooms: 4
Bathrooms: 2
Web ID: 756366

Rental Reg. # RP230430. This shingled Cape styled home offers over 2,000 square feet of living space with an eat-in kitchen, dining room, living room, screened in porch, four bedrooms, and 2 bathrooms. Outdoors is a large patio with outdoor dining, heated gunite pool with bluestone surround and lounge area. A great summer rental in Sag Harbor. Listing ID: 756366

June Rental: $25,000
July Rental: $45,000

Richard Finder
(631) 702-7511

Sag Harbor
$45,000

Sag Harbor, NY
Rental
Bedrooms: 5
Bathrooms: 4
Web ID: 755119

Rental Reg. # RP170415 Spend your summer in this beautiful and completely renovated home with bay views. Step into the first floor of the house which features a large living room with wood burning fireplace, large dining room, and sunny gourmet eat-in kitchen with breakfast bar. Custom kitchen cabinets, Carrara marble countertops, and high-end stainless steel appliances. There is a bedroom on the main floor with sliding glass doors which opens to the deck overlooking the backyard with a gunite heated pool. The upper level has a large master bedroom suite with vaulted ceilings and 4 piece bathroom with jetted bathtub. 3 additional bedrooms at the upper level. The lower level of the house is finished and includes an additional bedroom which is ideal for a housekeeper or nanny. There are a total of 5 bedrooms in this house. The lower level has additional recreational space and laundry. All this...

Custom Rental: $90,000
July Rental: $45,000
August Rental: $45,000
August - LD Rental: $50,000

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