365 Hamptons Rentals

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27 Notamiset Road
$58,000

Quiogue, NY
Rental
Bedrooms: 4
Bathrooms: 3
Web ID: 905306

Rental Reg. #:RP220968 Nestled on a private road in the charming hamlet of Quiogue, this one-of-a-kind residence is available for $25,000 for any two-week period between July 1, 2025 and September 1, 2025. If tenant requires two consecutive two-week periods, there will be an additional $10,000 charge. Optimally set on a picturesque park-like acre, the property features four bedrooms, three baths, a heated gunite saltwater pool, and a pool house. The historic farmhouse home, originally built c.1900, underwent a brand-new renovation that blends modern amenities with classic charm. French doors, wall of glass sliders, and skylights provide an abundance of natural light throughout. The spacious all-glass living room with fireplace and the kitchen/dining areas open to a bluestone patio surrounded by a custom masonry enclosure, perfect for dining al fresco. Also on the first level is a guest bedroom, full bath, and laundry area. The second floor features the primary...

July Rental: $58,000
August Rental: $62,000
Two Week Rental: $25,000

William F LeMaire
(631) 288-5208

East Hampton
$57,500

East Hampton, NY
Rental
Bedrooms: 4
Bathrooms: 5
Web ID: 754342

Rental Registration #24-134 Located on 7 acres in the Northwest Woods in East Hampton, this 5 bedroom/6 bathroom single level home with 3 car garage and loft space is the ideal home for a family looking to have an unforgettable hamptons vacation. This private oasis has a large outdoor deck, oversized heated pool, outdoor shower and hot tub, and private tennis court. Looking for a game of family football or soccer? The newly added expansive lawn is the perfect spot. Inside, the 5 bedrooms each have a private full bathroom (including the loft space) for maximum comfort. The 900s sq. ft. loft space above the garage is perfect for those who need a little more space or privacy. The true family gathering spot though is the open plan living room and kitchen/dining room. Here all can gather for big dinners or to watch...

May Rental: $30,000
MD - LD Rental: $130,000
June Rental: $37,500
July Rental: $57,500
July / Aug Rental: $110,000
August - LD Rental: $57,500
September Rental: $30,000
October Rental: $30,000
Two Week Rental: $31,000

Philip Judson
(631) 771-5328

128 Water Mill Towd Road
$57,000

Water Mill, NY
Rental
Bedrooms: 2
Bathrooms: 2
Web ID: 865245

RR #RP220736 Enjoy this contemporary designed cottage, six minutes from Southampton Village. The calm, tranquil interior, large recreation room, lush garden and heated gunite pool make it perfect for Summer living. Listing ID:865245

MD - LD Rental: $72,000
July / Aug Rental: $57,000

John P Vitello
(631) 204-2407

Springs
$55,000

Springs, NY
Rental
Bedrooms: 3
Bathrooms: 2
Web ID: 737534

Rental Reg. # 24-106. This single-level traditional is privately situated on a beautifully landscaped property. The house features a living room with wood burning fireplace, dining area, renovated eat-in kitchen with radiant heat floor; primary bedroom with gas fireplace and radiant heat floor in primary bathroom, and two additional bedrooms and one bath. Additional amenities include central-air-conditioning; washer and dryer, sprinkler system, a large mahogany deck with marble dining table, gas grill, salt water heated pool and pool house. Listing ID: 737534.

MD - LD Rental: $65,000
July / Aug Rental: $55,000

JB Jose B DosSantos
(631) 903-6147

Philip Judson
(631) 771-5328

Shinnecock Hills
$55,000

Shinnecock Hills, NY
Rental
Bedrooms: 5
Bathrooms: 4.5
Web ID: 736046

RR# RP240229. Elegant, beautifully furnished and well-appointed post-modern, situated on a landscaped half-acre of property with a pool and tennis court. Living room with fireplace, sitting room with fireplace, formal dining room, kitchen with breakfast area, 5 bedrooms, 4.5 baths, CAC and a 2 car garage. Listing ID:736046

June Rental: $45,000
July Rental: $55,000
July / Aug Rental: $95,000
August - LD Rental: $65,000
Two Week Rental: $30,000
Year Round: $210,000

John P Vitello
(631) 204-2407

Shelter Island
$55,000

Shelter Island, NY
Rental
Web ID: 905943

Enjoy the calm life on Shelter Island in this Designer/Builder's chic 2 bedroom, 2 bath dream beach house down the street from the water and Wade's Beach, one of many Shelter pristine beaches where you can also kayak, paddleboard or sail. Amenities include, a new 2 car detached garage with a charging station, and bikes for island cycle touring, Outdoor shower, outdoor dining area and grill outback. Visit the many new restaurants, Leon 1909, Vine Street Cafe,The Pridwin, The Chequit, Rams Head Inn, Isola, Sunset Beach, Slice, Ecentric Bagel, shops, Music presented by The Perlman Music Program, or visit the Historical Society, Sylvester Manor. Take day trips to the North Fork vineyards and the south fork ocean beaches and towns. Have the quintessential summer here. Not to be missed.

Year Round: $55,000

Cynthia R Barrett
(631) 537-4322

Village Of Southampton
$55,000

Village of Southampton, NY
Rental
Bedrooms: 4
Bathrooms: 3
Web ID: 736461

Traditional 4 bedroom, 3 bath home located in a quiet community south of the highway. State of the art kitchen, breakfast nook, formal dining room and living room. Bright and comfortable. Pool, CAC, finished basement. Great location and the perfect vacation house. Listing ID: 736461

July Rental: $55,000
August - LD Rental: $65,000

John P Vitello
(631) 204-2407

Springs
$55,000

Springs, NY
Rental
Bedrooms: 3
Bathrooms: 3
Web ID: 832854

Rental Reg. # 23-407. Newly renovated 3 bedroom, 3-bathroom home situated just a stone throw away from a private beach in the quiet community of Springs, East Hampton. Beautiful outdoor spaces for entertaining and dining. This beautifully renovated home is just a 10-minute drive from Amagansett or East Hampton towns and ocean beaches and just minutes from great restaurants. Wake up to views of the bay from spacious master bedroom, with en-suite bathroom complete with soaker tub and walk-in shower. Light-filled living room has views of the water as well as new flat screen tv. Great place to relax after a day at the beach. Second floor has an eat-in kitchen with brand new appliances, a guest bathroom stocked with bath and beach towels, and a full-size laundry room. This floor also has a guest bedroom with walk-in closet and an additional bedroom which can be...

MD - LD Rental: $55,000

Michael Petersohn
(631) 771-5336

East Hampton
$55,000

East Hampton, NY
Rental
Bedrooms: 3
Bathrooms: 2.5
Web ID: 880363

Rental Reg# 23-582. Envision your dreamy summer in the Hamptons at this enchanting 3-bedroom, 2.5-bathroom farmhouse. Tucked away just beyond East Hampton Village, this cozy home invites you to create lasting memories. Imagine laughter-filled gatherings with cherished friends and quiet moments on the balcony with breathtaking views. And remember the convenience of being close to exclusive boutiques, organic farms, and the sun-kissed beaches that define the magic of the Hamptons. Listing ID: 880363

MD - LD Rental: $55,000

Raul Guazhambo
(631) 903-6148

Southampton
$55,000

Southampton, NY
Rental
Bedrooms: 5
Bathrooms: 4.5
Web ID: 754635

RR# RP201338. On a quiet cul-de-sac, this beautifully renovated, three-level home offers a mature landscaped, private setting on 1.8 acres surrounded by a Peconic Land Trust reserve. 4,000 sf of Ipe decking leads to your tennis court, heated pool, outdoor dining and significant entertaining space.With the rear yard facing east, you are ensured of brilliant sun from dawn to late afternoon. The spacious, open floor plan on the main level offers a sun-drenched great room, a separate den, a junior master suite, dining area and chef's kitchen featuring top of the line appliances, wine/beverage fridge, double ovens and much more. Walk out onto your beautiful deck from both the kitchen and living areas. On the top level you'll find a very spacious master bedroom and bath with two additional guest bedrooms joined by a double sink, jack and jill bathroom. Down to the walk-out, lower level...

MD - LD Rental: $140,000
June Rental: $25,000
June/July Rental: $70,000
July Rental: $55,000
July / Aug Rental: $115,000
August - LD Rental: $60,000

Maritza Jimenez
(631) 204-2411

Southampton
$55,000

Southampton, NY
Rental
Bedrooms: 4
Bathrooms: 4
Web ID: 735801

RR #RP240241. This charming and private waterfront cottage features a living room with vaulted ceilings and fireplace, as well as a library, dining area, and new country kitchen. The decor is light and airy for a peaceful experience. All rooms open to an aged patio with teak furnishings. This beautiful home also includes a heated gunite pool, hot tub, and 20' dock. Separate guest bungalow comes complete with one bedroom and one bathroom. Two-car detached garage. The views offer vistas of open space that are mesmerizing. Lush vegetation in the backyard ensures privacy. Listing ID: 735801

MD - LD Rental: $99,000
July / Aug Rental: $85,000
August - LD Rental: $55,000
Year Round: $159,900

John P Vitello
(631) 204-2407

Village Of East Hampton
$55,000

Village of East Hampton, NY
Rental
Bedrooms: 3
Bathrooms: 3
Web ID: 735674

Welcome to 99 Egypt Lane! This prestigious East Hampton property boasts two spectacular one-level cottages and is conveniently situated walking distance to Wiborg and Maidstone Beach and East Hampton Village Shops and Restaurants. The well furnished 1920's traditional main house has two bedrooms and two baths, living/dining room, a new kitchen and central air-conditioning. The guest cottage has a master bedroom, bath, living room with fireplace, garden room and central air-conditioning. Topping it off is a 20x20 heated gunite pool with fabulous entertaining areas and mature garden and trees. Both cottages are luxuriously furnished with exquisite curated artwork, multiple comfortable living spaces with a beachy vibe and gorgeous patio and deck spaces anchoring the heated gunite pool. There is also an outdoor shower just outside the guest cottage. These cottages are jewelboxes, chockfull of charm and so close to world-class East Hampton Village shopping, dining and spectacular beaches.

MD - LD Rental: $105,000
June Rental: $35,000
July Rental: $55,000
August - LD Rental: $60,000

James Blueweiss
(631) 903-6133

Sagaponack
$55,000

Sagaponack, NY
Rental
Bedrooms: 3
Bathrooms: 3
Web ID: 742577

Possibly the best value in Sagaponack within a short distance to the ocean. Privately landscaped 1.5-acre property, with 3 bedrooms, 3 baths, fireplace, extensive decking, and a pool. Listing ID: 742577

MD - LD Rental: $135,000
June Rental: $40,000
June/July Rental: $90,000
July Rental: $55,000

Maritza Jimenez
(631) 204-2411

East Hampton
$55,000

East Hampton, NY
Rental
Bedrooms: 5
Bathrooms: 3
Web ID: 735652

Furnished contemporary privately situated on a beautifully landscaped parcel with mature trees and flower gardens. Living room with fireplace; dining room, kitchen, five bedrooms and three baths. Amenities include air-conditioning, cable television, patio, pool house (with recreation room, two bedrooms and bath), and a 20'x40' Gunite pool. Close to restaurants, Georgica and Main Beach. Listing ID: 735652

July Rental: $55,000
August - LD Rental: $60,000

JB Jose B DosSantos
(631) 903-6147

Bridgehampton
$55,000

Bridgehampton, NY
Rental
Bedrooms: 4
Bathrooms: 3.5
Web ID: 736492

Newly completed 4 bedroom 3.5 bath home has all the modern amenities, chic top of the line kitchen, French doors help create a private seating in a formal dining area. Backyard has a heated gunite pool and expansive lawn with mature hedges creating a private enjoyable setting.

Custom Rental: $30,000
June Rental: $30,000
July Rental: $55,000
August - LD Rental: $65,000
September Rental: $30,000

Cynthia R Barrett
(631) 537-4322

East Hampton
$55,000

East Hampton, NY
Rental
Bedrooms: 4
Bathrooms: 4
Web ID: 737579

Rental Registration #: 24-1104 This attractive four-bedroom, four-bath traditional is privately secluded on a beautiful 3-acre +/- property with a heated pool. Features include an enclosed porch, living room, dining room, Epicurean kitchen, two fireplaces, central air-conditioning, an oversized garage, hot tub and extensive decking. Listing ID: 737579.

MD - LD Rental: $130,000
June Rental: $20,000
July Rental: $55,000
August Rental: $65,000
September Rental: $20,000
Winter Rental: $10,000

Timothy R O'Connor
(631) 771-5321

Jeffrey C Carter
(631) 771-5323

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