405 Hamptons Rentals

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355 Midway Road
$18,000

Southold, NY
Rental
Bedrooms: 3
Bathrooms: 3
Web ID: 888811

This impeccable modern 3 bedroom, 3 bath home in Southold's coveted Cedar Beach district offers privacy, water views and a private neighborhood beach. The open plan includes a kitchen, dining area, den/office, and living room with fireplace. Sliding doors open to the bluestone patio with a gas grill and plenty of room for entertaining and sunning. The three bedrooms, including the primary suite, all have water views. A private beach is nearby and there's easy access to renowned North Fork wineries, farm stands, restaurants and shops. This home has everything needed for an exceptional East End retreat. Listing ID #888811

MD - LD Rental: $45,000
June Rental: $8,000
July Rental: $18,000
August - LD Rental: $20,000
September Rental: $8,000
Winter Rental: $6,000

Marianne Collins
(631) 734-2957

161 Norfolk Drive
$17,000

East Hampton, NY
Rental
Bedrooms: 3
Bathrooms: 2
Web ID: 917006

Rental Reg # 23-93 This sweet yet sophisticatedly updated Clearwater Beach Cottage is the perfect Hamptons getaway. The large open kitchen with oversized eating counter and adjacent dining offers options from casual to gourmet meal prep and dining. The comfy living room is a great space to relax and unwind or the expansive yard and covered patio area also offers shade on those hot summer days. The home has a primary bedroom with an ensuite bath and two additional guest rooms share a second full bath. The private gated residents-only Clearwater Beach Association is one of best kept secrets in The Hamptons with a stunning west facing lifeguarded sandy beach, picnic and grilling areas, plus storage for kayak/paddleboards and a launch. Summer sunsets await you!

MD - LD Rental: $42,000
June Rental: $10,000
July Rental: $17,000
July / Aug Rental: $34,000
August Rental: $17,000
August - LD Rental: $17,000

Timothy C Burch
(631) 771-5315

David Tenenbaum
(631) 771-5322

Southampton
$16,000

Southampton, NY
Rental
Bedrooms: 2
Bathrooms: 2
Web ID: 906802

RR# RP240614. Come spend your summer on St Andrews Circle; a charming, quiet, great location. This light filled single story is close to amenities and the beach, the perfect gateway to an enjoyable Hamptons season. Pool and tennis and wide open spaces. This unit has a lovely private back deck area, for grilling and sun bathing. Listing ID: 906802

July Rental: $16,000
July / Aug Rental: $30,000
August - LD Rental: $17,000

Richard Finder
(631) 702-7511

Sagaponack
$15,000

Sagaponack, NY
Rental
Bedrooms: 4
Bathrooms: 3
Web ID: 738071

RR#: RP180642 This fabulous totally renovated home is located a stone's throw to Wolffer Winery and 5 minutes to gorgeous ocean beaches, Sagg Main and Bridgehampton Village. The home boasts 4 spacious bedrooms and 3 tastefully redone bathrooms with brand new linens. Huge windows allow for ample natural light to flow through the large kitchen, dining room, family room as well as the separate living room. The entire house has been fitted with bright and beachy, all new modern furniture! Step outside to find a heated salt-water pool, mahogany deck with remote controlled retractable awning and a pool cabana with sofa. A perfect summer getaway! Listing ID: 738071

November Rental: $15,000
December Rental: $15,000

Cristina Matos
(631) 204-2408

East Hampton
$15,000

East Hampton, NY
Rental
Bedrooms: 4
Bathrooms: 4
Web ID: 880234

Rental Reg. # 24-0,936 - East Hampton Village Fringe 4 Bedrooms, 4 Baths, swimming pool, and finished lower level available for a relaxing summer. The spacious home is conveniently located just outside East Hampton Village providing easy access to all the village has to offer, including ocean beaches and bay beaches.

Winter Rental: $15,000

JB Jose B DosSantos
(631) 903-6147

Raul Guazhambo
(631) 903-6148

Springs
$15,000

Springs, NY
Rental
Bedrooms: 3
Bathrooms: 2.5
Web ID: 754272

Rental Registration #23- 0,115 - Charming country post and beam house just a short distance to private bay beach. Cathedral ceilings in living room, country kitchen, and wraparound covered porches overlooking sparkling pool. Well-appointed and beautifully decorated. Primary suite with marble bath and jacuzzi. 2 spacious additional guest bedrooms. A peaceful country setting close to Villages, bay beach, and Amagansett Ocean beach. Listing ID 754272

MD - LD Rental: $40,000
June Rental: $10,000
July Rental: $15,000
July / Aug Rental: $32,000
August - LD Rental: $20,000
September Rental: $8,000

Philip Judson
(631) 771-5328

JB Jose B DosSantos
(631) 903-6147

Shelter Island
$15,000

Shelter Island, NY
Rental
Bedrooms: 5
Bathrooms: 3
Web ID: 895344

Designers own fabulous reconstruction and renovation of the Classic and Iconic Captain Cartwright House in Shelter Island. This classic 5 bedroom home, detached garage, covered porches, blue stone patios and heated 20 x 40 gunite pool with all the bells and whistles is centrally located between the South and the North Ferries and across the street from the 2350 acre Mashomack Preserve on Shelter Island. The very private setting is ideal for relaxing by the chic lounging areas around the pool or entertaining summer guests on the beautifully landscaped grounds perfect for intimate dinners. An oversized outdoor shower is a show stopper. This so very special summer getaway is now available for the first time and will not last.

July Rental: $15,000
Winter Rental: $4,000

Cynthia R Barrett
(631) 537-4322

Rental Property at Other, Other, Hamptons, NY - Bedrooms: 4 
Bathrooms: 1.5  - $15,000 MO.

Other
$15,000

Other, NY
Rental
Bedrooms: 4
Bathrooms: 1.5
Web ID: 914367

Rental Reg. # 241179 This five bedroom Hampton bays rental is moments from town, contently located with easy access to neighboring hamlets. Amazing situation for staff housing needs. No frills staff housing.

January Rental: $15,000
February Rental: $15,000
March Rental: $15,000
April Rental: $15,000
May Rental: $15,000
June Rental: $15,000
November Rental: $15,000
December Rental: $15,000

Jared Schiavoni
(631) 537-4337

Anthony C Cerio
(631) 903-6151

123 Windward
$15,000

Springs, NY
Rental
Bedrooms: 3
Bathrooms: 2.5
Web ID: 743609

Rental Reg#: 24-524. This cozy 3 bdrm/2.5 bath Barnes Landing cottage is nestled in a quiet and private setting and is a short walk to the lovely Barnes Landing bay beach. The home features a breezy floor plan with a combined living room and a dining alcove. Sliders to the back deck make for easy outdoor lounging and dining. There's a spacious, well-stocked separate kitchen, a laundry room, as well as an over-sized outdoor & open-to-the sky shower for cooling off after a summer's day. This rental includes a three person kayak ready for your enjoyment at Barnes Landing Beach (locked storage at the beach for your easy access), beach chairs & umbrella, tennis racquets & balls (public tennis courts a 5 minute drive), and boogie boards. Everything you need for a fun summer in the Hamptons!

May Rental: $10,000
MD - LD Rental: $40,000
July Rental: $15,000
August - LD Rental: $20,000
Year Round: $80,000

James Blueweiss
(631) 903-6133

North Sea
$14,000

North Sea, NY
Rental
Bedrooms: 3
Bathrooms: 1.5
Web ID: 890606

RR# RP241116. Located moments from the sandy beaches of Peconic Bay, this charming bungalow is also convenient to shops and restaurants in the villages of Sag Harbor and Southampton. Featuring a living room, kitchen, den, 3 bedrooms, and 1 full bath, a cozy cabana in the back yard with electricity and water provides an additional half bath and private outdoor shower. The back patio and hedged yard offer privacy and shade for entertaining or relaxing on lazy summer days. Breathtaking sunsets are on regular display just 1 block away at the community bay beach. Listing ID: 890606

MD - LD Rental: $40,000
June Rental: $10,000
July Rental: $14,000
July / Aug Rental: $30,000
August - LD Rental: $16,000

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

1155 Old Harbor Road
$13,000

New Suffolk, NY
Rental
Bedrooms: 4
Bathrooms: 3
Web ID: 741545

New Suffolk Bayfront available winter through April 2025 and Fall 2025. Stunning views across Cutchogue Harbor and Peconic Bay will be yours at this spacious beachfront home, whether from the airy, glassed-in great room, the brick patio, or from your beachside deck. Tucked away down a quiet drive, this home offers peace and privacy in historic New Suffolk. There are 3 bedrooms and 2 baths upstairs, one bedroom and one bath downstairs, a sitting room with fireplace, full kitchen with breakfast bar, and water views from almost every room. A quintessential North Fork getaway. Listing ID #741545

October Rental: $13,000
Winter Rental: $6,000

Marianne Collins
(631) 734-2957

East Hampton
$12,000

East Hampton, NY
Rental
Bedrooms: 5
Bathrooms: 3.5
Web ID: 754246

Rental Reg. # 22-1260 This beautiful, airy 5 bedroom home is situated on a quiet road in the Northwest Woods just a few miles from the ocean and a mile from the bay. A guest suite on the ground floor sleeps 4 and has a perfectly appointed bathroom along with another bedroom with queen bed. The large living room with a screened-in porch is a perfect spot for entertaining. Upstairs there are 3 more bedrooms and two bathrooms. The home is filled with light and features skylights and a fireplace for cooler nights. There is a washer/dryer, dishwasher, and cable TV plus WiFi. The pool is heated and there is air conditioning throughout the home. Listing ID: 754246.

Winter Rental: $12,000

John Scott JT Thomas
(631) 771-5327

Village Of East Hampton
$12,000

Village of East Hampton, NY
Rental
Bedrooms: 2
Bathrooms: 2.5
Web ID: 758002

It doesn't get any easier or more convenient than being located just off of Newtown Lane in the heart of East Hampton Village and steps to all restaurants, boutique shopping, coffee shops, movie theater and public transportation. Literally... there's no need for a car. This immaculate duplex offers 2 bedrooms, 2.5 baths, kitchen with stainless appliances and Ceasar Stone counter tops, living room, laundry on bedroom level, lower level den/ home office, central air, central vac. Beautifully decorated and appointed. It's the perfect summer rental, or winter Pied-'a- Terre for enjoying the quiet winter months in East Hampton Village. Listing ID: 758002

December Rental: $12,000

Patricia Stanis
(631) 771-5318

East Hampton
$12,000

East Hampton, NY
Rental
Bedrooms: 3
Bathrooms: 3
Web ID: 736287

Rental Registration #: 23-1,266 - Come enjoy the long summer days in this light-filled postmodern home! It offers three bedrooms, three full baths, cathedral open living area with a beautiful fireplace, kitchen, and dining area. Amenities include a music/tv room, heated swimming pool, outdoor shower, primary bedroom with fireplace, and central air-conditioning. Ultra-private and pristine. Listing ID:736287

January Rental: $12,000
February Rental: $12,000
March Rental: $12,000

JB Jose B DosSantos
(631) 903-6147

Margaret Turner
(631) 771-5314

Village Of Southampton
$12,000

Village of Southampton, NY
Rental
Bedrooms: 2
Bathrooms: 1
Web ID: 758038

Restored 18th century manor house with a sense of Southampton history. Very spacious 2-bedroom, 1-bath with a fully equipped kitchen. Green lawns just half block to the village shops. Listing ID#: 758038

May Rental: $4,500
June Rental: $10,500
July Rental: $12,000
August - LD Rental: $12,000
Winter Rental: $4,000

Richard Finder
(631) 702-7511

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