Fair Housing Notice Standard Operating Procedure
631.765.5333

Seasonal Rentals

    to
     
     
     
    Search Search
    » Property Criteria
    » Features
    •  
    » Display Tools
    Search

    220  properties match your search;

    218 with Multiple photos ;  15 with Virtual Tour ;  0 with Videos

    Save Search
    Showing 111 - 120 of 220 results| view:  results per page« first|...|10|11|12|13|...|last »
    • Summer is here! Spend your days in this fully furnished 3 bed Classic North Fork Beach Home. Outdoor deck and covered patio seating area bring the living space outdoors. This seasonal rental is just 7 homes away from a private sandy Bay Beach. Situated on a spacious lot on a charming street, this quintessential home is yours to enjoy July/Aug/Sept/Oct. Relax or visit the many area wineries, breweries, shopping and beaches the area has to offer. Located between both the North and South Forks how will you choose to spend your days and nights? On the Island, of course!! 10
      30 Willow Street Aquebogue, NY 11931
      $10,000
      3 Bedrooms 1 Full Bath 1 Half Bath
      Single Family For Rent ML# 3561015
      Summer is here! Spend your days in this fully furnished 3 bed Classic North Fork Beach Home. Outdoor deck and covered patio seating area bring the living space outdoors. This seasonal rental is just 7 homes away from a private sandy Bay Beach. Situated on a spacious lot on a charming street, this quintessential home is yours to enjoy July/Aug/Sept/Oct. Relax or visit the many area wineries, breweries, shopping and beaches the area has to offer. Located between both the North and South Forks how will you choose to spend your days and nights? On the Island, of course!!
      Presented By: Corcoran  631-765-1300
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Permit# 1127. Seeing is believing! Newly renovated, this four bedroom, three full bath waterfront home features an elegant New England Costal vibe. Enjoy true outdoor living on the furnished patio or upper level deck dining room. Take advantage of the hot tub, outdoor shower, dock and all the beach toys (Canoe, kayak, paddle board). This is the first rental post the super high-end open concept renovation including a massive, fully appointed designer kitchen with an enormous island, a ground level family room that spills out onto the patio through French doors and full, luxurious bathroom renovations. Revel in the spectacular views from the elevated kitchen, dining room, comfy but elegant living room and upper deck outdoor dining as well as the amazing ground floor waterfront views from den, patio, and guest room. The owners’ 3rd floor retreat boasts an en suite master bath, two walk in closets and expansive views. There are plenty of work from home stations throughout the house. When it is not work time, head to nearby New Suffolk Beach or Veterans Beach, or pack up the canoe and paddle out to explore deserted and otherwise inaccessible bay beaches that you’ll never see any other way. Centrally located on the North Fork, close to Love Lane, farm stands, wineries and all the North Fork offers! 25
      505 Bungalow Lane Mattituck, NY 11952
      $10,000
      4 Bedrooms 3 Full Baths
      Single Family For Rent ML# 3553535
      Permit# 1127. Seeing is believing! Newly renovated, this four bedroom, three full bath waterfront home features an elegant New England Costal vibe. Enjoy true outdoor living on the furnished patio or upper level deck dining room. Take advantage of the hot tub, outdoor shower, dock and all the beach toys (Canoe, kayak, paddle board). This is the first rental post the super high-end open concept renovation including a massive, fully appointed designer kitchen with an enormous island, a ground level family room that spills out onto the patio through French doors and full, luxurious bathroom renovations. Revel in the spectacular views from the elevated kitchen, dining room, comfy but elegant living room and upper deck outdoor dining as well as the amazing ground floor waterfront views from den, patio, and guest room. The owners’ 3rd floor retreat boasts an en suite master bath, two walk in closets and expansive views. There are plenty of work from home stations throughout the house. When it is not work time, head to nearby New Suffolk Beach or Veterans Beach, or pack up the canoe and paddle out to explore deserted and otherwise inaccessible bay beaches that you’ll never see any other way. Centrally located on the North Fork, close to Love Lane, farm stands, wineries and all the North Fork offers!
      Presented By: Douglas Elliman Real Estate  631-354-8100
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Enjoy a beautiful airy and bright mint condition Bay Front Orient Contemporary home, perfect for relaxing and entertaining. This 4-bedroom 4.5 bath home has gourmet kitchen, fireplace, open common space for easy entertaining. First floor has access to bay side screened porch from living room and den (or 4th bedroom with full bath). Second floor master bedroom and a guest bedroom open onto upper bay side deck, a third bedroom with full bath completes the layout. Private stairs to the beach and deeded beach rights to association Bay beach just a short walk from the house. Property is close to all village amenities: Country Store, Post Office, Marinas, Bay and Sound beaches. Offered Aug 20-LD $13, 000; Sept $20, 000; Oct $15, 000; Nov $10, 000; Dec $10, 000. Permit# 1020. 14
      1390 Willow Terrace Lane Orient, NY 11957
      $10,000
      4 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 2800.00:#
      Single Family For Rent ML# 3550396
      Enjoy a beautiful airy and bright mint condition Bay Front Orient Contemporary home, perfect for relaxing and entertaining. This 4-bedroom 4.5 bath home has gourmet kitchen, fireplace, open common space for easy entertaining. First floor has access to bay side screened porch from living room and den (or 4th bedroom with full bath). Second floor master bedroom and a guest bedroom open onto upper bay side deck, a third bedroom with full bath completes the layout. Private stairs to the beach and deeded beach rights to association Bay beach just a short walk from the house. Property is close to all village amenities: Country Store, Post Office, Marinas, Bay and Sound beaches. Offered Aug 20-LD $13, 000; Sept $20, 000; Oct $15, 000; Nov $10, 000; Dec $10, 000. Permit# 1020.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-477-0013
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Direct waterfront North Fork farmhouse with private sandy beach on Southold Bay, part of the Peconic Estuary. Beautifully maintained, this large 4BR/ 2.55 BTH home benefits from many recent upgrades, including 2023 new chef’s kitchen with waterviews over the hedges, renovated powder room, screened in front porch and lovely back deck with large and private garden and vineyard views. Fabulous indoor/ outdoor North Fork Summer Living in the mature gardens with specimen trees, waterfront, private sandy beach and vineyard views, and your private sugar sand beach to swim, kayak, paddle board, boat and fish. Close to all area attractions. Pet friendly! Walk to vineyards and organic farms for North Fork farm to table dining. Close to fine dining restaurants, farms, and waterfront bars. Fun arts, crafts, yoga, juice bar, live music and water sports, Southold, Greenport Maritime Village and ferries to Shelter Island, Sag Harbor and the South Fork all close by and easy to reach. Southold Town Rental Permit 0631 22
      870 Bay Home Rd Southold, NY 11971
      $10,000
      4 Bedrooms 2 Full Baths 2 Half Baths Sq. Ft. 1784.00:#
      Misc For Rent ML# 3547704
      Direct waterfront North Fork farmhouse with private sandy beach on Southold Bay, part of the Peconic Estuary. Beautifully maintained, this large 4BR/ 2.55 BTH home benefits from many recent upgrades, including 2023 new chef’s kitchen with waterviews over the hedges, renovated powder room, screened in front porch and lovely back deck with large and private garden and vineyard views. Fabulous indoor/ outdoor North Fork Summer Living in the mature gardens with specimen trees, waterfront, private sandy beach and vineyard views, and your private sugar sand beach to swim, kayak, paddle board, boat and fish. Close to all area attractions. Pet friendly! Walk to vineyards and organic farms for North Fork farm to table dining. Close to fine dining restaurants, farms, and waterfront bars. Fun arts, crafts, yoga, juice bar, live music and water sports, Southold, Greenport Maritime Village and ferries to Shelter Island, Sag Harbor and the South Fork all close by and easy to reach. Southold Town Rental Permit 0631
      Presented By: Property Angels  631-252-5653
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • In this Luxurious home, you’ll have front-row seats to some incomparable Long Island Sounds sunsets. Sit on the large deck or sit directly on the beach for one-of-a-kind views. Or simply dip and relax in the hot tub and admire the view of the water. This 4-bedroom beach house sleeps 12. The master bedroom with a King bed and one of the Queen bedrooms has its own access to the balcony. The open floor concept allows you to move around the kitchen. The home also comes with central air/heating. There is a sunroom with wrap-around windows where you can have a spectacular view of the ocean from sunrise to sunset. A river rocks fireplace is always ready during cold nights and/or wintertime. You can also enjoy outdoor dining with an outdoor BBQ grill or have dinner inside in a large dining room that seats 12! Have a great time and have fun in the game room on a pool table, a foosball, and an air hockey table. You are guaranteed essential amenities including free parking, WIFI, and cable TV. Nearly all of our homes also come with kayaks to keep adventure close by. You are free to explore local destinations including the vineyards for wine tasting, farm stands to support local growers, a close-knit beach community, and nature reserves to explore. The five-star restaurants are minutes away as well as the Hamptons, Greenport, Montauk, and/or Shelter Island. 34
      224 Creek Wading River, NY 11792
      $10,000
      4 Bedrooms 2 Full Baths 2 Half Baths
      Misc For Rent ML# 3525410
      In this Luxurious home, you’ll have front-row seats to some incomparable Long Island Sounds sunsets. Sit on the large deck or sit directly on the beach for one-of-a-kind views. Or simply dip and relax in the hot tub and admire the view of the water. This 4-bedroom beach house sleeps 12. The master bedroom with a King bed and one of the Queen bedrooms has its own access to the balcony. The open floor concept allows you to move around the kitchen. The home also comes with central air/heating. There is a sunroom with wrap-around windows where you can have a spectacular view of the ocean from sunrise to sunset. A river rocks fireplace is always ready during cold nights and/or wintertime. You can also enjoy outdoor dining with an outdoor BBQ grill or have dinner inside in a large dining room that seats 12! Have a great time and have fun in the game room on a pool table, a foosball, and an air hockey table. You are guaranteed essential amenities including free parking, WIFI, and cable TV. Nearly all of our homes also come with kayaks to keep adventure close by. You are free to explore local destinations including the vineyards for wine tasting, farm stands to support local growers, a close-knit beach community, and nature reserves to explore. The five-star restaurants are minutes away as well as the Hamptons, Greenport, Montauk, and/or Shelter Island.
      Presented By: Colony Realty  631-722-5800
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Romance, elegance, and the bucolic backdrop of Oregon Road make this home a standout! Nestled within a vineyard, this 3 bedroom, 2 bath vintage farmhouse charmer lies on 2 acres with an in-ground pool and endless vineyard views. Short distance to tasting rooms, farm stands, renowned restaurants, vineyards, and fantastic beaches that the North Fork is known for. Permit # 0940 29
      2600 Oregon Rd Mattituck, NY 11952
      $10,000
      3 Bedrooms 2 Full Baths
      Single Family For Rent ML# 3494263
      Romance, elegance, and the bucolic backdrop of Oregon Road make this home a standout! Nestled within a vineyard, this 3 bedroom, 2 bath vintage farmhouse charmer lies on 2 acres with an in-ground pool and endless vineyard views. Short distance to tasting rooms, farm stands, renowned restaurants, vineyards, and fantastic beaches that the North Fork is known for. Permit # 0940
      Presented By: Corcoran  631-848-7730
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Welcome to your serene off-season retreat in -a stunning rental that epitomizes modern elegance and tranquil seclusion. This exceptional residence offers 4 spacious bedrooms and 3 luxurious bathrooms, all nestled on an expansive 43, 560 square foot lot. Step inside to discover a beautifully designed interior featuring a chef’s kitchen, perfect for culinary enthusiasts. The open-concept living spaces are bathed in natural light, creating an inviting atmosphere for both relaxation and entertainment. The primary suite is a true retreat, boasting ample space and refined finishes. Outside, enjoy exclusive beach rights making it effortless to indulge in coastal living. The property also features a heated pool, ideal for unwinding or entertaining guests. Surrounded by lush woodlands, this home offers unparalleled privacy and a peaceful ambiance. Discover the tranquility and charm of this extraordinary property. 13
      3475 Wunneweta Rd Cutchogue, NY 11935
      $9,500
      4 Bedrooms 3 Full Baths Sq. Ft. 3000.00:#
      Single Family For Rent ML# 3580422
      Welcome to your serene off-season retreat in -a stunning rental that epitomizes modern elegance and tranquil seclusion. This exceptional residence offers 4 spacious bedrooms and 3 luxurious bathrooms, all nestled on an expansive 43, 560 square foot lot. Step inside to discover a beautifully designed interior featuring a chef’s kitchen, perfect for culinary enthusiasts. The open-concept living spaces are bathed in natural light, creating an inviting atmosphere for both relaxation and entertainment. The primary suite is a true retreat, boasting ample space and refined finishes. Outside, enjoy exclusive beach rights making it effortless to indulge in coastal living. The property also features a heated pool, ideal for unwinding or entertaining guests. Surrounded by lush woodlands, this home offers unparalleled privacy and a peaceful ambiance. Discover the tranquility and charm of this extraordinary property.
      Presented By: Compass Greater NY LLC  631-251-8644
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Enjoy this Waterfront rental just steps to Goose Creek beach. Easy water access to Goose Creek from this private location, perfect for kayaking and paddle boarding. Features include 3 bedrooms including second floor primary en-suite with water views, 2 additional guest bedrooms, 2 additional guest baths and plenty of living space overlooking Goose Creek. Spacious bright kitchen, dining area with doors to waterside deck where you will experience beautiful sunsets. The perfect retreat for your summer fun or any other time of the year. Call for off-season rates. Close to all North Fork amenities. 35
      800 Goose Creek Lane Southold, NY 11971
      $9,500
      3 Bedrooms 3 Full Baths Sq. Ft. 2032.00:#
      Single Family For Rent ML# 3526789
      Enjoy this Waterfront rental just steps to Goose Creek beach. Easy water access to Goose Creek from this private location, perfect for kayaking and paddle boarding. Features include 3 bedrooms including second floor primary en-suite with water views, 2 additional guest bedrooms, 2 additional guest baths and plenty of living space overlooking Goose Creek. Spacious bright kitchen, dining area with doors to waterside deck where you will experience beautiful sunsets. The perfect retreat for your summer fun or any other time of the year. Call for off-season rates. Close to all North Fork amenities.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-734-5439
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Located on a private and serene 1.09 acre parcel of land and only 1/3 of a mile from McCabes Beach, with miles of Long Island Sound beach to traverse to the east and west, this charming and newly built two story home offers an open concept living space with plentiful natural light on the first floor with a half bathroom between the living and dining room, with a half bathroom off of the hallway leading to the eat-in-kitchen and den/tv room. The second floor provides a master bedroom with en-suite bathroom, two additional bedrooms and another full bathroom. There are large sliding glass doors in the kitchen that lead to a picturesque patio and outdoor sitting area with grill, tables and umbrella. Take in all the North Fork has to offer. Rental permit # 0343 19
      13595 Soundview Avenue Southold, NY 11971
      $9,000
      3 Bedrooms 2 Full Baths 1 Half Bath
      Single Family For Rent ML# 3587451
      Located on a private and serene 1.09 acre parcel of land and only 1/3 of a mile from McCabes Beach, with miles of Long Island Sound beach to traverse to the east and west, this charming and newly built two story home offers an open concept living space with plentiful natural light on the first floor with a half bathroom between the living and dining room, with a half bathroom off of the hallway leading to the eat-in-kitchen and den/tv room. The second floor provides a master bedroom with en-suite bathroom, two additional bedrooms and another full bathroom. There are large sliding glass doors in the kitchen that lead to a picturesque patio and outdoor sitting area with grill, tables and umbrella. Take in all the North Fork has to offer. Rental permit # 0343
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • North Fork. Bay Front Charmer On The Beach at 15 Downs Boulevard in Jamesport. In coveted Fairhaven Private Community. Vintage cottage right on sandy bay beachfront. Sept and October $9000 per month, 2025 Winter Months at only $6900 per (2 month minimum). Summer 2024: July $28, 000. Lovely and well kept getaway full of olde time appeal. Spacious open plan with water views, new central air, new waterside patio and outdoor furniture, sleek kitchen, stainless appliances, wood floors. The main floor offers 3 Bedrooms to include a water view primary en-suite (bath with walk in shower), and 2 additional guest bedrooms with a hall bath. Second level has 2 bedrooms (one is water view), a loft with dormitory style beds, and another hall guest bath. Swim, kayak, bring a small boat to moor. Sunbathe out your back door, or meander just one lane over to town facilities with expansive beach, tennis courts, playground and marina with 4 public boat ramps. The Sweetest Summer Vacation On The Open Bay! RP# 24-0271 25
      15 Downs Boulevard Jamesport, NY 11947
      $9,000
      5 Bedrooms 3 Full Baths Sq. Ft. 2700.00:#
      Single Family For Rent ML# 3277968
      North Fork. Bay Front Charmer On The Beach at 15 Downs Boulevard in Jamesport. In coveted Fairhaven Private Community. Vintage cottage right on sandy bay beachfront. Sept and October $9000 per month, 2025 Winter Months at only $6900 per (2 month minimum). Summer 2024: July $28, 000. Lovely and well kept getaway full of olde time appeal. Spacious open plan with water views, new central air, new waterside patio and outdoor furniture, sleek kitchen, stainless appliances, wood floors. The main floor offers 3 Bedrooms to include a water view primary en-suite (bath with walk in shower), and 2 additional guest bedrooms with a hall bath. Second level has 2 bedrooms (one is water view), a loft with dormitory style beds, and another hall guest bath. Swim, kayak, bring a small boat to moor. Sunbathe out your back door, or meander just one lane over to town facilities with expansive beach, tennis courts, playground and marina with 4 public boat ramps. The Sweetest Summer Vacation On The Open Bay! RP# 24-0271
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    Showing 111 - 120 of 220 results| view:  results per page« first|...|10|11|12|13|...|last »
    OneKey™ MLS The data relating to real estate for sale on this web site comes in part from the OneKey™ MLS. Real Estate listings held by brokerage firms other than Beninati are marked with the Broker Reciprocity logo and detailed information about them includes the name of the listing brokers.
    Office: (631) 765 5333 Fax (631) 765 5225 broker@beninatiassociates.com

    Questions? Just Ask!

     Submit
    Office: 52875 Main Road, Southold NY 11971
    631.765.5333     powered by eRealty Media | Admin