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Southold Homes for Rent

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    Showing 11 - 20 of 57 results| view:  results per page« 1|2|3|4|5|...|last »
    • Ideal North Fork Dream Home for Spring and Summer Living! Embrace the vibrant spirit of Southold with this spacious and inviting home. Boasting four generously sized bedrooms, three equipped with ensuite bathrooms and the first-floor bedroom conveniently offering access to a full bath across the hall, this residence ensures comfort and convenience. The heart of the home, the great room, showcases the second fireplace and opens up to the rear masonry deck, which overlooks the large, heated pool and the backyard. Just a few blocks away is an array of charming shops, cafes, and restaurants, adding to the allure of this perfect home base for your North Fork experience. Available Year Round at 10k per month. June: 30K July: 38k August: 45k. Memorial Day- Labor Day: 100k. Also available off season. 28
      315 Maple Lane Southold, NY 11971
      $30,000
      4 Bedrooms 4 Full Baths Sq. Ft. 3500.00:# Square Feet
      Single Family For Rent ML# 3528088
      Ideal North Fork Dream Home for Spring and Summer Living! Embrace the vibrant spirit of Southold with this spacious and inviting home. Boasting four generously sized bedrooms, three equipped with ensuite bathrooms and the first-floor bedroom conveniently offering access to a full bath across the hall, this residence ensures comfort and convenience. The heart of the home, the great room, showcases the second fireplace and opens up to the rear masonry deck, which overlooks the large, heated pool and the backyard. Just a few blocks away is an array of charming shops, cafes, and restaurants, adding to the allure of this perfect home base for your North Fork experience. Available Year Round at 10k per month. June: 30K July: 38k August: 45k. Memorial Day- Labor Day: 100k. Also available off season.
      Presented By: Compass Greater NY LLC  516-330-6086
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Spacious Open Floor Plan Newer Home. Inground Pool with Built in Hot Tub and Blue Stone Pool Surround. Screened Porch Overlooking Pool Area. Nice Yard. Wood Burning Fireplace. Good Wifi. Long Island Sound Beach and Historic Lighthouse Museum and Park Several Doors Away. Summer 2024 - Memorial Day through June $30, 000. Off Season Until End of April 2024 at $10, 000 Per Month (Single or Multiple Months Rental Considered). Permit #0537. 28
      590 Soundview Av Ext Southold, NY 11971
      $30,000
      4 Bedrooms 4 Full Baths 1 Half Bath
      Single Family For Rent ML# 3524504
      Spacious Open Floor Plan Newer Home. Inground Pool with Built in Hot Tub and Blue Stone Pool Surround. Screened Porch Overlooking Pool Area. Nice Yard. Wood Burning Fireplace. Good Wifi. Long Island Sound Beach and Historic Lighthouse Museum and Park Several Doors Away. Summer 2024 - Memorial Day through June $30, 000. Off Season Until End of April 2024 at $10, 000 Per Month (Single or Multiple Months Rental Considered). Permit #0537.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Rental permit 405. Dine Al Fresco! Enjoy The Spectacular Sunsets At This Waterfront Paradise. 3 Bedroom 2 bath Contemporary Home With 1st Floor Waterside Master Suite. New Soft padded Heated/Lighted Salt Water IG Pool W/Automatic Cover, Unobstructed Waterviews, Enclosed Outdoor Shower, Hi End Newly Built Kitchen. Enjoy Kayaking, Paddle Boarding and Fishing From Your Own Dock. Easy Direct Bay Access. Beautiful Goose Creek Beach Practically at Your Doorstep. Available October 24 - April 2025 Or July 2025. Exit Clean, Utility & Security Deposit Required. Leased For July 24 11
      470 Goose Creek Lane Southold, NY 11971
      $30,000
      3 Bedrooms 2 Full Baths Sq. Ft. 2000.00:# Square Feet
      Single Family For Rent ML# 3236473
      Rental permit 405. Dine Al Fresco! Enjoy The Spectacular Sunsets At This Waterfront Paradise. 3 Bedroom 2 bath Contemporary Home With 1st Floor Waterside Master Suite. New Soft padded Heated/Lighted Salt Water IG Pool W/Automatic Cover, Unobstructed Waterviews, Enclosed Outdoor Shower, Hi End Newly Built Kitchen. Enjoy Kayaking, Paddle Boarding and Fishing From Your Own Dock. Easy Direct Bay Access. Beautiful Goose Creek Beach Practically at Your Doorstep. Available October 24 - April 2025 Or July 2025. Exit Clean, Utility & Security Deposit Required. Leased For July 24
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Beachfront, located in Southold Shores, this architect’s own home is built with all the beautiful appointments you can imagine. Embracing the purity of architectural detail, together with a refined simplicity, this waterfront home offers a timeless elegance. Sweeping sunsets eye-catching angles and thoughtful details provide constant visual interest. A large 4 bedrooms with 4 baths ensuite, seaside floor to ceiling windows overlooking the Bayfront, Chefs kitchen leading to large outdoor deck and lovely garden. It is truly stunning. A special summer oasis. Available June $24K, August $45K, Sept $25K RP# 0857 8
      950 Blue Marlin Drive Southold, NY 11971
      $24,000
      4 Bedrooms 4 Full Baths Sq. Ft. 3200.00:# Square Feet
      Single Family For Rent ML# 3376195
      Beachfront, located in Southold Shores, this architect’s own home is built with all the beautiful appointments you can imagine. Embracing the purity of architectural detail, together with a refined simplicity, this waterfront home offers a timeless elegance. Sweeping sunsets eye-catching angles and thoughtful details provide constant visual interest. A large 4 bedrooms with 4 baths ensuite, seaside floor to ceiling windows overlooking the Bayfront, Chefs kitchen leading to large outdoor deck and lovely garden. It is truly stunning. A special summer oasis. Available June $24K, August $45K, Sept $25K RP# 0857
      Presented By: Town And Country Real Estate  631-477-5990
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Magnificent Waterfront with Pool! Enjoy the luxury of coastal living in this beautifully constructed home with its own private beach. Open and airy spaces with all the amenities for comfort and relaxation. Spacious kitchen, Dining Rm, Living Rm w/fp, Four generous sized bedrooms & 3.5 baths. The upstairs loft boasts an amazing recreational area with soaring ceilings & walls of glass overlooking spectacular views of the sound & sunsets. Close to shopping, vineyards, boating, world-class dining and more! Last two weeks of June (6/15-6/30): $23, 000. Full Month of July: $50, 000. First two weeks of August (8/1-8/15): $25, 000. 33
      18805 Soundview Avenue Southold, NY 11971
      $23,000
      4 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 3800.00:# Square Feet
      Single Family For Rent ML# 3529983
      Magnificent Waterfront with Pool! Enjoy the luxury of coastal living in this beautifully constructed home with its own private beach. Open and airy spaces with all the amenities for comfort and relaxation. Spacious kitchen, Dining Rm, Living Rm w/fp, Four generous sized bedrooms & 3.5 baths. The upstairs loft boasts an amazing recreational area with soaring ceilings & walls of glass overlooking spectacular views of the sound & sunsets. Close to shopping, vineyards, boating, world-class dining and more! Last two weeks of June (6/15-6/30): $23, 000. Full Month of July: $50, 000. First two weeks of August (8/1-8/15): $25, 000.
      Presented By: Compass Greater NY LLC  516-517-4751
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Incredibly charming North Fork rental complete with farm field views, in-ground pool, pool house, gas fire pit and more. Stylish and updated, this 3 bedroom home is flooded with natural light, has both interior and exterior fire places, farmhouse kitchen and charming period details. Enjoy the resort-like pool area with family and guests, taking in the beautiful views of the vineyards and farms on the neighboring lots. Plenty of extra guest space. Also available off season, please inquire. June- 22k July-28k August-35k Mem-LD- 80K 23
      2740 Main Bayview Rd Southold, NY 11971
      $22,000
      3 Bedrooms 3 Full Baths
      Single Family For Rent ML# 3531922
      Incredibly charming North Fork rental complete with farm field views, in-ground pool, pool house, gas fire pit and more. Stylish and updated, this 3 bedroom home is flooded with natural light, has both interior and exterior fire places, farmhouse kitchen and charming period details. Enjoy the resort-like pool area with family and guests, taking in the beautiful views of the vineyards and farms on the neighboring lots. Plenty of extra guest space. Also available off season, please inquire. June- 22k July-28k August-35k Mem-LD- 80K
      Presented By: Compass Greater NY LLC  516-330-6086
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Enjoy an experience on the North Fork of LI this summer. Whether a couple of weeks, a month, or the whole season, spend it nestled in a quiet spot that is near downtown Southold. Feel embraced by all the NOFO has to offer in this meticulously renovated, waterfront Cape, while enjoying the utmost in privacy and waterfront access. Step down into your own private swimming spot in clear Jockey Creek or enjoy your own private deep-water dock (bring your boat!). Kayak, canoe or paddle directly to Southold Bay, Shelter Island Sound and the extended fishing grounds of Greenport, Bug Light, Orient and beyond. Enjoy a quick ride into the charming downtown of Southold for elegant dining, shopping and easy access to LIRR/Jitney into NYC. Make lasting summer memories on this expansive idyllic, half acre, creekfront property which is perfect for quiet time, entertaining on the deck or play. 31
      3675 Wells Avenue Southold, NY 11971
      $23,500
      $22,000
      4 Bedrooms 2 Full Baths
      Single Family For Rent PRICE REDUCED ML# 3467464
      Enjoy an experience on the North Fork of LI this summer. Whether a couple of weeks, a month, or the whole season, spend it nestled in a quiet spot that is near downtown Southold. Feel embraced by all the NOFO has to offer in this meticulously renovated, waterfront Cape, while enjoying the utmost in privacy and waterfront access. Step down into your own private swimming spot in clear Jockey Creek or enjoy your own private deep-water dock (bring your boat!). Kayak, canoe or paddle directly to Southold Bay, Shelter Island Sound and the extended fishing grounds of Greenport, Bug Light, Orient and beyond. Enjoy a quick ride into the charming downtown of Southold for elegant dining, shopping and easy access to LIRR/Jitney into NYC. Make lasting summer memories on this expansive idyllic, half acre, creekfront property which is perfect for quiet time, entertaining on the deck or play.
      Presented By: Signature Premier Properties  631-765-6000
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Tranquil farm setting in the heart of North Fork, close to all. Centrally located to all the North Fork has to offer, but tucked away on quiet block surrounded by farms. Enjoy our newly furnished home with 5 beds, 2 baths, and an in-ground saltwater pool. Wake up and sip coffee on your front porch & enjoy the serene views with farm animals roaming in the background. 2 mins drive to Southold town. 4 mins drive to Horton Point lighthouse or Mcbain beach. 10 mins to Greenport Village. 21
      4200 Youngs Avenue Southold, NY 11971
      $21,500
      4 Bedrooms 2 Full Baths Sq. Ft. 2400.00:# Square Feet
      Single Family For Rent ML# 3534791
      Tranquil farm setting in the heart of North Fork, close to all. Centrally located to all the North Fork has to offer, but tucked away on quiet block surrounded by farms. Enjoy our newly furnished home with 5 beds, 2 baths, and an in-ground saltwater pool. Wake up and sip coffee on your front porch & enjoy the serene views with farm animals roaming in the background. 2 mins drive to Southold town. 4 mins drive to Horton Point lighthouse or Mcbain beach. 10 mins to Greenport Village.
      Presented By: Century 21 Albertson Realty  631-765-3800
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Quintessential 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 new chef’s kitchen, renovated powder room, screened in front porch and back deck. Fabulous indoor/ outdoor North Fork Summer Living in the mature gardens with specimen trees, waterfront 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 easy to reach. Southold Town Rental Permit 0631 23
      870 Bay Home Rd Southold, NY 11971
      $22,000
      $20,000
      4 Bedrooms 2 Full Baths 2 Half Baths Sq. Ft. 1784.00:# Square Feet
      Single Family For Rent PRICE REDUCED ML# 3475506
      Quintessential 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 new chef’s kitchen, renovated powder room, screened in front porch and back deck. Fabulous indoor/ outdoor North Fork Summer Living in the mature gardens with specimen trees, waterfront 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 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
    • Southold, North Fork - artful cottage located in Southold by Founder’s Landing Park/Wharf House. Opposite a fabulous bay beach sits this unique, furnished, one bedroom residence. Full kitchen with dishwasher, bright and sunny living room, comfortable bedroom... home is heated by natural gas. Park like property with outside sitting area. Privacy and pet friendly. Enjoy life on the east end in this furnished home ready for you and convenient to area restaurants, wineries, and all the North Fork has to offer. Permit #0107 13
      Southold, NY 11971
      $19,000
      1 Bedroom 1 Full Bath Sq. Ft. 750.00:# Square Feet
      Single Family For Rent ML# 3525718
      Southold, North Fork - artful cottage located in Southold by Founder’s Landing Park/Wharf House. Opposite a fabulous bay beach sits this unique, furnished, one bedroom residence. Full kitchen with dishwasher, bright and sunny living room, comfortable bedroom... home is heated by natural gas. Park like property with outside sitting area. Privacy and pet friendly. Enjoy life on the east end in this furnished home ready for you and convenient to area restaurants, wineries, and all the North Fork has to offer. Permit #0107
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    Showing 11 - 20 of 57 results| view:  results per page« 1|2|3|4|5|...|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

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    Office: 52875 Main Road, Southold NY 11971
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