Fair Housing Notice Standard Operating Procedure
631.765.5333

Southold Rentals

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

    610  properties match your search;

    584 with Multiple photos ;  29 with Virtual Tour ;  3 with Videos

    Save Search
    Showing 31 - 40 of 610 results| view:  results per page« first|...|2|3|4|5|...|last »
    • Charming 55+ Condominium Living. Unit 18D is a middle unit with 2 bedrooms and 2 bathrooms. In the front section of the home you will find the newly updated kitchen with bay window bump-out creating a breakfast nook. Kitchen appliances include; refrig, DW, oven/range, and built-in microwave. There is also a 2nd bedroom with large closet and 3/4 bath nearby. The rear of the home has a large living/dining room and the spacious primary bedroom has two closets and full bath. Fresh paint, new carpet. The first floor also has a coat closet, linen closet, washer/dryer and entrance to a full unfinished basement for lots of storage.. There is a brick patio in the back overlooking a neighboring farm. This unit is adjacent to the swimming pool and clubhouse. Founders Village is within walking distance to Village of Southold, train station, shopping and restaurants. Close to the LI Sound and the Peconic Bay for beach-goers. Central Air, Oil Heat. No pets.
      2555 Youngs Ave. Unit 18D Southold NY, 11971
      $2,800
      2 Bedrooms 2 Full Baths Sq. Ft. 1100.00:#
      Misc Sold ML# 3559664
      Charming 55+ Condominium Living. Unit 18D is a middle unit with 2 bedrooms and 2 bathrooms. In the front section of the home you will find the newly updated kitchen with bay window bump-out creating a breakfast nook. Kitchen appliances include; refrig, DW, oven/range, and built-in microwave. There is also a 2nd bedroom with large closet and 3/4 bath nearby. The rear of the home has a large living/dining room and the spacious primary bedroom has two closets and full bath. Fresh paint, new carpet. The first floor also has a coat closet, linen closet, washer/dryer and entrance to a full unfinished basement for lots of storage.. There is a brick patio in the back overlooking a neighboring farm. This unit is adjacent to the swimming pool and clubhouse. Founders Village is within walking distance to Village of Southold, train station, shopping and restaurants. Close to the LI Sound and the Peconic Bay for beach-goers. Central Air, Oil Heat. No pets.
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Planning a staycation? this Laughing Waters Association ranch is the perfect destination for a resort-style stay this year. Come experience the private bay beach, smell the salt air, and enjoy time boating/SUP/kayaking in the creek or try your luck clamming. The home is an easy and comfortable springboard to the North Fork lifestyle and features an open plan ideal for entertaining. Living room, Dining room, large kitchen to make the most serious cooks feel at home - plus an en suite bedroom with full bath and two additional bedrooms and full bath. Beyond the covered porch is a verdant and fully fenced in lawn area ideal for play, a bbq area, multiple sitting areas, a game room adjacent to the garage, a pool house with ’bar’ area and the most amazing outdoor, poolside shower. No detail for enjoyment has been overlooked - there is even a firepit for idle-hour! Available monthly, or weekly - inquire. Pets permited - fully fenced in property! Southold RP# 1149 expires 6/10/26 31
      50 Wabasso Street Southold, NY 11971
      $18,000
      3 Bedrooms 2 Full Baths Sq. Ft. 1200.00:#
      Single Family For Rent ML# 3559692
      Planning a staycation? this Laughing Waters Association ranch is the perfect destination for a resort-style stay this year. Come experience the private bay beach, smell the salt air, and enjoy time boating/SUP/kayaking in the creek or try your luck clamming. The home is an easy and comfortable springboard to the North Fork lifestyle and features an open plan ideal for entertaining. Living room, Dining room, large kitchen to make the most serious cooks feel at home - plus an en suite bedroom with full bath and two additional bedrooms and full bath. Beyond the covered porch is a verdant and fully fenced in lawn area ideal for play, a bbq area, multiple sitting areas, a game room adjacent to the garage, a pool house with ’bar’ area and the most amazing outdoor, poolside shower. No detail for enjoyment has been overlooked - there is even a firepit for idle-hour! Available monthly, or weekly - inquire. Pets permited - fully fenced in property! Southold RP# 1149 expires 6/10/26
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Spacious Open Plan Home with So Much to Offer near Several Great Beaches. Open Livingroom, Dining Room, Kitchen, a Separate Den and a Separate Office as well as a Good Size Bedroom and Bath on First Floor. The Spacious Kitchen Offers Sub Zero Refrigerator, a Wine Fridge and a Separate Fridge Dedicated to Drinks You Grab on Way to Pool. Primary Ensuite and Two Bedrooms and Hall Bath on Second Floor. Finished Lower Level Family Room offers TV with Gaming Hookup and a Closet Full of Games to Enjoy. Fully Fenced Large Back Yard. Additional Separate Fencing around Inground Heated Pool with Easy Automatic Solar Cover and Pool House. Large Stone Patio for BBQing, Dining and Lounging and Lots of Open Backyard Grass Area to Play the Yard Games Provided or to Simply Star Gaze at Night. Room for All. Available Single or Multiple Months 10/13/24 to 4/30/25 at $8, 000 Per Month and Summer 2025 - Memorial Day to Labor Day $90, 000; June $28, 000; July $32, 000; August to Labor Day $40, 000; Labor Day to end of September $10, 000. Pets Considered on Case-by-Case Basis. Permit #0913. 32
      450 Sterling Woods Lane Southold, NY 11971
      $8,000
      4 Bedrooms 3 Full Baths Sq. Ft. 3400.00:#
      Single Family For Rent ML# 3559564
      Spacious Open Plan Home with So Much to Offer near Several Great Beaches. Open Livingroom, Dining Room, Kitchen, a Separate Den and a Separate Office as well as a Good Size Bedroom and Bath on First Floor. The Spacious Kitchen Offers Sub Zero Refrigerator, a Wine Fridge and a Separate Fridge Dedicated to Drinks You Grab on Way to Pool. Primary Ensuite and Two Bedrooms and Hall Bath on Second Floor. Finished Lower Level Family Room offers TV with Gaming Hookup and a Closet Full of Games to Enjoy. Fully Fenced Large Back Yard. Additional Separate Fencing around Inground Heated Pool with Easy Automatic Solar Cover and Pool House. Large Stone Patio for BBQing, Dining and Lounging and Lots of Open Backyard Grass Area to Play the Yard Games Provided or to Simply Star Gaze at Night. Room for All. Available Single or Multiple Months 10/13/24 to 4/30/25 at $8, 000 Per Month and Summer 2025 - Memorial Day to Labor Day $90, 000; June $28, 000; July $32, 000; August to Labor Day $40, 000; Labor Day to end of September $10, 000. Pets Considered on Case-by-Case Basis. Permit #0913.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Romantic sweeping porch beauty, FACING the Creek and Beach Rest, and rewind, in a truly unique and bucolic setting. Even the children will love the magic. 7
      2975 N Bayview Rd Southold, NY 11971
      $25,000
      3 Bedrooms 3 Full Baths
      Single Family For Rent Withdrawn ML# 3559324
      Romantic sweeping porch beauty, FACING the Creek and Beach Rest, and rewind, in a truly unique and bucolic setting. Even the children will love the magic.
      Presented By: Carol A Bohn  631-831-2738
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • A North Fork Summer Time Oasis! Newly Renovated 4 Bedroom, 3 Bath Home with Heated Pool (20’ x 42’) and Near a Memorable Long Island Sound Beach. Marble Pool Surround Never Gets Hot. Additional Lower Level Living Room adjacent to the Wet Bar and Fridge Providing Easy Access for Pool Side Dining. Ice Machine, Gas Grill, Large Outdoor Sofa and Dining Table as Well as Lounges and Umbrellas. Everything You Need for Summer Time Fun. July $20, 000; August to Labor Day $25, 000. Also $5, 000 per Week with Two Week Minimum. Permit #0987. 26
      630 Wild Cherry Way Southold, NY 11971
      $20,000
      4 Bedrooms 3 Full Baths
      Single Family For Rent 99 ML# 3558852
      A North Fork Summer Time Oasis! Newly Renovated 4 Bedroom, 3 Bath Home with Heated Pool (20’ x 42’) and Near a Memorable Long Island Sound Beach. Marble Pool Surround Never Gets Hot. Additional Lower Level Living Room adjacent to the Wet Bar and Fridge Providing Easy Access for Pool Side Dining. Ice Machine, Gas Grill, Large Outdoor Sofa and Dining Table as Well as Lounges and Umbrellas. Everything You Need for Summer Time Fun. July $20, 000; August to Labor Day $25, 000. Also $5, 000 per Week with Two Week Minimum. Permit #0987.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Lovely spacious newly built Colonial just down the lane from 4 gorgeous LI Sound Beaches. Main Floor Primary Bedroom En-suite with private side entrance and it’s own deck. Second Primary Bedroom En-Suite on level 2 (has radiant heat floor and heat lamp). Two additional Bedrooms, a full Bath in the hall, and Laundry Room. Kitchen has huge island with seating, 6 burner or griddle dual fuel oven. Total 4 Bedrooms, 3.5 Baths, all hardwood floors, central air, patio, 2 decks. Amazing location just minutes to McCabes, Goldsmith, Kenneys, and Town Beach, as well as the great new beach side restaurant Little Fish. Fabulous Hamlet Downtown on Main Road with all your shopping needs, many more trendy restaurants, antique shops, art galleries, and vineyards with music. Enjoy the rental’s paddle board, 2 kayaks, and beach buggy wagon. July $17, 000, August to Labor Day $24, 000, September $12, 000. 30
      6430 Hortons Lane Southold, NY 11971
      $24,000
      4 Bedrooms 3 Full Baths 1 Half Bath
      Single Family For Rent ML# 3556906
      Lovely spacious newly built Colonial just down the lane from 4 gorgeous LI Sound Beaches. Main Floor Primary Bedroom En-suite with private side entrance and it’s own deck. Second Primary Bedroom En-Suite on level 2 (has radiant heat floor and heat lamp). Two additional Bedrooms, a full Bath in the hall, and Laundry Room. Kitchen has huge island with seating, 6 burner or griddle dual fuel oven. Total 4 Bedrooms, 3.5 Baths, all hardwood floors, central air, patio, 2 decks. Amazing location just minutes to McCabes, Goldsmith, Kenneys, and Town Beach, as well as the great new beach side restaurant Little Fish. Fabulous Hamlet Downtown on Main Road with all your shopping needs, many more trendy restaurants, antique shops, art galleries, and vineyards with music. Enjoy the rental’s paddle board, 2 kayaks, and beach buggy wagon. July $17, 000, August to Labor Day $24, 000, September $12, 000.
      Presented By: Town And Country Real Estate  631-288-3030
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Rental Permit # 0966Fantastic home set directly on Great Pond and a block (975 feet) from Kenney’s Beach with restaurant Little Fish just around the corner. This bright 3 bedroom and 2 full bathroom, with a 3 season room all window porch home has an expansive rear deck overlooking the fresh water pond. Watch osprey dive bomb for fresh water bass while geese, ducks and egrets meander across the water. In the evening, take in spectacular sunsets from the large bay window facing directly west or from the beach itself.
      315 Lake Drive Southold NY, 11971
      $3,800
      3 Bedrooms 2 Full Baths Sq. Ft. 1100.00:#
      Single Family Sold ML# 3554728
      Rental Permit # 0966Fantastic home set directly on Great Pond and a block (975 feet) from Kenney’s Beach with restaurant Little Fish just around the corner. This bright 3 bedroom and 2 full bathroom, with a 3 season room all window porch home has an expansive rear deck overlooking the fresh water pond. Watch osprey dive bomb for fresh water bass while geese, ducks and egrets meander across the water. In the evening, take in spectacular sunsets from the large bay window facing directly west or from the beach itself.
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • **June Special** 6/16-6/30 for $2950.00 (not including security & cleaning fee). Beach house with a modern farmhouse feel! Down the street from Founders Landing Beach, close to town & restaurants. Great location, open floor plan, perfect summer retreat! 11
      340 Locust Lane Southold, NY 11971
      $7,800
      3 Bedrooms 2 Full Baths
      Single Family For Rent Withdrawn ML# 3554527
      **June Special** 6/16-6/30 for $2950.00 (not including security & cleaning fee). Beach house with a modern farmhouse feel! Down the street from Founders Landing Beach, close to town & restaurants. Great location, open floor plan, perfect summer retreat!
      Presented By: Signature Premier Properties  631-765-6000
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Enjoy the Summer in this bright and airy cottage in Paradise Shores. Fully renovated, central air, vaulted ceilings, open floor plan and tons of natural light, this home is welcoming. Relax on the back deck after a day of fun in the sun. Private bay access one block away. Water views in the backyard. Rental Permit #0199, Additional information: Interior Features:Combo Kitchen 19
      2350 Paradise Shores Rd Southold, NY 11971
      $7,500
      2 Bedrooms 1 Full Bath
      Single Family For Rent Withdrawn ML# 3554180
      Enjoy the Summer in this bright and airy cottage in Paradise Shores. Fully renovated, central air, vaulted ceilings, open floor plan and tons of natural light, this home is welcoming. Relax on the back deck after a day of fun in the sun. Private bay access one block away. Water views in the backyard. Rental Permit #0199, Additional information: Interior Features:Combo Kitchen
      Presented By: Douglas Elliman Real Estate  631-354-8100
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Welcome! The moment you lay eyes on this expansive property, you will feel as though you’ve arrived to live out the summer of your dreams. An incredible 3-acre property nestled two blocks from the beach with lots of quiet roads for running, biking and exploring. Throughout the grounds, there are many areas to relax and entertain, including a gorgeous pool area with Wi-Fi, surrounded by hydrangea with an 18x50 gunite heated saltwater pool; double outdoor showers; furnished patio; 3 pergolas; kitchen garden with raised beds and cutting flowers; shade garden; screened-in front porch; playhouse with loft; fire pit; and great lawn. The main house has been lovingly restored and features 3+ bedrooms, 2 bathrooms, a fireplace, den, library, and a fabulous farmhouse kitchen with central HVAC and modern amenities throughout. Surrounded by the North Fork’s award-winning vineyards, marinas, renowned restaurants, farm stands, beaches and great shopping! Permit #1114 35
      50 Lighthouse Rd Southold, NY 11971
      $25,000
      3 Bedrooms 2 Full Baths
      Single Family For Rent Withdrawn ML# 3553592
      Welcome! The moment you lay eyes on this expansive property, you will feel as though you’ve arrived to live out the summer of your dreams. An incredible 3-acre property nestled two blocks from the beach with lots of quiet roads for running, biking and exploring. Throughout the grounds, there are many areas to relax and entertain, including a gorgeous pool area with Wi-Fi, surrounded by hydrangea with an 18x50 gunite heated saltwater pool; double outdoor showers; furnished patio; 3 pergolas; kitchen garden with raised beds and cutting flowers; shade garden; screened-in front porch; playhouse with loft; fire pit; and great lawn. The main house has been lovingly restored and features 3+ bedrooms, 2 bathrooms, a fireplace, den, library, and a fabulous farmhouse kitchen with central HVAC and modern amenities throughout. Surrounded by the North Fork’s award-winning vineyards, marinas, renowned restaurants, farm stands, beaches and great shopping! Permit #1114
      Presented By: Corcoran  631-848-7730
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    Showing 31 - 40 of 610 results| view:  results per page« first|...|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

    Questions? Just Ask!

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