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 1 - 10 of 610 results| view:  results per page« 1|2|3|4|5|...|last »
    • Looking for a true summer experience on the beautiful North Fork of Long Island? look no further. This Spacious home has the full spectrum of mother nature right on your own huge back yard on the great lake with 2 fire pits. Featuring 4 Bedrooms, 4 Bath, An Oversize Patio, Large Heated In ground pool. Your own fully equipped gym to help keep you in the best of shape! You may enjoy fishing in a lake only a few steps away, as well as close distance to Kenny’s Beach on the Sound. Ample of Marinas around the corners, as well as endless vegetable & fruit farms & stands, wineries, restaurants & shopping. Enjoy this rare find for a memorable summer experience! Permit no: 0080. Expire: 06/07/2025, Additional information: Interior Features: Guest Quarters 31
      1205 Lake Drive Southold, NY 11971
      $17,500
      4 Bedrooms 4 Full Baths Sq. Ft. 4000.00:# Square Feet
      Single Family For Rent NEW ML# 819358
      Looking for a true summer experience on the beautiful North Fork of Long Island? look no further. This Spacious home has the full spectrum of mother nature right on your own huge back yard on the great lake with 2 fire pits. Featuring 4 Bedrooms, 4 Bath, An Oversize Patio, Large Heated In ground pool. Your own fully equipped gym to help keep you in the best of shape! You may enjoy fishing in a lake only a few steps away, as well as close distance to Kenny’s Beach on the Sound. Ample of Marinas around the corners, as well as endless vegetable & fruit farms & stands, wineries, restaurants & shopping. Enjoy this rare find for a memorable summer experience! Permit no: 0080. Expire: 06/07/2025, Additional information: Interior Features: Guest Quarters
      Presented By: Douglas Elliman Real Estate  631-298-8000
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Come view this spacious and bright four-bedroom, three-full-bath home on Southold’s lovely Pine Neck. Centrally locatd, this home features an open floor plan with two large living rooms, one with brick fireplace. The large open updated kitchen has cast stone counters and stainless steel appliances. A large second-story deck over looks the large and private rear yard. CAC and private laundry equipment add comfort and convenience to your vacation experience.Full season (MD-LD) $24, 500June $6, 500 July $8800 August-LD $9500 12
      440 Pine Neck Rd Southold, NY 11971
      $24,500
      4 Bedrooms 3 Full Baths Sq. Ft. 2340.00:# Square Feet
      Single Family For Rent NEW ML# 818299
      Come view this spacious and bright four-bedroom, three-full-bath home on Southold’s lovely Pine Neck. Centrally locatd, this home features an open floor plan with two large living rooms, one with brick fireplace. The large open updated kitchen has cast stone counters and stainless steel appliances. A large second-story deck over looks the large and private rear yard. CAC and private laundry equipment add comfort and convenience to your vacation experience.Full season (MD-LD) $24, 500June $6, 500 July $8800 August-LD $9500
      Presented By: Douglas Elliman Real Estate  631-298-8000
      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. February 2025 to End of April 2025 at $10, 000 Per Month (Single or Multiple Months Rental Considered). Summer 2025 - June $25, 000; LD to End of September $20, 000. Permit #0537. 29
      590 Soundview Av Ext Southold, NY 11971
      $90,000
      $25,000
      4 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 3100.00:# Square Feet
      Single Family For Rent PRICE REDUCED ML# 813857
      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. February 2025 to End of April 2025 at $10, 000 Per Month (Single or Multiple Months Rental Considered). Summer 2025 - June $25, 000; LD to End of September $20, 000. Permit #0537.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Looking for the perfect year-round rental on the North Fork? This charming 3-bedroom, 1-bathroom home offers the ideal retreat, whether you’re a local resident or seeking a year-round getaway. Nestled in the heart of the North Fork, this home is just moments away from the area’s renowned beaches, picturesque wineries, charming hamlet shopping, and so much more. Spend your days savoring wine tastings, strolling through quaint villages, dining at top-notch restaurants, or relaxing on nearby sandy shores. The property features an eat-in kitchen, perfect for creating memorable meals, and a spacious back deck and firepit area designed for outdoor entertaining. With plenty of activities and amenities at your doorstep, this rental offers the perfect blend of comfort and convenience. Don’t miss your chance to live in one of the North Fork’s most sought-after locations. Call today for your private tour!Southold Town Permit #: 0828 12
      900 Cedar Drive Southold, NY 11971
      $3,200
      3 Bedrooms 1 Full Bath Sq. Ft. 1100.00:# Square Feet
      Single Family For Rent ML# 812595
      Looking for the perfect year-round rental on the North Fork? This charming 3-bedroom, 1-bathroom home offers the ideal retreat, whether you’re a local resident or seeking a year-round getaway. Nestled in the heart of the North Fork, this home is just moments away from the area’s renowned beaches, picturesque wineries, charming hamlet shopping, and so much more. Spend your days savoring wine tastings, strolling through quaint villages, dining at top-notch restaurants, or relaxing on nearby sandy shores. The property features an eat-in kitchen, perfect for creating memorable meals, and a spacious back deck and firepit area designed for outdoor entertaining. With plenty of activities and amenities at your doorstep, this rental offers the perfect blend of comfort and convenience. Don’t miss your chance to live in one of the North Fork’s most sought-after locations. Call today for your private tour!Southold Town Permit #: 0828
      Presented By: Signature Premier Properties  631-765-6000
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Impeccable, like new ranch for rent with quality features throughout in Harbor Lights with a deeded beach and park at the end of the street. There are three bedrooms, two full bathrooms, open floor plan from kitchen through the dining area into the vaulted ceiling living room, Enjoy the beautiful screened in porch which overlooks the private back yard with slate patio, grass lawn, and outdoor shower. Prime location for easy access to numerous beaches, wineries and town shops, restaurants and transportation. Available July and/or August $15, 000. Southold Town Rental Permit #0600, Additional information: Appearance: Mint 17
      1265 Brigantine Drive Southold, NY 11971
      $15,000
      3 Bedrooms 2 Full Baths Sq. Ft. 1750.00:# Square Feet
      Single Family For Rent ML# 810773
      Impeccable, like new ranch for rent with quality features throughout in Harbor Lights with a deeded beach and park at the end of the street. There are three bedrooms, two full bathrooms, open floor plan from kitchen through the dining area into the vaulted ceiling living room, Enjoy the beautiful screened in porch which overlooks the private back yard with slate patio, grass lawn, and outdoor shower. Prime location for easy access to numerous beaches, wineries and town shops, restaurants and transportation. Available July and/or August $15, 000. Southold Town Rental Permit #0600, Additional information: Appearance: Mint
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Rental Permit #0609 Enter a sanctuary of light and space in this beautifully designed home, where the grandeur of the Long Island Sound meets serene beachside living. As you enter, you’re greeted by a stunning wall of windows that invites the outside in, setting a tranquil tone throughout the residence. The first floor offers three well-appointed bedrooms, including a master with en-suite bathroom with its own private deck accessed through sliding glass doors-an ideal retreat for morning coffees or evening relaxation. Two additional bedrooms have a full bathroom across the hall. Additionally, a separate laundry room provides practical utility without compromising on style. Ascend to the second floor and discover the heart of the home: an open concept living area that combines the living room, dining room, and a modern kitchen equipped with granite countertops and new stainless steel appliances. Cathedral ceilings with exposed wooden beams accentuate the feeling of openness, further enhanced by plentiful natural light and two sliding glass doors that lead out to an impressive 1, 400 square foot wrap-around deck. Here, panoramic views of the Long Island Sound unfold in every direction, offering a breathtaking backdrop for entertaining or quiet reflection. Outside, the property is bordered by preserved land, ensuring unspoiled vistas and privacy. Just a direct half-mile down the street lies Kenney’s Beach, a sandy beach, rare for the Long Island Sound that stretches for miles. Whether heading east to Horton’s Point Lighthouse or west to Goldsmith’s Inlet, the journey is as stunning as the destination. The nearby 60-acre nature trail invites exploration, while this home offers peace, privacy, and breathtaking sunsets in a coveted private beach community. 30
      350 West Drive Southold, NY 11971
      $16,000
      3 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 1900.00:# Square Feet
      Single Family For Rent ML# 809819
      Rental Permit #0609 Enter a sanctuary of light and space in this beautifully designed home, where the grandeur of the Long Island Sound meets serene beachside living. As you enter, you’re greeted by a stunning wall of windows that invites the outside in, setting a tranquil tone throughout the residence. The first floor offers three well-appointed bedrooms, including a master with en-suite bathroom with its own private deck accessed through sliding glass doors-an ideal retreat for morning coffees or evening relaxation. Two additional bedrooms have a full bathroom across the hall. Additionally, a separate laundry room provides practical utility without compromising on style. Ascend to the second floor and discover the heart of the home: an open concept living area that combines the living room, dining room, and a modern kitchen equipped with granite countertops and new stainless steel appliances. Cathedral ceilings with exposed wooden beams accentuate the feeling of openness, further enhanced by plentiful natural light and two sliding glass doors that lead out to an impressive 1, 400 square foot wrap-around deck. Here, panoramic views of the Long Island Sound unfold in every direction, offering a breathtaking backdrop for entertaining or quiet reflection. Outside, the property is bordered by preserved land, ensuring unspoiled vistas and privacy. Just a direct half-mile down the street lies Kenney’s Beach, a sandy beach, rare for the Long Island Sound that stretches for miles. Whether heading east to Horton’s Point Lighthouse or west to Goldsmith’s Inlet, the journey is as stunning as the destination. The nearby 60-acre nature trail invites exploration, while this home offers peace, privacy, and breathtaking sunsets in a coveted private beach community.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Brand New Tastefully Renovated Furnished Apartment conveniently located in the heart of Southold. The apartment is Available to rent for Year Round or flexible time-frame(s). Public transportation is in near proximity, along with everything else the North Fork has to offer. 5
      53395 Route 25 Unit Apt 1 Southold, NY 11971
      $3,500
      $3,000
      1 Bedroom 1 Full Bath Sq. Ft. 750.00:# Square Feet
      Apartment For Rent PRICE REDUCED ML# 805184
      Brand New Tastefully Renovated Furnished Apartment conveniently located in the heart of Southold. The apartment is Available to rent for Year Round or flexible time-frame(s). Public transportation is in near proximity, along with everything else the North Fork has to offer.
      Presented By: Century 21 Albertson Realty  631-765-3800
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 16
      455 W Shore Drive Southold, NY 11971
      $5,000
      4 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 1625.00:#
      Single Family For Rent ML# 3591372
      Presented By: Corcoran  631-765-1300
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • This beautiful home with in-ground pool and ample private open space exudes beach resort ease and is rarely available for rent. Located in a quiet enclave off the vineyards mile of Southold on the north fork, it is within proximity to farms, town, beaches and restaurants. The home which entered via a tree lined drive, is comprised of two stories, plus a lower level. The first floor features a southeast facing double height living room with woodburning fireplace, a modern kitchen with breakfast counter, a formal dining area which opens to a vast deck for lounging and socializing. A private primary suite is on the first floor with a dedicated full bathroom and closet. Off of the main entry is half bath and another closet. There is an attached one care garage. The second floor has two bedrooms with peek-a-boo waterviews, each with a private balcony.There is a guest bath on this level. The lower level has full glass sliding doors from the family room to outside. There is also a full bath, wine closet, laundry and plenty of storage space. The fenced in backyard has a pool with large patio that provides secure and private space for recreation, and opportunities for gardening. Potential boat dock available. 31
      Southold, NY 11971
      $98,000
      3 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 2085.00:#
      Single Family For Rent ML# 3590555
      This beautiful home with in-ground pool and ample private open space exudes beach resort ease and is rarely available for rent. Located in a quiet enclave off the vineyards mile of Southold on the north fork, it is within proximity to farms, town, beaches and restaurants. The home which entered via a tree lined drive, is comprised of two stories, plus a lower level. The first floor features a southeast facing double height living room with woodburning fireplace, a modern kitchen with breakfast counter, a formal dining area which opens to a vast deck for lounging and socializing. A private primary suite is on the first floor with a dedicated full bathroom and closet. Off of the main entry is half bath and another closet. There is an attached one care garage. The second floor has two bedrooms with peek-a-boo waterviews, each with a private balcony.There is a guest bath on this level. The lower level has full glass sliding doors from the family room to outside. There is also a full bath, wine closet, laundry and plenty of storage space. The fenced in backyard has a pool with large patio that provides secure and private space for recreation, and opportunities for gardening. Potential boat dock available.
      Presented By: Compass Greater NY LLC  631-566-7463
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Contemporary Home with Heated Pool, Less then a 1/2 Mile from a Gorgeous Long Island Sound Beach. Come Enjoy the Great North Fork. The Perfect Getaway Does Exist! With 3 Bedrooms and 2 Full Baths, Close Proximity to the Beach, a Pool Integrated into the Deck, and a Separate Rooftop Deck, This Property Offers an Ideal Mix of Relaxation and Style. The Spacious Gourmet Kitchen (Sub-Zero Fridge, Meile Oven, Wolf Gas Range) and Multiple Living Areas Make it Great for Both Quiet Retreats and Entertaining Guests. The North Fork is Known for its Beautiful Landscapes, Beaches, Wineries, and Local Charm, So This Home is in a Prime Spot to Enjoy All it Has to Offer! Off Season $4, 000 Per Month; Year Round $4, 200 Per Month, Memorial Day to Labor Day $32, 000; June $8, 000; July $12, 000, August to Labor Day $15, 000; $3, 000 Weekly with 2 Week Minimum. Permit #1217. 30
      8200 Soundview Avenue Southold, NY 11971
      $4,000
      3 Bedrooms 2 Full Baths
      Single Family For Rent ML# 3590047
      Contemporary Home with Heated Pool, Less then a 1/2 Mile from a Gorgeous Long Island Sound Beach. Come Enjoy the Great North Fork. The Perfect Getaway Does Exist! With 3 Bedrooms and 2 Full Baths, Close Proximity to the Beach, a Pool Integrated into the Deck, and a Separate Rooftop Deck, This Property Offers an Ideal Mix of Relaxation and Style. The Spacious Gourmet Kitchen (Sub-Zero Fridge, Meile Oven, Wolf Gas Range) and Multiple Living Areas Make it Great for Both Quiet Retreats and Entertaining Guests. The North Fork is Known for its Beautiful Landscapes, Beaches, Wineries, and Local Charm, So This Home is in a Prime Spot to Enjoy All it Has to Offer! Off Season $4, 000 Per Month; Year Round $4, 200 Per Month, Memorial Day to Labor Day $32, 000; June $8, 000; July $12, 000, August to Labor Day $15, 000; $3, 000 Weekly with 2 Week Minimum. Permit #1217.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    Showing 1 - 10 of 610 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

    Questions? Just Ask!

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