Fair Housing Notice Standard Operating Procedure
631.765.5333

Southold Rentals

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

    565  properties match your search;

    536 with Multiple photos ;  26 with Virtual Tour ;  3 with Videos

    Save Search
    Showing 1 - 10 of 564 results| view:  results per page« 1|2|3|4|5|...|last »
    • 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:# Square Feet
      Single Family For Rent NEW 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
    • Large and bright 4 bedroom, 2.5 bath home with pool in a private waterfront community. Property has path that brings you ten houses from the most beautiful beach. A great place to spend any season and year-round. Great open kitchen with table that seats 8. Adjacent to the dining room which can seat 10+. Host the holidays. Primary suite is oversized with a seating area and a separate sunroom. Upstairs are all of the guest rooms and a den. The property is just shy of 3 acres and offers plenty of room to roam. A great escape from the city, and a tranquil place from which to work. Available multiple time periods; any two available weeks in the summer $8k/week, July12- Aug 8 $30k, Sept.3-30 $25k, Oct. $20k, Nov. $20k, Winter Sept. 3- May 1 $48k, may be available year-round after Labor Day. 25
      2600 Paradise Point Rd Southold, NY 11971
      $8,000
      4 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 3950.00:# Square Feet
      Single Family For Rent NEW ML# 3547691
      Large and bright 4 bedroom, 2.5 bath home with pool in a private waterfront community. Property has path that brings you ten houses from the most beautiful beach. A great place to spend any season and year-round. Great open kitchen with table that seats 8. Adjacent to the dining room which can seat 10+. Host the holidays. Primary suite is oversized with a seating area and a separate sunroom. Upstairs are all of the guest rooms and a den. The property is just shy of 3 acres and offers plenty of room to roam. A great escape from the city, and a tranquil place from which to work. Available multiple time periods; any two available weeks in the summer $8k/week, July12- Aug 8 $30k, Sept.3-30 $25k, Oct. $20k, Nov. $20k, Winter Sept. 3- May 1 $48k, may be available year-round after Labor Day.
      Presented By: Compass Greater NY LLC  631-251-8644
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Charming year-round rental in coveted Founders Landing! Just moments from a sugar sand Bay beach and a marina with deep water access. Nestled on a spacious 1/4 acre parcel perfect for outdoor activities. Featuring two cozy bedrooms and a well-appointed bath, this home offers plenty of room for entertaining while being easy to maintain. Conveniently close to shops, beaches, and dining. Don’t miss out on this great rental! Southold Town Rental Permit #1096 18
      1385 Old Shipyard Lane Southold, NY 11971
      $3,750
      2 Bedrooms 1 Full Bath Sq. Ft. 606.00:# Square Feet
      Single Family For Rent NEW ML# 3546984
      Charming year-round rental in coveted Founders Landing! Just moments from a sugar sand Bay beach and a marina with deep water access. Nestled on a spacious 1/4 acre parcel perfect for outdoor activities. Featuring two cozy bedrooms and a well-appointed bath, this home offers plenty of room for entertaining while being easy to maintain. Conveniently close to shops, beaches, and dining. Don’t miss out on this great rental! Southold Town Rental Permit #1096
      Presented By: Douglas Elliman Real Estate  631-354-8100
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Introducing your brand-new summer retreat! Available from July 2024, this stunning 4-bedroom, 3.5-bathroom waterfront oasis boasts the pinnacle of luxury living. Nestled on West Creek in Southold. Enjoy exclusive access to Peconic Bay via your private dock, perfect for soaking up the summer sun. Spanning approximately 3500 square feet of impeccable interior space, revel in the elegance of oak floors, a luxurious soaking tub, and high ceilings throughout. The first floor offers two primary ensuites, a spacious Great Room with a cozy fireplace, a convenient laundry room, and 2.5 baths. Plus, a two-car garage ensures ample parking for all your summer adventures. Ascend to the second floor to discover two additional bedrooms, a full bath, a second laundry area, and a sprawling bonus room-ideal for entertaining guests or unwinding after a day of exploration. Central air conditioning ensures comfort on even the hottest summer days, while a full basement provides plenty of storage space for your beach gear. Outside is your private paradise, complete with a refreshing 16 x 32 in-ground pool, currently being readied for the summer. Situated in the coveted Southold Park District, relish in access to Founder Landing and South Harbor Park, along with proximity to pristine bay beaches, renowned vineyards, charming farmstands, premier shopping destinations, and convenient public transportation. Don’t miss this unparalleled opportunity to experience the epitome of summer living and make memories to last a lifetime! Southold Town Rental Permit #1085. 30
      910 Glenn Rd Southold, NY 11971
      $35,000
      4 Bedrooms 3 Full Baths 1 Half Bath
      Single Family For Rent NEW ML# 3546491
      Introducing your brand-new summer retreat! Available from July 2024, this stunning 4-bedroom, 3.5-bathroom waterfront oasis boasts the pinnacle of luxury living. Nestled on West Creek in Southold. Enjoy exclusive access to Peconic Bay via your private dock, perfect for soaking up the summer sun. Spanning approximately 3500 square feet of impeccable interior space, revel in the elegance of oak floors, a luxurious soaking tub, and high ceilings throughout. The first floor offers two primary ensuites, a spacious Great Room with a cozy fireplace, a convenient laundry room, and 2.5 baths. Plus, a two-car garage ensures ample parking for all your summer adventures. Ascend to the second floor to discover two additional bedrooms, a full bath, a second laundry area, and a sprawling bonus room-ideal for entertaining guests or unwinding after a day of exploration. Central air conditioning ensures comfort on even the hottest summer days, while a full basement provides plenty of storage space for your beach gear. Outside is your private paradise, complete with a refreshing 16 x 32 in-ground pool, currently being readied for the summer. Situated in the coveted Southold Park District, relish in access to Founder Landing and South Harbor Park, along with proximity to pristine bay beaches, renowned vineyards, charming farmstands, premier shopping destinations, and convenient public transportation. Don’t miss this unparalleled opportunity to experience the epitome of summer living and make memories to last a lifetime! Southold Town Rental Permit #1085.
      Presented By: Douglas Elliman Real Estate  631-354-8100
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Stunning new construction with 110’ of Long Island Sound front and private stairs to your beach. 10ft ceilings throughout the first floor, open floor plan with panoramic views. The living room has an oversized fireplace, built in cabinets and coffered ceilings, glass doors that open directly to the patio. Viking full stainless steel appliance package, double dishwashers, gas stove with custom stainless hood, wine cooler and an oversized custom island with a built in microwave. 2 primary bedrooms one located on 1st floor with radiant heated floors in the bathroom, marble shower, free standing soaking tub, double custom vanity and a custom walk-in closet with illuminated hanging rods. Finished mud room & laundry room, powder room with gorgeous marble floors. Second floor features 3 bedrooms including another primary suite, full bath, a great room w/ a color changing LED fireplace. Full basement with BR&BA. This is a must see! Available July: $50K and Aug-Labor Day: $50K. Permit #: 1101 35
      17877 Soundview Avenue Southold, NY 11971
      $50,000
      5 Bedrooms 4 Full Baths 1 Half Bath
      Commercial For Rent ML# 3546351
      Stunning new construction with 110’ of Long Island Sound front and private stairs to your beach. 10ft ceilings throughout the first floor, open floor plan with panoramic views. The living room has an oversized fireplace, built in cabinets and coffered ceilings, glass doors that open directly to the patio. Viking full stainless steel appliance package, double dishwashers, gas stove with custom stainless hood, wine cooler and an oversized custom island with a built in microwave. 2 primary bedrooms one located on 1st floor with radiant heated floors in the bathroom, marble shower, free standing soaking tub, double custom vanity and a custom walk-in closet with illuminated hanging rods. Finished mud room & laundry room, powder room with gorgeous marble floors. Second floor features 3 bedrooms including another primary suite, full bath, a great room w/ a color changing LED fireplace. Full basement with BR&BA. This is a must see! Available July: $50K and Aug-Labor Day: $50K. Permit #: 1101
      Presented By: Corcoran  631-848-7730
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Introducing this charming 2 bedroom, 2 bathroom condo nestled in the picturesque town of Southold. This turn-key condo offers an ideal combination of convenience and comfort. The spacious and bright living area, high ceilings and fireplace create a warm and inviting atmosphere. The kitchen has been recently updated, and the updated bathrooms feature glass enclosed showers. There are beautiful hardwood doors and floors throughout. Additionally, residents have full access to the clubhouse and inground pool. This condo is the perfect blend of modern comfort, convenient amenities with close proximity to beautiful North Fork beaches. Permit #1106 19
      2555 Youngs Avenue Southold, NY 11971
      $3,100
      2 Bedrooms 2 Full Baths
      Condo For Rent NEW ML# 3546359
      Introducing this charming 2 bedroom, 2 bathroom condo nestled in the picturesque town of Southold. This turn-key condo offers an ideal combination of convenience and comfort. The spacious and bright living area, high ceilings and fireplace create a warm and inviting atmosphere. The kitchen has been recently updated, and the updated bathrooms feature glass enclosed showers. There are beautiful hardwood doors and floors throughout. Additionally, residents have full access to the clubhouse and inground pool. This condo is the perfect blend of modern comfort, convenient amenities with close proximity to beautiful North Fork beaches. Permit #1106
      Presented By: Engel & Volkers North Fork  631-298-7953
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Southold Shores Bayfront Community Contemporary Available Y/R Or Furnished For Summer 2018 Season... Flexible Dates/Rates - Inquire. Moments To Greenport Village Or Southold Amenities. Private Bay Beach Ass’n W/Possibility To Keep A Boat In The Ass’n Marina. Large, Light, Bright And Airy Home W/Front And Back Porches.... Available May 1.
      75 Tarpon Drive Southold NY, 11971
      $2,600 - $17,500
      4 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 2200.00:# Square Feet
      Single Family Sold ML# 3016868
      Southold Shores Bayfront Community Contemporary Available Y/R Or Furnished For Summer 2018 Season... Flexible Dates/Rates - Inquire. Moments To Greenport Village Or Southold Amenities. Private Bay Beach Ass’n W/Possibility To Keep A Boat In The Ass’n Marina. Large, Light, Bright And Airy Home W/Front And Back Porches.... Available May 1.
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Boating, Beach & Bay Views Aplenty From This Wonderful Waterfront Rental! Large Deck Will Be Fully And Attractively Furnished With Umbrella-Covered Tables, Plenty Of Seating And Serving Areas. Kitchen Side Porch/Patio Has Retractable Awning And Seating. Deep Water Dock And Private Beach Steps Away On Southold Bay!
      1705 Arshamomaque Avenue Southold NY, 11971
      $25,000
      4 Bedrooms 2 Full Baths 1 Half Bath Sq. Ft. 1800.00:# Square Feet
      Single Family Sold ML# 3012850
      Boating, Beach & Bay Views Aplenty From This Wonderful Waterfront Rental! Large Deck Will Be Fully And Attractively Furnished With Umbrella-Covered Tables, Plenty Of Seating And Serving Areas. Kitchen Side Porch/Patio Has Retractable Awning And Seating. Deep Water Dock And Private Beach Steps Away On Southold Bay!
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Harbor Lights, W/Docking Rights, 4 Bedrooms Including 2 Waterview Master Suites, 1 On Each Floor. Entertain All Of Your Guests With This Sun Filled Open Floor Plan, Which Boasts A Fireplace, In-Ground Pool, Privacy, And All On Shy 1/2 Acre. Enjoy Private Sandy Peconic Bay Beach, Assoc. Park And Your Very Own Dock, Who Could Ask For More!
      90 Windjammer Drive Southold NY, 11971
      $3,500 - $10,000
      4 Bedrooms 3 Full Baths Sq. Ft. 3000.00:# Square Feet
      Single Family Sold ML# 3008887
      Harbor Lights, W/Docking Rights, 4 Bedrooms Including 2 Waterview Master Suites, 1 On Each Floor. Entertain All Of Your Guests With This Sun Filled Open Floor Plan, Which Boasts A Fireplace, In-Ground Pool, Privacy, And All On Shy 1/2 Acre. Enjoy Private Sandy Peconic Bay Beach, Assoc. Park And Your Very Own Dock, Who Could Ask For More!
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Winter Waterview, Hilltop Setting, Private Road, Deeded Row To Beach, Recently Renovated From Top To Bottom, New Appliances And Mechanicals
      1975 Hyatt Rd Southold NY, 11971
      $24,000
      2 Bedrooms 2 Full Baths Sq. Ft. 450.00:# Square Feet
      Single Family Sold ML# 3008152
      Winter Waterview, Hilltop Setting, Private Road, Deeded Row To Beach, Recently Renovated From Top To Bottom, New Appliances And Mechanicals
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    Showing 1 - 10 of 564 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