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Southold Luxury Rentals

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    Showing 21 - 30 of 38 results| view:  results per page« 1|2|3|4 »
    • 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
    • Southold Goose Creek Waterfront. Immaculate sun-filled home with all you will need to relax and enjoy summer. Large living room, and dining room. Well equipped Kitchen with sliders to deck, Den with amazing water views. Ensuite bedroom with water views, 2 additional bedrooms and bathrooms. Furnished deck and large yard. There is a dock to fish, boat, paddle board or kayak (2 included) from your own dock. A perfect retreat close to all the best of the North Fork. Rental Permit 0691 26
      1175 Waterview Drive Southold, NY 11971
      $14,000
      3 Bedrooms 3 Full Baths Sq. Ft. 1800.00:# Square Feet
      Single Family For Rent ML# 3519239
      Southold Goose Creek Waterfront. Immaculate sun-filled home with all you will need to relax and enjoy summer. Large living room, and dining room. Well equipped Kitchen with sliders to deck, Den with amazing water views. Ensuite bedroom with water views, 2 additional bedrooms and bathrooms. Furnished deck and large yard. There is a dock to fish, boat, paddle board or kayak (2 included) from your own dock. A perfect retreat close to all the best of the North Fork. Rental Permit 0691
      Presented By: The Agency Northshore NY  631-870-0753
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 2024 Rates July $6, 750.00/week (two week minimum) or $27, 000.00 for the month: Brand New Modern Farmhouse Completed in 2021 and located in the heart Hog’s Neck in Southold Hamlet. This home features an impressive 20x50 heated pool w/ electric cover, out door shower and sprawling paver patio. The interior is open and airy w/ Chef’s Kitchen outfitted with Thermador appliances, large living room with built in shelving, gas fireplace and formal dining room. All four bedrooms are located on the second level: 1 Primary En-suite, 1 Junior Suite, 2 Guest Bedrooms and Full Hallway Bathroom. You will enjoy being within close proximity to Goose Creek, South Harbor Park Beach and Southold’s vibrant business district! 33
      75 Clearview Avenue Southold, NY 11971
      $32,500
      $27,000
      4 Bedrooms 3 Full Baths 1 Half Bath
      Single Family For Rent PRICE REDUCED ML# 3513782
      2024 Rates July $6, 750.00/week (two week minimum) or $27, 000.00 for the month: Brand New Modern Farmhouse Completed in 2021 and located in the heart Hog’s Neck in Southold Hamlet. This home features an impressive 20x50 heated pool w/ electric cover, out door shower and sprawling paver patio. The interior is open and airy w/ Chef’s Kitchen outfitted with Thermador appliances, large living room with built in shelving, gas fireplace and formal dining room. All four bedrooms are located on the second level: 1 Primary En-suite, 1 Junior Suite, 2 Guest Bedrooms and Full Hallway Bathroom. You will enjoy being within close proximity to Goose Creek, South Harbor Park Beach and Southold’s vibrant business district!
      Presented By: Daniel Gale Sothebys Intl Rlty  631-477-0013
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • This soothing beach house is so Zen, you will feel like you are at a spa retreat! Peaceful and perfectly appointed, the backyard features a fabulous lagoon style pool, with a waterfall and hot tub, an amazing outdoor kitchen and bar, bathroom and outdoor shower! 3 bedrooms, 2 baths, including a spacious primary suite with a gorgeous spa like bathroom. All this and steps to the association beach! Surrounded by marinas, award winning vineyards, restaurants, farm stands & great shopping. Make this absolutely mint home your North Fork summer rental, you will not want to leave! Rental Permit #1002 21
      355 Windjammer Drive Southold, NY 11971
      $70,000
      3 Bedrooms 2 Full Baths
      Single Family For Rent ML# 3513704
      This soothing beach house is so Zen, you will feel like you are at a spa retreat! Peaceful and perfectly appointed, the backyard features a fabulous lagoon style pool, with a waterfall and hot tub, an amazing outdoor kitchen and bar, bathroom and outdoor shower! 3 bedrooms, 2 baths, including a spacious primary suite with a gorgeous spa like bathroom. All this and steps to the association beach! Surrounded by marinas, award winning vineyards, restaurants, farm stands & great shopping. Make this absolutely mint home your North Fork summer rental, you will not want to leave! Rental Permit #1002
      Presented By: Corcoran  631-848-7730
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Welcome to your future summer retreat! This beautiful newly built home offers the perfect blend of comfort and luxury, featuring 4 spacious bedrooms and 4 full baths. First floor primary bedroom with luxurious ensuite bathroom. Inside, you’ll find ample space and modern amenities that cater to your every need. However, what truly sets this property apart is the outdoor paradise waiting for you in the backyard. Immerse yourself in the heated saltwater pool or unwind in the relaxing hot tub - it’s your private sanctuary. Don’t miss the chance to rent this exceptional home and experience a lifestyle of unparalleled indulgence. Close to the beach!! Permit# - 0980 36
      4004 Old North Rd Southold, NY 11971
      $45,000
      4 Bedrooms 4 Full Baths Sq. Ft. 2787.00:# Square Feet
      Single Family For Rent ML# 3510262
      Welcome to your future summer retreat! This beautiful newly built home offers the perfect blend of comfort and luxury, featuring 4 spacious bedrooms and 4 full baths. First floor primary bedroom with luxurious ensuite bathroom. Inside, you’ll find ample space and modern amenities that cater to your every need. However, what truly sets this property apart is the outdoor paradise waiting for you in the backyard. Immerse yourself in the heated saltwater pool or unwind in the relaxing hot tub - it’s your private sanctuary. Don’t miss the chance to rent this exceptional home and experience a lifestyle of unparalleled indulgence. Close to the beach!! Permit# - 0980
      Presented By: Douglas Elliman Real Estate  631-354-8100
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Room for All in this Spacious 6 Bedroom Luxurious Home with Gourmet Kitchen with 6 Burner Wolf Stove, Formal Dining Room. Large Living Room with Fireplace, a Separate Den and Large Bedrooms. Rainy Day Game Room and More in Lower Level. All set on 2.3 Acres with In Ground Pool, Nicely Finished Outdoor Space and Yard Area and Just a Short Distance to Kenneys and McCabes Beaches. Summer 2024 - June 1 to June 28 - $30, 000 or $8, 500 Per Week With Two Week Minimum. August 25 to September 8 (Two Weeks) $18, 500; September $30, 000 or $8, 500 per Week With Two Week Minimum. Off Season - October through April at $15, 000 Per month for Single or Multiple Month Rentals. Permit #0233. 26
      1820 Kenneys Rd Southold, NY 11971
      $15,000
      6 Bedrooms 4 Full Baths Sq. Ft. 5028.00:# Square Feet
      Single Family For Rent ML# 3505469
      Room for All in this Spacious 6 Bedroom Luxurious Home with Gourmet Kitchen with 6 Burner Wolf Stove, Formal Dining Room. Large Living Room with Fireplace, a Separate Den and Large Bedrooms. Rainy Day Game Room and More in Lower Level. All set on 2.3 Acres with In Ground Pool, Nicely Finished Outdoor Space and Yard Area and Just a Short Distance to Kenneys and McCabes Beaches. Summer 2024 - June 1 to June 28 - $30, 000 or $8, 500 Per Week With Two Week Minimum. August 25 to September 8 (Two Weeks) $18, 500; September $30, 000 or $8, 500 per Week With Two Week Minimum. Off Season - October through April at $15, 000 Per month for Single or Multiple Month Rentals. Permit #0233.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Welcome to 1355 Watersedge Way a delightful Bayfront home located on Little Peconic Bay in Southold. Inside you have a spacious living room with a smart TV and a wall of sliding glass doors the lead out to the waterside deck, eat in kitchen, two bedrooms and one bathroom. on the lower level there is a family room with wet bar and access to the yard and outdoor shower, one bedroom, a full bath, and washer and dryer. The house is located next to a nature preserve with 300 ft. of beach providing easy access to the water/bay and plenty of privacy. Enjoy the spectacular views of the water and sunsets! MD TO LD $50k, June$12k, July $23K; August 1 to LD $24K, off season $7k for 30 days. House is available from May to November with a minimum of four weeks that does not need to align with the calendar month. RP# 0929 32
      1355 Watersedge Way Southold, NY 11971
      $7,000 - $50,000
      3 Bedrooms 2 Full Baths
      Single Family For Rent ML# 3501928
      Welcome to 1355 Watersedge Way a delightful Bayfront home located on Little Peconic Bay in Southold. Inside you have a spacious living room with a smart TV and a wall of sliding glass doors the lead out to the waterside deck, eat in kitchen, two bedrooms and one bathroom. on the lower level there is a family room with wet bar and access to the yard and outdoor shower, one bedroom, a full bath, and washer and dryer. The house is located next to a nature preserve with 300 ft. of beach providing easy access to the water/bay and plenty of privacy. Enjoy the spectacular views of the water and sunsets! MD TO LD $50k, June$12k, July $23K; August 1 to LD $24K, off season $7k for 30 days. House is available from May to November with a minimum of four weeks that does not need to align with the calendar month. RP# 0929
      Presented By: Town And Country Real Estate  631-477-5990
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Permit #493 Newly Renovated Farmhouse Centrally Located In Southold With Easy Access By Bus, Train or Car. Enjoy Your Morning Coffee As The Sun Rises Over The Farmfield. Spend An Afternoon Exploring The Beauty of the North Fork, Soak in the Sun at one of the Beautiful Peconic Bay or Long Island Sound Beaches, Enjoy Live Music at Numerous Wineries and/or Breweries, Browse unique local finds at One of Many Antique and/or Quaint Shops, and Don’t Forget to Stop by Our Bountiful Farm Stands. Cool Off With a Dip in the Heated Saltwater Pool, Enjoy Dinner Under the Stars and Reminisce Around the Fire Pit. Utilities Included. 10% Security & Exit Clean. Enjoy Summer On The North Fork! 25
      3400 Youngs Avenue Southold, NY 11971
      $40,000
      4 Bedrooms 2 Full Baths
      Single Family For Rent ML# 3489027
      Permit #493 Newly Renovated Farmhouse Centrally Located In Southold With Easy Access By Bus, Train or Car. Enjoy Your Morning Coffee As The Sun Rises Over The Farmfield. Spend An Afternoon Exploring The Beauty of the North Fork, Soak in the Sun at one of the Beautiful Peconic Bay or Long Island Sound Beaches, Enjoy Live Music at Numerous Wineries and/or Breweries, Browse unique local finds at One of Many Antique and/or Quaint Shops, and Don’t Forget to Stop by Our Bountiful Farm Stands. Cool Off With a Dip in the Heated Saltwater Pool, Enjoy Dinner Under the Stars and Reminisce Around the Fire Pit. Utilities Included. 10% Security & Exit Clean. Enjoy Summer On The North Fork!
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • NEW TO THE RENTAL MARKET! JUST A DREAM BOAT! NEWLY RENOVATED, LIGHT AND BRIGHT, BEAUTIFULLY APPOINTED, EVERY CONVENIENCE - 2 BEDROOMS, 2 BATHS. PLUS - CONVERTIBLE QUEEN SOFABED! BEAUTIFUL OUTDOOR DINING, FIRE PIT, PORCH, ENCLOSED SHOWER! PRICED RIGHT! STEPS TO POPULAR KENNEY’S BEACH - JUST BRING YOUR LITTLE RED WAGON AND STROLL TO THE BEACH AND ENJOY! 29
      250 Wesland Rd Southold, NY 11971
      $6,000 - $10,500
      2 Bedrooms 2 Full Baths Sq. Ft. 1400.00:# Square Feet
      Single Family For Rent ML# 3478213
      NEW TO THE RENTAL MARKET! JUST A DREAM BOAT! NEWLY RENOVATED, LIGHT AND BRIGHT, BEAUTIFULLY APPOINTED, EVERY CONVENIENCE - 2 BEDROOMS, 2 BATHS. PLUS - CONVERTIBLE QUEEN SOFABED! BEAUTIFUL OUTDOOR DINING, FIRE PIT, PORCH, ENCLOSED SHOWER! PRICED RIGHT! STEPS TO POPULAR KENNEY’S BEACH - JUST BRING YOUR LITTLE RED WAGON AND STROLL TO THE BEACH AND ENJOY!
      Presented By: Beninati Associates  631-765-5333
      Call Today: 631-765-5333, 631-235-8980, or  Email: Marie Beninati
      Call Today: 631-765-5333, or  Email: Lee Beninati
    • Located in a gorgeous Bay beach private community, just a stone’s throw from Southold Bay. Waterviews from many rooms and the sprawling backyard. Immaculate, light filled, 5 bedroom/2 bath charmer with room for all. Features include walkout deck, a library, sunroom w/gorgeous Bay views, outdoor showerhouse. Super convenient to fine dining, shopping & wineries - just 5 minutes to either Southold or Greenport....even 3 stellar farm stands just up the road including a CSA. Farm to table heaven! Located within the Park District with access to Founders’ Landing Park’s treasured sandy Bay beach. Everything you need to enjoy your summer on the amazing North Fork! Rental permit #0392; Expiration date 4/7/25. 20
      695 Rogers Rd Southold, NY 11971
      $15,000
      5 Bedrooms 2 Full Baths Sq. Ft. 1800.00:# Square Feet
      Single Family For Rent ML# 3470466
      Located in a gorgeous Bay beach private community, just a stone’s throw from Southold Bay. Waterviews from many rooms and the sprawling backyard. Immaculate, light filled, 5 bedroom/2 bath charmer with room for all. Features include walkout deck, a library, sunroom w/gorgeous Bay views, outdoor showerhouse. Super convenient to fine dining, shopping & wineries - just 5 minutes to either Southold or Greenport....even 3 stellar farm stands just up the road including a CSA. Farm to table heaven! Located within the Park District with access to Founders’ Landing Park’s treasured sandy Bay beach. Everything you need to enjoy your summer on the amazing North Fork! Rental permit #0392; Expiration date 4/7/25.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    Showing 21 - 30 of 38 results| view:  results per page« 1|2|3|4 »
    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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