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Southold Luxury Rentals

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    Showing 1 - 10 of 41 results| view:  results per page« 1|2|3|4|5 »
    • 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
      3 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
    • Welcome to your perfect summer getaway nestled in the heart of North Fork wine country. This recently renovated Southold rental offers the epitome of luxury and comfort, greeting you with a bright and airy living space, adorned with top-of-the-line appliances, furnishings and tasteful decor. The open-concept layout seamlessly connects the living area to the fully equipped kitchen, boasting state-of-the-art appliances that make cooking a joy. Whether you’re preparing a gourmet meal or simply brewing your morning coffee, you’ll appreciate the convenience and style of these modern amenities. With three cozy bedrooms and two pristine bathrooms, there’s ample space for the whole family or friends to unwind and recharge after a day of exploring. Outside, a spacious yard beckons you to soak up the summer sun or savor al fresco dining amid the lush greenery of the landscaped garden. Whether you’re hosting a barbecue with loved ones or simply enjoying a quiet moment, this outdoor oasis provides the perfect backdrop for making memories. As if that weren’t enough, this summer rental includes all utilities, so you can relax and enjoy your stay without worrying about additional costs. The only thing you’ll need to arrange is housekeeping, required every two weeks to maintain the pristine condition of this exquisite retreat. Don’t miss your chance to experience the best of Southold living in this impeccably designed summer rental (Southold Town rental permit #1074) 25
      145 Custer Avenue Southold, NY 11971
      $9,750
      3 Bedrooms 2 Full Baths
      Single Family For Rent ML# 3542805
      Welcome to your perfect summer getaway nestled in the heart of North Fork wine country. This recently renovated Southold rental offers the epitome of luxury and comfort, greeting you with a bright and airy living space, adorned with top-of-the-line appliances, furnishings and tasteful decor. The open-concept layout seamlessly connects the living area to the fully equipped kitchen, boasting state-of-the-art appliances that make cooking a joy. Whether you’re preparing a gourmet meal or simply brewing your morning coffee, you’ll appreciate the convenience and style of these modern amenities. With three cozy bedrooms and two pristine bathrooms, there’s ample space for the whole family or friends to unwind and recharge after a day of exploring. Outside, a spacious yard beckons you to soak up the summer sun or savor al fresco dining amid the lush greenery of the landscaped garden. Whether you’re hosting a barbecue with loved ones or simply enjoying a quiet moment, this outdoor oasis provides the perfect backdrop for making memories. As if that weren’t enough, this summer rental includes all utilities, so you can relax and enjoy your stay without worrying about additional costs. The only thing you’ll need to arrange is housekeeping, required every two weeks to maintain the pristine condition of this exquisite retreat. Don’t miss your chance to experience the best of Southold living in this impeccably designed summer rental (Southold Town rental permit #1074)
      Presented By: Douglas Elliman Real Estate  631-354-8100
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • New Construction with all high end finishes. First Floor Primary Suite. Three additional oversized bedrooms - all ensuite. 2 King beds, 2 Queen beds. Den/Office facing inground pool, Huge 2nd Fl Bonus Room, 5.5 Luxurious Baths. Every detail has been carefully considered and designed to accommodate multiple guests. Close to shopping, multiple parks, beaches, golf and fine dining. This is Truly an Entertainer’s Delight! Dogs allowed up to 10 lbs. Tenant pays utilities and pool care. 32
      630 Calves Neck Rd Southold, NY 11971
      $35,000 - $65,000
      4 Bedrooms 5 Full Baths 1 Half Bath Sq. Ft. 4400.00:# Square Feet
      Single Family For Rent ML# 3542038
      New Construction with all high end finishes. First Floor Primary Suite. Three additional oversized bedrooms - all ensuite. 2 King beds, 2 Queen beds. Den/Office facing inground pool, Huge 2nd Fl Bonus Room, 5.5 Luxurious Baths. Every detail has been carefully considered and designed to accommodate multiple guests. Close to shopping, multiple parks, beaches, golf and fine dining. This is Truly an Entertainer’s Delight! Dogs allowed up to 10 lbs. Tenant pays utilities and pool care.
      Presented By: Compass Greater NY LLC  516-319-3274
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Beautifully decorated, charming 4 bedroom, 2 bath home with custom details throughout. Complete with an outdoor shower, enjoy the tranquil setting relaxing on the patio or in the luxurious sauna. Revel in the great location conveniently located near sandy beaches, wineries, restaurants, and public transportation. Available for August. Rental Permit #0639. 8
      170 Laurel Avenue Southold, NY 11971
      $12,000
      4 Bedrooms 2 Full Baths
      Single Family For Rent ML# 3539926
      Beautifully decorated, charming 4 bedroom, 2 bath home with custom details throughout. Complete with an outdoor shower, enjoy the tranquil setting relaxing on the patio or in the luxurious sauna. Revel in the great location conveniently located near sandy beaches, wineries, restaurants, and public transportation. Available for August. Rental Permit #0639.
      Presented By: Town And Country Real Estate  631-477-5990
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Summer Beckons At This Spacious Retreat In A Private, Park-Like Setting In A Very Desirable Cul-de-Sac Community Of Southold. Featuring Large Gunite Swimming Pool, Deeded Beach, Multiple Bedrooms, Large Sun-Drenched Living Areas That Open To Backyard. Rental Available First 2 Weeks Of August. Come And Get It. Permit#0848 29
      1075 Clipper Drive Southold, NY 11971
      $13,000
      5 Bedrooms 4 Full Baths Sq. Ft. 3600.00:# Square Feet
      Single Family For Rent ML# 3537644
      Summer Beckons At This Spacious Retreat In A Private, Park-Like Setting In A Very Desirable Cul-de-Sac Community Of Southold. Featuring Large Gunite Swimming Pool, Deeded Beach, Multiple Bedrooms, Large Sun-Drenched Living Areas That Open To Backyard. Rental Available First 2 Weeks Of August. Come And Get It. Permit#0848
      Presented By: Douglas Elliman Real Estate  631-354-8100
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Escape to this idyllic waterfront haven. This summer retreat includes 3-bedrooms and 3-bathrooms, blending luxury and comfort seamlessly. Enjoy modern amenities including a fully equipped Chefs kitchen, and an open concept living space with floor to ceiling windows. Kayak, or Paddle Board from your private dock to the local sandy beach. The property also features a generous outdoor space, perfect for relaxation and entertaining and a Tesla charging station adding additional convenience. Don’t miss the opportunity to make this waterfront sanctuary your summer getaway! 14
      50 Oak Avenue Southold, NY 11971
      $18,000
      3 Bedrooms 3 Full Baths Sq. Ft. 2328.00:# Square Feet
      Single Family For Rent OPEN HOUSE ML# 3536769
      Escape to this idyllic waterfront haven. This summer retreat includes 3-bedrooms and 3-bathrooms, blending luxury and comfort seamlessly. Enjoy modern amenities including a fully equipped Chefs kitchen, and an open concept living space with floor to ceiling windows. Kayak, or Paddle Board from your private dock to the local sandy beach. The property also features a generous outdoor space, perfect for relaxation and entertaining and a Tesla charging station adding additional convenience. Don’t miss the opportunity to make this waterfront sanctuary your summer getaway!
      Presented By: Compass Greater NY LLC  917-848-5102
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
      Upcoming Open House View Location
      04/28/2024 - 04/28/2024 1:30PM - 2:30PM
    • Immacualte 5 bedroom, 4 bath pool home only two houses away from Goose Creek. Lush landscaping and heated in-ground pool recently added. Three levels of living with bedrooms on each floor. Perfect home for entertaining. Fully finished lower level opens to pool. Main level has a screened porch and bbq porch that overlook the pool Enjoy the outdoors in the pool, on the newly built social area, or from the outdoor dining area. Truly a special jewel for the month of August-LD. 26
      675 Birch Avenue Southold, NY 11971
      $40,000
      5 Bedrooms 4 Full Baths Sq. Ft. 3100.00:# Square Feet
      Single Family For Rent ML# 3535739
      Immacualte 5 bedroom, 4 bath pool home only two houses away from Goose Creek. Lush landscaping and heated in-ground pool recently added. Three levels of living with bedrooms on each floor. Perfect home for entertaining. Fully finished lower level opens to pool. Main level has a screened porch and bbq porch that overlook the pool Enjoy the outdoors in the pool, on the newly built social area, or from the outdoor dining area. Truly a special jewel for the month of August-LD.
      Presented By: Compass Greater NY LLC  631-251-8644
      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
    • Nestled beside Great Pond, a natural fresh water expanse that is more resemblant of a lake, this three bedroom home is filled with natural light from sunrise to set through large bay windows and sliding glass doors leading out to an expansive rear deck, both that frame the pond and the lush surroundings, inviting the calm of the dawn and the beauty of twilight. Rental Permit # 59-5-21 Kenney’s Beach, less than 1, 000 feet from the home, offers miles of unobstructed sandy shores. To the west, more than a mile of beach abuts 60 acres of the Peconic Dunes nature trails, conserved land open to the public and ends at Goldsmith’s Inlet, and to the east, it reaches all the way to the historic Horton’s Point Lighthouse. This stretch of beach is perfect for leisurely exploration or simply enjoying the panoramic Long Island Sound views. Inside, the home is bathed in light, with expansive bay windows that capture the essence of the pond and its verdant surroundings. Sunrise and sunset are daily spectacles here, painting the sky with colors that infuse the space with warmth. The deck in the rear, generous and well-appointed, stands ready for your tranquil afternoons or friendly gatherings. Great Pond-a vast freshwater expanse where the serenity of a lake meets the vitality of a natural habitat. This charming home is an idyllic base for those who revel in the splendor of the outdoors and the spectacle of wildlife. The pond is alive with swans, ducks, geese, and ospreys that dive down to fish, while egrets grace the water’s edge, all against the backdrop of lush greenery. 16
      425 Lake Drive Southold, NY 11971
      $10,500
      3 Bedrooms 1 Full Bath Sq. Ft. 1530.00:# Square Feet
      Single Family For Rent ML# 3533354
      Nestled beside Great Pond, a natural fresh water expanse that is more resemblant of a lake, this three bedroom home is filled with natural light from sunrise to set through large bay windows and sliding glass doors leading out to an expansive rear deck, both that frame the pond and the lush surroundings, inviting the calm of the dawn and the beauty of twilight. Rental Permit # 59-5-21 Kenney’s Beach, less than 1, 000 feet from the home, offers miles of unobstructed sandy shores. To the west, more than a mile of beach abuts 60 acres of the Peconic Dunes nature trails, conserved land open to the public and ends at Goldsmith’s Inlet, and to the east, it reaches all the way to the historic Horton’s Point Lighthouse. This stretch of beach is perfect for leisurely exploration or simply enjoying the panoramic Long Island Sound views. Inside, the home is bathed in light, with expansive bay windows that capture the essence of the pond and its verdant surroundings. Sunrise and sunset are daily spectacles here, painting the sky with colors that infuse the space with warmth. The deck in the rear, generous and well-appointed, stands ready for your tranquil afternoons or friendly gatherings. Great Pond-a vast freshwater expanse where the serenity of a lake meets the vitality of a natural habitat. This charming home is an idyllic base for those who revel in the splendor of the outdoors and the spectacle of wildlife. The pond is alive with swans, ducks, geese, and ospreys that dive down to fish, while egrets grace the water’s edge, all against the backdrop of lush greenery.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
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    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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