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Southold Homes for Rent

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    Showing 31 - 40 of 61 results| view:  results per page« first|...|3|4|5|6|7 »
    • This home at 4845 South Harbor Road, Southold, is a truly unique and meticulously renovated craftsman cottage that is comfortable and charming. You are steps away from one of the finest beaches on the North Fork, South Harbor beach. Popular wineries Croteaux and Mattabella are down the street, and Greenport Village is ten-minute drive. The house has a lovely wraparound porch plus a screened in porch. The backyard has a spacious back patio, gas grill, and dining table with chairs. This is really a fantastic location to enjoy the North Fork! RP# 0424 26
      4845 S Harbor Rd Southold, NY 11971
      $13,500
      3 Bedrooms 2 Full Baths Sq. Ft. 1366.00:# Square Feet
      Single Family For Rent ML# 3528985
      This home at 4845 South Harbor Road, Southold, is a truly unique and meticulously renovated craftsman cottage that is comfortable and charming. You are steps away from one of the finest beaches on the North Fork, South Harbor beach. Popular wineries Croteaux and Mattabella are down the street, and Greenport Village is ten-minute drive. The house has a lovely wraparound porch plus a screened in porch. The backyard has a spacious back patio, gas grill, and dining table with chairs. This is really a fantastic location to enjoy the North Fork! RP# 0424
      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
    • 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
    • Enjoy this Waterfront rental just steps to Goose Creek beach. Easy water access to Goose Creek from this private location, perfect for kayaking and paddle boarding. Features include 3 bedrooms including second floor primary en-suite with water views, 2 additional guest bedrooms, 2 additional guest baths and plenty of living space overlooking Goose Creek. Spacious bright kitchen, dining area with doors to waterside deck where you will experience beautiful sunsets. The perfect retreat for your summer fun or any other time of the year. Close to all North Fork amenities. Permit # 1023 35
      800 Goose Creek Lane Southold, NY 11971
      $12,000
      3 Bedrooms 3 Full Baths Sq. Ft. 2032.00:# Square Feet
      Single Family For Rent ML# 3526789
      Enjoy this Waterfront rental just steps to Goose Creek beach. Easy water access to Goose Creek from this private location, perfect for kayaking and paddle boarding. Features include 3 bedrooms including second floor primary en-suite with water views, 2 additional guest bedrooms, 2 additional guest baths and plenty of living space overlooking Goose Creek. Spacious bright kitchen, dining area with doors to waterside deck where you will experience beautiful sunsets. The perfect retreat for your summer fun or any other time of the year. Close to all North Fork amenities. Permit # 1023
      Presented By: Daniel Gale Sothebys Intl Rlty  631-734-5439
      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
    • Chic ranch at 600 Corey Creek Lane, Southold. Featuring a beautiful wood-burning fireplace centered in the living room with high vaulted ceilings. 3 beds and 2 baths complete this home with an updated kitchen flowing into the dining area. Outside is a generous-sized patio with a firepit perfect for unwinding and having a relaxing night. Great location; close to town with shops and restaurants plus access to Corey Creek at the end of the road and sandy South Harbor beach minutes away! Fully furnished. RP# 0512 23
      600 Corey Creek Lane Southold, NY 11971
      $10,000
      3 Bedrooms 2 Full Baths
      Single Family For Rent ML# 3525143
      Chic ranch at 600 Corey Creek Lane, Southold. Featuring a beautiful wood-burning fireplace centered in the living room with high vaulted ceilings. 3 beds and 2 baths complete this home with an updated kitchen flowing into the dining area. Outside is a generous-sized patio with a firepit perfect for unwinding and having a relaxing night. Great location; close to town with shops and restaurants plus access to Corey Creek at the end of the road and sandy South Harbor beach minutes away! Fully furnished. RP# 0512
      Presented By: Town And Country Real Estate  631-477-5990
      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
    • Welcome to this fabulous vacation home located at 1275 The Esplanade, in Southold’s coveted Angel Shores private bay beach community. The private bay beach is so close you can hear the waves and feel the bay breeze from your porch. There is a glorious free form, heated, saltwater pool, with a sparkling fountain and waterfall. Outdoor shower, patio fire pit, BBQ and plenty of outdoor lounge areas complete the private backyard. The interior is stunning! Stylish decor and furnishings, central air and a house generator, a huge sun room that overlooks the pool. Sleek and spacious rooms, with hardwood floors throughout. The first floor was totally renovated , completed in April 2024. The large kitchen has quartz countertops and high-end appliances, open concept living room, spacious dining area, and a brand-new powder room. The second floor was renovated in 2023 with upscale spa like bathrooms and a second-floor laundry room for your convenience. The finished lower level has an entertainment area and game room with a pool table and arcade game. Also, there are 3 kayaks and 5 bicycles available for you to fully enjoy all the North Fork has to offer. Available 2024 ...April $8, 500, May $8, 500, Memorial Day Weekend Thru June $16, 500 (5 Weeks). Your Best Summer Vacation Poolside and By the Sea Shore! 34
      Southold, NY 11971
      $8,500
      4 Bedrooms 2 Full Baths 1 Half Bath
      Single Family For Rent ML# 3289709
      Welcome to this fabulous vacation home located at 1275 The Esplanade, in Southold’s coveted Angel Shores private bay beach community. The private bay beach is so close you can hear the waves and feel the bay breeze from your porch. There is a glorious free form, heated, saltwater pool, with a sparkling fountain and waterfall. Outdoor shower, patio fire pit, BBQ and plenty of outdoor lounge areas complete the private backyard. The interior is stunning! Stylish decor and furnishings, central air and a house generator, a huge sun room that overlooks the pool. Sleek and spacious rooms, with hardwood floors throughout. The first floor was totally renovated , completed in April 2024. The large kitchen has quartz countertops and high-end appliances, open concept living room, spacious dining area, and a brand-new powder room. The second floor was renovated in 2023 with upscale spa like bathrooms and a second-floor laundry room for your convenience. The finished lower level has an entertainment area and game room with a pool table and arcade game. Also, there are 3 kayaks and 5 bicycles available for you to fully enjoy all the North Fork has to offer. Available 2024 ...April $8, 500, May $8, 500, Memorial Day Weekend Thru June $16, 500 (5 Weeks). Your Best Summer Vacation Poolside and By the Sea Shore!
      Presented By: Town And Country Real Estate  631-477-5990
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Adorable ranch across from the water in Laughing Waters Community. Association beach available to tenants. Enjoy a summer vacation in this 2 bdr, 1 bth ranch with porch/den, kit, Lr and patio. Garage/ shed not included in lease. Swim, kayak , relax in this special place. 15
      3205 Minnehaha Boulevard Southold, NY 11971
      $8,000
      2 Bedrooms 1 Full Bath
      Single Family For Rent ML# 3531881
      Adorable ranch across from the water in Laughing Waters Community. Association beach available to tenants. Enjoy a summer vacation in this 2 bdr, 1 bth ranch with porch/den, kit, Lr and patio. Garage/ shed not included in lease. Swim, kayak , relax in this special place.
      Presented By: Colony Realty  631-722-5800
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Impressive Goose Creek home with water views and large heated in-ground pool! This four bedroom, three bath house features a first floor primary bedroom with en-suite, a gourmet kitchen and open living space. The newly designed landscape is ideal for entertaining or relaxing. Enjoy its large fire pit and BBQ grill after an afternoon of Kayaking. Close to Southold town and Corey Creek Beach. Permit #0290 28
      485 Hickory Avenue Southold, NY 11971
      $8,000
      4 Bedrooms 3 Full Baths
      Single Family For Rent ML# 3446952
      Impressive Goose Creek home with water views and large heated in-ground pool! This four bedroom, three bath house features a first floor primary bedroom with en-suite, a gourmet kitchen and open living space. The newly designed landscape is ideal for entertaining or relaxing. Enjoy its large fire pit and BBQ grill after an afternoon of Kayaking. Close to Southold town and Corey Creek Beach. Permit #0290
      Presented By: Daniel Gale Sothebys Intl Rlty  631-734-5439
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    Showing 31 - 40 of 61 results| view:  results per page« first|...|3|4|5|6|7 »
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    Office: (631) 765 5333 Fax (631) 765 5225 broker@beninatiassociates.com

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