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Southold Homes for Rent

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    Showing 1 - 10 of 51 results| view:  results per page« 1|2|3|4|5|...|last »
    • 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
    • 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 - Memorial Day to Labor Day $90, 000; June 25, 000; July 36, 000; August to LD 42, 00; LD to End of September $20, 000. Permit #0537. 29
      590 Soundview Av Ext Southold, NY 11971
      $90,000
      4 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 3100.00:# Square Feet
      Single Family For Rent NEW 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 - Memorial Day to Labor Day $90, 000; June 25, 000; July 36, 000; August to LD 42, 00; 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
    • Southold, North Fork: This beautiful estate, bayfront home offers complete privacy in a peaceful woodland setting with a historic provenance and featuring a sugar sand beach. Despite its private location, it is conveniently close to the village and North Fork amenities. Croteaux is just up the lane, and NoFo table is a short bike ride away. The estate house has a broad porch, a living room with a fireplace, a formal dining room, a den, a large kitchen, and a pantry. Upstairs, there are five bedrooms, three baths, PLUS, an outdoor shower convenient for all to enjoy. The outbuilding, known as The Birdhouse, offers dormitory space for overflow guests with a private bathroom. The estate has a direct beachfront setting, with sugar sand and carefree days awaiting visitors in an old-fashioned East End seaside cottage. MD-LD $75, 000; June $20, 000; July $25, 000; August-LD $30, 000; September $15, 000; October $15, 000 Permit# 0996 32
      1695 Old Woods Path Southold, NY 11971
      $75,000
      6 Bedrooms 4 Full Baths Sq. Ft. 3000.00:# Square Feet
      Single Family For Rent ML# 3212687
      Southold, North Fork: This beautiful estate, bayfront home offers complete privacy in a peaceful woodland setting with a historic provenance and featuring a sugar sand beach. Despite its private location, it is conveniently close to the village and North Fork amenities. Croteaux is just up the lane, and NoFo table is a short bike ride away. The estate house has a broad porch, a living room with a fireplace, a formal dining room, a den, a large kitchen, and a pantry. Upstairs, there are five bedrooms, three baths, PLUS, an outdoor shower convenient for all to enjoy. The outbuilding, known as The Birdhouse, offers dormitory space for overflow guests with a private bathroom. The estate has a direct beachfront setting, with sugar sand and carefree days awaiting visitors in an old-fashioned East End seaside cottage. MD-LD $75, 000; June $20, 000; July $25, 000; August-LD $30, 000; September $15, 000; October $15, 000 Permit# 0996
      Presented By: Town And Country Real Estate  631-298-0600
      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 place... you will not want to leave! Permit #1002, Additional information: Appearance:Mint 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 place... you will not want to leave! Permit #1002, Additional information: Appearance:Mint
      Presented By: Corcoran  631-848-7730
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Stunning new construction with 110’ of Long Island Sound front & 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 & 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! July: $50, 000.00 // August-Labor Day: $50, 000.00. Permit #: 1101 35
      17877 Soundview Avenue Southold, NY 11971
      $50,000
      5 Bedrooms 4 Full Baths 1 Half Bath
      Single Family For Rent ML# 3546351
      Stunning new construction with 110’ of Long Island Sound front & 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 & 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! July: $50, 000.00 // August-Labor Day: $50, 000.00. Permit #: 1101
      Presented By: Corcoran  631-848-7730
      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, Additional information: Appearance:excellent, Lease Term:August-Labor Day, July, July-August, June, Memorial-Labor, Off Season 32
      1355 Watersedge Way Southold, NY 11971
      $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, Additional information: Appearance:excellent, Lease Term:August-Labor Day, July, July-August, June, Memorial-Labor, Off Season
      Presented By: Town And Country Real Estate  631-477-5990
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Permit 816. Beautiful New Construction In Private Beach Community. Creekfront Beach Access Along With 20x40 Heated Saltwater Pool. Ideal For Large Groups & Perfect For Entertaining, This Property Has It All. 8 Bedrooms And 7 Bathrooms Set On Lush Manicured Grounds, Provides Spacious Accommodations For Up To 16 Guests. Spend Afternoons Lounging By The Pool & Evenings Gathering With Family And Friends. Deeded Beach Rights, Minutes To Wineries & Just A Short Bike Ride To Restaurants And Shops In Town. Three 50amp lv2 EV Chargers Available. 14 Day Minimum., Additional information: Appearance:MINT, Lease Term:Flexible, Weekly, Weekly Rent Amt:12500, Interior Features:Separate Thermostat 34
      650 Pine Avenue Southold, NY 11971
      $50,000
      8 Bedrooms 7 Full Baths Sq. Ft. 5400.00:#
      Single Family For Rent ML# 3466368
      Permit 816. Beautiful New Construction In Private Beach Community. Creekfront Beach Access Along With 20x40 Heated Saltwater Pool. Ideal For Large Groups & Perfect For Entertaining, This Property Has It All. 8 Bedrooms And 7 Bathrooms Set On Lush Manicured Grounds, Provides Spacious Accommodations For Up To 16 Guests. Spend Afternoons Lounging By The Pool & Evenings Gathering With Family And Friends. Deeded Beach Rights, Minutes To Wineries & Just A Short Bike Ride To Restaurants And Shops In Town. Three 50amp lv2 EV Chargers Available. 14 Day Minimum., Additional information: Appearance:MINT, Lease Term:Flexible, Weekly, Weekly Rent Amt:12500, Interior Features:Separate Thermostat
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Sublime Sound front home overlooking miles of beachfront with stairs to private beach. Stunning views through floor to ceiling windows and spacious sound front backyard. Newly added in-ground pool with retractable cover. Fully furnished 4 bedrooms, 3.5 baths, both formal living room and family room have wood burning fireplaces. Fully finished basement. Tesla hook up in the garage. The best that the North fork has to offer. 14
      16125 Soundview Avenue Southold, NY 11971
      $40,000
      4 Bedrooms 3 Full Baths 1 Half Bath
      Misc For Rent ML# 3564391
      Sublime Sound front home overlooking miles of beachfront with stairs to private beach. Stunning views through floor to ceiling windows and spacious sound front backyard. Newly added in-ground pool with retractable cover. Fully furnished 4 bedrooms, 3.5 baths, both formal living room and family room have wood burning fireplaces. Fully finished basement. Tesla hook up in the garage. The best that the North fork has to offer.
      Presented By: Brown Harris Stevens N Fork  631-477-0551
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 2025 Rates: July $32, 500. Brand New Modern Farmhouse Completed in 2021 and located in the heart Hog’s Neck in Southold Hamlet. This home features an impressive 20 x 50 heated pool with electric cover, out door shower and sprawling paver patio. The interior is open and airy with 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!, Additional information: Appearance:Pristine 31
      75 Clearview Avenue Southold, NY 11971
      $32,500
      4 Bedrooms 3 Full Baths 1 Half Bath
      Single Family For Rent ML# 3582922
      2025 Rates: July $32, 500. Brand New Modern Farmhouse Completed in 2021 and located in the heart Hog’s Neck in Southold Hamlet. This home features an impressive 20 x 50 heated pool with electric cover, out door shower and sprawling paver patio. The interior is open and airy with 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!, Additional information: Appearance:Pristine
      Presented By: Daniel Gale Sothebys Intl Rlty  631-477-0013
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Southold, North Fork: Delightful cottage just up from Founder’s Landing Park, the beach, and the Wharf House. A super convenient ’in town’ location allows instant access to an easy lifestyle. Charming, well-cared-for home features an open floor plan with a large, comfortable living room/dining room, eat-in kitchen with gas range, laundry room, and full bath on primary, plus an additional bath on the second floor with two large bedrooms (queen bed in one, twins and futon in other). Private terrace with firepit, outdoor dining, and bbq area. Onsite parking. Moments to the beach, boating, public transportation, and such popular places as the North Fork Table, North Fork Roasting Co, Einstein Square, and Greenport Village in addition to the numerous wineries and events the North Fork is known for. Flexible rates all year long - whether a winter rental, Summer 2025 or the shoulder season... owner offers a furnished year-round rental - $4200 per mo. Rental Permit# 1216., Additional information: ExterioFeatures:Tennis, year rent:4200 26
      150 Hobart Rd Southold, NY 11971
      $30,000
      2 Bedrooms 2 Full Baths Sq. Ft. 1300.00:# Square Feet
      Single Family For Rent ML# 3588931
      Southold, North Fork: Delightful cottage just up from Founder’s Landing Park, the beach, and the Wharf House. A super convenient ’in town’ location allows instant access to an easy lifestyle. Charming, well-cared-for home features an open floor plan with a large, comfortable living room/dining room, eat-in kitchen with gas range, laundry room, and full bath on primary, plus an additional bath on the second floor with two large bedrooms (queen bed in one, twins and futon in other). Private terrace with firepit, outdoor dining, and bbq area. Onsite parking. Moments to the beach, boating, public transportation, and such popular places as the North Fork Table, North Fork Roasting Co, Einstein Square, and Greenport Village in addition to the numerous wineries and events the North Fork is known for. Flexible rates all year long - whether a winter rental, Summer 2025 or the shoulder season... owner offers a furnished year-round rental - $4200 per mo. Rental Permit# 1216., Additional information: ExterioFeatures:Tennis, year rent:4200
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    Showing 1 - 10 of 51 results| view:  results per page« 1|2|3|4|5|...|last »
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    Office: (631) 765 5333 Fax (631) 765 5225 broker@beninatiassociates.com

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