Fair Housing Notice Standard Operating Procedure
631.765.5333

North Fork Short Term Rentals

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

    226  properties match your search;

    226 with Multiple photos ;  15 with Virtual Tour ;  0 with Videos

    Save Search
    Showing 41 - 50 of 226 results| view:  results per page« first|...|3|4|5|6|...|last »
    • Open Bay Front Right On The Beach! Stunner mid century modern, see rates below. Sand in your toes right out your door, walls of glass, gorgeous open bay views from every room. Sparkling hot tub spa for 6 adds to the resort style amenities, a small putting green on premise, oversized outdoor shower, kayak, paddleboard, and beach toys. Secluded private beach in the coveted Fairhaven Community, swim and sunbathe, clam for dinner, kayak, moor a boat. Stellar sunrise and sunset skies, watch the sail boats go by. This lovely offering has a total of 5 bedrooms, and 3 full baths. The spacious private wing primary en-suite is on the main floor, as is a new bedroom with twin beds and a hall bath for the Nanny or Grandma. There are three additional water view guest bedrooms and a full hall bath on level 2. Open water view granite kitchen and dining, central air, huge waterside deck with retractable sun awning, covered shady porch (dine outdoors on rainy days). Public tennis, playground, marina with 4 public boat ramps only 2 lanes away. Great Open Waterfront Vacation! 2025 August 1st thru Labor Day Tues $35, 000, Winter months 2025 at $6, 900 per month. 34
      11 Beach Rd Jamesport, NY 11947
      $35,000
      5 Bedrooms 3 Full Baths Sq. Ft. 2700.00:# Square Feet
      Single Family For Rent ML# 3524823
      Open Bay Front Right On The Beach! Stunner mid century modern, see rates below. Sand in your toes right out your door, walls of glass, gorgeous open bay views from every room. Sparkling hot tub spa for 6 adds to the resort style amenities, a small putting green on premise, oversized outdoor shower, kayak, paddleboard, and beach toys. Secluded private beach in the coveted Fairhaven Community, swim and sunbathe, clam for dinner, kayak, moor a boat. Stellar sunrise and sunset skies, watch the sail boats go by. This lovely offering has a total of 5 bedrooms, and 3 full baths. The spacious private wing primary en-suite is on the main floor, as is a new bedroom with twin beds and a hall bath for the Nanny or Grandma. There are three additional water view guest bedrooms and a full hall bath on level 2. Open water view granite kitchen and dining, central air, huge waterside deck with retractable sun awning, covered shady porch (dine outdoors on rainy days). Public tennis, playground, marina with 4 public boat ramps only 2 lanes away. Great Open Waterfront Vacation! 2025 August 1st thru Labor Day Tues $35, 000, Winter months 2025 at $6, 900 per month.
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Welcome to this exceptional waterfront oasis! This stunning 4 bedroom, 3 bathroom home is a true gem nestled along the water’s edge, offering unparalleled relaxation and breathtaking views. Step inside and be greeted by an abundance of natural light, illuminating the spacious open-concept living area. The chic design, with its stylish finishes, creates a warm and inviting atmosphere throughout with panoramic windows that showcase the picturesque waterfront scenery. The gourmet kitchen is a chef’s delight, equipped with top-of-the-line appliances, ample counter space, and custom cabinetry. Prepare culinary masterpieces while enjoying the tranquil water views, or simply gather around the large island for casual dining and lively conversations. As you make your way to the bedrooms, you’ll find four generously sized bedrooms, each offering a cozy haven for relaxation and rest. The primary suite is a true sanctuary, featuring its own private balcony overlooking the water, a spacious walk-in closet, and a luxurious en-suite bathroom adorned with premium fixtures and finishes. The highlight of this property is undoubtedly the heated waterside saltwater pool. Whether you’re hosting lively poolside gatherings or enjoying a serene evening dip, the pool area will undoubtedly become your favorite spot to create lasting memories. This waterfront paradise also has a deepwater dock and offers direct access to the water, making it perfect for water enthusiasts. Imagine launching your boat, kayak or paddleboard right from your backyard, or simply enjoying a leisurely boat ride to explore the nearby coves and beaches. Enjoy the tranquility and serenity of waterfront living, while still being just a short drive away from local amenities, restaurants, and entertainment options. Your dream waterfront retreat awaits! Permit 1001, Additional information: Appearance:Platinum, Lease Term:12 Months, August-Labor Day, July, Memorial-Labor, Monthly, year rent:7500. 34
      900/1 Fox Hollow Rd Mattituck, NY 11952
      $35,000
      4 Bedrooms 3 Full Baths
      Single Family For Rent ML# 3514394
      Welcome to this exceptional waterfront oasis! This stunning 4 bedroom, 3 bathroom home is a true gem nestled along the water’s edge, offering unparalleled relaxation and breathtaking views. Step inside and be greeted by an abundance of natural light, illuminating the spacious open-concept living area. The chic design, with its stylish finishes, creates a warm and inviting atmosphere throughout with panoramic windows that showcase the picturesque waterfront scenery. The gourmet kitchen is a chef’s delight, equipped with top-of-the-line appliances, ample counter space, and custom cabinetry. Prepare culinary masterpieces while enjoying the tranquil water views, or simply gather around the large island for casual dining and lively conversations. As you make your way to the bedrooms, you’ll find four generously sized bedrooms, each offering a cozy haven for relaxation and rest. The primary suite is a true sanctuary, featuring its own private balcony overlooking the water, a spacious walk-in closet, and a luxurious en-suite bathroom adorned with premium fixtures and finishes. The highlight of this property is undoubtedly the heated waterside saltwater pool. Whether you’re hosting lively poolside gatherings or enjoying a serene evening dip, the pool area will undoubtedly become your favorite spot to create lasting memories. This waterfront paradise also has a deepwater dock and offers direct access to the water, making it perfect for water enthusiasts. Imagine launching your boat, kayak or paddleboard right from your backyard, or simply enjoying a leisurely boat ride to explore the nearby coves and beaches. Enjoy the tranquility and serenity of waterfront living, while still being just a short drive away from local amenities, restaurants, and entertainment options. Your dream waterfront retreat awaits! Permit 1001, Additional information: Appearance:Platinum, Lease Term:12 Months, August-Labor Day, July, Memorial-Labor, Monthly, year rent:7500.
      Presented By: Engel & Volkers North Fork  631-298-7953
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Pristine and private post-modern home in Jamesport now available for the Off Season from October 1, 2024 through April 30, 2025 and August through Labor Day 2025. Nestled away on a pin-drop quiet cul-de-sac and situated on a shy acre of meticulously landscaped property. All just around the corner from the coveted Iron Pier Beach and Park. This grand and incredibly spacious home boasts beautiful natural light throughout. All tastefully decorated with high-end finishings. Meticulously appointed throughout for the most decerning guest. The home features a fully stocked eat-in chef’s kitchen perfect for entertaining. The home lends to multiple entertainment and living spaces for making wonderful memories with family and friends. With lush bedrooms and baths, the home comfortably sleeps up to 12 guests. The backyard is truly an oasis featuring a huge outdoor kitchen, lounge and dining area overlooking the in-ground heated pool and hot tub with waterfall. Gather around the large fire-pit area all year long. Treat yourself and guests to the North Fork this coming season. You are guaranteed to fall in love. The utilities are not included for the winter rental. Ground care is included. Snow removal is not included. Pets are permitted on a case-by-case scenario and service animals are exempt. Tenant application and credit required via Rentspree: https://apply.link/47aAygL Rental Permit # 23-0222, Additional information: Appearance:Pristine, Interior Features:Separate Thermostat 36
      39 Smugglers Path Jamesport, NY 11947
      $35,000
      3 Bedrooms 4 Full Baths Sq. Ft. 3655.00:#
      Single Family For Rent ML# 3510531
      Pristine and private post-modern home in Jamesport now available for the Off Season from October 1, 2024 through April 30, 2025 and August through Labor Day 2025. Nestled away on a pin-drop quiet cul-de-sac and situated on a shy acre of meticulously landscaped property. All just around the corner from the coveted Iron Pier Beach and Park. This grand and incredibly spacious home boasts beautiful natural light throughout. All tastefully decorated with high-end finishings. Meticulously appointed throughout for the most decerning guest. The home features a fully stocked eat-in chef’s kitchen perfect for entertaining. The home lends to multiple entertainment and living spaces for making wonderful memories with family and friends. With lush bedrooms and baths, the home comfortably sleeps up to 12 guests. The backyard is truly an oasis featuring a huge outdoor kitchen, lounge and dining area overlooking the in-ground heated pool and hot tub with waterfall. Gather around the large fire-pit area all year long. Treat yourself and guests to the North Fork this coming season. You are guaranteed to fall in love. The utilities are not included for the winter rental. Ground care is included. Snow removal is not included. Pets are permitted on a case-by-case scenario and service animals are exempt. Tenant application and credit required via Rentspree: https://apply.link/47aAygL Rental Permit # 23-0222, Additional information: Appearance:Pristine, Interior Features:Separate Thermostat
      Presented By: Douglas Elliman Real Estate  631-298-8000
      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
    • Escape to your private Cutchogue oasis this summer! This stunning home boasts four bedrooms, including two en-suite, and 3.5 baths, offering luxurious accommodations for your getaway. Unwind in the in-ground pool or lounge on the wrap-around porch overlooking a tranquil creek. Two living rooms and an open-concept kitchen provide ample space for entertaining, while the wooded lot ensures complete privacy. With coveted Nassau Point beach access less than a mile away, sun and sand are just moments from your door. Book your stay and experience the ultimate summer escape! Seasonal Rates: June $15K July $30K August $30K MD-LD $70K September $15K 25
      250 Pine Tree Court Cutchogue, NY 11935
      $30,000
      4 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 2800.00:# Square Feet
      Single Family For Rent NEW ML# 818066
      Escape to your private Cutchogue oasis this summer! This stunning home boasts four bedrooms, including two en-suite, and 3.5 baths, offering luxurious accommodations for your getaway. Unwind in the in-ground pool or lounge on the wrap-around porch overlooking a tranquil creek. Two living rooms and an open-concept kitchen provide ample space for entertaining, while the wooded lot ensures complete privacy. With coveted Nassau Point beach access less than a mile away, sun and sand are just moments from your door. Book your stay and experience the ultimate summer escape! Seasonal Rates: June $15K July $30K August $30K MD-LD $70K September $15K
      Presented By: Daniel Gale Sothebys Intl Rlty  631-734-5439
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Contemporary private, secluded home in bucolic Browns Hill, Orient with Panoramic views over gardens, fields and bays from Montauk to Shelter Island. Enter through a welcoming space from the foyer to the living room with wood burning fireplace, updated gourmet kitchen and dining room with panoramic farm and bay views. Three levels of living space with one bedroom & full bath on each floor Lower-level bedroom with deck, ground floor master ensuite bedroom with full bath and deck, second floor loft/bedroom and full bath. Heated/saltwater/gunite 12 x 25 pool with deck & patio overlooking farm fields with distant bay view. Outdoor shower. A short walk to association sound beach. Offered Aug-LD $30, 000. All inclusive. Permit # 0174. 38
      255 South View Drive Orient, NY 11957
      $30,000
      3 Bedrooms 3 Full Baths Sq. Ft. 1846.00:# Square Feet
      Single Family For Rent ML# 812977
      Contemporary private, secluded home in bucolic Browns Hill, Orient with Panoramic views over gardens, fields and bays from Montauk to Shelter Island. Enter through a welcoming space from the foyer to the living room with wood burning fireplace, updated gourmet kitchen and dining room with panoramic farm and bay views. Three levels of living space with one bedroom & full bath on each floor Lower-level bedroom with deck, ground floor master ensuite bedroom with full bath and deck, second floor loft/bedroom and full bath. Heated/saltwater/gunite 12 x 25 pool with deck & patio overlooking farm fields with distant bay view. Outdoor shower. A short walk to association sound beach. Offered Aug-LD $30, 000. All inclusive. Permit # 0174.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-477-0013
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Gorgeous contemporary home, impeccably designed and furnished with seaside style. Spacious kitchen with island, Large fenced backyard with covered porch and dining area, and balconies on 2nd floor to overlook it all. Private association beach is a short walk away. Available August 2-September 2 14
      185 Rockcove Court Greenport, NY 11944
      $30,000
      4 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 2600.00:# Square Feet
      Single Family For Rent ML# 805936
      Gorgeous contemporary home, impeccably designed and furnished with seaside style. Spacious kitchen with island, Large fenced backyard with covered porch and dining area, and balconies on 2nd floor to overlook it all. Private association beach is a short walk away. Available August 2-September 2
      Presented By: Signature Premier Properties  631-765-6000
      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
    • 2025 Rates: June $30, 000, July $60, 000, July-August $125, 000 and August-Labor Day $65, 000. This stunning two-story home sits on 3.44 acres of beautiful lawns and trees, featuring a circular driveway and a double-arched covered porch with bluestone patio. Inside, the foyer opens to a light filled dining room and great room with 10 foot coffered ceilings, exquisite details, and an elegant chef’s kitchen equipped with Crownpoint custom cabinetry and top -of-the-line Wolf and Sub-Zero appliances. French doors lead to a covered porch overlooking the pool and yard. The second floor has 3 bedrooms each with a private bath and 9 foot ceilings. A separate staircase leads to a den with pull out sofa, wet-bar with ref/freezer and it’s own full bath. Additional features include a Gunite heated pool with electric cover, full house generator, alarm system, and two smart tv’s. This home is close proximity to Wades Beach and Mashomack Preserve., Additional information: Appearance:Exquisite, Interior Features:Separate Thermostat 36
      104 S Ferry Rd Shelter Island, NY 11964
      $30,000
      5 Bedrooms 5 Full Baths 1 Half Bath Sq. Ft. 4040.00:#
      Single Family For Rent ML# 3585239
      2025 Rates: June $30, 000, July $60, 000, July-August $125, 000 and August-Labor Day $65, 000. This stunning two-story home sits on 3.44 acres of beautiful lawns and trees, featuring a circular driveway and a double-arched covered porch with bluestone patio. Inside, the foyer opens to a light filled dining room and great room with 10 foot coffered ceilings, exquisite details, and an elegant chef’s kitchen equipped with Crownpoint custom cabinetry and top -of-the-line Wolf and Sub-Zero appliances. French doors lead to a covered porch overlooking the pool and yard. The second floor has 3 bedrooms each with a private bath and 9 foot ceilings. A separate staircase leads to a den with pull out sofa, wet-bar with ref/freezer and it’s own full bath. Additional features include a Gunite heated pool with electric cover, full house generator, alarm system, and two smart tv’s. This home is close proximity to Wades Beach and Mashomack Preserve., Additional information: Appearance:Exquisite, Interior Features:Separate Thermostat
      Presented By: Daniel Gale Sothebys Intl Rlty  631-749-1155
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • This absolutely stunning contemporary home is the place for your North Fork getaway! Features galore include a chef’s dream eat in kitchen, spacious living room with gas fireplace, and 3 available bedrooms. The first floor primary suite is enormous, with a soaking tub as well as shower in the gorgeous bathroom, plus a connected additional bedroom. The 2 guest suites, one with 2 queen beds, have their own beautiful bathrooms plus a there’s a TV in every bedroom. Step out to the backyard paradise, with luxurious pool, cushy furniture, large dining table and firepit. Swim, relax, or enjoy the sunset at Iron Pier beach, just a block away, or visit the nearby farm stands or golf courses. You will not be disappointed! 17
      43 Smugglers Path Jamesport, NY 11947
      $30,000
      3 Bedrooms 3 Full Baths 1 Half Bath
      Single Family For Rent ML# 3563342
      This absolutely stunning contemporary home is the place for your North Fork getaway! Features galore include a chef’s dream eat in kitchen, spacious living room with gas fireplace, and 3 available bedrooms. The first floor primary suite is enormous, with a soaking tub as well as shower in the gorgeous bathroom, plus a connected additional bedroom. The 2 guest suites, one with 2 queen beds, have their own beautiful bathrooms plus a there’s a TV in every bedroom. Step out to the backyard paradise, with luxurious pool, cushy furniture, large dining table and firepit. Swim, relax, or enjoy the sunset at Iron Pier beach, just a block away, or visit the nearby farm stands or golf courses. You will not be disappointed!
      Presented By: Signature Premier Properties  631-765-6000
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    Showing 41 - 50 of 226 results| view:  results per page« first|...|3|4|5|6|...|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