Fair Housing Notice Standard Operating Procedure
631.765.5333

Seasonal Rentals

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

    15  properties match your search;

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

    Save Search
    Showing 1 - 10 of 15 results| view:  results per page« 1|2 »
    • 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. 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.
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      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:6700 34
      900/1 Fox Hollow Rd Mattituck, NY 11952
      $35,000
      4 Bedrooms 3 Full Baths
      Commercial 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:6700
      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: 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
    • Escape to your own piece of paradise in this stunning bayfront home, offering the ultimate in relaxation and luxury. Nestled on the scenic North Fork, this charming 4-bedroom, 2-bath residence boasts breathtaking bay views and direct access to your very own private beach. Imagine unwinding on the expansive deck, sipping your morning coffee while gazing at the tranquil waters, or heading down to the beach to dip your toes in the sand. This home is a true oasis, perfect for outdoor entertaining and water activities. Whether you’re swimming, kayaking, paddleboarding, or simply lounging on the giant anchored raft, there’s something for everyone. The lush, hydrangea-filled gardens provide a sense of privacy and serenity, making this retreat incredibly enticing. With two spacious living areas and options for dining indoors or out, this home is designed for both relaxation and entertainment. Enjoy cozy evenings by the beach or star gazing, roasting marshmallows over a fire and making memories to last a lifetime. Discover the perfect North Fork getaway, where charm, character, and coastal living come together in harmony. 32
      1429 Peconic Bay Boulevard Laurel, NY 11948
      $25,000
      4 Bedrooms 2 Full Baths 1 Half Bath
      Single Family For Rent ML# 3575176
      Escape to your own piece of paradise in this stunning bayfront home, offering the ultimate in relaxation and luxury. Nestled on the scenic North Fork, this charming 4-bedroom, 2-bath residence boasts breathtaking bay views and direct access to your very own private beach. Imagine unwinding on the expansive deck, sipping your morning coffee while gazing at the tranquil waters, or heading down to the beach to dip your toes in the sand. This home is a true oasis, perfect for outdoor entertaining and water activities. Whether you’re swimming, kayaking, paddleboarding, or simply lounging on the giant anchored raft, there’s something for everyone. The lush, hydrangea-filled gardens provide a sense of privacy and serenity, making this retreat incredibly enticing. With two spacious living areas and options for dining indoors or out, this home is designed for both relaxation and entertainment. Enjoy cozy evenings by the beach or star gazing, roasting marshmallows over a fire and making memories to last a lifetime. Discover the perfect North Fork getaway, where charm, character, and coastal living come together in harmony.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-298-4130
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Enjoy an experience on the North Fork of LI this summer. Whether a couple of weeks, a month, or the whole season, spend it nestled in a quiet spot that is near downtown Southold. Feel embraced by all the NOFO has to offer in this meticulously renovated, waterfront Cape, while enjoying the utmost in privacy and waterfront access. Step down into your own private swimming spot in clear Jockey Creek or enjoy your own private deep-water dock (bring your boat!). Kayak, canoe or paddle directly to Southold Bay, Shelter Island Sound and the extended fishing grounds of Greenport, Bug Light, Orient and beyond. Enjoy a quick ride into the charming downtown of Southold for elegant dining, shopping and easy access to LIRR/Jitney into NYC. Make lasting summer memories on this expansive idyllic, half acre, creekfront property which is perfect for quiet time, entertaining on the deck or play., Additional information: Appearance:excellent 30
      3675 Wells Avenue Southold, NY 11971
      $20,500
      4 Bedrooms 2 Full Baths
      Single Family For Rent ML# 3467464
      Enjoy an experience on the North Fork of LI this summer. Whether a couple of weeks, a month, or the whole season, spend it nestled in a quiet spot that is near downtown Southold. Feel embraced by all the NOFO has to offer in this meticulously renovated, waterfront Cape, while enjoying the utmost in privacy and waterfront access. Step down into your own private swimming spot in clear Jockey Creek or enjoy your own private deep-water dock (bring your boat!). Kayak, canoe or paddle directly to Southold Bay, Shelter Island Sound and the extended fishing grounds of Greenport, Bug Light, Orient and beyond. Enjoy a quick ride into the charming downtown of Southold for elegant dining, shopping and easy access to LIRR/Jitney into NYC. Make lasting summer memories on this expansive idyllic, half acre, creekfront property which is perfect for quiet time, entertaining on the deck or play., Additional information: Appearance:excellent
      Presented By: Signature Premier Properties  631-765-6000
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • This Beautifully Appointed Seasonal Rental Home is Now Available for September 5 - October 5 of 2024/2025 and July - Labor Day 2025. Close to All in Mattituck. Custom Built for Comfort and Enjoyment by All. Perfect for Entertaining Family and Guests. The Home Boasts 4 Large Bedrooms, 3 Full Baths, a Custom Eat-In Kitchen with All High-End Stainless Appliances with Room for Everyone and Everything! The First Floor and Entry are Fully Handicap Accessible. An Enclosed Patio Area Lends Additional Enjoyment and Cozy Lounge Space with Bar and Outdoor Shower. Built-In BBQ and Outdoor Jacuzzi in Deck. Grand Rear Patio with Firepit with Ample Entertaining Space. Central Vac, Central Air and Hardwood Floors Throughout. Utilities Included (with a Cap), Lawn, Garbage and Jacuzzi Care are Included. All Nestled on a Shy Acre of Private, Lush Property. Close to All We Love on the North Fork! Rental Permit #472. All Prospective Tenants to Complete an Application Via Rentspree. Link to be Provided Upon Inquiry 36
      105 Ole Jule Lane Mattituck, NY 11952
      $17,500
      4 Bedrooms 3 Full Baths Sq. Ft. 2500.00:#
      Single Family For Rent ML# 3572497
      This Beautifully Appointed Seasonal Rental Home is Now Available for September 5 - October 5 of 2024/2025 and July - Labor Day 2025. Close to All in Mattituck. Custom Built for Comfort and Enjoyment by All. Perfect for Entertaining Family and Guests. The Home Boasts 4 Large Bedrooms, 3 Full Baths, a Custom Eat-In Kitchen with All High-End Stainless Appliances with Room for Everyone and Everything! The First Floor and Entry are Fully Handicap Accessible. An Enclosed Patio Area Lends Additional Enjoyment and Cozy Lounge Space with Bar and Outdoor Shower. Built-In BBQ and Outdoor Jacuzzi in Deck. Grand Rear Patio with Firepit with Ample Entertaining Space. Central Vac, Central Air and Hardwood Floors Throughout. Utilities Included (with a Cap), Lawn, Garbage and Jacuzzi Care are Included. All Nestled on a Shy Acre of Private, Lush Property. Close to All We Love on the North Fork! Rental Permit #472. All Prospective Tenants to Complete an Application Via Rentspree. Link to be Provided Upon Inquiry
      Presented By: Douglas Elliman Real Estate  631-298-8000
      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. Call for off-season rates. Close to all North Fork amenities. 35
      800 Goose Creek Lane Southold, NY 11971
      $9,500
      3 Bedrooms 3 Full Baths Sq. Ft. 2032.00:#
      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. Call for off-season rates. Close to all North Fork amenities.
      Presented By: Daniel Gale Sothebys Intl Rlty  631-734-5439
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 25
      40 Overlook Drive Aquebogue, NY 11931
      $8,000
      4 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 3800.00:#
      Single Family For Rent ML# 3592652
      Presented By: Kerrigan Country Realty  631-288-9600
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Greenport Village. Beautifully Renovated Vintage Bungalow with New Kitchen and Baths While Keeping Original Charm and Character. Hardwood Floors Throughout. Inviting Front Porch, Patio and Yard. Off Season Rental. Available January 2025 thru April 2025 Only at $5, 000 per Month. Permit#24-023. 28
      446 6th Street Greenport, NY 11944
      $5,000
      4 Bedrooms 1 Full Bath 1 Half Bath Sq. Ft. 1400.00:# Square Feet
      Single Family For Rent NEW ML# 802278
      Greenport Village. Beautifully Renovated Vintage Bungalow with New Kitchen and Baths While Keeping Original Charm and Character. Hardwood Floors Throughout. Inviting Front Porch, Patio and Yard. Off Season Rental. Available January 2025 thru April 2025 Only at $5, 000 per Month. Permit#24-023.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    Showing 1 - 10 of 15 results| view:  results per page« 1|2 »
    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