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Southold Luxury Rentals

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    Showing 1 - 10 of 29 results| view:  results per page« 1|2|3 »
    • 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  631-251-8644
      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
    • Located on a private and serene 1.09 acre parcel of land and only 1/3 of a mile from McCabes Beach, with miles of Long Island Sound beach to traverse to the east and west, this charming and newly built two story home offers an open concept living space with plentiful natural light on the first floor with a half bathroom between the living and dining room, with a half bathroom off of the hallway leading to the eat-in-kitchen and den/tv room. The second floor provides a master bedroom with en-suite bathroom, two additional bedrooms and another full bathroom. There are large sliding glass doors in the kitchen that lead to a picturesque patio and outdoor sitting area with grill, tables and umbrella. Take in all the North Fork has to offer. Rental permit # 0343 19
      13595 Soundview Avenue Southold, NY 11971
      $9,000
      3 Bedrooms 2 Full Baths 1 Half Bath
      Single Family For Rent ML# 3587451
      Located on a private and serene 1.09 acre parcel of land and only 1/3 of a mile from McCabes Beach, with miles of Long Island Sound beach to traverse to the east and west, this charming and newly built two story home offers an open concept living space with plentiful natural light on the first floor with a half bathroom between the living and dining room, with a half bathroom off of the hallway leading to the eat-in-kitchen and den/tv room. The second floor provides a master bedroom with en-suite bathroom, two additional bedrooms and another full bathroom. There are large sliding glass doors in the kitchen that lead to a picturesque patio and outdoor sitting area with grill, tables and umbrella. Take in all the North Fork has to offer. Rental permit # 0343
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 2025 Rates: July $32, 500, July-August $67, 500 and August-Labor Day $35, 000. 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! 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, July-August $67, 500 and August-Labor Day $35, 000. 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!
      Presented By: Daniel Gale Sothebys Intl Rlty  631-477-0013
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Now Available for Off Season Rental Until March 31, 2025 and Post Labor Day 2025. Rented June 1 - September 30th. Set Creekfront with Private Dock and Associated Bay Beach Access in Community. The Extensive Rear Patio Area is Impressive with an Inground Pool and Jacuzzi. All Creekfront with a Beautiful View. The Home is Grand and Designed to Entertain. Boasting 5 Bedrooms and 4 Baths. 2 Large Living Rooms, Well Appointed Kitchen with All High-End Appliances. 6 Burner Wolf Stove for Cooking. All Overlooking Dining, Living and Bar Area. All Utilities (Except Electric), Cleaning, Pool, Jacuzzi and Exterior Maintenance Provided by Landlord. Ample Parking. The Home Also Includes a Bocce Court, Ping-Pong and Shuffleboard Tables. All Prospective Tenants to Provide a Completed Application Via RentSpree. Link to be Provided. Rental Permit # 1180, Additional information: Appearance: Beautiful, Interiorr Features: Efficiency Kitchen, Guest Quarters, Interior Features: Separate Thermostat 36
      425 Cedar Point Drive E Southold, NY 11971
      $15,000
      5 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 3700.00:#
      Single Family For Rent ML# 3573270
      Now Available for Off Season Rental Until March 31, 2025 and Post Labor Day 2025. Rented June 1 - September 30th. Set Creekfront with Private Dock and Associated Bay Beach Access in Community. The Extensive Rear Patio Area is Impressive with an Inground Pool and Jacuzzi. All Creekfront with a Beautiful View. The Home is Grand and Designed to Entertain. Boasting 5 Bedrooms and 4 Baths. 2 Large Living Rooms, Well Appointed Kitchen with All High-End Appliances. 6 Burner Wolf Stove for Cooking. All Overlooking Dining, Living and Bar Area. All Utilities (Except Electric), Cleaning, Pool, Jacuzzi and Exterior Maintenance Provided by Landlord. Ample Parking. The Home Also Includes a Bocce Court, Ping-Pong and Shuffleboard Tables. All Prospective Tenants to Provide a Completed Application Via RentSpree. Link to be Provided. Rental Permit # 1180, Additional information: Appearance: Beautiful, Interiorr Features: Efficiency Kitchen, Guest Quarters, Interior Features: Separate Thermostat
      Presented By: Douglas Elliman Real Estate  631-298-8000
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Enjoy water views and Long Island Sound sunsets from this magnificent new construction home for rent! Perfectly situated on 1.5 scenic acres, this home offers exclusivity and privacy. The beautiful eat-in-kitchen features high-end amenities including a Viking refrigerator and 8 burner range, double ovens, dual Bosch dishwashers plus two wine coolers. The airy and spacious living room is accented with dramatic vaulted ceilings, fireplace and wet bar. A wall of oversized sliding glass doors allow for plenty of natural light and lead to a 2, 000 sq. ft mahogany deck and heated gunite pool - ideal for comfort and relaxation. Two generously sized bedrooms and 1.5 baths complete the first floor. The second floor boasts an expansive primary suite with two walk-in closets and a luxurious bath including radiant heated floors, soaking tub, water closet, rain shower & body jets. Enjoy an early morning cup of coffee or star gaze in the evenings from your private water view balcony, making this room the perfect retreat. You will also find two additional bedrooms and two full baths on this floor. Enjoy all the North Fork has to offer and more with the deeded right of way that comes with this home which provides convenient access to sought-after McCabe’s Beach! Kenney’s Beach is also just a stone’s throw away! Don’t miss the opportunity to create a vacation to remember with this special home! Two-week terms are also available. Appearance: Mint 15
      11925 Soundview Avenue Southold, NY 11971
      $12,500
      5 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 3600.00:#
      Single Family For Rent ML# 3571029
      Enjoy water views and Long Island Sound sunsets from this magnificent new construction home for rent! Perfectly situated on 1.5 scenic acres, this home offers exclusivity and privacy. The beautiful eat-in-kitchen features high-end amenities including a Viking refrigerator and 8 burner range, double ovens, dual Bosch dishwashers plus two wine coolers. The airy and spacious living room is accented with dramatic vaulted ceilings, fireplace and wet bar. A wall of oversized sliding glass doors allow for plenty of natural light and lead to a 2, 000 sq. ft mahogany deck and heated gunite pool - ideal for comfort and relaxation. Two generously sized bedrooms and 1.5 baths complete the first floor. The second floor boasts an expansive primary suite with two walk-in closets and a luxurious bath including radiant heated floors, soaking tub, water closet, rain shower & body jets. Enjoy an early morning cup of coffee or star gaze in the evenings from your private water view balcony, making this room the perfect retreat. You will also find two additional bedrooms and two full baths on this floor. Enjoy all the North Fork has to offer and more with the deeded right of way that comes with this home which provides convenient access to sought-after McCabe’s Beach! Kenney’s Beach is also just a stone’s throw away! Don’t miss the opportunity to create a vacation to remember with this special home! Two-week terms are also available. Appearance: Mint
      Presented By: Compass Greater NY LLC  516-517-4751
      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
    • Planning a staycation? this Laughing Waters Association ranch is the perfect destination for a resort-style stay this year. Come experience the private bay beach, smell the salt air, and enjoy time boating/SUP/kayaking in the creek or try your luck clamming. The home is an easy and comfortable springboard to the North Fork lifestyle and features an open plan ideal for entertaining. Living room, Dining room, large kitchen to make the most serious cooks feel at home - plus an en suite bedroom with full bath and two additional bedrooms and full bath. Beyond the covered porch is a verdant and fully fenced in lawn area ideal for play, a bbq area, multiple sitting areas, a game room adjacent to the garage, a pool house with ’bar’ area and the most amazing outdoor, poolside shower. No detail for enjoyment has been overlooked - there is even a firepit for idle-hour! Available monthly, or weekly - inquire. Pets permited - fully fenced in property! Southold RP# 1149 expires 6/10/26 31
      50 Wabasso Street Southold, NY 11971
      $18,000
      3 Bedrooms 2 Full Baths Sq. Ft. 1200.00:#
      Single Family For Rent ML# 3559692
      Planning a staycation? this Laughing Waters Association ranch is the perfect destination for a resort-style stay this year. Come experience the private bay beach, smell the salt air, and enjoy time boating/SUP/kayaking in the creek or try your luck clamming. The home is an easy and comfortable springboard to the North Fork lifestyle and features an open plan ideal for entertaining. Living room, Dining room, large kitchen to make the most serious cooks feel at home - plus an en suite bedroom with full bath and two additional bedrooms and full bath. Beyond the covered porch is a verdant and fully fenced in lawn area ideal for play, a bbq area, multiple sitting areas, a game room adjacent to the garage, a pool house with ’bar’ area and the most amazing outdoor, poolside shower. No detail for enjoyment has been overlooked - there is even a firepit for idle-hour! Available monthly, or weekly - inquire. Pets permited - fully fenced in property! Southold RP# 1149 expires 6/10/26
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Lovely spacious newly built Colonial just down the lane from 4 gorgeous LI Sound Beaches. Main Floor Primary Bedroom En-suite with private side entrance and it’s own deck. Second Primary Bedroom En-Suite on level 2 (has radiant heat floor and heat lamp). Two additional Bedrooms, a full Bath in the hall, and Laundry Room. Kitchen has huge island with seating, 6 burner or griddle dual fuel oven. Total 4 Bedrooms, 3.5 Baths, all hardwood floors, central air, patio, 2 decks. Amazing location just minutes to McCabes, Goldsmith, Kenneys, and Town Beach, as well as the great new beach side restaurant Little Fish. Fabulous Hamlet Downtown on Main Road with all your shopping needs, many more trendy restaurants, antique shops, art galleries, and vineyards with music. Enjoy the rental’s paddle board, 2 kayaks, and beach buggy wagon. July $17, 000, August to Labor Day $24, 000, September $12, 000. 30
      6430 Hortons Lane Southold, NY 11971
      $24,000
      4 Bedrooms 3 Full Baths 1 Half Bath
      Single Family For Rent ML# 3556906
      Lovely spacious newly built Colonial just down the lane from 4 gorgeous LI Sound Beaches. Main Floor Primary Bedroom En-suite with private side entrance and it’s own deck. Second Primary Bedroom En-Suite on level 2 (has radiant heat floor and heat lamp). Two additional Bedrooms, a full Bath in the hall, and Laundry Room. Kitchen has huge island with seating, 6 burner or griddle dual fuel oven. Total 4 Bedrooms, 3.5 Baths, all hardwood floors, central air, patio, 2 decks. Amazing location just minutes to McCabes, Goldsmith, Kenneys, and Town Beach, as well as the great new beach side restaurant Little Fish. Fabulous Hamlet Downtown on Main Road with all your shopping needs, many more trendy restaurants, antique shops, art galleries, and vineyards with music. Enjoy the rental’s paddle board, 2 kayaks, and beach buggy wagon. July $17, 000, August to Labor Day $24, 000, September $12, 000.
      Presented By: Town And Country Real Estate  631-288-3030
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Welcome to your perfect summer getaway located in the desirable Claves Neck neighborhood of Southold. This comfortable Ranch has ample space for the whole family to unwind and recharge after a day of exploring the North Fork. The home offers a fully equipped kitchen, spacious living, and dining rooms, three pleasant bedrooms, two pristine bathrooms. Outside, a savor al fresco dining amid the lush greenery surrounding the screened in porch and brick patio with outdoor dining area and gas BBQ. Whether you are hosting a barbecue with loved ones or simply enjoying a quiet moment, this outdoor oasis provides the perfect backdrop for making memories. Popular beaches, restaurants, and wineries are all close by. Do not miss your chance to experience the best of Southold living (Southold Town rental permit #49090) Available for 2 weeks @ $3000 per week., Additional information: Appearance:Rxcellent, Weekly Renta Amt:3000 27
      400 Hill Rd Southold, NY 11971
      $12,000
      3 Bedrooms 2 Full Baths Sq. Ft. 1620.00:#
      Single Family For Rent ML# 3549421
      Welcome to your perfect summer getaway located in the desirable Claves Neck neighborhood of Southold. This comfortable Ranch has ample space for the whole family to unwind and recharge after a day of exploring the North Fork. The home offers a fully equipped kitchen, spacious living, and dining rooms, three pleasant bedrooms, two pristine bathrooms. Outside, a savor al fresco dining amid the lush greenery surrounding the screened in porch and brick patio with outdoor dining area and gas BBQ. Whether you are hosting a barbecue with loved ones or simply enjoying a quiet moment, this outdoor oasis provides the perfect backdrop for making memories. Popular beaches, restaurants, and wineries are all close by. Do not miss your chance to experience the best of Southold living (Southold Town rental permit #49090) Available for 2 weeks @ $3000 per week., Additional information: Appearance:Rxcellent, Weekly Renta Amt:3000
      Presented By: Town And Country Real Estate  631-477-5990
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    Showing 1 - 10 of 29 results| view:  results per page« 1|2|3 »
    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

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    Office: 52875 Main Road, Southold NY 11971
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