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Southold Luxury Rentals

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    Showing 11 - 20 of 38 results| view:  results per page« 1|2|3|4 »
    • Permit #: 0160. This Superb 3-Bedroom, 2-Bathroom Ranch Home Showcases Gorgeous Water Views And Is Strategically Located Near Goose Creek Beach And The Pulsating Heart Of Southold, Allowing You To Enjoy The Best Of Both Worlds. The Interior Is Beautifully Designed With A Minimalist Aesthetic, Offering A Serene Retreat From The Every Day Hustle And Bustle. The Open Layout Allows For Easy Movement And A Seamless Blend Of Indoor And Outdoor Living Spaces. Its Picturesque Waterfront Setting Serving As A Constant Reminder Of The Beauty That Surrounds You. Here, You Can Start Your Day With A Refreshing Morning Jog, Entertain Guests With A Backyard Barbecue, Or Unwind With A Glass Of Wine While Watching The Sunset Over The Water. 1100 Pine Ave Is More Than Just An Address; It’s The Perfect Summer Getaway. Call Today To Schedule Your Private Tour. 19
      1100 Pine Avenue Southold, NY 11971
      $5,000 - $28,000
      3 Bedrooms 2 Full Baths
      Single Family For Rent ML# 3532447
      Permit #: 0160. This Superb 3-Bedroom, 2-Bathroom Ranch Home Showcases Gorgeous Water Views And Is Strategically Located Near Goose Creek Beach And The Pulsating Heart Of Southold, Allowing You To Enjoy The Best Of Both Worlds. The Interior Is Beautifully Designed With A Minimalist Aesthetic, Offering A Serene Retreat From The Every Day Hustle And Bustle. The Open Layout Allows For Easy Movement And A Seamless Blend Of Indoor And Outdoor Living Spaces. Its Picturesque Waterfront Setting Serving As A Constant Reminder Of The Beauty That Surrounds You. Here, You Can Start Your Day With A Refreshing Morning Jog, Entertain Guests With A Backyard Barbecue, Or Unwind With A Glass Of Wine While Watching The Sunset Over The Water. 1100 Pine Ave Is More Than Just An Address; It’s The Perfect Summer Getaway. Call Today To Schedule Your Private Tour.
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Ideal summer getaway in the heart of the North Fork with 5 bed and 4.5 baths. The home sits on a shy half acre complete with accessory office/gym structure, inground gunite pool and has incredible views of the neighboring North Fork vineyard. The first floor features an open floor plan with a large eat-in kitchen, dining area, living room and family room. There are four bedrooms in the main portion of home and an accessory attached apartment with an additional bedroom, family room and kitchenette. Enjoy close proximity to downtown Southold, beaches and wineries. Renovated top to bottom in 2021. June- 25K, July 35K. 27
      45805 Main Rd Southold, NY 11971
      $35,000
      5 Bedrooms 4 Full Baths 1 Half Bath Sq. Ft. 3600.00:# Square Feet
      Single Family For Rent ML# 3532208
      Ideal summer getaway in the heart of the North Fork with 5 bed and 4.5 baths. The home sits on a shy half acre complete with accessory office/gym structure, inground gunite pool and has incredible views of the neighboring North Fork vineyard. The first floor features an open floor plan with a large eat-in kitchen, dining area, living room and family room. There are four bedrooms in the main portion of home and an accessory attached apartment with an additional bedroom, family room and kitchenette. Enjoy close proximity to downtown Southold, beaches and wineries. Renovated top to bottom in 2021. June- 25K, July 35K.
      Presented By: Compass Greater NY LLC  516-330-6086
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Magnificent Waterfront with Pool! Enjoy the luxury of coastal living in this beautifully constructed home with its own private beach. Open and airy spaces with all the amenities for comfort and relaxation. Spacious kitchen, Dining Rm, Living Rm w/fp, Four generous sized bedrooms & 3.5 baths. The upstairs loft boasts an amazing recreational area with soaring ceilings & walls of glass overlooking spectacular views of the sound & sunsets. Close to shopping, vineyards, boating, world-class dining and more! Last two weeks of June (6/15-6/30): $23, 000. Full Month of July: $50, 000. First two weeks of August (8/1-8/15): $25, 000. 33
      18805 Soundview Avenue Southold, NY 11971
      $23,000
      4 Bedrooms 3 Full Baths 1 Half Bath Sq. Ft. 3800.00:# Square Feet
      Single Family For Rent ML# 3529983
      Magnificent Waterfront with Pool! Enjoy the luxury of coastal living in this beautifully constructed home with its own private beach. Open and airy spaces with all the amenities for comfort and relaxation. Spacious kitchen, Dining Rm, Living Rm w/fp, Four generous sized bedrooms & 3.5 baths. The upstairs loft boasts an amazing recreational area with soaring ceilings & walls of glass overlooking spectacular views of the sound & sunsets. Close to shopping, vineyards, boating, world-class dining and more! Last two weeks of June (6/15-6/30): $23, 000. Full Month of July: $50, 000. First two weeks of August (8/1-8/15): $25, 000.
      Presented By: Compass Greater NY LLC  516-517-4751
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 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
    • Public Remarks:If you are looking for a true summer experience on the beautiful North Fork of Long Island, look no further. This Spacious home has the full spectrum of mother nature right on your own huge back yard on the great lake with 2 fire pits. Featuring 4 Bedrooms, 4 Bath, An Oversize Patio, Large Heated In ground pool. Your own fully equipped gym to help keep you in the best of shape! You may enjoy fishing in a lake only a few steps away, as well as close distance to Kenny’s Beach on the Sound. Ample of Marinas around the corners, as well as endless Vegetable & Fruit Farms & Stands, Wineries, Restaurants & Shopping. Enjoy this rare find for a memorable summer experience! Permit no: 0080 Expire: 06/07/2025 - JULY & AUGUST ARE NO LONGER AVAILABLE . 28
      1205 Lake Drive Southold, NY 11971
      $17,500 - $25,000
      4 Bedrooms 4 Full Baths
      Single Family For Rent ML# 3528933
      Public Remarks:If you are looking for a true summer experience on the beautiful North Fork of Long Island, look no further. This Spacious home has the full spectrum of mother nature right on your own huge back yard on the great lake with 2 fire pits. Featuring 4 Bedrooms, 4 Bath, An Oversize Patio, Large Heated In ground pool. Your own fully equipped gym to help keep you in the best of shape! You may enjoy fishing in a lake only a few steps away, as well as close distance to Kenny’s Beach on the Sound. Ample of Marinas around the corners, as well as endless Vegetable & Fruit Farms & Stands, Wineries, Restaurants & Shopping. Enjoy this rare find for a memorable summer experience! Permit no: 0080 Expire: 06/07/2025 - JULY & AUGUST ARE NO LONGER AVAILABLE .
      Presented By: Douglas Elliman Real Estate  631-298-8000
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Ideal North Fork Dream Home for Spring and Summer Living! Embrace the vibrant spirit of Southold with this spacious and inviting home. Boasting four generously sized bedrooms, three equipped with ensuite bathrooms and the first-floor bedroom conveniently offering access to a full bath across the hall, this residence ensures comfort and convenience. The heart of the home, the great room, showcases the second fireplace and opens up to the rear masonry deck, which overlooks the large, heated pool and the backyard. Just a few blocks away is an array of charming shops, cafes, and restaurants, adding to the allure of this perfect home base for your North Fork experience. Available Year Round at 10k per month. June: 30K July: 38k August: 45k. Memorial Day- Labor Day: 100k. Also available off season. 28
      315 Maple Lane Southold, NY 11971
      $30,000
      4 Bedrooms 4 Full Baths Sq. Ft. 3500.00:# Square Feet
      Single Family For Rent ML# 3528088
      Ideal North Fork Dream Home for Spring and Summer Living! Embrace the vibrant spirit of Southold with this spacious and inviting home. Boasting four generously sized bedrooms, three equipped with ensuite bathrooms and the first-floor bedroom conveniently offering access to a full bath across the hall, this residence ensures comfort and convenience. The heart of the home, the great room, showcases the second fireplace and opens up to the rear masonry deck, which overlooks the large, heated pool and the backyard. Just a few blocks away is an array of charming shops, cafes, and restaurants, adding to the allure of this perfect home base for your North Fork experience. Available Year Round at 10k per month. June: 30K July: 38k August: 45k. Memorial Day- Labor Day: 100k. Also available off season.
      Presented By: Compass Greater NY LLC  516-330-6086
      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
    • Bring your swim suit, flip flops, and summer vibe! This amazing property located in a private beachfront community across the street from a beautiful sandy bay beach. The community is set far off the main rd providing a great ambience of being away from it all! Great place to relax, boat, entertain, dine al fresco, and all things fun in the sun. Lovely updated, immaculate home with 3beds and 2 full baths, office space, living room, dining room, outdoor deck with bay views! Pack some extra clothes, you will not want to go home! 23
      2445 Minnehaha Boulevard Southold, NY 11971
      $14,000
      3 Bedrooms 2 Full Baths
      Single Family For Rent ML# 3526587
      Bring your swim suit, flip flops, and summer vibe! This amazing property located in a private beachfront community across the street from a beautiful sandy bay beach. The community is set far off the main rd providing a great ambience of being away from it all! Great place to relax, boat, entertain, dine al fresco, and all things fun in the sun. Lovely updated, immaculate home with 3beds and 2 full baths, office space, living room, dining room, outdoor deck with bay views! Pack some extra clothes, you will not want to go home!
      Presented By: Compass Greater NY LLC  631-251-8644
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Southold, North Fork - artful cottage located in Southold by Founder’s Landing Park/Wharf House. Opposite a fabulous bay beach sits this unique, furnished, one bedroom residence. Full kitchen with dishwasher, bright and sunny living room, comfortable bedroom... home is heated by natural gas. Park like property with outside sitting area. Privacy and pet friendly. Enjoy life on the east end in this furnished home ready for you and convenient to area restaurants, wineries, and all the North Fork has to offer. Permit #0107 13
      Southold, NY 11971
      $19,000
      1 Bedroom 1 Full Bath Sq. Ft. 750.00:# Square Feet
      Single Family For Rent ML# 3525718
      Southold, North Fork - artful cottage located in Southold by Founder’s Landing Park/Wharf House. Opposite a fabulous bay beach sits this unique, furnished, one bedroom residence. Full kitchen with dishwasher, bright and sunny living room, comfortable bedroom... home is heated by natural gas. Park like property with outside sitting area. Privacy and pet friendly. Enjoy life on the east end in this furnished home ready for you and convenient to area restaurants, wineries, and all the North Fork has to offer. Permit #0107
      Presented By: Town And Country Real Estate  631-298-0600
      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
    Showing 11 - 20 of 38 results| view:  results per page« 1|2|3|4 »
    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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