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Southold Luxury Rentals

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    Showing 21 - 29 of 29 results| view:  results per page« 1|2|3 »
    • NEW TO THE RENTAL MARKET! JUST A DREAM BOAT! NEWLY RENOVATED, LIGHT AND BRIGHT, BEAUTIFULLY APPOINTED, EVERY CONVENIENCE - 2 BEDROOMS, 2 BATHS. PLUS - CONVERTIBLE QUEEN SOFABED! BEAUTIFUL OUTDOOR DINING, FIRE PIT, PORCH, ENCLOSED SHOWER! PRICED RIGHT! STEPS TO POPULAR KENNEY’S BEACH - JUST BRING YOUR LITTLE RED WAGON AND STROLL TO THE BEACH AND ENJOY!, Additional information: Appearance:excellent!, Lease Term:August-Labor Day, July, July-August, June, Memorial-Labor, Off Season, Weekly, Weekly Rent Amt:3000 29
      250 Wesland Rd Southold, NY 11971
      $10,500
      2 Bedrooms 2 Full Baths Sq. Ft. 1400.00:#
      Single Family For Rent ML# 3478213
      NEW TO THE RENTAL MARKET! JUST A DREAM BOAT! NEWLY RENOVATED, LIGHT AND BRIGHT, BEAUTIFULLY APPOINTED, EVERY CONVENIENCE - 2 BEDROOMS, 2 BATHS. PLUS - CONVERTIBLE QUEEN SOFABED! BEAUTIFUL OUTDOOR DINING, FIRE PIT, PORCH, ENCLOSED SHOWER! PRICED RIGHT! STEPS TO POPULAR KENNEY’S BEACH - JUST BRING YOUR LITTLE RED WAGON AND STROLL TO THE BEACH AND ENJOY!, Additional information: Appearance:excellent!, Lease Term:August-Labor Day, July, July-August, June, Memorial-Labor, Off Season, Weekly, Weekly Rent Amt:3000
      Presented By: Beninati Associates  631-765-5333
      Call Today: 631-235-8980, 631-765-5333, or  Email: Marie Beninati
      Call Today: 631-765-5333, or  Email: Lee Beninati
    • Located in a gorgeous Bay beach private community, just a stone’s throw from Southold Bay. Waterviews from many rooms and the sprawling backyard. Immaculate, light filled, 5 bedroom/2 bath charmer with room for all. Features include walkout deck, a library, sunroom w/gorgeous Bay views, outdoor showerhouse. Super convenient to fine dining, shopping & wineries - just 5 minutes to either Southold or Greenport....even 3 stellar farm stands just up the road including a CSA. Farm to table heaven! Located within Southold’s Park District, includes access to Founders’ Landing treasured sandy Bay beach park & playground. Everything you need for a fantastic North Fork vacation. Rental permit #0392; Expiration date 4/18/2025, Additional information: Appearance:Excellent, Weekly Rent Amt:2500 20
      695 Rogers Rd Southold, NY 11971
      $15,000
      5 Bedrooms 2 Full Baths Sq. Ft. 1800.00:#
      Single Family For Rent ML# 3470466
      Located in a gorgeous Bay beach private community, just a stone’s throw from Southold Bay. Waterviews from many rooms and the sprawling backyard. Immaculate, light filled, 5 bedroom/2 bath charmer with room for all. Features include walkout deck, a library, sunroom w/gorgeous Bay views, outdoor showerhouse. Super convenient to fine dining, shopping & wineries - just 5 minutes to either Southold or Greenport....even 3 stellar farm stands just up the road including a CSA. Farm to table heaven! Located within Southold’s Park District, includes access to Founders’ Landing treasured sandy Bay beach park & playground. Everything you need for a fantastic North Fork vacation. Rental permit #0392; Expiration date 4/18/2025, Additional information: Appearance:Excellent, Weekly Rent Amt:2500
      Presented By: Douglas Elliman Real Estate  631-477-2220
      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
    • 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
    • Available seasonally, this impeccable modern 3 bedroom 3 bath home in Southold’s coveted Cedar Beach district offers privacy, water views and a private neighborhood beach. The open plan includes kitchen, dining area, den/office, and living room with fireplace. Sliding doors open to the bluestone patio with gas grill and plenty of room for entertaining and sunning. The three bedrooms, including a primary suite, all have water views. The private bay beach is a short stroll away. Easy access to renowned North Fork wineries, farmstands, restaurants and shops. Memorial Day-Labor Day $45, 000; June $8000; July $18, 000; August-LD $20, 000. 22
      355 Midway Rd Southold, NY 11971
      $20,000
      3 Bedrooms 3 Full Baths
      Single Family For Rent ML# 3389441
      Available seasonally, this impeccable modern 3 bedroom 3 bath home in Southold’s coveted Cedar Beach district offers privacy, water views and a private neighborhood beach. The open plan includes kitchen, dining area, den/office, and living room with fireplace. Sliding doors open to the bluestone patio with gas grill and plenty of room for entertaining and sunning. The three bedrooms, including a primary suite, all have water views. The private bay beach is a short stroll away. Easy access to renowned North Fork wineries, farmstands, restaurants and shops. Memorial Day-Labor Day $45, 000; June $8000; July $18, 000; August-LD $20, 000.
      Presented By: Brown Harris Stevens N Fork  631-477-0551
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Permit 681 .Enjoy This Beautifully Renovated 4 Bedroom, 3 Bath Ranch Style Home With Heated Pool. Open Floor Plan Includes LR With Cathedral Ceilings, High End EIK, Dining Area & Outdoor Shower. Plenty of Room For The Whole Family & Guests. Beautiful Goose Creek Beach Just 0.2 Miles Down The Road. Minutes To Local Wineries, Shopping & Dining. Make Memories In This Wonderful Summer Rental! 26
      215 Northfield Lane Southold, NY 11971
      $14,000
      4 Bedrooms 3 Full Baths Sq. Ft. 2300.00:#
      Single Family For Rent ML# 3386926
      Permit 681 .Enjoy This Beautifully Renovated 4 Bedroom, 3 Bath Ranch Style Home With Heated Pool. Open Floor Plan Includes LR With Cathedral Ceilings, High End EIK, Dining Area & Outdoor Shower. Plenty of Room For The Whole Family & Guests. Beautiful Goose Creek Beach Just 0.2 Miles Down The Road. Minutes To Local Wineries, Shopping & Dining. Make Memories In This Wonderful Summer Rental!
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Beachfront, located in Southold Shores, this architect’s own home is built with all the beautiful appointments you can imagine. Embracing the purity of architectural detail, together with a refined simplicity, this waterfront home offers a timeless elegance. Sweeping sunsets eye-catching angles and thoughtful details provide constant visual interest. A large 4 bedrooms with 4 baths ensuite, seaside floor to ceiling windows overlooking the Bayfront, Chefs kitchen leading to large outdoor deck and lovely garden. It is truly stunning. A special summer oasis. Available August $40K, Sept $20K RP# 0857 34
      950 Blue Marlin Drive Southold, NY 11971
      $20,000
      4 Bedrooms 4 Full Baths Sq. Ft. 3200.00:#
      Single Family For Rent ML# 3376195
      Beachfront, located in Southold Shores, this architect’s own home is built with all the beautiful appointments you can imagine. Embracing the purity of architectural detail, together with a refined simplicity, this waterfront home offers a timeless elegance. Sweeping sunsets eye-catching angles and thoughtful details provide constant visual interest. A large 4 bedrooms with 4 baths ensuite, seaside floor to ceiling windows overlooking the Bayfront, Chefs kitchen leading to large outdoor deck and lovely garden. It is truly stunning. A special summer oasis. Available August $40K, Sept $20K RP# 0857
      Presented By: Town And Country Real Estate  631-477-5990
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • Rental permit 405. Dine Al Fresco! Enjoy The Spectacular Sunsets At This Waterfront Paradise. 3 Bedroom 2 bath Contemporary Home With 1st Floor Waterside Master Suite. New Soft padded Heated/Lighted Salt Water IG Pool W/Automatic Cover, Unobstructed Waterviews, Enclosed Outdoor Shower, Hi End Newly Built Kitchen. Enjoy Kayaking, Paddle Boarding and Fishing From Your Own Dock. Easy Direct Bay Access. Beautiful Goose Creek Beach Practically at Your Doorstep. 11
      470 Goose Creek Lane Southold, NY 11971
      $30,000
      3 Bedrooms 2 Full Baths Sq. Ft. 2000.00:#
      Single Family For Rent ML# 3236473
      Rental permit 405. Dine Al Fresco! Enjoy The Spectacular Sunsets At This Waterfront Paradise. 3 Bedroom 2 bath Contemporary Home With 1st Floor Waterside Master Suite. New Soft padded Heated/Lighted Salt Water IG Pool W/Automatic Cover, Unobstructed Waterviews, Enclosed Outdoor Shower, Hi End Newly Built Kitchen. Enjoy Kayaking, Paddle Boarding and Fishing From Your Own Dock. Easy Direct Bay Access. Beautiful Goose Creek Beach Practically at Your Doorstep.
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      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. Permit# 0996 32
      1695 Old Woods Path Southold, NY 11971
      $30,000
      6 Bedrooms 4 Full Baths
      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. Permit# 0996
      Presented By: Town And Country Real Estate  631-298-0600
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    Showing 21 - 29 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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