Southold Luxury Rentals

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    Showing 21 - 30 of 36 results| view:  results per page« 1|2|3|4 »
    • 355 Windjammer Drive Southold, NY 11971
      $70,000
      3 Bedrooms 2 Full Baths
      Single Family For Rent ML# 3513704
      This soothing beach house is so Zen, you will feel like you are at a spa retreat! Peaceful and perfectly appointed, the backyard features a fabulous lagoon style pool, with a waterfall and hot tub, an amazing outdoor kitchen and bar, bathroom and outdoor shower! 3 bedrooms, 2 baths, including a spacious primary suite with a gorgeous spa like bathroom. All this and steps to the association beach! Surrounded by marinas, award winning vineyards, restaurants, farm stands & great shopping. Make this absolutely mint home your North Fork summer rental, you will not want to leave! Rental Permit #1002
      Presented By: Corcoran  631-848-7730
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 4004 Old North Rd Southold, NY 11971
      $45,000
      4 Bedrooms 4 Full Baths Sq. Ft. 2787.00:# Square Feet
      Single Family For Rent ML# 3510262
      Welcome to your future summer retreat! This beautiful newly built home offers the perfect blend of comfort and luxury, featuring 4 spacious bedrooms and 4 full baths. First floor primary bedroom with luxurious ensuite bathroom. Inside, you’ll find ample space and modern amenities that cater to your every need. However, what truly sets this property apart is the outdoor paradise waiting for you in the backyard. Immerse yourself in the heated saltwater pool or unwind in the relaxing hot tub - it’s your private sanctuary. Don’t miss the chance to rent this exceptional home and experience a lifestyle of unparalleled indulgence. Close to the beach!! Permit# - 0980
      Presented By: Douglas Elliman Real Estate  631-354-8100
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 1820 Kenneys Rd Southold, NY 11971
      $15,000
      6 Bedrooms 4 Full Baths Sq. Ft. 5028.00:# Square Feet
      Single Family For Rent ML# 3505469
      Room for All in this Spacious 6 Bedroom Luxurious Home with Gourmet Kitchen with 6 Burner Wolf Stove, Formal Dining Room. Large Living Room with Fireplace, a Separate Den and Large Bedrooms. Rainy Day Game Room and More in Lower Level. All set on 2.3 Acres with In Ground Pool, Nicely Finished Outdoor Space and Yard Area and Just a Short Distance to Kenneys and McCabes Beaches. Summer 2024 - June 1 to June 28 - $30, 000 or $8, 500 Per Week With Two Week Minimum. August 25 to September 8 (Two Weeks) $18, 500; September $30, 000 or $8, 500 per Week With Two Week Minimum. Off Season - October through April at $15, 000 Per month for Single or Multiple Month Rentals. Permit #0233.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 1355 Watersedge Way Southold, NY 11971
      $55,000
      $7,000 - $50,000
      3 Bedrooms 2 Full Baths
      Single Family For Rent PRICE REDUCED ML# 3501928
      Welcome to 1355 Watersedge Way a delightful Bayfront home located on Little Peconic Bay in Southold. Inside you have a spacious living room with a smart TV and a wall of sliding glass doors the lead out to the waterside deck, eat in kitchen, two bedrooms and one bathroom. on the lower level there is a family room with wet bar and access to the yard and outdoor shower, one bedroom, a full bath, and washer and dryer. The house is located next to a nature preserve with 300 ft. of beach providing easy access to the water/bay and plenty of privacy. Enjoy the spectacular views of the water and sunsets! MD TO LD $50k, June$12k, July $23K; August 1 to LD $24K, off season $7k for 30 days. House is available from May to November with a minimum of four weeks that does not need to align with the calendar month. RP# 0929
      Presented By: Town And Country Real Estate  631-477-5990
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 3400 Youngs Avenue Southold, NY 11971
      $40,000
      4 Bedrooms 2 Full Baths
      Single Family For Rent ML# 3489027
      Permit #493 Newly Renovated Farmhouse Centrally Located In Southold With Easy Access By Bus, Train or Car. Enjoy Your Morning Coffee As The Sun Rises Over The Farmfield. Spend An Afternoon Exploring The Beauty of the North Fork, Soak in the Sun at one of the Beautiful Peconic Bay or Long Island Sound Beaches, Enjoy Live Music at Numerous Wineries and/or Breweries, Browse unique local finds at One of Many Antique and/or Quaint Shops, and Don’t Forget to Stop by Our Bountiful Farm Stands. Cool Off With a Dip in the Heated Saltwater Pool, Enjoy Dinner Under the Stars and Reminisce Around the Fire Pit. Utilities Included. 10% Security & Exit Clean. Enjoy Summer On The North Fork!
      Presented By: Thomas J McCarthy Real Estate  631-765-5815
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 250 Wesland Rd Southold, NY 11971
      $12,000
      $6,000 - $10,500
      2 Bedrooms 2 Full Baths Sq. Ft. 1400.00:# Square Feet
      Single Family For Rent PRICE REDUCED 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!
      Presented By: Beninati Associates  631-765-5333
      Call Today: 631-765-5333, 631-235-8980, or  Email: Marie Beninati
      Call Today: 631-765-5333, or  Email: Lee Beninati
    • 870 Bay Home Rd Southold, NY 11971
      $22,000
      4 Bedrooms 2 Full Baths 2 Half Baths Sq. Ft. 1784.00:# Square Feet
      Single Family For Rent ML# 3475506
      Quintessential waterfront North Fork farmhouse with private sandy beach on Southold Bay, part of the Peconic Estuary. Beautifully maintained, this large 4BR/ 2.55 BTH home benefits from many recent upgrades, including new chef’s kitchen, renovated powder room, screened in front porch and back deck. Fabulous indoor/ outdoor North Fork Summer Living in the mature gardens with specimen trees, waterfront and vineyard views, and your private sugar sand beach to swim, kayak, paddle board, boat and fish. Close to all area attractions. Pet friendly! Walk to vineyards and organic farms for North Fork farm to table dining. Close to fine dining restaurants, farms, and waterfront bars. Fun arts, crafts, yoga, juice bar, live music and water sports, Southold, Greenport Maritime Village and ferries to Shelter Island, Sag Harbor and the South Fork easy to reach. Southold Town Rental Permit 0631
      Presented By: Property Angels  631-252-5653
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 695 Rogers Rd Southold, NY 11971
      $18,000
      5 Bedrooms 2 Full Baths Sq. Ft. 1800.00:# Square Feet
      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 spacious backyard. Immaculate, light filled, 5 bedroom/2 bath charmer with room for all. Features incl library, sunroom w/gorgeous Bay view, 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 the Park District with access to Founders’ Landing Park. Everything you need to enjoy the amazing North Fork! Rental permit #0392; Expiration date 4/7/25.
      Presented By: Douglas Elliman Real Estate  631-477-2220
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 3675 Wells Avenue Southold, NY 11971
      $25,000
      $23,500
      4 Bedrooms 2 Full Baths
      Single Family For Rent PRICE REDUCED 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.
      Presented By: Signature Premier Properties  631-765-6000
      Call Today: (631) 765 5333, or  Email: Beninati Associates Real Estate
    • 650 Pine Avenue Southold, NY 11971
      $50,000
      8 Bedrooms 7 Full Baths Sq. Ft. 5400.00:# Square Feet
      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
    Showing 21 - 30 of 36 results| view:  results per page« 1|2|3|4 »
    OneKeyâ„¢ MLS The data relating to real estate for sale on this web site comes in part from the OneKeyâ„¢ 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.

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