Newest Homes for Rent in Southold, NY

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  $10,000 Per Month

  • 3 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • House for Rent

  275 Maier Place, Southold, NY 11971

  Seasonal Rental in Scenic Southold, NY – 3 Bed, 3 Bath RetreatEscape to the heart of the North Fork with this beautifully appointed 3-bedroom, 2-bath seasonal rental in picturesque Southold, NY. Nestled among the region's famed vineyards, farm stands, and white sand beaches, this home offers the perfect blend of charm, comfort, and convenience.Inside, you'll find a spacious and

  Mary Terry MCKENNASHEA LLC

  275 Maier Place, Southold, NY 11971
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  /20

  $5,000 Per Month

  • 3 Beds
  • 1 Bath
  • 1,200 Sq Ft
  • House for Rent

  145 Founders Path, Southold, NY 11971

  Beautiful Charming Cottage Located in the Coveted Community of Founders. Close to a gorgeous sandy beach, grocery shopping, coffee shop, restaurants, jitney stop, and all things North Fork. Three bedrooms, one bath, LR, kitchen, outdoor deck, fire pit, outdoor shower. Available Sept. $5000, Oct & Nov $4000, Dec through March $3,000, April $3,500. May $5,000, June $6,000 and August $12,000.

  Diane Mollica Compass Greater NY LLC

  145 Founders Path, Southold, NY 11971
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  /20

  $6,000 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,750 Sq Ft
  • House for Rent

  1854 N Bayview Rd, Southold, NY 11971

  Year round lease. Amazing location with private beach, amazing waterviews and a private dock! Home is fully furnished and has 2 bedrooms, 2 full bathrooms and a 1/2 bathroom. Bring your boat or kayaks!

  Isaac Israel Richmond Realty Corp

  1854 N Bayview Rd, Southold, NY 11971
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  /20

  $19,000 Per Month

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Apartment for Rent

  475 Youngs Ave Unit c, Southold, NY 11971

  Southold, North Fork: Discover the epitome of easy living at Unit C "Baldwin T. Payne" in Southold, North Fork. This condo-like residence, part of the North Fork Resident's Inn, offers a one-of-a-kind opportunity to embrace a modern lifestyle in a historic setting. The unit boasts a spacious layout with direct garden access, abundant natural light, and contemporary furnishings. With upscale

  Nicholas Planamento William Raveis New York LLC

  475 Youngs Ave Unit c, Southold, NY 11971
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  $4,900 Per Month

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • House for Rent

  6710 Soundview Ave, Southold, NY 11971

  Enjoy Southold this Summer at a Sleek Scandinavian Style Farm Ranch. Available for Bi-Weekly Rental Only. The Rate is Weekly at a Bi-Weekly Minimum. Nestled on Shy 2.5 Acres of Private Wooded Property You Can Truly Get Away from It All. Constructed in 2022 for Elegance and Comfort. Complete One Level Living at Its Finest. The Home Boasts a Grand Open Layout with Vaulted Ceilings Throughout.

  Rene Giacobbe Douglas Elliman Real Estate

  6710 Soundview Ave, Southold, NY 11971
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  /30

  $10,000 Per Month

  • 3 Beds
  • 1.5 Baths
  • 1,578 Sq Ft
  • House for Rent

  425 Old Shipyard Ln, Southold, NY 11971

  Southold-Enjoy the North Fork in this adorable cottage. Located in Founder's Landing Southold beach community. Three bedrooms, living room, kitchen with dining area and sunroom overlooking yard and pool. This charming home has everything you need for a great summer getaway. Close to community beach and Park. Close to town, restaurants, shopping, The giving room yoga and juice bar, Southold fish

  Amy Kirincic The Agency Northshore NY

  425 Old Shipyard Ln, Southold, NY 11971
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  /21

  $10,000 Per Month

  • 5 Beds
  • 7 Baths
  • 3,500 Sq Ft
  • House for Rent

  495 N Parish Dr, Southold, NY 11971

  Southold, North Fork.Experience the beauty of seasonal living on Southold Bay. This newly renovated contemporary bayfront estate home invites you to bask in its light and bright ambiance, perfect for relaxation and rejuvenation. With its Zen-inspired organic design, you’ll find comfort and privacy combined with the conveniences of modern life.Nestled near the Southold Yacht Club, just

  Nicholas Planamento William Raveis New York LLC

  495 N Parish Dr, Southold, NY 11971
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  /23

  $18,000 Per Month

  • 3 Beds
  • 3 Baths
  • 3,100 Sq Ft
  • House for Rent

  1685 Peconic Ln, Peconic, NY 11958

  The Jefferson House, built in 1750, beautifully renovated and brought back to life in 2021. This historic home is the perfect place to stay this summer and welcome family and friends. Truly the most unique home offered for rent on the North Fork. Situated on 7 acres of natural and manicured gardens with specimen trees, fruit orchards and an outdoor patio – all nestled between vineyards and town

  Barbara Poliwoda Douglas Elliman Real Estate

  1685 Peconic Ln, Peconic, NY 11958
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  $7,500 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • House for Rent

  485 Pine Rd, Southold, NY 11971

  2026 Rates: September $7500; October $10,000: Discover your perfect getaway in this expansive and meticulously updated ranch home, designed for relaxation and rejuvenation. Experience a resort-like atmosphere with the stunning gunite, heated saltwater pool, complemented by a beautiful stone surround and convenient outdoor shower. Step inside to find high vaulted ceilings that create an airy

  William Walters Daniel Gale Sothebys Intl Rlty

  485 Pine Rd, Southold, NY 11971
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  /17

  $9,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • House for Rent

  1265 Brigantine Dr, Southold, NY 11971

  Impeccable, like new ranch for rent with quality features throughout in Harbor Lights with a deeded beach and park at the end of the street. There are three bedrooms, two full bathrooms, open floor plan from kitchen through the dining area into the vaulted ceiling living room, Enjoy the beautiful screened in porch which overlooks the private back yard with slate patio, grass lawn, and outdoor

  Barbara Poliwoda Douglas Elliman Real Estate

  1265 Brigantine Dr, Southold, NY 11971
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  /31

  $16,000 Per Month

  • 4 Beds
  • 3.5 Baths
  • House for Rent

  75 Clearview Ave, Southold, NY 11971

  2026 Rates: NO AVAILABILITY 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

  William Walters Daniel Gale Sothebys Intl Rlty

  75 Clearview Ave, Southold, NY 11971
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  $25,000 Per Month

  • 4 Beds
  • 3.5 Baths
  • House for Rent

  910 Glenn Rd, Southold, NY 11971

  Introducing your perfect retreat! This stunning 4-bed, 3.5-bath waterfront oasis nestled on West Creek in Southold. Enjoy access to Peconic Bay via your private dock. Spanning approx 3500 sq ft, revel in the elegance of oak floors, a luxurious soaking tub, and high ceilings throughout. The 1st floor has 2 primary ensuites, a spacious Great Room with cozy fireplace, laundry, and 2.5 baths +2-car

  Andrea Parks Douglas Elliman Real Estate

  910 Glenn Rd, Southold, NY 11971
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  /19

  $28,000 Per Month

  • 3 Beds
  • 2 Baths
  • House for Rent

  1100 Pine Ave, Southold, NY 11971

  Permit #: 0160. Superb 3-Bedroom, 2-Bathroom Ranch Home Showcases Gorgeous Water Views And Is Perfectly Located Near Goose Creek Beach And The Pulsating Heart Of Southold. 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

  Colin McCarthy Thomas J McCarthy Real Estate

  1100 Pine Ave, Southold, NY 11971
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  /13

  $7,000 Per Month

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • House for Rent

  Unlisted Address

  Experience the charm of this delightful rental cottage nestled in Southold, North Fork, just a stone’s throw from Founder's Landing Park and Wharf House, with one of the most amazing sugar sand beaches in our community. This unique, fully furnished one-bedroom retreat features flexible rental periods and competitive rates throughout the year.Imagine waking up to the serene views of a

  Nicholas Planamento William Raveis New York LLC

  Unlisted Address
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  /19

  $4,000 Per Month

  • 3 Beds
  • 2 Baths
  • House for Rent

  1975 Youngs Ave, Southold, NY 11971

  This beautifully furnished farmhouse offers you a warm welcome home on the North Fork. Amazing decor throughout every room for you to enjoy your stay. There are three bedrooms and two full bathrooms, hardwood floors, central air conditioning, and a back deck overlooking a fenced in yard. Great location just one block from the town restaurants, shops, and all transportation. Numerous beaches to

  Barbara Poliwoda Douglas Elliman Real Estate

  1975 Youngs Ave, Southold, NY 11971
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  /21

  $60,000 Per Month

  • 3 Beds
  • 2 Baths
  • House for Rent

  355 Windjammer Dr, Southold, NY 11971

  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!

  Sheri Winter Parker Corcoran

  355 Windjammer Dr, Southold, NY 11971
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  /27

  $19,500 Per Month

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • House for Rent

  1355 Watersedge Way, Southold, NY 11971

  Welcome to 1355 Watersedge Way, a delightful Bayfront home offering breathtaking water and sunset views in Southold. Nestled next to a nature preserve with 300 feet of private beach, this home provides both serenity and direct water access.Inside, the spacious living room features a a wall of sliding glass doors that open to a waterside deck, perfect for enjoying the bay breeze. The eat-in

  Jeanmarie Bay William Raveis New York LLC

  1355 Watersedge Way, Southold, NY 11971
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  /28

  $7,500 Per Month

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • House for Rent

  3400 Youngs Ave, Southold, NY 11971

  Nobody comes to the North Fork because they're looking for excitement, they come because they're looking for something they've been missing. Time slows here. Not dramatically, but quietly. You notice it on the first morning when you realize you've finished your coffee without checking your phone. The windows are open, the breeze carries the scent of nearby fields, and the only thing on the agenda

  Thomas McCarthy Thomas J McCarthy Real Estate

  3400 Youngs Ave, Southold, NY 11971
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  /29

  $12,000 Per Month

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • House for Rent

  250 Wesland Rd, Southold, NY 11971

  JUST A DREAM BOAT! NEWLY RENOVATED, LIGHT AND BRIGHT, BEAUTIFULLY APPOINTED, EVERY CONVENIENCE - 2 BEDROOMS, 2 BATHS. PLUS -SUPER COMFORTABLE CONVERTIBLE QUEEN SOFABED! BEAUTIFUL OUTDOOR DINING, FIRE PIT, PORCH, ENCLOSED SHOWER! PRICED RIGHT! STEPS TO POPULAR KENNEY'S BEACH - JUST BRING OUR LITTLE RED WAGON AND STROLL TO THE BEACH AND ENJOY! Additional information: Appearance excellent! Lease

  Marie Beninati Beninati Associates

  250 Wesland Rd, Southold, NY 11971
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  $30,000 Per Month

  • 8 Beds
  • 7 Baths
  • 5,400 Sq Ft
  • House for Rent

  650 Pine Ave, Southold, NY 11971

  Masterfully crafted resort style property, where coastal luxury meets effortless living. Tucked within a coveted private beach community with beach access, this resort-style property was designed for gathering, entertaining, and unwinding in total privacy. The home features a show-stopping 20’ x 40’ heated saltwater pool, framed by lush, manicured grounds that feel both serene and indulgent.

  Colin McCarthy Thomas J McCarthy Real Estate

  650 Pine Ave, Southold, NY 11971
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  /15

  $3,500 Per Month

  • 2 Beds
  • 1 Bath
  • House for Rent

  3825 S Harbor Rd, Southold, NY 11971

  Classic North Fork Beach home located just 10 homes away from South Harbor Beach and Park, Amazing comfort and privacy on this acre plus setting. Home is crisp, clean, and fully furnished ready for you to enjoy. South Harbors expansive beach offers an inlet to paddle board, kayak, fish, and relax on the water. Please call for availability; 2025 Rates: January- April $3500, May $5000, June $7000,

  Barbara Poliwoda Douglas Elliman Real Estate

  3825 S Harbor Rd, Southold, NY 11971
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  /24

  $8,000 Per Month

  • 3 Beds
  • 3 Baths
  • House for Rent

  355 Midway Rd, Southold, NY 11971

  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

  Marianne Collins Brown Harris Stevens N Fork

  355 Midway Rd, Southold, NY 11971
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  $20,000 Per Month

  • 4 Beds
  • 4 Baths
  • 3,200 Sq Ft
  • House for Rent

  950 Blue Marlin Dr, Southold, NY 11971

  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,

  Lori Feilen William Raveis New York LLC

  950 Blue Marlin Dr, Southold, NY 11971
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  /21

  $6,000 Per Month

  • 4 Beds
  • 3 Baths
  • House for Rent

  1155 Old Harbor Rd, Southold, NY 11971

  Quintessential North Fork sandy bay beachfront rental. Stunning views across Cutchogue Harbor and Peconic Bay will be yours at this spacious waterfront home, whether from the airy great room, the brick patio, or from the beachside deck. Tucked away down a quiet drive, this home offers peace and privacy in historic New Suffolk. There are 3 bedrooms and 2 baths upstairs, one bedroom and one bath

  Marianne Collins Brown Harris Stevens N Fork

  1155 Old Harbor Rd, Southold, NY 11971
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  $10,000 Per Month

  • 4 Beds
  • 2.5 Baths
  • House for Rent

  1275 the Esplanade, Southold, NY 11971

  July 2 Weeks $12,000!, Full Month $22,000! (details below)...Fabulous Lux Vacations on the coveted Esplanade in "Angel Shores". This Striking 4BR/2.5B Designer Style Home has just undergone an entire first floor renovation thru early 2025. Enjoy your private deeded sandy bay beach and heated freeform lagoon pool with a zen waterfall. Property is fully fenced and enclosed by lush mature specimen

  Kate Carpluk William Raveis New York LLC

  1275 the Esplanade, Southold, NY 11971
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  $30,000 Per Month

  • 6 Beds
  • 4 Baths
  • 3,000 Sq Ft
  • House for Rent

  1695 Old Woods Path, Southold, NY 11971

  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

  Nicholas Planamento William Raveis New York LLC

  1695 Old Woods Path, Southold, NY 11971

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