Pet-Friendly Homes for Rent in Southold, NY

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  $14,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,693 Sq Ft
  • House for Rent

  4525 S Harbor Rd, Southold, NY 11971

  2026 Availability: July $12,000; August $14,000. Newly renovated Southold home offering 3 bedrooms and 2 full baths, ideally located just 0.2 miles from South Harbor beach. An open concept kitchen and living room, anchored by a fireplace and filled with natural light offers the perfect place to unwind after a day of exploring the North Fork. Outdoors, a patio with dining area, built in barbecue,

  Bridget Elkin Compass Greater NY LLC

  4525 S Harbor Rd, Southold, NY 11971
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  $12,000 Per Month

  • 4 Beds
  • 3 Baths
  • 2,900 Sq Ft
  • House for Rent

  110 Sleepy Hollow Ln, Southold, NY 11971

  Discover this stunningly renovated 4-bedroom, 3-bath home, offering an expansive open floor plan, a cozy den, and a versatile bonus room. Designed for both comfort and style, the chef’s kitchen includes a massive eat-in-quartz island and boasts top-of-the-line Fisher & Paykel appliances, including a double-drawer dishwasher, induction cooktop, and convection oven. Perfect for entertaining and

  Paul Loeb Douglas Elliman Real Estate

  110 Sleepy Hollow Ln, Southold, NY 11971
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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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  /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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  $30,000 Per Month

  • 4 Beds
  • 3 Baths
  • 2,350 Sq Ft
  • House for Rent

  485 Hickory Ave, Southold, NY 11971

  Impressive Goose Creek home with water views and large heated in-ground pool! This four bedroom, three bath house features a first floor primary bedroom with en-suite, a gourmet kitchen and open living space. The newly designed landscape with outdoor kitchen (not pictured) is ideal for entertaining or relaxing. Enjoy its large fire pit and BBQ grill after an afternoon of Kayaking. Close to

  Mackenzie Needham Daniel Gale Sothebys Intl Rlty

  485 Hickory Ave, Southold, NY 11971
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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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  /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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