North Fork Houses for Rent with Pool

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  $6,000 per month

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • House for Rent

  285 Oyster Ponds Ln, Orient, NY 11957

  Orient village mid century gem with pool. This newly renovated, well appointed residence is perfectly located and offers 3 bright and spacious bedrooms and 2 full baths, chefs kitchen, dining room, living room and screened in porch. The yard and pool area are fenced. The garden features a pool house and stone patio perfect for alfresco dining, overlooking the beautiful pool, specimen trees and

  Lori Feilen William Raveis New York LLC

  285 Oyster Ponds Ln, Orient, NY 11957
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  $32,500 per month

  • 4 Beds
  • 3.5 Baths
  • House for Rent

  75 Clearview Ave, Southold, NY 11971

  2026 Rates To Come: Brand 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 dining

  William Walters Daniel Gale Sothebys Intl Rlty

  75 Clearview Ave, Southold, NY 11971
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  /25

  $38,500 per month

  • 3 Beds
  • 2.5 Baths
  • 2,110 Sq Ft
  • House for Rent

  27840 Main Rd, Orient, NY 11957

  CHIC RETREAT! A glamorous getaway! You won't know if you are tucked away in Tuscany or the South of France! This recently renovated modernist home is nestled amongst your own private vineyard with incredible farm vistas, imparting a spa retreat vibe. A large pool reaching out towards the horizon. Cozy up by the firepit or have lunch alfresco under the vineyard pergola and enjoy incredible

  Sheri Winter Parker Corcoran

  27840 Main Rd, Orient, NY 11957
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  $32,000 per month

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

  1080 Lands End Rd, Orient, NY 11957

  Very spacious, natural light filled custom designed beauty just 3 minutes to gorgeous, private community LI Sound beach. 44' x 24' heated, saltwater pool. Bright & airy open concept design LR/DR/KI with sliders to expansive deck overlooking private, fully fenced, park-like grounds. Upstairs has a large, 2nd living room with billiards, foosball, large tv plus sliders to private deck. 2 primary

  Kathleen Travers Douglas Elliman Real Estate

  1080 Lands End Rd, Orient, NY 11957
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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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  $14,000 per month

  • 4 Beds
  • 3 Baths
  • 2,700 Sq Ft
  • House for Rent

  560 Grandview Dr, Orient, NY 11957

  Come to the beautiful North Fork and spend your summer in this outstanding, stylish home in private sound front community at 560 Grandview Drive, Orient. Large bright home with 4 bedrooms and 3 baths, great room with fireplace, primary bedroom en-suite with fireplace, 2, additional bedrooms with en-suite Bathroom, super spacious light filled floor plan and chic furnishings, set on 1 acre, heated

  Lori Feilen William Raveis New York LLC

  560 Grandview Dr, Orient, NY 11957
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  $19,000 per month

  • 3 Beds
  • 2 Baths
  • House for Rent

  300 Marion Place, East Marion, NY 11939

  Private, peaceful home on a serene acre of property. Just renovated, featuring open modern Kitchen/Dining combo for casual entertaining. Separate family room across open foyer with fireplace and loads of puzzles & games. Charming covered front porch looks out onto front yard. Back deck with grill overlooks pool and backyard. Three bedrooms: 1 Queen, 2 full beds and primary with king bed and

  Laura Wanamaker Prime Properties Long Island

  300 Marion Place, East Marion, NY 11939
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  $9,000 per month

  • 4 Beds
  • 3.5 Baths
  • 3,500 Sq Ft
  • House for Rent

  950 Tasker Ln, Greenport West, NY 11944

  2025 Rates: September $25,000; October $23,000/ 2026 Rates: May $26,000; June $29,000; July $36,000; September $27,000; October $24,000. Experience North Fork summer living in this newly constructed gem! Nestled in the sought-after Stirling Eastern Shores community, this impeccably designed modern farmhouse offers exclusive access to a private Long Island Sound beach, just a five minute walk from

  William Walters Daniel Gale Sothebys Intl Rlty

  950 Tasker Ln, Greenport West, NY 11944
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  $20,000 per month

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

  1460 Hillcrest Dr, Orient, NY 11957

  This home has it all! Experience luxurious North Fork living with this incredible one-of-a-kind resort-style property. Gorgeous professionally designed 1-acre fully enclosed rear yard. Multiple tiers, huge 20x40 heated pool, outdoor shower, expansive rear patios with tons of seating and space to lounge, relax and have fun including a sports court - basketball and badminton, tree swing, fire pit,

  Nicole Pappas Compass Greater NY LLC

  1460 Hillcrest Dr, Orient, NY 11957
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  $13,500 per month

  • 5 Beds
  • 3.5 Baths
  • 2,400 Sq Ft
  • House for Rent

  155 Bridge St, Greenport, NY 11944

  2025 Rates are as follows: May 1 - 22: $10,000 or $3,500 per week; May 23 - June 27: $20,000 or $5,000 per week; July 13-31 $20K; Sept 4 - 30: $20,000 or $5,000 per week: Rare new construction on a quiet side street in Greenport Village, this modern luxury home is the perfect base to explore the beaches, wineries, and farm-to-table dining of the North Fork. Walking distance to downtown Greenport

  William Walters Daniel Gale Sothebys Intl Rlty

  155 Bridge St, Greenport, NY 11944
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  $70,000 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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  $7,500 per month

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

  3400 Youngs Ave, Southold, NY 11971

  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

  Thomas McCarthy Thomas J McCarthy Real Estate

  3400 Youngs Ave, 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

  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

  Colin McCarthy Thomas J McCarthy Real Estate

  650 Pine Ave, Southold, NY 11971
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  /11

  $4,000 per month

  • 3 Beds
  • 1.5 Baths
  • 1,600 Sq Ft
  • House for Rent

  2420 Plum Island Ln, Orient, NY 11957

  Year Round ONLY $4000 Per Month!! Welcome To Plum Island Lane In The Much Sought After Community Of 'Orient By The Sea' - Which Is A Stones Throw From The Private Beach! This Perfect Get Away Home Consists Of 3 Large Bedrooms, 1.5 Bathrooms, A Spacious EIK, Bright Open-Plan Living Room, Laundry And Recently Installed In-Ground 20 x 40 Saltwater Swimming Pool! This Gem Of A Home Was Completely

  Pete Halpin Douglas Elliman Real Estate

  2420 Plum Island Ln, Orient, NY 11957
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  $25,000 per month

  • 4 Beds
  • 5 Baths
  • 5,000 Sq Ft
  • House for Rent

  2055 Grandview Dr, Orient, NY 11957

  Available for Sept. 3-30. $25,000. Amazing North Fork home with heated salt water gunite pool located in Grandview Estates featuring 4 bedrooms (1st floor bedroom with ensuite, 2 en suite guest bedroom on the second floor with 1 additional guest bedroom and guest bathroom) office/den also located on the second floor with a large sitting area and balcony at the landing of the second floor, large,

  JoAnn Wind Daniel Gale Sothebys Intl Rlty

  2055 Grandview Dr, Orient, NY 11957
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  $10,000 per month

  • 4 Beds
  • 2.5 Baths
  • House for Rent

  1275 the Esplanade, Southold, NY 11971

  STUNNER 4BR DESIGNER HOME ~ PET FRIENDLY, HEATED POOL & BEACH!August 2 Weeks Only $15,000 and $18,000! First Time Offered! (see below) Fabulous vacations on the coveted Esplanade in "Angel Shores", with a deeded sandy bay beach and heated freeform lagoon pool with a waterfall. Property is fully fenced and private, with many lounge areas for sunning, a shady pergola when needed, and a great

  Kate Carpluk William Raveis New York LLC

  1275 the Esplanade, Southold, NY 11971
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  $7,000 per month

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

  470 Goose Creek Ln, Southold, NY 11971

  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 Spectacular Waterviews, Enclosed Outdoor Shower, Hi End Newly Built Kitchen. Enjoy Kayaking, Paddle Boarding and Fishing From Your Own Dock. Easy

  Thomas McCarthy Thomas J McCarthy Real Estate

  470 Goose Creek Ln, Southold, NY 11971

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