19

Southold, NY Houses for Rent with Private Pool

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  • /16

    $35,000 per month

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

    3693 Pine Neck Rd, Southold, NY 11971

    Elegant Waterfront Retreat on the North Fork - Welcome guests in style at this exquisite waterfront residence, where timeless design meets relaxed coastal living. Overlooking serene, protected waters, this expansive home features a sparkling waterside pool, private dock, and inviting fire pit—creating an idyllic setting for summer entertaining.Thoughtfully designed living and gathering spaces

    Eric Frend Corcoran

    3693 Pine Neck Rd, Southold, NY 11971
  • /30

    $26,000 per month

    • 4 Beds
    • 3.5 Baths
    • 3,800 Sq Ft
    • House for Rent

    365 Chablis Path, Southold, NY 11971

    Space, Luxury, and Privacy Await in This Stunning Contemporary Home! Experience the perfect blend of elegance and comfort in this beautiful home, offering an expansive backyard ideal for dining, lounging, and entertaining. Enjoy endless hours of relaxation in the inground pool, or gather with loved ones in the spacious yard. A charming gazebo provides a welcome retreat from the sun, weather, or

    Diane Arpaia Signature Premier Properties

    365 Chablis Path, Southold, NY 11971
  • /17

    $9,000 per month

    • 4 Beds
    • 5.5 Baths
    • 102,802 Sq Ft
    • House for Rent

    525 S Harbor Rd, Southold, NY 11971

    NORTH FORK FALL RENTAL! Enjoy this Privately Situated Home in the Heart of Southold Yet Close to All that the North Fork Has to Offer- Visit the Farms, Vineyards and Shopping. Open Concept Liv Rm, Din Rm, Updated Kit, Renovated 4 Bed/5.5 Bath Home With Family and Guests in Mind. Windowed Doors Lead Out to a Fabulous Resort Style Yard. Enjoy The North Fork At This Unforgettable Poolside Paradise.

    Teresa Rogers Douglas Elliman Real Estate

    525 S Harbor Rd, Southold, NY 11971
  • /25

    $40,000 per month

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

    1160 Goose Creek Ln, Southold, NY 11971

    Step back in time-without sacrificing comfort-in this beautifully preserved 5-bedroom, 3-bath home brimming with charm and nestled along the tranquil banks of Goose Creek. Surrounded by water on two sides and set on a private road, this unique property offers a rare blend of historic character and modern amenities. From the moment you arrive, you'll be captivated by the timeless architecture,

    Sheri Winter Parker Corcoran

    1160 Goose Creek Ln, Southold, NY 11971
  • /42

    $3,500 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
  • /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
  • /46

    $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

    Paul Loeb Douglas Elliman Real Estate

    110 Sleepy Hollow Ln, Southold, NY 11971
  • /28

    $10,000 per month

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

    9325 Main Bayview Rd, Southold, NY 11971

    2025 Rates: Last two weeks of June: $10,000.00, September 2-30 $15,000.00, October $12,500.00, Off season $6,000.00/month: Stunning New Construction in Southold's Hog Neck community. Enjoy open living w/ high vaulted ceilings in this sprawling modern farm house. Grand room features a combination of living room w/ gas fireplace, dining room, sun-soaked eat-in-kitchen w/ center island and shaker

    Bill Walters Daniel Gale Sothebys Intl Rlty

    9325 Main Bayview Rd, Southold, NY 11971
  • /39

    $10,000 per month

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

    485 Pine Rd, Southold, NY 11971

    2025 Rates: MDW- End Of June $10,000; July $22,000;September $10,000; October $7,500: 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

    Bill Walters Daniel Gale Sothebys Intl Rlty

    485 Pine Rd, Southold, NY 11971
  • /27

    $35,000 per month

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

    485 Hickory Ave, Southold, NY 11971

    Beautiful Goose Creek view home with large heated in-ground pool! This 4 bedroom, 3 bath house features a 1st floor primary with en-suite, a gourmet kitchen and open living space. The outdoor living space has newly designed landscape and is ideal for entertaining or relaxing. Fire pit and grill. Lawn is sprayed for ticks. Close to Southold town and Corey Creek Beach. Pricing is for August 2025

    Mackenzie Needham Daniel Gale Sothebys Intl Rlty

    485 Hickory Ave, Southold, NY 11971
  • /36

    $15,000 per month

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

    1205 Lake Dr, Southold, NY 11971

    Looking to create a beautiful memory of true summer experience on the beautiful North Fork of Long Island? look no further. This Spacious home has the full spectrum of mother nature right on your own huge back yard on the great lake with 2 fire pits. Featuring 4 Bedrooms, 4 Bath, An Oversize Patio, Large Heated In ground pool. Your own fully equipped gym to help keep you in the best of

    Chrisand Castella Douglas Elliman Real Estate

    1205 Lake Dr, Southold, NY 11971
  • /29

    $9,000 per month

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

    590 Soundview Ave, Southold, NY 11971

    Spacious Open Floor Plan Newer Home. Inground Pool with Built in Hot Tub and Blue Stone Pool Surround. Screened Porch Overlooking Pool Area. Nice Yard. Wood Burning Fireplace. Good Wifi. Long Island Sound Beach and Historic Lighthouse Museum and Park Several Doors Away. October $20,000, Winter Rental (November 2025 to April 2026) $9,000 Per Month for Single or Multiple Months; Summer 2026 -

    Paul Loeb Douglas Elliman Real Estate

    590 Soundview Ave, Southold, NY 11971
  • /31

    $34,500 per month

    • 4 Beds
    • 3.5 Baths
    • House for Rent

    75 Clearview Ave, Southold, NY 11971

    2026 Rates: July $34,500; August 1-LD $44,500: 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

    Bill Walters Daniel Gale Sothebys Intl Rlty

    75 Clearview Ave, Southold, NY 11971
  • /33

    $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
  • /21

    $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 Farm Field. 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

    Thomas McCarthy Thomas J McCarthy Real Estate

    3400 Youngs Ave, Southold, NY 11971
  • /34

    $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
  • /40

    $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
  • /11

    $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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