$3,200 per month
- 2 Beds
- 2 Baths
- 1,000 Sq Ft
- House for Rent
1855 Kenneys Rd, Southold, NY 11971
1855 Kenneys Rd, Southold, NY 11971$3,200 per month
1855 Kenneys Rd, Southold, NY 11971
1855 Kenneys Rd, Southold, NY 11971$8,438 per month
810 Waterview Dr Unit ID1261529P, Southold, NY 11971
Feel at home in Steve’s Place, a charming Southold retreat. This 3-bedroom, 1.5-bath home sleeps 6 comfortably.The remodeled kitchen is fully equipped and opens to a cozy living area with ample seating. The living room is ideal for movie nights, reading, or quiet evenings. Outdoors, the fenced yard is a private retreat featuring a heated pool, poolside loungers, a gas grill, and covered deck
$15,000 per month
935 Corey Creek Ln, Southold, NY 11971
Experience the ultimate North Fork summer in this stunning new construction home, designed for effortless entertaining and elevated coastal living. Professionally decorated and impeccably finished, this residence offers three bedrooms, four full bathrooms, a bonus room, and a beautifully finished lower level with an additional private half bath. Step outside to your own private retreat featuring
Melissa Principi Douglas Elliman Real Estate
$6,500 per month
845 Budds Pond Rd, Southold, NY 11971
845 Budds Pond Road offers a rare bayfront year-round rental with exceptional access to both Greenport and Southold, placing the best of the North Fork just minutes away while maintaining the privacy of a quiet cul-de-sac setting. This turn-key waterfront residence is modern, thoughtfully updated, and designed for effortless year-round living. The home features a spacious primary suite, two
Kieran Collings Douglas Elliman Real Estate
$30,000 per month
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
$4,000 per month
825 Oak Dr, Southold, NY 11971
Year round rental available in the private beach community of Reydon Shores. This comfortable home features a spacious kitchen which leads out into a grand deck for outdoor dining. There are 4 bedrooms and 3 bathrooms. On the first floor of this home there is a first-floor master en suite, an additional bedroom, a living room/dining room, a large family room and a laundry room. On the second
Barbara Poliwoda Douglas Elliman Real Estate
$14,000 per month
60 Water Terrace, Southold, NY 11971
Settle into summer on the North Fork in this beautifully maintained and updated 4 bedroom, 3 full bath home located in the Angel Shores community of Southold. The layout is ideal for entertaining or just enjoying the lazy days of summer. This special home offers a 1st floor bedroom and full bath, along with a 2nd story spacious primary en-suite and 2 additional bedrooms to comfortably accommodate
Natalie Hough Daniel Gale Sothebys Intl Rlty
$100,000 per month
450 Sterling Woods Ln, Southold, NY 11971
Spacious Open Plan Home with So Much to Offer near Several Great Beaches. Open Livingroom, Dining Room, Kitchen, a Separate Den and a Separate Office as well as a Good Size Bedroom and Bath on First Floor. The Spacious Kitchen Offers Sub Zero Refrigerator, a Wine Fridge and a Separate Fridge Dedicated to Drinks You Grab on Way to Pool. Primary Ensuite and Two Bedrooms and Hall Bath on Second
Paul Loeb Douglas Elliman Real Estate
$20,000 per month
580 Gin Ln, Southold, NY 11971
Wonderful opportunity to spend time in the wonderful Southold community of Bay Haven. Choose to spend the sunny days by your own pool, or head down the block to the community's private bay beach. There is more than ample space to host in this brightly renovated cape with room for everyone. The main level is comprised of a lounge area with fireplace and dry bar, an open kitchen and a large great
Scott Bortzner Compass Greater NY LLC
$13,000 per month
215 Northfield Ln, Southold, NY 11971
Permit 0681- Enjoy This Beautifully Renovated 4 Bedroom, 3 Bath Ranch Style Home With Heated Pool. Open Floor Plan Includes LR With Cathedral Ceilings, High End EIK, Dining Area & Outdoor Shower. Plenty of Room For The Whole Family & Guests. Beautiful Goose Creek Beach Just 0.2 Miles Down The Road. Minutes To Local Wineries, Shopping & Dining. BOOK NOW FOR SUMMER 2025. Terms: May $13,000, June
Mitch Pickman Thomas J McCarthy Real Estate
$22,500 per month
270 N Sea Dr, Southold, NY 11971
Southold, North Fork: Endless sunsets await at this exceptional vacation rental, available year-round with flexible terms and rates. Ideally located in the sought-after Kenny’s Beach community, this sun-drenched home is surrounded by wide sandy dunes perfect for walking, birdwatching, swimming, and relaxing days by the shore.Immaculately maintained, the residence offers 4 bedrooms and 3 full
Nicholas Planamento William Raveis New York LLC
$35,000 per month
Unlisted Address
This beautiful home with in-ground pool and ample private open space exudes beach resort ease and is rarely available for rent. Located in a quiet enclave off the vineyards mile of Southold on the north fork, it is within proximity to farms, town, beaches and restaurants. The home which entered via a tree lined drive, is comprised of two stories, plus a lower level. The first floor features a
Scott Bortzner Compass Greater NY LLC
$4,000 per month
310 Old Shipyard Ln, Southold, NY 11971
Southold Village Rental Charming and well-located, this 3-bedroom, 1-bath residence offers easy North Fork living just moments from the heart of Southold. A short distance to Southold Town, local shops, dining, and the waterfront, as well as close proximity to Founders Beach for swimming, sunsets, and seaside relaxation. The home features a comfortable layout with light-filled living spaces,
Eric Frend Corcoran
$3,800 per month
5125 Main Bayview Rd, Southold, NY 11971
Experience easy one-level living in this immaculate home in Southold! Clean and airy throughout along with a lovely yard with plenty of privacy. Set in the sought after Goose Creek Estates with its own sandy beach down the road. The welcoming front porch opens to an inviting and comfortable living room and spacious den with hardwood floors and a wood burning fireplace. The dining area leads to
Suzette Reiss Douglas Elliman Real Estate
$35,000 per month
610 Wildberry Ln, Southold, NY 11971
Start your summer in pure luxury by securing this brand-new multi-level, beautifully decorated, modern farmhouse rental in Southold for the month of June, perfectly situated on the desirable North Fork of Long Island. This pristine property offers an exceptional outdoor oasis featuring an in-ground pool surrounded by a spacious patio for relaxation and entertaining; inside, the light-filled main
Mackenzie Needham Daniel Gale Sothebys Intl Rlty
$3,200 per month
49925 Main Rd, Southold, NY 11971
Southold Town Rental Permit #0787. NEWLY RENOVATED Light, Bright And Airy 2nd Floor YEAR ROUND Apartment With 2 Bedrooms And A Full Bath In Southold's Historic Corridor, Gorgeous Grounds And Landscaping, Close To All!, Additional information: Appearance:Excellent
Thomas McCarthy Thomas J McCarthy Real Estate
$30,000 per month
11925 Soundview Ave, Southold, NY 11971
.Enjoy water views and Long Island Sound sunsets from this magnificent new construction home for rent! Perfectly situated on 1.5 scenic acres, this home offers exclusivity and privacy. The beautiful eat-in-kitchen features high-end amenities including a Viking refrigerator and 8 burner range, double ovens, dual Bosch dishwashers plus two wine coolers. The airy and spacious living room is accented
Nicholas Liappas Compass Greater NY LLC
$30,000 per month
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
$5,000 per month
1000 Rambler Rd, Southold, NY 11971
Available Year-Round or Seasonal: Beautiful like new colonial just 500 feet from sandy bay beach. Four bedrooms plus a lovely sunroom. Enjoy your morning coffee on the bedroom balcony. Outside shower and gas grill off backyard deck. Bicycles and a kayak with trailer included. A perfect beach house. Year-Round $5000/month plus utilities. Memorial Day-Labor Day $65,000, or July & August $50,000
Pamela Hunt Colony Realty
$25,000 per month
425 Cedar Point Dr E, Southold, NY 11971
Now Available for June 2026. This Impressive Home is Set Creekfront with Private Dock with Peconic Bay Access and Associated Bay Beach within the Community. The Extensive Rear Patio Area is Impressive with an Inground Pool and Jacuzzi. All Creekfront with a Beautiful View. The Home is Grand and Designed to Entertain. Boasting 5 Bedrooms and 4 Baths. 2 Large Living Rooms, Well Appointed Kitchen
Rene Giacobbe Douglas Elliman Real Estate
$3,800 per month
775 Hummel Ave Unit A, Southold, NY 11971
This Freshly Renovated Apartment is centrally located in Southold Village. The Two Family Home is in proximity to everything the North Fork has to offer. Three upstairs Bedrooms are comfortably separated from a large kitchen and entertainment area. The move-in ready apartment is located within Southold School District, and provides for the perfect year round home or North Fork Retreat. Additional
Joseph Divello Century 21 Albertson Realty
$55,000 per month
7635 Main Bayview Rd, Southold, NY 11971
Elegant Historic Home in Southold – Coastal Charm Meets Modern Luxury Escape to the North Fork and enjoy this beautifully restored historic Southold home, perfectly blending timeless elegance with every modern comfort. This spacious retreat features 5 bedrooms and 3.5 baths, ideal for families or groups seeking a serene getaway. Enjoy central air conditioning, high-speed internet, and five smart
Mary Terry MCKENNASHEA LLC
$25,000 per month
345 Colonial Rd, Southold, NY 11971
Tucked away on a private setting in a peaceful North Fork neighborhood just minutes from Corey Creek, Croteaux Vineyards and Greenport Brewery, this exceptional colonial offers the perfect backdrop for an unforgettable summer. With approximately 2,700 sq. ft. of bright, inviting living space across two levels, there is ample room for family and friends to gather and create lasting memories. Step
Gloria Scrocco STOEBE & CO
$25,000 per month
525 S Harbor Rd, Southold, NY 11971
The Ultimate North Fork Retreat! This recently renovated home offers 4 ensuite bedrooms including a ground floor primary suite, with a total of 5.5 baths. The sprawling and very private 2.4 acre property features resort-like amenities including a 20 x 50 heated pool, fully equipped outdoor kitchen, multiple seating areas and more. Inside, the open floor plan flows from the living room with a gas
Thomas Perry Brown Harris Stevens W Hampton
$35,000 per month
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
$10,000 per month
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
$5,000 per month
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
$15,000 per month
1854 N Bayview Rd, Southold, NY 11971
Last Minute deal on Summer rental. 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
$30,000 per month
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
$50,000 per month
1160 Goose Creek Ln, Southold, NY 11971
Available: July $50,000; Aug - LD: $55,000; July/Aug-LD $85,000Step 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
Sheri Winter Parker Corcoran
$3,000 per month
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
$3,500 per month
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
$10,000 per month
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
$10,000 per month
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
$10,000 per month
485 Pine Rd, Southold, NY 11971
2026 Rates: MDW- June $12,000; July 23,500 A1-LD $25,000; September $12,000; 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
William Walters Daniel Gale Sothebys Intl Rlty
$38,000 per month
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. Winter Rental (November 2025 to April 2026) $9,000 Per Month for Single or Multiple Months; Summer 2026 - Memorial Day to Labor
Paul Loeb Douglas Elliman Real Estate
$9,000 per month
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
$34,500 per month
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
William Walters Daniel Gale Sothebys Intl Rlty
$8,000 per month
400 Hill Rd, Southold, NY 11971
Welcome to your perfect summer getaway located in the desirable Claves Neck neighborhood of Southold. This comfortable Ranch has ample space for the whole family to unwind and recharge after a day of exploring the North Fork. The home offers a fully equipped kitchen, spacious living, and dining rooms, three pleasant bedrooms, two pristine bathrooms. Outside, a savor al fresco dining amid the lush
Jeanmarie Bay William Raveis New York LLC
$25,000 per month
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
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