$50,000 per month
1000 Rambler Rd, Southold, NY 11971
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. Memorial Day-Labor Day $65,000, or July & August $50,000.
Pamela Hunt Colony Realty
$4,300 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
$3,200 per month
1855 Kenneys Rd, Southold, NY 11971
1855 Kenneys Rd, Southold, NY 11971
$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 $10,000.
Diane Mollica Compass Greater NY LLC
$3,200 per month
2555 Youngs Ave Unit 4D, Southold, NY 11971
Introducing this charming 2 bedroom, 2 bathroom condo nestled in the picturesque town of Southold. This turn-key condo offers an ideal combination of convenience and comfort. The spacious and bright living area, high ceilings and fireplace create a warm and inviting atmosphere. The kitchen has been recently updated, and the updated bathrooms feature glass enclosed showers. There are beautiful
Susan Orioli Engel & Volkers North Fork
$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
$5,000 per month
215 Leon Rd, Southold, NY 11971
Enjoy this spacious vacation rental located just a short distance from Southold Town Beach. With room for the whole family, this home features three en-suite bedrooms plus an additional bedroom and full bath. The well-equipped kitchen opens to the dining and living rooms, where a cozy fireplace adds charm and warmth. Sliding glass doors lead to a deck overlooking a large backyard, perfect for
Jeanmarie Bay William Raveis New York LLC
$26,000 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
$6,500 per month
400 Town Creek Ln, Southold, NY 11971
400 Town Creek Ln, Southold, NY 11971
$50,000 per month
1160 Goose Creek Ln, Southold, NY 11971
Available: July $50,000; Aug - LD: $50,000; 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
$3,500 per month
315 Lake Dr, Southold, NY 11971
Rental Permit # 0966 Fantastic home set directly on Great Pond and a block (975 feet) from Kenney's Beach with restaurant Little Fish just around the corner. This bright 3 bedroom and 2 full bathroom, with a 3 season room all window porch home has an expansive rear deck overlooking the fresh water pond. Watch osprey dive bomb for fresh water bass while geese, ducks and egrets meander across the
Alexander Aquino Douglas Elliman Real Estate
$3,250 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
$40,000 per month
57305 Route 48, Greenport, NY 11944
Spectacular, contemporary seasonal rental home with pool and Jacuzzi on the Long Island Sound front. 150 feet of direct waterfront and beach, with incredible view. Meticulously renovated and professionally designed. 6 bedrooms, 5.5 bathrooms. Hamptons luxury in North Fork. Home situated on 1 acre, 6,600 square feet. One master bedroom has jacuzzi and steam room and two extra bedrooms with full
Zepur Diktas Compass Greater NY 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
$18,000 per month
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
Kenneth Poliwoda Douglas Elliman Real Estate
$10,000 per month
780 Minnehaha Blvd, Southold, NY 11971
Welcome to this high-quality beach home to stay for a couple of weeks in the summer or for a few months in the offseason. This custom designed impeccable home contains four bedrooms and four full bathrooms. There is an open floor plan with vaulted ceilings, from the chef's kitchen to the dining and living room. Enjoy a barbecue in the enclosed porch. Beautiful tranquil setting with views of
Kenneth Poliwoda Douglas Elliman Real Estate
$8,000 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
$10,000 per month
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
William Walters Daniel Gale Sothebys Intl Rlty
$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
$35,000 per month
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.
Mackenzie Needham Daniel Gale Sothebys Intl Rlty
$26,900 per month
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 shape! You
Chrisand Castella Douglas Elliman Real Estate
$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
$10,000 per month
455 W Shore Dr, Southold, NY 11971
Welcome to 455 West Shore Road, Southold, NY. This charming 4-bedroom, 2. 5-bathroom rental property offers 1,600 square feet of comfortable living space. Nestled in a serene location, the home provides exclusive beach rights, perfect for summer enjoyment. The spacious layout includes a well-appointed kitchen, inviting living areas, and ample storage. The property is ideal for those seeking a
Eric Frend Corcoran
$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
$24,000 per month
6430 Hortons Ln, Southold, NY 11971
Lovely spacious newly built Colonial just down the lane from 4 gorgeous LI Sound Beaches. Main Floor Primary Bedroom En-suite with private side entrance and it's own deck. Second Primary Bedroom En-Suite on level 2 (has radiant heat floor and heat lamp). Two additional Bedrooms, a full Bath in the hall, and Laundry Room. Kitchen has huge island with seating, 6 burner or griddle dual fuel oven.
Kate Carpluk William Raveis New York LLC
$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
$28,000 per month
1100 Pine Ave, Southold, NY 11971
Permit #: 0160. This Superb 3-Bedroom, 2-Bathroom Ranch Home Showcases Gorgeous Water Views And Is Strategically Located Near Goose Creek Beach And The Pulsating Heart Of Southold, Allowing You To Enjoy The Best Of Both Worlds. 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
Colin McCarthy Thomas J McCarthy Real Estate
$7,000 per month
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
$17,000 per month
1175 Waterview Dr, Southold, NY 11971
Southold Goose Creek Waterfront Home. Immaculate sun-filled home with all you will need to relax and enjoy summer. Large living room, and dining room. Well equipped Kitchen with sliders to deck, Den with amazing water views. Ensuite bedroom with water views, 2 additional bedrooms and bathrooms. Furnished deck and large yard. There is a dock to fish, boat, paddle board or kayak (2 included) from
Amy Kirincic The Agency Northshore NY
$6,500 per month
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
Kenneth Poliwoda Douglas Elliman Real Estate
$24,000 per month
400 Diamond Ln, Peconic, NY 11958
Enjoy stunning water views and all-season access to the Sound from this charming 3-bedroom, 1-bathroom waterfront home. This cozy home channels happy, mid-century vibes. Large living room with fireplace, dining nook, and sunroom, all with breathtaking views of the water. The patio with BBQ is the perfect spot to relax and enjoy the outdoors, and the path to the Sound makes it easy to access the
Sheri Winter Parker Corcoran
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