$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 rental. 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
$12,000 per month
425 Old Shipyard Ln, Southold, NY 11971
Rent Includes Utilities
Amy Kirincic The Agency Northshore NY
$70,000 per month
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!
$25,500 per month
45 Budds Pond Rd, Southold, NY 11971
Escape to your dream Southold summer in this spacious 5-bedroom, 2-bathroom home boasting an in-ground heated pool and convenient dock space. Bathed in natural light and surrounded by lush gardens, this home offers ample space for entertaining and ensuring guests feel right at home. Spend sunny afternoons basking by the pool under the awning or take a leisurely stroll to the private beach access,
Mackenzie Needham Daniel Gale Sothebys Intl Rlty
$18,000 per month
455 W Shore Dr, Southold, NY 11971
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 tranquil retreat with convenient access to local
$25,000 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 Town And Country Real Estate
$20,000 per month
580 Gin Ln, Southold, NY 11971
Wonderful opportunity to spend all or part of the summer 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
Scott Bortzner Compass Greater NY LLC
$99,000 per month
56765 County Road 48, Greenport, NY 11944
Beautiful 3bd 2bath spacious home with pool on the Sound. Modern finishes and open floor plan help make this a special place to spend the summer months. Close proximity to local beaches, shops, and restaurants. Available Memorial Day- Labor Day.
Shannon Oshea East End Luxury Ltd
$16,000 per month
2160 N Bayview Road Extension, Southold, NY 11971
Are you ready for some peace and tranquility? Step back from the insanity and enjoy this serene, elegant property that offers the perfect combination of restful seclusion and easy accessibility to all the North Fork has to offer. On a quiet road, tucked away from town, you can enjoy the sounds of silence. Harvest veggies from your own garden, paddle (or do laps) in the 50' heated salt water pool,
Regan Battuello The Agency Northshore NY
$13,500 per month
295 Beckwith Ave, Southold, NY 11971
Experience the perfect North Fork summer in this stunning designer-curated home, where historic charm blends seamlessly with modern convenience. Thoughtfully restored with nods to its rich past, this home offers a stylish and comfortable retreat with every contemporary amenity you need.Ideally located near Southold’s charming Main Road, you’ll have effortless access to boutique shops,
Andrea Parks Douglas Elliman Real Estate
$22,500 per month
270 N Sea Dr, Southold, NY 11971
Indulge in a sun-drenched Southold summer at this immaculate 4-bedroom, 3-bath retreat, where Kenny's Beach views paint a picturesque backdrop from the primary suite's private porch. A bright, comfortable atmosphere permeates the home, featuring seamless indoor/outdoor dining, a sprawling porch/decking, and a luxurious saltwater pool. Enjoy the added perks of "toys" provided by the owner,
Mackenzie Needham Daniel Gale Sothebys Intl Rlty
$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
$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
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
$3,000 per month
2555 Youngs Ave Unit 2A, Southold, NY 11971
Welcome to Founders Village a 55 and over community complete with a clubhouse and pool. This fabulous end unit offers plenty of private space with a scenic view and sunshine is available for a one-year lease. Inside you will find a large and welcoming living room with cathedral ceilings, a wood burning fireplace, dining area, and sliding glass doors which lead out to a private patio. This year
Kenneth Poliwoda Douglas Elliman Real Estate
$4,200 per month
380 Eds Rd, Southold, NY 11971
Discover a wonderful opportunity for year-round rental in the heart of Southold. This beautifully renovated home exudes style and comfort, featuring exquisite hardwood floors and a seamless flow from the kitchen/dining room to an inviting deck—perfect for entertaining or relaxing. With two newly updated bathrooms, this home is fresh, clean, and ready for move-in.Enjoy the convenience of a
Diane Mollica Compass Greater NY LLC
$15,000 per month
54505 County Road 48 Aka Rd N, Southold, NY 11971
**Southold, North Fork:** Picture yourself enjoying the most enchanting summer in this exquisite beach house situated on the sparkling Long Island Sound. With 100 feet of private waterfront beach and stunning sunset views, this home promises an unforgettable summer or vacation escape. Experience affordable luxury and peace as you relax in this tranquil setting, conveniently located near the
Nicholas Planamento Town And Country Real Estate
$10,000 per month
485 Pine Rd, Southold, NY 11971
2025 Rates: MDW- End Of June $10,000; July $22,000; A1-LD $23,500;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
William Walters Daniel Gale Sothebys Intl Rlty
$28,000 per month
630 Wild Cherry Way, Southold, NY 11971
A North Fork Summertime Oasis! Newly Renovated 4 Bedroom, 3 Bath Home with Heated Pool (20' x 42') Located Near a Memorable Long Island Sound Beach. The Marble Pool Surround Never Gets Hot. An Additional Lower-Level Living Room adjacent to a Wet Bar and Fridge Provides Easy Access for Pool Side Dining. Ice Machine, Gas Grill, Large Outdoor Sofa and Dining Table as Well as Lounge Chairs and
Paul Loeb Douglas Elliman Real Estate
$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. Pricing is for August 2025
Mackenzie Needham Daniel Gale Sothebys Intl Rlty
$17,500 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
Chrisand Castella Douglas Elliman Real Estate
$6,250 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. March 2025 to End of April 2025 at $10,000 Per Month (Single or Multiple Months Rental Considered). Summer 2025 - June
Paul Loeb Douglas Elliman Real Estate
$3,100 per month
900 Cedar Dr, Southold, NY 11971
Looking for the perfect year-round rental on the North Fork? This charming 3-bedroom, 1-bathroom home offers the ideal retreat, whether you’re a local resident or seeking a year-round getaway. Nestled in the heart of the North Fork, this freshly painted home with new carpet, is just moments away from the area’s renowned beaches, picturesque wineries, charming hamlet shopping, and so much more.
Diane Arpaia Signature Premier Properties
$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
$3,000 per month
53395 New York State Route 25 Unit 1, Southold, NY 11971
Brand New Tastefully Renovated Furnished Apartment conveniently located in the heart of Southold. The apartment is Available to rent for Year Round or flexible time-frame(s). Public transportation is in near proximity, along with everything else the North Fork has to offer.
Joseph Divello Century 21 Albertson Realty
$4,200 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
$98,000 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
$7,000 per month
475 Youngs Ave Unit B, Southold, NY 11971
Southold, North Fork - centrally located (no car needed) 1 bedroom apartment in legal 3-family building. Unit is completely separate and independent of other units. Fully furnished. Tenant responsible for utilities, security, etc and is to carry insurance. Pets on individual basis. A perfect pied-a-terre in wine country whether short stay, vacation, or possibly year-round...comfortably furnished
Nicholas Planamento Town And Country Real Estate
$30,000 per month
150 Hobart Rd, Southold, NY 11971
Southold, North Fork: Delightful cottage just up from Founder's Landing Park, the beach, and the Wharf House. A super convenient 'in town' location allows instant access to an easy lifestyle. Charming, well-cared-for home features an open floor plan with a large, comfortable living room/dining room, eat-in kitchen with gas range, laundry room, and full bath on primary, plus an additional bath
Nicholas Planamento Town And Country Real Estate
$9,000 per month
13595 Soundview Ave, Southold, NY 11971
Located on a private and serene 1.09 acre parcel of land and only 1/3 of a mile from McCabes Beach, with miles of Long Island Sound beach to traverse to the east and west, this charming and newly built two story home offers an open concept living space with plentiful natural light on the first floor with a half bathroom between the living and dining room, with a half bathroom off of the hallway
Alexander Aquino Douglas Elliman Real Estate
$4,800 per month
13595 Soundview Ave, Southold, NY 11971
Located on a private and serene 1.09 acre parcel of land and only 1/3 of a mile from McCabes Beach, with miles of Long Island Sound beach to traverse to the east and west, this charming and newly built two story home offers an open concept living space with plentiful natural light on the first floor with a half bathroom between the living and dining room, with a half bathroom off of the hallway
Alexander Aquino Douglas Elliman Real Estate
$32,500 per month
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
$3,500 per month
45 Baywater Ave, Southold, NY 11971
**off-season rental only. Charming home, originally built in approximately 1905. Main Rd, South onto South Harbor Road, Left on to Baywater Ave. Close proximity all the North Fork has to offer. Down the road to Croteaux Vinyards and South Harbor Park for swimming, kayaking and boating. Close to the best North Fork restaurants, marinas and farm stands.
Mackenzie Needham Daniel Gale Sothebys Intl Rlty
$37,000 per month
935 Corey Creek Ln, Southold, NY 11971
Southold Luxe New Construction Home with Dreamy Backyard, In Ground Pool and Pool House! Make memories and enjoy entertaining this summer in this professionally decorated three bedroom, four bathroom home. Bonus space includes finished basement, huge pool house, outdoor kitchen, in-ground pool. Launch kayaks just a few steps away in the private creek access or bring your beach chair to nearby
Melissa Principi Douglas Elliman Real Estate
$15,000 per month
425 Cedar Point Dr E, Southold, NY 11971
Now Available for Off Season Rental Until March 31, 2025 and Post Labor Day 2025. Rented June 1 - September 30th. Set Creekfront with Private Dock and Associated Bay Beach Access in 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
Rene Giacobbe Douglas Elliman Real Estate
$3,900 per month
5650 N Bayview Rd, Southold, NY 11971
Historic Main Bayview schoolhouse converted to country residence located at 5650 N Bayview Road, Southold. Available for winter rental, September 3, 2024 - May 31, 2025 $3,900 per mo plus utilities, etc Country residence features 5 bedrooms in historic Main Bayview Schoolhouse converted to residence - sleeps max 10 people. Pet friendly. Equidistant to Cedar Beach and Goose Creek Beach. Moments to
Nicholas Planamento Town And Country Real Estate
$40,000 per month
16125 Soundview Ave, Southold, NY 11971
Sublime Sound front home overlooking miles of beachfront with stairs to private beach. Stunning views through floor to ceiling windows and spacious sound front backyard. Newly added in-ground pool with retractable cover. Fully furnished 4 bedrooms, 3.5 baths, both formal living room and family room have wood burning fireplaces. Fully finished basement. Tesla hook up in the garage. The best that
Jessica Koenig Brown Harris Stevens N Fork
$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
$10,000 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 Town And Country Real Estate
$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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