$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
Charming 2-Bedroom, 1-Bath Cottage in Southold – Perfect for Seasonal or Annual RentalsExperience the idyllic escape of this enchanting cottage, offering endless charm and privacy on a beautiful 1.5-acre property in sought-after Southold. This cozy residence features two inviting bedrooms and a well-appointed bathroom, making it ideal for relaxing getaways or year-round living.Private and
Nicholas Accardi Hartford Homes & Estates of LI
$14,000 per month
525 S Harbor Rd, Southold, NY 11971
Serenity Now! Enjoy this Privately Situated Home in the Heart of Southold Yet Close to All that the North Fork Has to Offer. Open Concept Liv Rm, Din Rm, Updated Kit, Renovated 4 Bd/5.5 Bth Home With Family and Guests in Mind. Windowed Doors Lead Out to a Fabulous Resort Style Yard. Enjoy Your Summer At This Unforgettable Poolside Paradise. Available: 14,000/2 wk minimum; Aug-LD 24,000.
Teresa Rogers Douglas Elliman Real Estate
$5,600 per month
3175 Kenneys Rd, Southold, NY 11971
Lakefront vacation property with a fantastic view, central air and hot tub. This space is open and updated with 3 bedrooms, and bonus room. Walk to Kenney's Beach with all beach gear included. This Neighborhood is close to restaurants, wineries, farm stands and music.
Jason Romaniello Blue Shark Realty Group Inc
$50,000 per month
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
$3,800 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
$4,500 per month
8340 Main Bayview Rd, Southold, NY 11971
Year round, creekfront rental in Southold. This spacious four bedroom, 2.5 Bathroom home was designed by well-known East Hampton architect and custom built with a layout that flows from room to room. Large first floor primary with huge walk-in closet with built ins. Second floor has three bedrooms and one large hall bathroom. State of the art mechanicals and extremely well maintained. Spacious
Melissa Principi Douglas Elliman Real Estate
$4,850 per month
775 Hickory Rd, Southold, NY 11971
Delightful North Fork Year-Round Rental located at 775 Hickory Road, Southold. Completely furnished, high end appliances, radiant heat, updated electric, and more. The large eat in kitchen is open to the dining & living area with a fireplace and sliding doors that lead you out to the expansive patios, where you will relax and enjoy the sea breeze. There is a master suite with full bath, guest
Jeanmarie Bay William Raveis New York LLC
$12,000 per month
425 Lake Dr, Southold, NY 11971
Welcome to Paradise!! 425 Lake Drive is a magical lake-front beach home located in Southold on the North Fork. Adventure abounds on beautiful fresh-water Great Pond. Explore the lake on two kayaks, two canoes, take a swim, or just relax in the hammock and then enjoy the refreshing outdoor shower. This 3-bedroom, 1-bathroom home comes fully equipped and comfortably furnished. Dine al fresco on the
Robert Wilner Douglas Elliman Real Estate
$4,000 per month
8515 Soundview Ave, Southold, NY 11971
Tucked away on the peaceful edge of freshwater Great Pond in Southold, this delightful 2-bedroom, 1-bath cottage offers the perfect blend of comfort and charm. Enjoy quiet mornings with water views and spend your days kayaking, paddle boarding, or fishing right from your backyard. Barbecue and dine on the spacious deck with a sunset view of the lake. Ideally situated just moments from Kenny's
Nicole Fitzgerald Signature Premier Properties
$5,000 per month
8415 Soundview Ave, Southold, NY 11971
Step inside this charming 2 bedroom, 1 bath bungalow nestled on the serene shores of Great Pond in Southold. This cozy waterfront retreat offers tranquil water views and is just around the corner from Kenny's Beach and the popular Little Fish restaurant. Enjoy kayaking, paddle boarding, and fishing right from your backyard. Centrally located in the heart of the North Fork, you're perfectly
Nicole Fitzgerald Signature Premier Properties
$7,500 per month
6710 Soundview Ave, Southold, NY 11971
Enjoy Southold this Summer at a Scandinavian Farm Ranch. 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. Incredible Natural Light in the Home. The Kitchen is Simple and Sleek Overlooking All. The Large
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
$22,000 per month
45 Budds Pond Rd, Southold, NY 11971
Available for two week rentals! 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
Mackenzie Needham Daniel Gale Sothebys Intl Rlty
$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 moments
Nicholas Planamento William Raveis New York LLC
$15,000 per month
580 Gin Ln, Southold, NY 11971
Wonderful opportunity to spend 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 kitchen
Scott Bortzner Compass Greater NY LLC
$35,000 per month
56765 Route 48, Southold, NY 11971
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.
Shannon Oshea East End Luxury Ltd
$15,000 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
$12,000 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
$4,000 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 fully
Diane Mollica Compass Greater NY LLC
$12,000 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 William Raveis New York LLC
$10,000 per month
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
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
$15,000 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. May 2025 $10,000. Summer 2025 - June $25,000 or $6,250 Weekly with Two Week Minimum; LD to End of September $20,000 or
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
$75,000 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
$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 William Raveis New York LLC
$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
$15,000 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 with bonus room and private half bath in the beautifully finished basement. Entertain and have fun this summer! Fully finished pool house with bathroom, outdoor kitchen, in-ground pool. Launch
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
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