$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!
$3,400 per month
516 Main St Unit CARRIAGE HOUSE, Greenport, NY 11944
Updated and Historic carriage house available for rent!...Completely separate, private space and entrance located on Carpenter Street features charming, yet updated features and within close proximity to the Village. Private garden area and private parking make this home even more convenient and appealing. Owner intends on making additional upgrades to house, including 1-new floors throughout
Joshua Weinman Keller Williams NYC
$12,000 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
$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
$15,000 per month
3825 Stars Rd, East Marion, NY 11939
Come spend your summer at one of the best beach communities in East Marion on the North Fork. Nestled in a peaceful community, with sunsets on the beach and a pool in your private backyard. 3 bedrooms, 2 baths, full finished basement and an outdoor shower. You will never want to leave. Surrounded by North Fork renowned farm stands, restaurants, beaches, marinas, boating, award winning wineries
$3,900 per month
4225 Stars Rd, East Marion, NY 11939
East Marion Rental! This immaculate high ranch home has a deeded private beach located less than 400 ft. away. It features an updated eat-in kitchen, separate dining room, three spacious bedrooms, three full baths and two living rooms - one on the main level and the other located on the lower walk-out level. The expansive rear yard is ideal for entertaining and enjoying summer bbq's and those
Connie Liappas Compass Greater NY LLC
$10,000 per month
540 2nd St, Greenport, NY 11944
Be a part of the action in Grernport Village. Lovely 2 bedroom 1.5 bath house, with a 3rd pass through bedroom. Central air. Gas stove. Renovated in 2023. All modern appliances and bathrooms. Combining the charm of an antique home with modern comfort. Quiet location, yet close to all that Greenport offers. [[Rental Registration # R25-046]]
$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
$12,000 per month
64230 County Road 48, Greenport, NY 11944
Enjoy summer fun on the North Fork in this MINT farmhouse on beautiful sprawling property! There's plenty of room for family and friends in this spacious home with 4 large bedrooms, 3 full baths, aneat-in-kitchen perfect for gatherings, impressive primary ensuite, den/home office and laundry room. Additionally, the basement is fully finished with a large and fun recreation room, full bathroom
Donald Bracken Thomas J McCarthy Real Estate
$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
$10,000 per month
3650 Bay Shore Rd, Greenport, NY 11944
Your Fabulous Beach House Vacation! 2 Week Rentals or Monthly! Spacious summer house in the coveted Peconic Bay Estates private beach community on the Bay. A darling hidden path brings you to the sweetest surprise little wooden bridge to cross over to arrive on the sandy beach. Fun! No shirt, no shoes, lazy day, Yes! Very quiet water front cove, lots of area biking, kayaking, taking beach
Kate Carpluk William Raveis New York LLC
$12,000 per month
39595 Main Rd, Orient, NY 11957
Spacious Traditional Home with 4 bedrooms, 2.5 baths near Orient State Park and Cross Sound Ferry.The private landscaped backyard features a pool with patio and lounge chairs and a large deck with glass doors to the kitchen. The first floor has a private living room space and a kitchen/family room open plan for entertainment. The second floor has a master ensuite with full bath overlooking the
Janet Markarian Daniel Gale Sothebys Intl Rlty
$7,375 per month
2700 Sound Dr, Greenport, NY 11944
2025 Rates: September 1-30 $29,500; October $25,000: Escape to this exceptional seasonal rental, perfectly situated on the shores of the Long Island Sound. This beautifully appointed waterfront home offers the ultimate coastal living experience, featuring private stairs leading directly to the beach, an in-ground heated gunite pool, and panoramic water views from nearly every room. With 4
William Walters Daniel Gale Sothebys Intl Rlty
$15,000 per month
157 Central Ave, Greenport, NY 11944
Available August - LD $15,000. Two week minimum rental. This charming 2 bed, 3 bath Greenport Village Colonial offers a perfect blend of historic charm and modern elegance. Step inside to find beautifully preserved character details complemented by contemporary updates. A sun-drenched kitchen and dining area open to a peaceful and private patio and garden. An additional den/yoga room provides the
Shane Hafer Compass Greater NY LLC
$15,000 per month
63615 North Rd, Greenport, NY 11944
Rental Permit # 1304 Chalet-Style Retreat with Private Soundfront Beach – Summer Rental in Greenport, NYNestled on 2.52 secluded acres along the North Fork’s coveted Soundfront, this architectural chalet-style home offers the ultimate summer escape. Featuring 3 oversized bedrooms and 4 full bathrooms, this expansive and warm retreat blends rustic charm with modern luxury.Soaring
Marco Maida Compass Greater NY LLC
$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
$8,500 per month
1745 Stars Rd, East Marion, NY 11939
2025 Rates: 6/16-6/23 $8,500/week; Month of July $35,000 or $9,000/week; 8/4-8/18 $20K. Spend your summer in style at this exquisite brand-new modern farmhouse, offering the perfect blend of luxury, comfort, and North Fork charm. Located just minutes from Greenport Village, local farmstands, renowned wineries, and pristine beaches, this home is the ideal summer retreat. Set on a full 1-acre lot,
William Walters Daniel Gale Sothebys Intl Rlty
$35,000 per month
Unlisted Address
Sound Front Contemporary Octagonal Home with Private Beach. Contemporary and chic, mint condition 1970's modular octagonal home located on a breath-taking sound front walk-out private beach in Orient. Three bedrooms, each with a full bath and an additional powder room. Updated kitchen and bathrooms. Every room is furnished with period mid-C style furniture. Living room has original Malm wood
Janet Markarian Daniel Gale Sothebys Intl Rlty
$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
$4,500 per month
345 Cemetery Rd, East Marion, NY 11939
Classic Cape with Open Front Porch on Quiet Side Street. 3 Bedrooms, 2.5 Baths. Primary Bedroom and Bath on First Floor. Wood Burning Fireplace. Nice Yard.
Paul Loeb Douglas Elliman Real Estate
$4,500 per month
22950 Main Rd, Orient, NY 11957
Orient Village Area - Bright, Spacious And Updated Unfurnished Year Round 3 Bedroom/2 Bath Ranch Rental With Family Room, Central Air Conditioning, Heated In Ground Saltwater Pool And Nice Yard. Located Close To Village Lane, Oysterpond's School, Young's Road Public Long Island Sound Beach And New York City Transportation. Permit #0132.
Paul Loeb Douglas Elliman Real Estate
$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
580 Stars Rd, East Marion, NY 11939
YEAR ROUND RENTAL! Step into stylish comfort with this beautifully designed modern farmhouse, offered fully furnished and move-in ready. This stunning 4-bedroom, 3.5-bath home combines rustic charm with contemporary elegance, perfect for comfortable family living or entertaining in style.Inside, you’ll find rich hardwood floors throughout and an open-concept living space that flows seamlessly
William Walters Daniel Gale Sothebys Intl Rlty
$42,000 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
$5,000 per month
30675 Main Rd, Orient, NY 11957
Spacious and grand, historic Terry Mulford House C. 1716, set on 5.8 private acres, fully renovated, with 5 bedrooms and 4 new full baths. New eat-in kitchen, living room with piano and flat screen TV. Relax on the wrap-around porch or rear courtyard. A short trip to Orient and Greenport Village, Orient State Park, marinas, sound, and bay beaches. Price includes utilities. Mid-term & departure
Janet Markarian Daniel Gale Sothebys Intl Rlty
$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
$4,200 per month
8325 Main Rd, East Marion, NY 11939
Authentic Craftsman was built in 1918. Featuring covered front porch, 2 bedrooms, full bath, living room with wood burning fireplace, eat-in kitchen, formal dining room, office/day bed, powder room/laundry, glass door to rear patio, private off-street parking. Starting Oct $4,200/mo. year-round. Permit# 1048
Janet Markarian Daniel Gale Sothebys Intl Rlty
$16,000 per month
12680 Main Rd, East Marion, NY 11939
Immaculate French Country Farmhouse with heated, saltwater pool. Featuring living room with gas fireplace, dining room spacious eat-in kitchen with glass door to patio, powder room, laundry room, ground floor master ensuite bedroom with bath, office/parlor. Second floor with 2 bedrooms – one with bay view – and a full bath. The spacious, manicured grounds boast a saltwater pool, pool house,
Janet Markarian Daniel Gale Sothebys Intl Rlty
$50,000 per month
555 Soundview Rd, Orient, NY 11957
Enjoy spectacular unobstructed vistas of the Long Island Sound from this exclusive 4 bedroom, 3.5 bath beachfront home! Experience coastal living at its finest with your very own private beach, beautiful inground pool and spa - making this the perfect summer retreat for the ultimate in luxury and relaxation. Convenient to all the North Fork has to offer...world class restaurants, vineyards,
Connie Liappas Compass Greater NY LLC
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