$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!
$3,900 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
$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
$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
$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
$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
$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
$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
$4,500 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
$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
$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
$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
$30,000 per month
308 Wiggins St, Greenport, NY 11944
FULLY TURNKEY from furnishings, bedding / linens, towels, to all kitchen ware, 100K artwork Maintenance team including house cleaner, pool care and landscaper are at your disposal. 2 minute walk into town - best location in Greenport, across from LIRR train and Hampton Jitney. Must honor all current Airbnb and VRBO bookings. MAIN HOUSE GROUND LEVEL: Living room with wood burning
Josh Shenkle EAST END ALLIANCE REAL ESTATE AND DEVELOPMENT LLC
$14,500 per month
730 Bay Ave, East Marion, NY 11939
Escape to the serene beauty of the North Fork in this beautifully updated East Marion retreat. Embrace your summer vacation in this charming home, featuring a modern, sun-drenched kitchen, a spacious living room with a cozy fireplace, and an elegant formal dining room perfect for friendly gatherings. Unwind on the screened-in porch, your personal oasis, or bask in the sunshine on the expansive
JoAnn Wind Daniel Gale Sothebys Intl Rlty
$8,000 per month
300 Fiddler Ln, Greenport, NY 11944
Like-new Greenport beauty with every amenity including a saltwater pool. Room for all indoors with a living room, reading room and large media room and outdoors with a dining area and lounging area poolside. Located in a lovely, quiet neighborhood just a few minutes to a gorgeous, sandy Bay beach, a beautiful Sound beach and Greenport's vibrant downtown with its waterfront park, cafes &
Kathleen Travers Douglas Elliman Real Estate
$16,000 per month
1500 Trumans Path, East Marion, NY 11939
Charming and chic 3 bedroom, 1.5 bath Cottage on Lake Marion with many charming original features. Open, sunny floor plan with common area that opens onto spacious lakefront deck perfect for relaxing, grilling & dining. Wood burning fireplace, fully equipped cook's kitchen, private dock, outdoor shower, & easy stroll to association bay beach. Offered June $8,000; Aug $16,000. Permit# 0692.
Janet Markarian Daniel Gale Sothebys Intl Rlty
$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
$6,000 per month
3825 Stars Rd, East Marion, NY 11939
FUN IN THE SUN! 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
Sheri Winter Parker Corcoran
$17,500 per month
495 Maple Ln, Orient, NY 11957
Entertain poolside in this stylish Mid-C Modern set on 2 acres, with views of Orient Harbor & the Sound. Handsomely furnished with master bedroom with full bath plus 2 additional bedrooms & full bath, large gourmet kitchen, den, spacious living room/dining room/common space opening to wrap-around deck overlooking pool. Walk to Village, Latham's farm stand. Aug 1-16 $17,500. Permit# 0321.
Janet Markarian Daniel Gale Sothebys Intl Rlty
$15,000 per month
165 Sterling St, Greenport, NY 11944
Tucked Away Along Sterling Harbor in Greenport's Historic District On the Village's Most Desired Street. This Lovely 3 BR, 2 BA Cottage Is Only A Block From the Maritime Village With Its Many Restaurants, Cafes, Shops, Mitchell Park & Carousel. Enjoy Your Morning Coffee & Evening Cocktails On The Waterview Deck. Close to All Transportation, Beaches & Wineries., Additional information: Appearance:
Mitch Pickman Thomas J McCarthy Real Estate
$7,000 per month
790 Oyster Ponds Ln, Orient, NY 11957
Authentic 1770 Cottage in the heart of Orient Village. Lovingly restored & maintained Village home on beautifully landscaped lot, offering private grounds & distant views of sunsets over the bay. Furnished in period antiques, screened-in porch off kitchen, first floor bedroom. Walk to amenities, bay beach, Yacht Club, marina, farm stand & Jitney. Offered Sept 3-Oct 1 $7,000. Permit #0091.
Janet Markarian Daniel Gale Sothebys Intl Rlty
$7,000 per month
1620 Aquaview Ave, East Marion, NY 11939
Mid-Century Contemporary with views of Long Island Sound in a private community with association beach across the road. Cathedral ceilings & large windows add to the bright & open feeling of the communal area. Water view deck for relaxing and entertaining. 1000 sf of living area plus 800 sf walk-out basement converted to a fully renovated recreation room/office with recessed lighting, new
Janet Markarian Daniel Gale Sothebys Intl Rlty
$30,000 per month
255 S View Dr, Orient, NY 11957
Contemporary private, secluded home in bucolic Browns Hill, Orient with Panoramic views over gardens, fields and bays from Montauk to Shelter Island. Enter through a welcoming space from the foyer to the living room with wood burning fireplace, updated gourmet kitchen and dining room with panoramic farm and bay views. Three levels of living space with one bedroom & full bath on each floor
Janet Markarian Daniel Gale Sothebys Intl Rlty
$11,000 per month
1855 Village Ln, Orient, NY 11957
Impeccably restored 19th Century gem located in the heart of Orient Village with bay views. Close to bay and sound beaches, and a stroll to all village amenities. Featuring 2 parlors, 3 bedrooms, library, office, eat-in kitchen, updated baths, charming garden, out-door dining, and grill, out-door shower. Offered May $7,000; June $11,000; Sept $10,000; Oct $7,000; Nov $6,000. Permit #0483.
Janet Markarian Daniel Gale Sothebys Intl Rlty
$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
$55,000 per month
1050 King St, Orient, NY 11957
Vineyard Views. Modern Farmhouse on private 1 acre located on the only private, working vineyard in Orient Village. 16x32 heated pool, newly renovated chef's kitchen & baths. The home features 3 bedrooms, 3 full baths. Ground floor designed with open common space and designer furnishings for luxurious entertaining, featuring living room with cathedral ceiling with sliders to pool and deck, eat-in
Janet Markarian Daniel Gale Sothebys Intl Rlty
$15,000 per month
231 5th Ave, Greenport, NY 11944
Located in the heart of Greenport Village, this charming home offers an open concept first level and has a first floor bedroom, half bathroom with washer and dryer and an expansive rear deck, covered by canvas for shade, overlooking a manicured and private rear yard. The second floor has two spacious bedrooms with a walk in closet and a full bathroom with a separate shower and large bathtub.
Alexander Aquino Douglas Elliman Real Estate
$16,000 per month
905 9th St, Greenport, NY 11944
With the addition of a new 20' x 40' heated, salt water in-ground pool in private yard, this fully renovated Greenport home has been stylishly decorated and features a large, eat-in kitchen, expansive living room, 3 bedrooms with two ensuite full bathrooms and a third full standalone bathroom. The residence has a large side yard and patio on a 1/3 of an acre and is third of a mile to the heart of
Alexander Aquino Douglas Elliman Real Estate
$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
$50,000 per month
2620 Orchard St, Orient, NY 11957
Discover the finest rental property in the charming hamlet of Orient, on Long Island's desirable North Fork. Built in 2017, this exceptional home combines a clean, contemporary aesthetic with breathtaking architectural detail, perfect for discerning guests.The first floor features an open-concept living space with soaring ceilings, anchored by a gourmet chef's kitchen with premium appliances and
Lisa Gillooly Compass Greater NY LLC
$15,000 per month
1970 Village Ln, Orient, NY 11957
Enjoy living in the crown jewel of Orient Village, the Shaw House built in 1730. Restored & meticulously maintained with original exposed beams, wide-plank floors, period hardware, 3 updated wood burning fireplaces, custom cabinetry & woodwork. 2 large decks span the back of the house overlooking Orient Harbor & Yacht Club. Offered Sept $15,000; Oct $8,000; Nov $8,000; Dec $6,000. Permit #0293.
Janet Markarian Daniel Gale Sothebys Intl Rlty
$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
$6,000 per month
285 Oyster Ponds Ln, Orient, NY 11957
Orient village mid century gem with pool. This newly renovated, well appointed residence is perfectly located and offers 3 bright and spacious bedrooms and 2 full baths, chefs kitchen, dining room, living room and screened in porch. The yard and pool area are fenced. The garden features a pool house and stone patio perfect for alfresco dining, overlooking the beautiful pool, specimen trees and
Lori Feilen William Raveis New York LLC
$4,200 per month
3670 Rocky Point Rd, East Marion, NY 11939
Beautifully Renovated in 2023. 3 Bedrooms/2 Bathroom. One Floor Living with Deck and Nice Yard. Fully Furnished. August to Labor Day $12,000 or $3,000 Per Week with Two Week Minimum. September $6,000; October $6,000, Off Season - November 2025 to May 2026 $3,000. Year Round $4,200. Rental Permit #0946.
Paul Loeb Douglas Elliman Real Estate
$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
$38,500 per month
27840 Main Rd, Orient, NY 11957
CHIC RETREAT! A glamorous getaway! You won't know if you are tucked away in Tuscany or the South of France! This recently renovated modernist home is nestled amongst your own private vineyard with incredible farm vistas, imparting a spa retreat vibe. A large pool reaching out towards the horizon. Cozy up by the firepit or have lunch alfresco under the vineyard pergola and enjoy incredible
Sheri Winter Parker Corcoran
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