$38,500 per month
27840 Ny-25, Orient, NY 11957
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 privacy! 3
$12,000 per month
425 Old Shipyard Ln, Southold, NY 11971
Rent Includes Utilities
Amy Kirincic The Agency Northshore NY
$35,000 per month
6 South St, Shelter Island Heights, NY 11965
Charm, history, location. Built as a carriage house circa 1890, this little gem has been meticulously restored and decorated. First time offered as a rental since it's restoration was completed in 2021.This is a chance to live and enjoy a part of Shelter Island history. bounded on two sides by preserved land and an estuary, the woodland setting provides year-round beauty and tranquility in the
$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
$22,000 per month
1710 Gull Pond Ln, Greenport, NY 11944
North Fork Lovers do not miss this opportunity to rent a renovated Contemporary Cabin. Inside this spacious 3 Bedroom - 2 Full Bathroom home that hold up to 8 people, you'll find an entertainer's paradise with a sun-soaked open concept kitchen, Granite Countertop, and Stainless Steel Appliances. The property also offers the best of both worlds: Private 2400 Sq Ft On 3.89 Acres, Nature Preserve
$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
$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
$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
$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!
$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. Offered Apr $4,200; May $5,000; July $12,000; year-round $4,200. Permit# 1048
Janet Markarian Daniel Gale Sothebys Intl Rlty
$150,000 per month
79 Silver Ln, Bridgehampton, NY 11944
Large contemporary house in Bridgehampton, south of the highway of the famous Ocean Road, 3 min. drive to the ocean. Just off Ocean Road on private street close to the ocean, completely renovated light filled chic 6 bedroom 5 and a half bath home with heated gunite pool and tennis court in private estate setting over looking farm with mature trees. Brand new gourmet Italian kitchen and all new
$32,000 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
$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
$70,000 per month
2315 Mill Ln, Peconic, NY 11958
Discover your perfect getaway at this stunning 3-bedroom, 2-full-bathroom rental, ideally situated near the pristine shores of Goldsmith's Inlet Beach on the North Fork. Step inside to find a fully renovated interior that boasts high-quality finishes and contemporary design. The rental includes two expansive living rooms, with a 24 ft high soaring cathedral ceiling in the great room seamlessly
Susan Orioli Engel & Volkers North Fork
$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
$4,800 per month
620 The Greenway, East Marion, NY 11939
Pebble Beach Farms Year round rental. Immaculate home inside and out. Set on manicured 1/2 acre property bordering Island's End Golf Course. Sunny and bright living room, dining room and kitchen. New stainless steel appliances. Second floor en-suite primary bedroom with 2 additional bedrooms. Full basement with washer and dryer and plenty of storage. Large back deck overlooking yard bordering
Amy Kirincic The Agency Northshore NY
$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
$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
$15,000 per month
695 Edwards Ln, Orient, NY 11957
Travel down a private road to a Farmhouse on 2.13 acres of serene. park-like grounds. Featuring living room with wood burning fireplace, kitchen/dining area, 3 bedrooms, 2 full bathrooms, screened porch. Enjoy summer in this quiet, private home near North Fork beaches and amenities. Offered June $9,000; July $15,000; Aug $15,000; Sept $10,000.
Janet Markarian Daniel Gale Sothebys Intl Rlty
$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
$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
$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
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
$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
$20,000 per month
415 6th Ave, Greenport, NY 11944
ADORABLE CAPE WITH POOL & HOT TUB IN THE HEART OF GREENPORTNestled in the Village of Greenport, this charming 4-bedroom Cape has been freshly painted and offers the perfect blend of modern comfort and coastal charm. The first floor includes 2 bedrooms, a cozy living room, an eat-in kitchen, and a full bath, while the second floor boasts 2 additional bedrooms and another full bath—plenty of
Jeanmarie Bay Town And Country Real Estate
$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
$7,000 per month
1110 Gillette Dr, East Marion, NY 11939
Perfect summer rental, Short Stroll to beautiful Bay Beach, Charming 4 br, 2ba Cape, Family room, views to the West over preserved land, totally upgraded and recently renovated, flexible rental times, 14 days minimum. Rental Permit # 1269
Tom Uhlinger Douglas Elliman Real Estate
$55,000 per month
1390 Demarest Rd, Orient, NY 11957
Spacious & immaculate Sound front Contemporary home sitting on a hilltop in Orient, overlooking Long Island Sound to the north & farm fields to the south. Meticulously renovated & professionally designed 4 bedrooms, 5.5 baths with 128 ft of private beach. The ground floor has a large family room with glass doors to a blue stone patio, lawn, & stairs to the beach. This level includes an ensuite
Janet Markarian Daniel Gale Sothebys Intl Rlty
$65,000 per month
1920 The Strand, East Marion, NY 11939
Serene, private, and tranquil oasis perfect for those looking to relax, unwind and unplug. A beautifully landscaped property overlooking the Long Island Sound with private beach access and breathtaking views from all levels of the home. Ground Level has 4 B/R's, 2 Baths, Laundry Room and Family Room which opens to Deck, Pool, and Bluff. Enjoy majestic sunsets from an additional deck perched at
Elena Ermogenous Century 21 Unique Realty
$12,000 per month
36 Stirling Cove Unit B, Greenport, NY 11944
Just a ferry ride from Sag Harbor and the Hampton's, take in expansive waterfront views of the bay and Greenport harbor from the second floor balcony in this renovated open concept waterfront condo located in the private Stirling Cove condominium association. This light filled townhouse offers a private beach, 60' x 30' heated pool overlooking the bay, two tennis courts, private parking and is
Alexander Aquino Douglas Elliman Real Estate
$2,750 per month
880 Wiggins St, Greenport, NY 11944
Beautiful like new second floor furnished apartment to rent year-round. Desirable location within reach of village shops, restaurants, beaches, park, school, and transportation. This apartment offers an updated kitchen with stainless steel appliances, oak hardwood flooring, open living room with dining area, large bedroom, and a clean full bathroom. There is a balcony deck, paver patio, and a
Kenneth Poliwoda Douglas Elliman Real Estate
$50,000 per month
505 Plum Island Ln, Orient, NY 11957
Available for summer 2025! Modern farmhouse with 4 bedrooms, all with ensuite baths. Get away from it all in this hotel-like Orient home. Open concept kitchen, dining, living with beautiful light filled bedrooms. Enormous blue stone patio leads to in-ground pool and beautifully landscaped yard beyond. Minutes from the private association beach, Orient State Park and Duryeas Restaurant & Bar. Past
Bridget Elkin Compass Greater NY LLC
$20,000 per month
185 Wiggins Ln, Greenport, NY 11944
An outdoor oasis is one element of this extraordinary property. This one of a kind 5 bedroom, 3.5 bath residence is the perfect home to make special memories this season. The perfect rental with one of the most extraordinary pool and garden areas on the North Fork. Features a 20' x 50' heated Gunite pool with waterfall, extensive hand cut stone patios, stone walls and numerous outdoor sitting
Nancy Cervelli Daniel Gale Sothebys Intl Rlty
$4,000 per month
424 4th St, Greenport, NY 11944
Welcome to your very own pied-a-terre cottage nestled on the world renowned grounds of Harbor Knoll guesthouse.Bask in this waterfront, private and secluded oasis of calm, while still being within arms reach of everything Greenport Village has to offer.This quaint cottage boasts, hardwood floors, ductless air-conditioning, an eat in kitchen, primary suite and a pullout sofa bed in
Pete Halpin 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
$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
Showing Results 1 - 40, Page 1 of 4
North Fork, located on a 30-mile peninsula opposite the Hamptons, is surrounded by the Long Island Sound, beaches, and farmland, offering a distinct alternative to its more famous neighbor. The area features nine parks, some with beach access, like Founders Landing Park, which has a lifeguard during summer months and an event hall for rent. Inlet Pond County Park offers a mature oak forest and a butterfly garden, while Southold Dog Park provides off-leash play areas for dogs. Housing styles in North Fork include Cape Cods, historic homes, and new builds, set on tree-lined streets without sidewalks. The community hosts a variety of events, such as Winterfest and Lobsterfest, and boasts over 60 local businesses, including unique shops like Lydia’s Antique & Stained Glass. Dining options are abundant, with A Lure Chowder House & Oysteria and Michelangelo Southold among the highlights. The area is also home to 20 wineries, including Bedell Cellars. While there are no chain stores on the peninsula, residents can find larger retailers 3 miles away in Riverhead. The Southold Union Free School District offers schools with a favorable student-to-teacher ratio. Commuting is facilitated by two Long Island Rail Road stations and bus stations within 10 minutes of the hamlet, with North Road and Highway 25 serving as main thoroughfares.
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