$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
$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
$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
$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
$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 space
Jeanmarie Bay William Raveis New York LLC
$2,500 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. June $7,000.00july $9,000.00 or $2,500.00 weekly 14 day minimum, August till LD, $12,000.00 or $3,500.00 weekly 14 day minimum
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
$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
$4,000 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
$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
$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
$25,000 per month
1000 Sound Dr, Greenport, NY 11944
Immaculate shingle-style home perched above the Long Island Sound. Enjoy endless water views and breathtaking sunsets from the heated pool and private beach. Open floor plan with EIK and fireplace, bedrooms across three floors, including first and second-floor primary suites with private waterside balconies. The large finished basement features a media/game room. The private office is ideal for
Eric Elkin Compass Greater NY LLC
$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
$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
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
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
$15,000 per month
2905 Private Rd, East Marion, NY 11939
4 Bedroom, 2.5-Bath Expanded Ranch with Large Deck and a 20' x 45' Heated Inground Gunite Pool. All Set on 3+ Wooded Acres with Mini Vineyard Adjacent to Preserved Land for Privacy. Central Airconditioning, Updated Baths, Hardwood Floors and Attached 2-Car Garage. Parks District Beach Rights to Beautiful Truman's Beach on the Long Island Sound. Farmstands, Islands End Golf, a Waterfront
Paul Loeb Douglas Elliman Real Estate
$35,000 per month
2100 Youngs Rd, Orient, NY 11957
Stunning waterfront shingle style home overlooking Long Island Sound with private beach access. Waterview, heated pool. Wrap-around porch. Original beach stone fireplace, vintage beadboard walls, large, updated gourmet kitchen, open common area, 5 bedrooms, 3 bathrooms, large master ensuite with private screen water view balcony. Beautiful interior furnishings, with teak rocking chairs, chaise
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
$35,000 per month
1390 Willow Terrace Ln, Orient, NY 11957
Enjoy a beautiful airy and bright mint condition Bay Front Orient Contemporary home, perfect for relaxing and entertaining. This 4-bedroom 4.5 bath home has gourmet kitchen, fireplace, open common space for easy entertaining. First floor has access to bay side screened porch from living room and den (or 4th bedroom with full bath). Second floor master bedroom and a guest bedroom open onto upper
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
$40,000 per month
2840 Stars Rd, East Marion, NY 11939
PRIVACY AND LUXURY COLLIDE! Down a private driveway with breathtaking views of the sea, privacy and luxury collide! This impressive beach estate rests on 12.3 acres and 460' of waterfront beach tucked away in a protected cove on the Long Island Sound. 6 bedrooms include their own ensuite bathroom, plus two half baths, a gourmet eat-in kitchen that is truly a chef's domain with multiple seating
Sheri Winter Parker Corcoran
$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
$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
$35,000 per month
300 Latham Ln, Orient, NY 11957
Experience breathtaking views of Long Island Sound and Orient Point County Park from this spacious open-concept home. Beautifully updated 4-bed, 4-bath home offers private 20x40 heated saltwater pool and serene backyard. Host memorable gatherings in the spacious kitchen, perfect for indoor & outdoor dining. The expansive master suite boasts breathtaking views, king-size bed, office nook, dressing
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
$25,000 per month
840 Southern Blvd, East Marion, NY 11939
Bright and spacious Contemporary summer rental on the North Fork. Featuring floor to ceiling windows, great room, 6 bedrooms, 3.5 bathrooms, eat-in kitchen, recreation room. Private back yard with 40x20 salt water heated pool. Offered June 1 - 28 $25,000; June 29 - July 18 $33,000; July (2 weeks) $24,000; Sept 4 - Oct 2 $30,000. Permit #1230.
Janet Markarian Daniel Gale Sothebys Intl Rlty
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