$3,500 per month
49925 Main Rd Unit 2nd Floor, Southold, NY 11971
Southold Town Rental Permit #0787. NEWLY RENOVATED Light, Bright And Airy 2nd Floor Apartment With 2 Bedrooms And A Full Bath In Southold's Historic Corridor, Gorgeous Grounds And Landscaping, Close To All!, Additional information: Appearance:Excellent
Thomas McCarthy Thomas J McCarthy Real Estate
$7,500 per month
1460 Hillcrest Dr, Orient, NY 11957
Year-round rental! Experience luxury North Fork living with this incredible fully furnished, designer decorated, long-term rental. What sets this home apart is it's resort-style, professionally landscaped property with fully enclosed rear yard, multiple tiers and expansive paved patios. Huge 20x40 heated pool, outdoor shower, sports court - basketball & badminton, tree swing, fire pit, BBQ,
Nicole Pappas Compass Greater NY LLC
$54,500 per month
25 Miami Ave, 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
$30,000 per month
11925 Soundview Ave, Southold, NY 11971
.Enjoy water views and Long Island Sound sunsets from this magnificent new construction home for rent! Perfectly situated on 1.5 scenic acres, this home offers exclusivity and privacy. The beautiful eat-in-kitchen features high-end amenities including a Viking refrigerator and 8 burner range, double ovens, dual Bosch dishwashers plus two wine coolers. The airy and spacious living room is accented
Nicholas Liappas Compass Greater NY LLC
$9,301 per month
810 Waterview Dr Unit ID1261529P, Southold, NY 11971
Feel at home in this beautifully and professionally decorated 3-bedroom, 1.5-bathroom North Fork vacation home, just a ten-minute drive to both the town and the beach. This home offers everything you need for a wonderful stay, including a remodeled kitchen perfect for the chef in the family.This home comfortably sleeps six with three queen-sized beds and features a beautiful, remodeled
$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 and
Paul Loeb Douglas Elliman Real Estate
$50,000 per month
1000 Rambler Rd, Southold, NY 11971
Beautiful like new colonial just 500 feet from sandy bay beach. Four bedrooms plus a lovely sunroom. Enjoy your morning coffee on the bedroom balcony. Outside shower and gas grill off backyard deck. Bicycles and a kayak with trailer included. A perfect beach house. Memorial Day-Labor Day $65,000, or July & August $50,000.
Pamela Hunt Colony Realty
$3,600 per month
380 Eds Rd, Southold, NY 11971
Discover a rare year-round rental opportunity in the heart of Southold that delivers exceptional value and everyday practicality. This light and bright renovated home features airy living spaces, beautifully refinished hardwood floors, and a clean, modern layout designed for low-maintenance living. The sun-filled kitchen and dining area flow seamlessly onto a spacious deck overlooking a large,
Colin McCarthy Thomas J McCarthy Real Estate
$50,000 per month
400 Youngs Rd, Orient, NY 11957
Stunning Orient retreat with a private heated gunite pool; enjoy an ideal location with a beach and village just down the block. This tranquil home features soaring ceilings, two fireplaces, four ensuite guest rooms, a private office, an enormous eat-in kitchen, a light-filled dining room, a hotel-like master suite with a second-floor balcony, charming front porch, two living rooms, and beautiful
Bridget Elkin Compass Greater NY LLC
$25,000 per month
425 Cedar Point Dr E, Southold, NY 11971
Now Available for June 2026. This Impressive Home is Set Creekfront with Private Dock with Peconic Bay Access and Associated Bay Beach within the 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 Living Rooms, Well Appointed Kitchen
Rene Giacobbe Douglas Elliman Real Estate
$65,000 per month
2180 Kerwin Blvd, Greenport, NY 11944
Welcome to coastal living. This fully furnished, expanded Cape sits on a quiet, shy acre, offering privacy and tranquility. Spend summer days relaxing around the in-ground pool, or enjoy the association bay beach access for swimming, paddleboarding, and beach combing. The cozy living room with wood-burning fireplace invites relaxation, while the kitchen, featuring a Viking stove, inspires
JoAnn Wind Daniel Gale Sothebys Intl Rlty
$10,000 per month
123 Sterling Ave Unit 12, Greenport, NY 11944
**2026 Rates:** May 23 - June 30: $18,000; July: $20,000; August 1 - Labor Day: $22,000; Memorial Day - Labor Day: $49,500Welcome to the 123 Sterling Boat Lofts! This exceptional property, situated on Sterling Harbor in the heart of Greenport Village, represents the perfect East End retreat. Thoughtfully designed with a spacious open floor plan, this third-floor corner unit offers stunning
William Walters Daniel Gale Sothebys Intl Rlty
$4,300 per month
775 Hummel Ave Unit A, Southold, NY 11971
This Freshly Renovated Apartment is centrally located in Southold Village. The Two Family Home is in proximity to everything the North Fork has to offer. Three upstairs Bedrooms are comfortably separated from a large kitchen and entertainment area. The move-in ready apartment is located within Southold School District, and provides for the perfect year round home or North Fork Retreat. Additional
Joseph Divello Century 21 Albertson Realty
$4,000 per month
517 Flint St, Greenport, NY 11944
Discover the charm of this beautifully maintained 2-bedroom, 1-bath home located in the heart of Greenport, NY. Perfect for year-round living, this cozy residence offers comfort, style, and the peaceful charm of the North Fork. Nestled on a quiet street, this home is just minutes from Greenport Village’s boutique shops, restaurants, beaches, and the LIRR station. Enjoy everything the North Fork
Crystal Bolling Realty Connect USA LI Inc
$55,000 per month
7635 Main Bayview Rd, Southold, NY 11971
Elegant Historic Home in Southold – Coastal Charm Meets Modern Luxury Escape to the North Fork and enjoy this beautifully restored historic Southold home, perfectly blending timeless elegance with every modern comfort. This spacious retreat features 5 bedrooms and 3.5 baths, ideal for families or groups seeking a serene getaway. Enjoy central air conditioning, high-speed internet, and five smart
Mary Terry MCKENNASHEA LLC
$3,200 per month
1855 Kenneys Rd, Southold, NY 11971
1855 Kenneys Rd, Southold, NY 11971
$25,000 per month
345 Colonial Rd, Southold, NY 11971
Tucked away on a private setting in a peaceful North Fork neighborhood just minutes from Corey Creek, Croteaux Vineyards and Greenport Brewery, this exceptional colonial offers the perfect backdrop for an unforgettable summer. With approximately 2,700 sq. ft. of bright, inviting living space across two levels, there is ample room for family and friends to gather and create lasting memories. Step
Gloria Scrocco STOEBE & CO
$20,000 per month
485 Sutton Place, Greenport, NY 11944
Welcome to 485 Sutton Place, Greenport – a newly renovated gem that effortlessly combines modern luxury with timeless charm. Every detail of this stunning home has been thoughtfully designed to create a harmonious blend of comfort, style, and sophistication. Step inside to discover two sunlit levels of living. The first floor features two generously sized bedrooms and a full bathroom with tub. A
Gloria Scrocco STOEBE & CO
$12,000 per month
312 5th Ave, Greenport, NY 11944
2026 Rates: April $7,500; May $12K; June $15K; July $25K; A1-LD $27,500; Sept $12,500; October $10K: This beautifully curated home away from home, blends modern design with warmth and style. Experience elegant comfort in your private retreat with natural light, modern decor and thoughtful touches throughout. Nestled on a quiet, tree lined street, this special haven features a front porch, fully
William Walters Daniel Gale Sothebys Intl Rlty
$25,000 per month
525 S Harbor Rd, Southold, NY 11971
The Ultimate North Fork Retreat! This recently renovated home offers 4 ensuite bedrooms including a ground floor primary suite, with a total of 5.5 baths. The sprawling and very private 2.4 acre property features resort-like amenities including a 20 x 50 heated pool, fully equipped outdoor kitchen, multiple seating areas and more. Inside, the open floor plan flows from the living room with a gas
Thomas Perry Brown Harris Stevens W Hampton
$2,650 per month
317 South St, Greenport, NY 11944
Public RemarksDiscover your perfect WINTER escape at 317 South Street, Greenport. This charming 4-bedroom, 1.5-bathroom home offers modern comfort with classic appeal. Available from November 1, 2025, to May 15, 2026, it's an ideal seasonal retreat.?Enjoy hardwood floors throughout, a spacious formal dining room, and a cozy living area. The kitchen boasts modern appliances, including a
Jennifer Benton Compass Greater NY LLC
$18,000 per month
3600 Rocky Point Rd, East Marion, NY 11939
Stylish and comfortable home with plenty of space to relax indoors and out, featuring a covered porch, a sunny deck and a large yard. Just a short distance to a Long Island Sound beach. Summer 2026 - Memorial Day to Labor Day $52,000, Memorial Day thru June $14,000, July $18,000 (or $4,500 Per Week with Two Week Minimum); August to Labor Day $22,000 (or $4,500 Per Week with Two Minimum).
Paul Loeb Douglas Elliman Real Estate
$10,000 per month
1075 Inlet Ln, Greenport, NY 11944
So Very Close to a Beautiful Bay Beach! 3 Bedrooms/2 Baths. Central Air Conditioning. 2 Large Decks. Nice Yard! FALL 2025 - November 2025 to April 2026 -$4,000 Per Month for Single or Multiple Months. SUMMER 2026 - Memorial Day to Labor Day $29,000; June $8,000; July $10,000; August to Labor Day $12,500. Permit #0497.,
Paul Loeb Douglas Elliman Real Estate
$35,000 per month
3693 Pine Neck Rd, Southold, NY 11971
Elegant Waterfront Retreat on the North Fork - Welcome guests in style at this exquisite waterfront residence, where timeless design meets relaxed coastal living. Overlooking serene, protected waters, this expansive home features a sparkling waterside pool, private dock, and inviting fire pit—creating an idyllic setting for summer entertaining.Thoughtfully designed living and gathering spaces
Eric Frend Corcoran
$3,000 per month
360 Flint St, Greenport, NY 11944
Welcome to 360 Flint Street, your cozy winter retreat in the charming village of Greenport, NY. This beautifully appointed home offers 2,400 square feet of living space, thoughtfully designed for comfort and modern living. Step into the warm and welcoming foyer, where high ceilings and hardwood floors set the tone for a relaxing getaway. The home features three spacious bedrooms, each providing
Jennifer Benton Compass Greater NY LLC
$16,000 per month
3045 Rocky Point Rd, East Marion, NY 11939
3 Bedroom/2 Bath Home with Heated Inground Pool and Several Beaches Nearby. Open Floor Plan and Vaulted Ceilings. Enjoy the Days of Summer on the Back Deck, Fenced Lawn and Pool. Several Nearby Beaches Too! Winter Rental (November 2025 to April 2026) Single or Multiple Months Considered at $5,000 Per Month. Summer 2026 - Memorial Day to Labor Day $45,000; June $12,000; July $16,000; August to
Paul Loeb Douglas Elliman Real Estate
$10,000 per month
275 Maier Place, Southold, NY 11971
Seasonal Rental in Scenic Southold, NY – 3 Bed, 3 Bath RetreatEscape to the heart of the North Fork with this beautifully appointed 3-bedroom, 2-bath seasonal rental in picturesque Southold, NY. Nestled among the region's famed vineyards, farm stands, and white sand beaches, this home offers the perfect blend of charm, comfort, and convenience.Inside, you'll find a spacious and
Mary Terry MCKENNASHEA LLC
$20,000 per month
1060 Willow Terrace Ln, Orient, NY 11957
STUNNING BAYFRONT Local Art Filled Home, with Mooring (Boat Lovers Welcome), Private BAY Beach and 5 min WALK to VILLAGE!Over 4500 sqft of immaculate contemporary, gorgeous furnishings with a local artist's own artwork make this home perfect for your own enjoyment and summer entertainment. The only bayfront rental fully set up for your boating and swimming needs. Light, bright and mint, 4
Janet Markarian Daniel Gale Sothebys Intl Rlty
$7,000 per month
1800 Village Ln, Orient, NY 11957
Available for a full year --enjoy the best of both worlds with your own weekend retreat and the perfect summer getaway all in one! This beautifully maintained residence, originally built in the 1800s, offers the perfect blend of historic character and contemporary comfort. With water views of scenic Orient Harbor, this home features soaring ceilings, abundant natural light, and stunning hardwood
Lisa Gillooly Compass Greater NY LLC
$6,000 per month
2435 Cedar Ln, East Marion, NY 11939
Newly renovated, unfurnished year-round 4-bedroom, 3-bath waterfront cottage with a deep-water dock in a private community offering two residents-only bay beaches. Features include a brand-new kitchen and baths, a wood-burning fireplace, central air conditioning, a waterside deck and yard, outdoor shower, and storage shed. Enjoy Quality North Fork living with the perfect setting for boating,
Paul Loeb Douglas Elliman Real Estate
$2,500 per month
1145 Major Pond Rd, Orient, NY 11957
This Charming Second-floor (Above Garage) apartment offers a light-filled, tranquil retreat surrounded by nature. Spanning approximately 700 Sq. ft., it features a spacious bedroom, an oversized bathroom, and a bonus room ideal for an office or extra storage. The practical kitchen flows into a cozy dining and living area, all designed for comfort and ease. With Private entrance, Private Yard and
Chrisand Castella Douglas Elliman Real Estate
$5,000 per month
145 Founders Path, Southold, NY 11971
Beautiful Charming Cottage Located in the Coveted Community of Founders. Close to a gorgeous sandy beach, grocery shopping, coffee shop, restaurants, jitney stop, and all things North Fork. Three bedrooms, one bath, LR, kitchen, outdoor deck, fire pit, outdoor shower. Available Sept. $5000, Oct & Nov $4000, Dec through March $3,000, April $3,500. May $5,000, June $6,000 and August $10,000.
Diane Mollica Compass Greater NY LLC
$14,000 per month
21 Stirling Cove Unit E, Greenport, NY 11944
Welcome to your ultimate retreat in the charming village of Greenport, NY. This luxurious condo offers both relaxation and adventure, with stunning bay views and private beach access. The open layout features elegant hardwood floors and central air conditioning, seamlessly blending indoor and outdoor living with a private space for entertaining or unwinding. During the bright summer, enjoy your
Jennifer Benton Compass Greater NY LLC
$10,000 per month
4630 Blue Horizon Bluffs, Peconic, NY 11958
It's all about the view! Perched on a bluff overlooking the Long Island Sound this home is a retreat and nature lovers paradise. Summer rental available for August or September, two week minimum or reserve for the 2026 season. Easy beach access with your own private staircase, you'll enjoy morning walks looking for beach glass and driftwood then spend the evenings watching breathtaking sunsets.
Melissa Principi Douglas Elliman Real Estate
$4,600 per month
1155 Tasker Ln, Greenport, NY 11944
one of a most desirable spot at Greenport - Super Spacious !. This charming home offers generous rooms, ample storage, and a detached 2-car garage with a full-size loft—perfect for a studio or extra storage. Located in the heart of Greenport, a quaint, short distance to seaside village filled with shops, galleries, quiet rustic storefronts, and picturesque harbor scenes. Enjoy true beach
Chrisand Castella Douglas Elliman Real Estate
$11,200 per month
750 Kerwin Blvd, Greenport, NY 11944
Greenport-Immaculate and spacious home. A welcoming front porch leads to the sunny Living room and dining room. A fully equipped gourmet kitchen with Thermador appliances with sliding doors to back deck, family room with vaulted ceilings also has access to large back deck, there is another den/office, a full bathroom with shower and laundry all on the first floor. The second floor there are two
Amy Kirincic The Agency Northshore NY
$3,200 per month
2555 Youngs Ave Unit 4D, Southold, NY 11971
Introducing this charming 2 bedroom, 2 bathroom condo nestled in the picturesque town of Southold. This turn-key condo offers an ideal combination of convenience and comfort. The spacious and bright living area, high ceilings and fireplace create a warm and inviting atmosphere. The kitchen has been recently updated, and the updated bathrooms feature glass enclosed showers. There are beautiful
Susan Orioli Engel & Volkers North Fork
$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
$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
$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
Showing Results 1 - 40, Page 1 of 3
Copyright © 2025 CoStar Group
