Southold NY Real Estate & Homes for Rent

Stunning Southold Luxe New Construction Rental with Dreamy Backyard. Make memories and have fun in this three bedroom, four bathroom home with finished basement, huge pool house, outdoor kitchen, in-ground pool. Meticulously landscaped outside and luxury decor and amenities throughout. Professional Rental Permit #0515

Renovated North Fork getaway situated on a lush 5 acre property. The tranquil setting is perfect in all seasons. 3 beds, 2 baths, nursery/office, plenty of living space, chef's kitchen and close to all the North Fork has to offer. Walking distance to coveted Cedar Beach. North fork with a New England vibe.

This completely renovated and fully furnished home has been transformed with picturesque views from every window! Your main floor is entirely open concept with vineyard views in the front and water views in the back. This home sits on a shy acre at the end of Goose Creek with unparalleled views from your own private dock. Featuring four bedrooms and 2.5 bathrooms, including your primary suite with ensuite and balcony, this home is not to be missed. Other upgrades include a stunning floating modern staircase, indoor garden, Chef's Kitchen with quartz countertops, wraparound deck for incredible outdoor dining and more! Escape, relax and enjoy your North Fork retreat with all the vineyards, beaches, farms and more that the East End is known for!

This Incredible Home is Now Available for Off Season Rental from September 1, 2024 - March 31, 2025 and Memorial - Labor Day 2025. Set Creekfront with Private Dock and Associated Bay Beach Access in 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 with All High-End Appliances. 6 Burner Wolf Stove for Cooking. All Overlooking Dining, Living and Bar Area. All Utilities, Cleaning, Pool, Jacuzzi and Exterior Maintenance Provided by Landlord. Ample Parking. The Home Also Includes a Bocce Court, Ping-Pong and Shuffleboard Tables. All Prospective Tenants to Provide a Completed Application Via RentSpree. Link to be Provided. Rental Permit # 1180

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 with dramatic vaulted ceilings, fireplace and wet bar. A wall of oversized sliding glass doors allow for plenty of natural light and lead to a 2,000 sq. ft mahogany deck and heated gunite pool - ideal for comfort and relaxation. Two generously sized bedrooms and 1.5 baths complete the first floor. The second floor boasts an expansive primary suite with two walk-in closets and a luxurious bath including radiant heated floors, soaking tub, water closet, rain shower & body jets. Enjoy an early morning cup of coffee or star gaze in the evenings from your private water view balcony, making this room the perfect retreat. You will also find two additional bedrooms and two full baths on this floor. Enjoy all the North Fork has to offer and more with the deeded right of way that comes with this home which provides convenient access to sought-after McCabe's Beach! Kenney's Beach is also just a stone's throw away! Don't miss the opportunity to create a vacation to remember with this special home! Two-week terms are also available.

Historic Main Bayview schoolhouse converted to country residence located at 5650 N Bayview Road, Southold. Available for winter rental, September 3, 2024 - June 30, 2025 $3,900 per mo plus utilities, etc Country residence features 5 bedrooms in historic Main Bayview Schoolhouse converted to residence - sleeps max 10 people. Pet friendly. Equidistant to Cedar Beach and Goose Creek Beach. Moments to village of Southold, North Fork wine trail, area shops and top tier restaurants. An ideal vacation destination OR winter residence. Private fenced yard. Living room features woodstove. Finished lower level offers playspace or make it a home office. Rental Permit #0336

Sublime Sound front home overlooking miles of beachfront with stairs to private beach. Stunning views through floor to ceiling windows and spacious sound front backyard. Newly added in-ground pool with retractable cover. Fully furnished 4 bedrooms, 3.5 baths, both formal living room and family room have wood burning fireplaces. Fully finished basement. Tesla hook up in the garage. The best that the North fork has to offer.

Home is Where the Heart is. Charming Updated Cedar Shake Ranch on Paradise Shores Road with Deeded Beach Rights. Home Features Open Concept Kitchen, Living and Dining Room with 3 Bedrooms, 1 1/2 Bath. Lucky to be in paradise on Paradise Shores Road!

Introducing a charming and inviting year-round rental in the heart of Southold's beautiful Colonial Village, an exclusive 55 and up adult community. This newly renovated 1st-floor apartment offers the perfect blend of comfort and convenience, boasting freshly repainted walls, new floors, and a modern kitchen in pristine condition. Step inside to discover a spacious layout featuring 2 bedrooms, 1 bath, and a welcoming entryway that flows seamlessly into the cozy living room. The adjacent eat-in kitchen provides a delightful space for preparing meals and entertaining guests. Nestled within a serene and well-maintained community, this residence offers a peaceful retreat for those seeking a relaxed and maintenance-free lifestyle. Don't miss the opportunity to make Colonial Village your home and enjoy the best of 55+ living in Southold.

Planning a staycation? this Laughing Waters Association ranch is the perfect destination for a resort-style stay this year. Come experience the private bay beach, smell the salt air, and enjoy time boating/SUP/kayaking in the creek or try your luck clamming. The home is an easy and comfortable springboard to the North Fork lifestyle and features an open plan ideal for entertaining. Living room, Dining room, large kitchen to make the most serious cooks feel at home - plus an en suite bedroom with full bath and two additional bedrooms and full bath. Beyond the covered porch is a verdant and fully fenced in lawn area ideal for play, a bbq area, multiple sitting areas, a game room adjacent to the garage, a pool house with 'bar' area and the most amazing outdoor, poolside shower. No detail for enjoyment has been overlooked - there is even a firepit for idle-hour! Available monthly, or weekly - inquire. Pets permited - fully fenced in property! Southold RP# 1149 expires 6/10/26

Spacious Open Plan Home with So Much to Offer near Several Great Beaches. Open Livingroom, Dining Room, Kitchen, a Separate Den and a Separate Office as well as a Good Size Bedroom and Bath on First Floor. The Spacious Kitchen Offers Sub Zero Refrigerator, a Wine Fridge and a Separate Fridge Dedicated to Drinks You Grab on Way to Pool. Primary Ensuite and Two Bedrooms and Hall Bath on Second Floor. Finished Lower Level Family Room offers TV with Gaming Hookup and a Closet Full of Games to Enjoy. Fully Fenced Large Back Yard. Additional Separate Fencing around Inground Heated Pool with Easy Automatic Solar Cover and Pool House. Large Stone Patio for BBQing, Dining and Lounging and Lots of Open Backyard Grass Area to Play the Yard Games Provided or to Simply Star Gaze at Night. Room for All. Available Single or Multiple Months 10/13/24 to 4/30/25 at $8,000 Per Month. Pets Considered on Case by Case Basis. Permit #0913.

A North Fork Summer Time Oasis! Newly Renovated 4 Bedroom, 3 Bath Home with Heated Pool (20' x 42') and Near a Memorable Long Island Sound Beach. Marble Pool Surround Never Gets Hot. Additional Lower Level Living Room adjacent to the Wet Bar and Fridge Providing Easy Access for Pool Side Dining. Ice Machine, Gas Grill, Large Outdoor Sofa and Dining Table as Well as Lounges and Umbrellas. Everything You Need for Summer Time Fun. July $20,000; August to Labor Day $25,000. Also $5,000 per Week with Two Week Minimum. Permit #0987.

Lovely spacious newly built Colonial just down the lane from 4 gorgeous LI Sound Beaches. Main Floor Primary Bedroom En-suite with private side entrance and it's own deck. Second Primary Bedroom En-Suite on level 2 (has radiant heat floor and heat lamp). Two additional Bedrooms, a full Bath in the hall, and Laundry Room. Kitchen has huge island with seating, 6 burner or griddle dual fuel oven. Total 4 Bedrooms, 3.5 Baths, all hardwood floors, central air, patio, 2 decks. Amazing location just minutes to McCabes, Goldsmith, Kenneys, and Town Beach, as well as the great new beach side restaurant Little Fish. Fabulous Hamlet Downtown on Main Road with all your shopping needs, many more trendy restaurants, antique shops, art galleries, and vineyards with music. Enjoy the rental's paddle board, 2 kayaks, and beach buggy wagon. July $17,000, August to Labor Day $24,000, September $12,000.

Enjoy the Summer in this bright and airy cottage in Paradise Shores. Fully renovated, central air, vaulted ceilings, open floor plan and tons of natural light, this home is welcoming. Relax on the back deck after a day of fun in the sun. Private bay access one block away. Water views in the backyard. Rental Permit #0199

Welcome! The moment you lay eyes on this expansive property, you will feel as though you've arrived to live out the summer of your dreams. An incredible 3-acre property nestled two blocks from the beach with lots of quiet roads for running, biking and exploring. Throughout the grounds, there are many areas to relax and entertain, including a gorgeous pool area with Wi-Fi, surrounded by hydrangea with an 18x50 gunite heated saltwater pool; double outdoor showers; furnished patio; 3 pergolas; kitchen garden with raised beds and cutting flowers; shade garden; screened-in front porch; playhouse with loft; fire pit; and great lawn. The main house has been lovingly restored and features 3+ bedrooms, 2 bathrooms, a fireplace, den, library, and a fabulous farmhouse kitchen with central HVAC and modern amenities throughout. Surrounded by the North Fork's award-winning vineyards, marinas, renowned restaurants, farm stands, beaches and great shopping! Permit #1114

Southold, North Fork: Discover the epitome of easy living at Unit C "Baldwin T. Payne" in Southold, North Fork. This condo-like residence, part of the North Fork Resident's Inn, offers a one-of-a-kind opportunity to embrace a modern lifestyle in a historic setting. The unit boasts a spacious layout with direct garden access, abundant natural light, and contemporary furnishings. With upscale appliances (including gas range, refrigerator/freezer with ice maker, dishwasher, on-site laundry, and more), wide plank floors, and elegant marble touches, every detail has been carefully considered. The property is conveniently located near public transportation, quality shopping, parks, and beaches, making it an ideal choice for anyone seeking a convenient and comfortable living space. With flexible rates throughout the year (MD-LD $24k; June $6k; July $7500, Aug-LD $10k, Bal of Sept or October $5k; November through April $4k) and the possibility of bringing pets with landlord approval, this property is a standout option for those looking to vacation or settle into the North Fork lifestyle. Broker/Owner. Rental Permit #0171.

Rental Permit #0609 Enter a sanctuary of light and space in this beautifully designed home, where the grandeur of the Long Island Sound meets serene beachside living. As you enter, you're greeted by a stunning wall of windows that invites the outside in, setting a tranquil tone throughout the residence. The first floor offers three well-appointed bedrooms, including a master with en-suite bathroom with its own private deck accessed through sliding glass doors-an ideal retreat for morning coffees or evening relaxation. Two additional bedrooms have a full bathroom across the hall. Additionally, a separate laundry room provides practical utility without compromising on style. Ascend to the second floor and discover the heart of the home: an open concept living area that combines the living room, dining room, and a modern kitchen equipped with granite countertops and new stainless steel appliances. Cathedral ceilings with exposed wooden beams accentuate the feeling of openness, further enhanced by plentiful natural light and two sliding glass doors that lead out to an impressive 1,400 square foot wrap-around deck. Here, panoramic views of the Long Island Sound unfold in every direction, offering a breathtaking backdrop for entertaining or quiet reflection. Outside, the property is bordered by preserved land, ensuring unspoiled vistas and privacy. Just a direct half-mile down the street lies Kenney's Beach, a sandy beach, rare for the Long Island Sound that stretches for miles. Whether you are meandering east towards Horton's Point Lighthouse or west towards Goldsmith's Inlet, the journey is as captivating as the destination. The nearby 60-acre nature trail just down the beach invites leisurely exploration, enhancing the natural allure of the area. Perfect for those who cherish peace, privacy, and the unique beauty of coastal living, this home offers promising unforgettable sunsets and a tranquil lifestyle nestled in a coveted private beach community.

Spend Your Summer in this Cozy 2 Bedroom, 1 Bath, Fully Furnished Cottage. Available through October, 2024. Close to Beautiful North Fork Beaches and Parks. Close to Area Shops.

Escape to this 4 bedroom, 3 bath waterfront North Fork Retreat with expansive views across Hashamomuck to Peconic Bay. The back yard features a deck with private stairs leading down to the water, perfect for kayaking and paddle boarding. End the day entertaining around the fire or with a sunset stroll on your deeded Long Island Sound beach just a block away. Make this home your jumping point to enjoy the beaches, parks, restaurants, vineyards, farm stands, golf courses, and the many other activities the East End has to offer. The list is endless and is awaiting your arrival! Rental Permit #0477

Welcome to your perfect summer getaway located in the desirable Claves Neck neighborhood of Southold. This comfortable Ranch has ample space for the whole family to unwind and recharge after a day of exploring the North Fork. The home offers a fully equipped kitchen, spacious living, and dining rooms, three pleasant bedrooms, two pristine bathrooms. Outside, a savor al fresco dining amid the lush greenery surrounding the screened in porch and brick patio with outdoor dining area and gas BBQ. Whether you are hosting a barbecue with loved ones or simply enjoying a quiet moment, this outdoor oasis provides the perfect backdrop for making memories. Popular beaches, restaurants, and wineries are all close by. Do not miss your chance to experience the best of Southold living (Southold Town rental permit #49090) Available for 2 weeks @ $3000 per week.

Large and bright 4 bedroom, 2.5 bath home with pool in a private waterfront community. Property has path that brings you ten houses from the most beautiful beach. A great place to spend any season and year-round. Great open kitchen with table that seats 8. Adjacent to the dining room which can seat 10+. Host the holidays. Primary suite is oversized with a seating area and a separate sunroom. Upstairs are all of the guest rooms and a den. The property is just shy of 3 acres and offers plenty of room to roam. A great escape from the city, and a tranquil place from which to work. Available multiple time periods; any two available weeks in the summer $8k/week, July12- Aug 8 $30k, Sept.3-30 $25k, Oct. $20k, Nov. $20k, Winter Sept. 3- May 1 $48k, may be available year-round after Labor Day.

Direct waterfront North Fork farmhouse with private sandy beach on Southold Bay, part of the Peconic Estuary. Beautifully maintained, this large 4BR/ 2.55 BTH home benefits from many recent upgrades, including 2023 new chef's kitchen with waterviews over the hedges, renovated powder room, screened in front porch and lovely back deck with large and private garden and vineyard views. Fabulous indoor/ outdoor North Fork Summer Living in the mature gardens with specimen trees, waterfront, private sandy beach and vineyard views, and your private sugar sand beach to swim, kayak, paddle board, boat and fish. Close to all area attractions. Pet friendly! Walk to vineyards and organic farms for North Fork farm to table dining. Close to fine dining restaurants, farms, and waterfront bars. Fun arts, crafts, yoga, juice bar, live music and water sports, Southold, Greenport Maritime Village and ferries to Shelter Island, Sag Harbor and the South Fork all close by and easy to reach. Southold Town Rental Permit 0631

Introducing your brand-new summer retreat! Available from July 2024, this stunning 4-bedroom, 3.5-bathroom waterfront oasis boasts the pinnacle of luxury living. Nestled on West Creek in Southold. Enjoy exclusive access to Peconic Bay via your private dock, perfect for soaking up the summer sun. Spanning approximately 3500 square feet of impeccable interior space, revel in the elegance of oak floors, a luxurious soaking tub, and high ceilings throughout. The first floor offers two primary ensuites, a spacious Great Room with a cozy fireplace, a convenient laundry room, and 2.5 baths. Plus, a two-car garage ensures ample parking for all your summer adventures. Ascend to the second floor to discover two additional bedrooms, a full bath, a second laundry area, and a sprawling bonus room-ideal for entertaining guests or unwinding after a day of exploration. Central air conditioning ensures comfort on even the hottest summer days, while a full basement provides plenty of storage space for your beach gear. Outside is your private paradise, complete with a refreshing 16 x 32 in-ground pool, currently being readied for the summer. Situated in the coveted Southold Park District, relish in access to Founder Landing and South Harbor Park, along with proximity to pristine bay beaches, renowned vineyards, charming farmstands, premier shopping destinations, and convenient public transportation. Don't miss this unparalleled opportunity to experience the epitome of summer living and make memories to last a lifetime! Southold Town Rental Permit #1085.

New Construction with all high end finishes. First Floor Primary Suite. Three additional oversized bedrooms - all ensuite. 2 King beds, 2 Queen beds. Den/Office facing inground pool, Huge 2nd Fl Bonus Room, 5.5 Luxurious Baths. Every detail has been carefully considered and designed to accommodate multiple guests. Close to shopping, multiple parks, beaches, golf and fine dining. This is Truly an Entertainer's Delight!

Stunning new construction with 110' of Long Island Sound front and private stairs to your beach. 10ft ceilings throughout the first floor, open floor plan with panoramic views. The living room has an oversized fireplace, built in cabinets and coffered ceilings, glass doors that open directly to the patio. Viking full stainless steel appliance package, double dishwashers, gas stove with custom stainless hood, wine cooler and an oversized custom island with a built in microwave. 2 primary bedrooms one located on 1st floor with radiant heated floors in the bathroom, marble shower, free standing soaking tub, double custom vanity and a custom walk-in closet with illuminated hanging rods. Finished mud room & laundry room, powder room with gorgeous marble floors. Second floor features 3 bedrooms including another primary suite, full bath, a great room w/ a color changing LED fireplace. Full basement with BR&BA. This is a must see! Permit #: 1101