Houses for Rent in Southold, NY

Enjoy the North Fork lifestyle in this fully furnished beach home just steps from South Harbor Beach and Park. Set on over an acre, this 2-bedroom, 1-bathroom ranch-style home offers a serene retreat. Paddleboard, kayak, or fish nearby, and relax in this peaceful setting. Available for seasonal rental with flexible lease terms from 1-6 months.

This delightful 3-bedroom, 2-bath cottage offers a relaxed, beachy vibe perfect for summer living. Spanning 1,000 sq. ft., it features bright interiors, cozy spaces, and a large back patio for effortless entertaining. Enjoy direct access to Goose Creek for kayaking and nearby sandy bays for relaxation. Embrace the North Fork lifestyle with farm stands, vineyards, and vibrant dining just moments away, making this cottage the ultimate summer retreat. Rental permit 1185.

This turn-key, contemporary home features 3 bedrooms and 2.5 baths, offering an ideal blend of modern living and coastal charm in a serene cul-de-sac. Expansive water views from the primary suite and two additional bedrooms enhance the light-filled interiors. Enjoy a spacious waterfront deck perfect for outdoor dining and morning coffee while embracing the best of North Fork living with easy access to Greenport and Southold.

This stunning 4-bedroom, 3-bath colonial home is just 500 feet from sandy bay beach, offering a perfect year-round or seasonal getaway. Enjoy a sunroom, balcony for morning coffee, outdoor shower, and a backyard deck with a gas grill. With bicycles and a kayak included, this beach house is ready for summer fun. Spacious at 2,700 sq ft, it blends comfort with coastal living, making it a fantastic choice for beach lovers.

Embrace serene living in this stunning 4-bedroom, 2-bath Scandinavian-style farm ranch, set on 2.5 acres of private woods. Built in 2022, the home features a grand open layout with vaulted ceilings and abundant natural light. The sleek kitchen overlooks an inviting living space with a flat-screen TV, while a covered patio and fenced saltwater pool provide outdoor enjoyment. Relax in the hot tub, and explore nearby Kenney’s Beach and local vineyards. Luxury living awaits!

Immaculate 5-bedroom, 2-bath home offers stunning Bay views and ample space for family and friends. Features include a sunroom, large backyard, and outdoor showerhouse. Enjoy easy access to nearby sandy beaches, fine dining, shopping, and local farm stands. Perfect for a fantastic North Fork vacation, this light-filled charmer is just moments from all the North Fork has to offer, combining comfort with convenience.

This beautifully maintained 3-bedroom, 3-bath home offers a perfect North Fork escape with access to private beaches. Enjoy summer afternoons by the large in-ground pool, or entertain on the expansive patio and gazebo. Indoor spaces are designed for relaxation, featuring a cozy living room with a fireplace and an updated kitchen with granite countertops. A serene wellness loft and a bonus room enhance this inviting home, just minutes from vineyards, farmstands, and waterfront dining.

Experience serene living in this cozy 2-bedroom, 1-bath bungalow by Great Pond. Enjoy stunning water views and easy access to Kenny's Beach and Little Fish. Perfect for kayaking, paddle boarding, and fishing, this retreat is centrally located to explore North Fork's farm stands, vineyards, and boutiques. Boasting 900 sq. ft. of comfort, this property is ideal for those seeking tranquility with an active outdoor lifestyle.

This delightful 2-bedroom, 1-bath cottage is perfectly situated on the edge of freshwater Great Pond, offering serene water views. Enjoy kayaking, paddle boarding, and fishing right from the backyard. A spacious deck provides the ideal spot for barbecues with breathtaking sunset vistas. Located just moments from Kenny's Beach and local dining gems, this charming retreat captures the essence of North Fork living, making it a perfect weekend escape or full-time haven.

This spacious 4-bedroom, 4.5-bath home features an open floor plan with two living areas, a chef’s kitchen, and a stylish dining table. The resort-style outdoor space is perfect for entertaining, boasting an inground pool with a built-in hot tub, a shaded dining area, and a convenient poolside half bath. Relax on the deck with stunning waterviews or enjoy the large screened porch. Just a short walk to Long Island Sound Beach, this North Fork summer retreat blends comfort with coastal living.

This stunningly renovated 4-bedroom, 3-bath Colonial home offers a spacious 2,900 sq. ft. layout featuring an open floor plan, cozy den, and versatile bonus room. The chef's kitchen is a highlight, featuring a large quartz island and top-tier Fisher & Paykel appliances. Enjoy multiple dining areas, a heated 18’ x 36’ pool, and beautifully landscaped grounds close to beaches and local attractions. A perfect blend of modern elegance and coastal charm awaits!

This superb 3-bed, 2-bath ranch home offers breathtaking water views near Goose Creek Beach. Its minimalist design provides a peaceful retreat, while the open layout seamlessly connects indoor and outdoor spaces. Enjoy activities like morning jogs, backyard barbecues, and sunset views, making it the perfect summer getaway. Flexible lease terms available.

This impressive 5-bedroom, 4-bath home offers a luxurious creekfront experience, complete with a private dock and Peconic Bay access. Designed for entertainment, it features two spacious living areas, a well-appointed kitchen with high-end appliances, and an extensive rear patio with an inground pool and jacuzzi. Enjoy a bocce court and gaming tables for fun-filled gatherings. Utilities, cleaning, and maintenance provided—experience ultimate convenience in this exquisite 3,700 sqft modern retreat.

Experience elevated coastal living in this stunning new construction home. This beautifully finished residence features 3 bedrooms, 4 bathrooms, and a completed lower level. Enjoy summer days by the heated in-ground pool or hosting in the outdoor kitchen and pool house. The meticulously landscaped grounds offer privacy, while direct access to a private creek invites kayaking and paddleboarding adventures. Ideal for memorable gatherings and relaxation in North Fork's luxurious summer atmosphere.

This spacious 4-bedroom, 3-bath residence offers a flexible open floor plan with a cozy den and office. The kitchen features a Sub Zero refrigerator and wine fridge, perfect for entertaining. Enjoy leisure in the finished lower-level family room equipped for gaming, and outdoors, the fully fenced yard boasts an in-ground heated pool with a convenient patio for dining and relaxation. Ample space for summer fun and stargazing awaits!

Stunning updates shine in this 1,400 sq ft retreat, featuring 2 bedrooms, 2 baths, and a convertible queen sofa bed. Enjoy outdoor dining, a fire pit, and an enclosed shower just steps from Kenney's Beach. Perfect for summer stays, this Southold haven invites relaxation and beachside strolls with every convenience at your fingertips.

This stunning 4-bedroom, 3.5-bath contemporary home spans 3,800 sq ft, featuring two luxurious ensuite bedrooms and charming Juliet balconies. The expansive backyard boasts an inground pool, ideal for entertaining and relaxation, along with a gazebo for shaded retreats. Located in Chardonnay Estates, this property is just minutes from the beautiful Sound beaches and the vibrant Greenport Village. Perfect for those seeking space, luxury, and privacy!

This beautifully renovated 4-bedroom, 3-bath ranch home encompasses 2,300 sq. ft. of vibrant living space featuring cathedral ceilings and a high-end kitchen. Enjoy the indoor-outdoor flow with a dining area and outdoor shower. Relax in the heated pool or take a short stroll to beautiful Goose Creek Beach, just 0.2 miles away. Perfect for family gatherings and close to local wineries, shopping, and dining. Summer 2025 is calling!

Embrace North Fork living in this fully furnished, beautifully decorated farmhouse with 3 bedrooms and 2 baths. Central air, hardwood floors, and a scenic deck overlooking a fenced yard make this home a perfect seasonal retreat. Enjoy a prime location a block from town amenities and nearby beaches. Available for flexible, short-term leases from November through October.

This delightful 3-bedroom, 1-bath home offers North Fork living with a bright and inviting layout. Just moments from Southold's shops, dining, and Founders Beach, it perfectly combines village charm with seaside access. Ideal for monthly or seasonal stays, enjoy the comfort of a well-located residence designed for relaxation and beachside fun. Embrace the essence of coastal living in this quaint retreat!

This mint-condition beach house features a serene ambiance, complemented by a stunning lagoon-style pool with a waterfall, hot tub, outdoor kitchen, and bar. It has 3 bedrooms and 2 baths, including a primary suite with spa-like amenities. Just steps to the association beach, surrounded by marinas, vineyards, and shopping, it's a perfect North Fork retreat.

This beautifully preserved 5-bedroom, 3-bath Colonial home boasts historic charm and modern comforts. Set along the serene banks of Goose Creek, it offers direct water access with a private dock for kayaking or fishing. Enjoy spacious open-concept living areas perfect for entertaining, complemented by a fabulous waterside pool and a generous yard. Wood floors and timeless architecture create a warm, inviting atmosphere in this unique retreat, making it ideal for family gatherings and leisurely living.

Enjoy versatile living in this 2,340 sq ft ranch-style home featuring four bedrooms and three full baths. The open floor plan includes two spacious living rooms and an updated kitchen with cast stone counters. The second-story deck overlooks a private yard, and hardwood floors create a warm upper level. Enhanced by amenities like central air, fireplace, and private laundry, this charming property offers comfort and convenience. A pet may be considered.

Discover a serene waterfront oasis in Southold, boasting 4 beds, 3.5 baths, high ceilings, and oak floors. Enjoy a private dock on West Creek, a 16x32 in-ground pool, and elegant primary ensuites on the first floor. A cozy fireplace enhances the spacious Great Room, and a sprawling bonus room awaits on the second floor. Close to bay beaches, vineyards, and restaurants, this retreat offers luxurious summer living.

Permit #493. Experience the charm of a newly renovated 4-bed, 2-bath farmhouse in Southold. Enjoy stunning sunrises over farm fields, explore local wineries, and relax in the heated saltwater pool. Features include a panoramic view, insulated doors, and hardwood floors. Flexible lease options. Utilities included. Perfect for summer and fall getaways on the North Fork.

This exquisite 8-bedroom, 7-bathroom home offers a perfect blend of relaxation and entertainment in a private beach community. Spanning 5,400 sq ft, it features a magnificent 20' x 40' heated saltwater pool and expansive living areas ideal for gatherings. Enjoy beach access, world-class wineries nearby, and modern amenities, including multiple climate zones and EV chargers. Perfect for 16 guests, this impeccably maintained property promises unforgettable memories by the water.

Impeccable ranch-style 3-bed, 2-bath home offering an open floor plan, vaulted ceilings, and quality finishes throughout. Enjoy a screened porch overlooking a private yard with a slate patio. Located in Harbor Lights with deeded beach access, it's close to beaches, wineries, and local shops. Available for July and August rentals at $15,000.

Nestled on an acre, this charming cedar log chalet offers a serene getaway with a heated saltwater pool and an elegant rustic vibe. Featuring 2 spacious bedrooms, a loft, and artistic craftsmanship throughout, the home includes a wrap-around porch, unique smokehouse, and two garages. Delight in proximity to a private beach, kayaking spots, and the North Fork's vibrant local offerings. Perfect for a secluded vacation escape.