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.

A 3,100 sq ft masterpiece, this 4-bed, 4.5-bath home features an open floor plan, an inground pool with hot tub, and a screened porch offering tranquil pool views. Just steps from Long Island Sound Beach and the Historic Lighthouse Museum and Park, enjoy the cozy wood-burning fireplace and seamless connectivity with good Wi-Fi. Ideal for short-term rentals, this versatile property offers both relaxation and adventure.

Experience the allure of North Fork in this stunning 4-bedroom, 5.5-bathroom contemporary home. With an open-concept living and dining area, the recently renovated kitchen is perfect for entertaining. The fabulous resort-style yard features a luxurious pool, ideal for enjoying sunny days. Comfort is emphasized with central air and multiple living spaces, ensuring family and guests feel at home. Conveniently located near farms, vineyards, and shopping, this is the ultimate getaway.

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!

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.

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.

Embrace the ultimate summer retreat in this expansive 4-bedroom, 4-bath home on a stunning lakefront. Spanning 4,000 sqft, it features an oversized patio, large heated pool, and a fully equipped gym. Enjoy fishing just steps from your door and close proximity to Kenny's Beach, marinas, and charming local farms and wineries. Perfect for making lasting memories in a tranquil, beautiful setting.

This beautifully renovated 4-bedroom, 3-bath Colonial offers an expansive layout featuring a cozy den and bonus room. The chef’s kitchen shines with a quartz island and top-tier Fisher & Paykel appliances. Ideal for gatherings, enjoy multiple dining areas, a heated 18' x 36' pool, and a lush yard on nearly an acre. Located on a tranquil street, this home is close to beaches and local hot spots, blending modern living with coastal charm.

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.

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.

Experience refined summer living in this chic 3-bedroom, 3-bath home in Southold. Nestled on serene grounds, the modern interior features a grand primary suite with spa bathroom and vaulted ceilings. Enjoy beach access nearby and a fenced backyard perfect for pets. Entertain on the spacious deck or unwind in the elegant living spaces. The property's layout offers both luxury and convenience near Goose Creek Beach.

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.

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.

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.

Nestled in a private beach community, this stunning new construction offers 8 bedrooms and 7 bathrooms across 5,400 sq. ft., making it perfect for group gatherings. Enjoy the heated saltwater pool and beach access, with nearby wineries and easy bike rides to local restaurants and shops. With deeded beach rights and EV chargers, it’s a dream for relaxation and entertaining alike. Flexible lease terms available.

Embrace the ultimate waterfront lifestyle in this stunning contemporary 3-bedroom, 2-bath home, featuring a first-floor master suite and breathtaking waterviews. Highlights include a newly built high-end kitchen, a heated saltwater pool, an enclosed outdoor shower, and your own dock for kayaking and fishing. With Goose Creek Beach just steps away, this property is perfect for enjoying sunsets and outdoor adventures year-round. Available May, June, and September to December.

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 custom-designed beach home features 4 bedrooms and 4 bathrooms within 2,082 sq ft, offering an open layout with vaulted ceilings. The chef's kitchen flows seamlessly to the dining and living areas, perfect for entertaining. An enclosed porch is ideal for barbecues while enjoying tranquil water views. Located a short walk from the community beach, with rental options for summer or offseason stays. Experience beach life in comfort and style.

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 by Great Pond, this charming 3-bedroom, 2-bathroom cottage offers serene water views and an expansive rear deck perfect for relaxation. Enjoy the bright 3-season room, captivating sunsets through the large bay window, and the short walk to Kenney's Beach for beachside dining. Witness local wildlife at your doorstep as osprey and ducks grace the pond. Embrace peaceful lakeside living in this delightful retreat!

This inviting 4-bedroom, 2.5-bath home spans 1,625 square feet, providing a perfect summer getaway. Enjoy exclusive beach rights and spacious living areas, making it ideal for relaxation. The well-appointed kitchen and ample storage enhance the comfort. Set in a serene location, this rental offers a wonderful balance of tranquility and access to local amenities, making it a prime choice for seasonal living.

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.

Experience serene North Fork living at this meticulously renovated 4-bed, 2-bath Cape Cod home. Nestled on a half-acre creekfront property, it offers privacy with direct water access. Enjoy your private dock, perfect for boating or kayaking to local fishing spots. Just minutes to charming downtown Southold for dining and shopping. Ideal for a summer escape, with space for entertaining or simply relaxing by the water.