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.

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 beautifully renovated ranch offers a serene Sound front escape, perfect for year-round living or seasonal retreats. Spanning 1,400 sq. ft., this cottage-style home features an open concept design that showcases stunning views of the Long Island Sound from nearly every angle. With 3 bedrooms and 2 baths, complemented by hardwood floors, central air, and modern appliances, this property awaits personal touches to enhance its inviting charm.

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 immaculate 3-bedroom, 2-bathroom ranch home spans 1,450 sq ft and offers easy one-level living in Southold. With a welcoming front porch, spacious living areas featuring hardwood floors, and a cozy wood-burning fireplace, comfort abounds. Enjoy a large kitchen with stainless steel appliances, a primary ensuite, and a peaceful back deck overlooking a lovely yard. Benefit from a garage for storage, plus sandy beach access just down the road for a perfect North Fork getaway.

Experience luxury in this stunning new construction home featuring breathtaking water views and serene Long Island Sound sunsets. Spanning 3,600 sq. ft. on 1.5 private acres, this Colonial-style residence boasts a gourmet eat-in kitchen with high-end appliances, a spacious living room with vaulted ceilings and fireplace, and an expansive primary suite with a lavish bath and private balcony. Enjoy relaxing on the 2,000 sq. ft. mahogany deck with a heated gunite pool and nearby beach access.

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 beautiful 4-bedroom, 3-bath colonial home boasts 2,700 sq ft of lovely living space, just 500 feet from the beach. Features include a sunroom, a private balcony for morning coffee, an outdoor shower, and a backyard deck with a gas grill. Enjoy complimentary bicycles and a kayak for seaside adventures, making it an ideal beach getaway for the summer season!

This impressive 5-bedroom, 4-bath Mediterranean home boasts 3,700 sq ft of elegant living space, perfect for entertaining. Features include high-end appliances, large living areas, and expansive outdoor patios with a pool, jacuzzi, and private dock with Peconic Bay access. Enjoy fun activities with a bocce court and games galore! Utilities (except electric), cleaning, and maintenance are included for a hassle-free lifestyle.

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.

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 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.

This elegant 6-bedroom, 4-bathroom waterfront retreat offers 3,000 sq. ft. of contemporary living space designed for effortless coastal enjoyment. With serene views, a sparkling pool, and a private dock, ideal for kayaking or boating, this home is perfect for summer gatherings. Flowing indoor and outdoor spaces complement the tranquil setting, while proximity to North Fork vineyards and beaches enhances the experience of relaxed, sophisticated living.

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!

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!

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.

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.

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 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.

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.