Houses for Rent in Southold, NY

Right in Southold, NY, this 4-bed, 4.5-bath house offers 3,100 sqft with an open floor plan and treetop water views. The resort-style backyard features an inground pool with hot tub, bluestone surround, and poolside kitchenette. Located just doors from a Long Island Sound beach and historic lighthouse, with hardwood floors and central air throughout.

Quietly set in Southold, NY, this new construction 3-bed, 3-bath house spans 1,800 sqft across two floors with hardwood throughout. The property features a heated in-ground pool, fully equipped pool house with bathroom, and outdoor kitchen for entertaining. Direct creek access allows kayak launches, while nearby South Harbor Beach adds classic North Fork appeal.

Right in Southold, NY, this colonial-style 4-bed, 3-bath house offers 2,900 sqft with an open floor plan and chef's kitchen featuring Fisher & Paykel appliances. The heated 18' x 36' pool sits on nearly an acre with multiple dining areas including a screened porch. A cozy den and bonus room provide work-from-home flexibility, while the quiet residential location puts you minutes from beaches, downtown shops, and local wineries.

Set in Southold, NY, this contemporary 4-bed, 2-bath house sits on 2.5 private wooded acres with saltwater pool and hot tub. The 2,000 sqft layout features vaulted ceilings, hardwood floors, and a sleek kitchen with large island. A fit for remote workers with quiet surroundings and natural light throughout. Utilities included, plus moments from beaches and North Fork vineyards.

Quietly set in Southold, NY, this newly renovated 2-bed, 2-bath house sits steps from popular Kenney's Beach. The 1,400 sqft cedar-frame layout features hardwood floors, central air, in-unit laundry, and dishwasher across two floors. Outdoor amenities include a fire pit, enclosed shower, and dining area perfect for beach getaways.

4-bed house in Southold, NY, featuring a renovated North Fork farmhouse with heated saltwater pool and detached pool house. The 2,000 sqft layout spans two floors with hardwood flooring, central air, and in-unit laundry. Multiple indoor/outdoor entertaining spaces, expansive lawn, and dramatic landscape lighting create resort-style living minutes from beaches and wineries.

In Southold, NY, this 3-bed, 3-bath townhouse in the Cedar Beach district offers water views from all bedrooms and access to a private neighborhood beach. The open-plan layout includes a kitchen, dining area, den/office, and living room with fireplace, plus sliding doors to a bluestone patio with gas grill. Easy access to North Fork wineries and farm stands.

Sitting in Southold, NY, this fully furnished 4-bed, 3-bath colonial house sits just 500 feet from sandy bay beach. The 2,700 sqft layout includes a sunroom, bedroom balcony, hardwood floors, and central air across two floors. Outside shower, gas grill, backyard deck, and garage parking complete the setup, with bicycles and kayak included. Utilities covered.

Quietly set in Southold, NY, this 3-bed, 3-bath house offers access to two private beaches in the exclusive Goose Bay Estates community. The 2,280 sqft layout features an updated kitchen with granite counters, fireplace, and sliding doors to a heated pool and outdoor cooking area. A second-floor balcony and wellness loft add space for relaxation, while the two-car garage and basement laundry provide convenience just minutes from North Fork vineyards and farmstands.

In Southold, NY, this ranch-style 3-bed, 2-bath house offers gorgeous water views and sits near Goose Creek Beach. The open layout features hardwood floors, central air, and a minimalist design that blends indoor and outdoor living spaces. With three parking spaces and outdoor space for entertaining, it's ideal for a summer getaway on the North Fork.

Sitting in Southold, NY, this renovated ranch-style house offers 4-bed, 3-bath living with cathedral ceilings and an open floor plan. The 2,300 sqft layout includes a high-end kitchen, dining area, hardwood floors, and central air. A heated pool and outdoor shower add seasonal appeal, with beautiful Goose Creek Beach just 0.2 miles away and local wineries minutes from the door.

Located in Southold, NY, this furnished 3-bed, 2-bath farmhouse offers a warm welcome on the North Fork with hardwood floors, central air, and a back deck overlooking a fenced yard. Just one block from town restaurants and shops, with numerous beaches nearby for exploring. Available for flexible seasonal stays from 2 weeks to 6 months.

Quietly set in Southold, NY, this ranch-style 3-bed, 1-bath house offers easy North Fork living moments from the village center. The 1,100 sqft layout features light-filled living spaces, dishwasher, in-unit laundry, and central air with a basement for storage. Close proximity to Founders Beach for swimming and sunsets, plus local shops and dining within walking distance.

House in Southold, NY, this Cape Cod-style 3-bed, 2-bath house sits steps from the association beach with a lagoon-style pool, waterfall, and hot tub. The outdoor kitchen and bar pair with a spa-like primary suite bathroom and hardwood floors throughout. Surrounded by award-winning vineyards, marinas, and farm stands.

Set in Southold, NY, this 4-bed, 3.5-bath waterfront house sits on West Creek with private dock access to Peconic Bay. The two-story layout features oak floors, high ceilings, dual primary suites on the first floor, and a great room with fireplace. Outside adds a 16x32 in-ground pool, 2-car garage, and full basement storage, with bay beaches and local vineyards nearby.

This 8-bed, 7-bath house in Southold offers 5,400 sqft with deeded beach access and a 20' x 40' heated saltwater pool on manicured grounds. The three-floor layout includes individually controlled climate zones, three EV chargers, and accommodates up to 16 guests. Minutes from North Fork wineries with flexible weekly lease terms and 14-day minimum stay.

Set in Southold, NY, this furnished 2-bed, 1-bath ranch-style house sits just 10 homes from South Harbor Beach and Park on an acre-plus setting. The fully furnished layout includes hardwood floors, in-unit laundry, dishwasher, and ductless heating for seasonal comfort. Beach access offers paddleboarding, kayaking, and fishing with expansive waterfront relaxation.

Set in Southold, NY, this ranch-style 3-bed, 2-bath house offers deeded beach access at the end of the street in Harbor Lights. The 1,750 sqft open floor plan flows from kitchen to vaulted ceiling living room, plus a screened porch overlooking a private backyard with slate patio and outdoor shower. Hardwood floors, central air, in-unit laundry, and prime location near wineries and town shops.

Right in Southold, NY, this 2-bed, 2-bath cedar log chalet offers 1,500 sqft with a heated saltwater pool and wrap-around porch. The open floor plan features hardwood floors, a loft bedroom, and master craftsman details throughout. Set on a private acre with attached 2-car garage plus detached garage, it's minutes from Cedar Beach and Peconic Bay for kayaking.