Southold: Vacation Rental By Owner

Set on a magical one-acre promontory, jutting into beautiful Long Creek with spectacular water views from every room, this light and airy 4 bedroom, 2.5 bath... ...more

Completely updated three bedroom midcentury ranch. Eat-in kitchen with new appliances, living room with vaulted ceiling and brick fireplace, dining room, master... ...more

This stunning luxury home is everything you could possibly want in a vacation rental! -6 Bedrooms -4 Bathrooms -Huge 2 Acre Yard -Over sized pool with a built in... ...more

Charming 1920s farmhouse in the heart of Southold Village. Minutes drive to beaches, wineries and local village shops. Situated on just over a half acre, there is... ...more

Waterfront retreat in quiet, tree lined neighborhood. Enjoy Summer days out on the spacious wrap-around deck, go upsstairs to roof deck or relax inside in the sun... ...more

Pristine, spacious, oceanview home 5 minutes from the beach. Sunset view from every bedroom and living room, and deck with grill. 3 bedrooms with full size beds... ...more

Our creekside home is one of the best places to spend a summer on the North Fork of Long Island. Located steps from a sandy beach in a private community facing... ...more

Stunning waterfront home, on 2 private acres, in Paradise Point. Brand new renovation! All new baths, updated kitchen, new hardwood floors throughout. Room for... ...more

Three Bedroom, two bath house with full kitchen, big yard and screened in porch. Down the street from the beach. Near wineries, restaurants, town of Southold and... ...more

Our home is on a 10 acre private field surrounded by beaches, farms and local wineries. We have a large fenced pool with an outdoor shower, a fire pit, outdoor... ...more

Newly built home in Long Island wine county, near beaches, hiking and fine dining. Beautifully appointed interior with a sunny open floor plan and cook's... ...more

Guests are sure to enjoy a memorable vacation in this fully furnished, 5 bedroom/3.5 bath newly renovated expansive modern contemporary property. This property is... ...more

5 bedroom house, 200yds from beautiful sandy beach, 1.5 acres of lawn, 4 bikes, canoe, kayak, 2paddle boards, koi pond, heated pool, hot tub, 3 full baths,... ...more

This stunning house was built in the 1940's and recently renovated by the artist/designer owner. The 1.5 acre waterfront property lies at the end of a long dirt... ...more

Enjoy our tranquil home in the private beach community of Southold Shores. Located on a half acre of private land, this home has all the amenities you will need... ...more

Waterfront (with dock) beach house located on Goose Creek, Southold (North Fork, LI). This custom-built new construction (2014) 2,000 sq.ft. home exudes that... ...more

Newly renovated contemporary farmhouse. 4 bedrooms, 2 ½ baths, heated salt-water gunite pool. Open, light-filled floor plan. Central AC. New appliances including... ...more

Our home is a hidden gem tucked away in a beautiful and quiet neighborhood in Southold, NY. With beautiful water views and just steps from the beach, it is a... ...more

Contact owner for any special requests, bookings or monthly rentals. This house is beautifully decorated and comfortable, light and spacious with it's wooden... ...more

Welcome to our home. We are located in the historic Founders Landing Community of Southold, up the block from the pristine waters of the Peconic Bay. Founders... ...more