Southold: Vacation Rental By Owner

Showing 20 Of 48 Vacation Rentals
  • Property-1 Image 1
    House $460 / Nightly
    • 4 Bed
    • 3 Baths
    • (6) Exceptional
    Southold, NY

    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

  • Property-2 Image 1
    House $480 / Nightly
    • 3 Bed
    • 1 Baths
    • (7) Exceptional
    Southold, NY

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

  • Property-3 Image 1
    House $1,361 / Nightly
    • 6 Bed
    • 5 Baths
    • (8) Wonderful
    Southold, NY

    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

  • Property-4 Image 1
    Farmhouse $343 / Nightly
    • 4 Bed
    • 2 Baths
    • (1) Exceptional
    Southold, NY

    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

  • Property-5 Image 1
    House Select Dates for Price
    • 3 Bed
    • 2 Baths
    • (1) Exceptional
    Southold, NY

    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

  • Property-6 Image 1
    House $400 / Nightly
    • 3 Bed
    • 4 Baths
    • (1) Exceptional
    Southold, NY

    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

  • Property-7 Image 1
    House $392 / Nightly
    • 5 Bed
    • 2 Baths
    Southold, NY

    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

  • Property-8 Image 1
    House Select Dates for Price
    • 6 Bed
    • 4 Baths
    Southold, NY

    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

  • Property-9 Image 1
    House Select Dates for Price
    • 3 Bed
    • 2 Baths
    Southold, NY

    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

  • Property-10 Image 1
    House $1,720 / Nightly
    • 6 Bed
    • 5 Baths
    Southold, NY

    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

  • Property-11 Image 1
    House $646 / Nightly
    • 4 Bed
    • 4 Baths
    Southold, NY

    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

  • Property-12 Image 1
    House $753 / Nightly
    • 5 Bed
    • 4 Baths
    • (3) Excellent
    Southold, NY

    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

  • Property-13 Image 1
    House $868 / Nightly
    • 5 Bed
    • 3 Baths
    • (1) Exceptional
    Southold, NY

    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

  • Property-14 Image 1
    House $847 / Nightly
    • 4 Bed
    • 4 Baths
    • (3) Exceptional
    Southold, NY

    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

  • Property-15 Image 1
    House Select Dates for Price
    • 3 Bed
    • 2 Baths
    • (13)
    Southold, NY

    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

  • Property-16 Image 1
    House $513 / Nightly
    • 4 Bed
    • 4 Baths
    • (2) Exceptional
    Southold, NY

    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

  • Property-17 Image 1
    House $557 / Nightly
    • 5 Bed
    • 3 Baths
    • (1) Exceptional
    Southold, NY

    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

  • Property-18 Image 1
    House $448 / Nightly
    • 3 Bed
    • 3 Baths
    • (1) Exceptional
    Southold, NY

    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

  • Property-19 Image 1
    House $719 / Nightly
    • 4 Bed
    • 3 Baths
    • (28) Exceptional
    Southold, NY

    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

  • Property-20 Image 1
    House $747 / Nightly
    • 4 Bed
    • 3 Baths
    • (18) Exceptional
    Southold, NY

    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

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Vacation Rental Filters are an easy way to help you personalize your search to find the ideal rental in Southold. Many accommodations in Southold provide "Non Smoking Only", there are 74, or there are 66 of Vacation Rentals in Southold with a "Children Welcome", there are also 58 with "Pets Not Allowed", which is another great reason to visit Southold.

We analyzed price data and rendered them in this graph, which shows vacation rental prices for the next twelve months in Southold. The most expensive month of the next 12 months is in June, where prices hit an average of $343 a night. In July, prices will hit an average low of $591 per night.