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  1. Waterfront, Pool, Golf, 5 Star
    Waterfront, Heated Pool, Golf, Elegance, Come for Celebrations and Holidays — Property 253123

    Vacation House rental in Southold area
    • House
    • 5 bedrooms , sleeps 10
    • 5 bathrooms
    • 1 half bathroom
    • beach, waterfront
    • daily maid service
    Rates (shown in USD)
    $2500 - $6250 per property per week

  2. Cute 2 Bedroom Apartment in Historic Home near town, beaches and vineyards (WBH) — Property 185644

    Vacation Apartment rental in Southold area
    • Apartment
    • 2 bedrooms , sleeps 5
    • 1 bathroom
    • beach, village
    • garden
    Rates (shown in USD)

  3. Waterfront House with Dock
    Charming Waterfront Home with Private Dock Close to Vineyards & Beaches — Property 237018

    Vacation House rental in Southold area
    • House
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • beach, waterfront
    • terrace
    Rates (shown in USD)
    $1490 - $1808 per property per week

  4. Lakefront Cottage, Walk to Beach, Hot Tub, Beautiful Sunsets — Property 115439

    Vacation House rental in Southold area
    • House
    • 2 bedrooms , sleeps 4
    • beach, waterfront
    • garden
    Rates (shown in USD)
    $1000 - $1500 per property per week

  5. The Southold Beach House
    Waterfront home with 480ft private beach and floating dock. — Property 16968

    Vacation rental in Southold area
    • 4 bedrooms , sleeps 8
    • 2 bathrooms
    • beach, waterfront
    • garden
    Rates (shown in USD)
    $1400 - $4750 per property per week

  6. Cute Cottage Apartment Near town, beaches and vineyards (WBH) — Property 174265

    Vacation Cottage rental in Southold area
    • Cottage
    • 2 bedrooms , sleeps 5
    • 1 bathroom
    • beach, village
    • pets considered
    Rates (shown in USD)
    $750 per property per week

  7. Water View Beach House with central AC located in Wine Country — Property 111053

    Vacation House rental in Southold area
    • House
    • 3 bedrooms , sleeps 7
    • 2 bathrooms
    • beach, resort
    • garden
    Rates (shown in USD)
    $1600 per property per week

  8. Secluded, 3 BR House Steps from Private Sound Beach — Property 221784

    Vacation House rental in Southold area
    • House
    • 3 bedrooms , sleeps 8
    • 2 bathrooms
    • satellite or cable
    • TV
    Rates (shown in USD)

  9. Old Bay Home
    Historic vineyard farmhouse with fabulous sandy bay beach — Property 235741

    Vacation Farmhouse rental in Southold area
    • Farmhouse
    • 4 bedrooms , sleeps 8
    • 1 bathroom
    • 2 half bathroom
    • beach, rural
    • garden
    Rates (shown in USD)
    $1800 - $3750 per property per week

  10. Deeded Bay Beach Home — Property 184107

    Vacation House rental in Southold area
    • House
    • 3 bedrooms , sleeps 6
    • 2 bathrooms
    • beach, rural
    • air-conditioning
    Rates (shown in USD)
    $1400 - $2000 per property per week

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