Vacation Rentals by Owner

Southold Vacation Rentals Show this location only Back to top

•   Spectacular, Brand New North Fork Beach - Wine Country Home 5BR+/4BA – Sleeps 10 – Southold #324021
  8
  $300-$750/nt - $2000-$4000/wk

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•   Newly Renovated Colonial a Block from Beach & Close to Many Vineyards 4BR/2.5BA – Sleeps 8-10 – Southold #461019
  0
  Rates from $2900/wk - $13500/mo

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•   Charming Cottage a Block from Beach, Town, & Close to Vineyards 3BR+/1BA – Sleeps 6 – Southold #365948
  5
  Weekly from $2,000, Monthy from $7,500

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•   Beautiful House and Garden, Guest House and Pool 4BR+/3BA – Sleeps 4-6 – Southold #360292
  1
  $15,000.00

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•   Waterview 3 BR Luxury Beach House for Less Than a Hotel Room 3BR+/2BA – Sleeps 7 – Southold #12068
  49
  $1600- $2400/wk

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•   Southold Soundfront Private Beach 2BR+/1BA – Sleeps 4-6 – Southold #57035
  1
  $300 - $1500 per night 1 night min stay

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•   Beach Front in Southold; Newly Renovated/Baths/Kitchen/2nd Floor Family Room! 4BR/2BA – Sleeps 8-10 – Southold #340957ha
  3
  $100 - $686 per night

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•   Spectacular Contemporary Sound Front Beach House = Perfection 3BR/2BA – Sleeps 6 – Southold #171575
  12
  $2950/ November and December

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•   Enchanting Cottage and Cabin on Sound - Chic and Secluded 4BR+/3.75BA – Sleeps 7-8 – Southold #286118
  1
  $2,000-$6,000/wk - $6,000-$22,000/mo

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•   Charming Victorian Country Home: Near Beaches and Vineyards 3BR/2.5BA – Sleeps 6 – Southold #343817
  1
  From $7500 - $8500/mo. $2000 - $2300/wk U. S. Dollars

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•   Beautifully Restored Historic Country Home on Li Near Beaches 4BR/2.25BA – Sleeps 2-8 – Southold #403810
  0
  $1,200- $2,500/wk

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•   Waterfront Designer Luxury, Southold, Magnificent Views, 2 Beaches 3BR+/3BA – Sleeps 6-8 – Southold #304511
  1
  From $800/nt - $3,750/wk - $16,000/mo

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• Special offer Memorial Day Weekend Special May 24, 2013 to May 27, 2013
    Renovated Cottage in Private North Fork Beach Community 2BR+/1.5BA – Sleeps 5 – Southold #255932
  1
  $1600/wk

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•   Adorable, Renovated 1890's Farmhouse; Walk to Beaches & Town! 3BR/2BA – Sleeps 6 – Southold #368762
  6
  $1204 - $2400 per week 7 night min stay

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•   John Andrew's Boutique Cottage in the Heart of Wine Country 1BR/1BA – Sleeps 2-4 – Southold #425647
  1
  $200 - $250 per night 2 night min stay

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•   Sunny 4 Bed / 2 Bath Summer Home Steps from Private Beach 4BR/2BA – Sleeps 8 – Southold #397255
  7
  $2400 - $3000 per week 7 night min stay

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•   Southold Water Front Chalet 3BR+/2BA – Sleeps 2-8 – Southold #296774
  6
  $295 per night 2 night min stay

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•   Southold Waterfront Floating Dock Walk to Beach Boat Ramp 3BR+/2BA – Sleeps 10-12 – Southold #356134
  4
  $2500- $3000 wk

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•   Waterfront Paradise Awaits! Gorgeous, Spacious, Beachfront Home! 5BR+/4BA – Sleeps 14 – Southold #435533
  2
  $1200 per night 2 night min stay

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•   Gentle Sparkler - 5 BR 5BR+/2.5BA – Sleeps 8-10 – Southold #469580
  0
  $600 - $700 per night 2 night min stay

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•   Charming 2BR in Heart of North Fork. Walk to Sandy Bay Beach 2BR+/1BA – Sleeps 6 – Southold #329122
  10
  $315 per night 3-7 night min stay

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•   Secluded Cottage on Great Pond (Swim & Boat) Walk to Sound Beach 2BR/1.5BA – Sleeps 6 – Southold #426188
  27
  1,500/wk to 2,000/wk

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•   Ten Year Old Colonial in Laughing Waters. Has Central Ac. 3BR+/2.5BA – Sleeps 6-10 – Southold #359599
  0
  $300 per night 6 night min stay

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•   Charming Antique Farmhouse on Private Bayfront Beach 5BR/2.75BA – Sleeps 9 – Southold #226043
  0
  $20,000- $25,000/mo

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•   Beautiful Cape in Park District on North Fork 3BR/2BA – Sleeps 6 – Southold #461983
  0
  $195 - $255 per night 14-30 night min stay

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•   100 Acres, Water, Heated Pool, Golf, Gourmet Kitchen and More! 5BR+/5.5BA – Sleeps 10-12 – Southold #256774
  122
  From $250/nt $1500nt

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•   Secluded, 3 BR House Steps from Private Sound Beach 3BR+/2BA – Sleeps 8 – Southold #32629
  4
  From $275/nt - $2000/wk - $8000/mo

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•   Water View Summer Rental Cottage 3BR+/2BA – Sleeps 4 – Southold #186582
  3
  $1800-$2000/wk - $6000-$7500/mo. summer

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•   Long Island/North Fork Vacation - Get Away 4BR+/3BA – Sleeps 8-10 – Southold #293831
  13
  $3,000 to $4,000

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•   Walk Barefoot to the Beach... 3BR+/2BA – Sleeps 8 – Southold #459784
  0
  $400 - $600 per night 3 night min stay

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•   July and August Monthly Special!!! Contact Today 2BR+/2BA – Sleeps 3-9 – Southold #422156
  5
  $1500- $2000 per week, weekends $600-400

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•   Waterfront Home/ Private Beachcommunity/ Heart of Wine Country 3BR/2BA – Sleeps 7-8 – Southold #356226
  0
  From $3,000/wk

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•   Charming Cottage Long Island Sound Separate Studio. Pets Ok! 3BR+/1BA – Sleeps 5 – Southold #415114
  0
  2 weeks $5600 1 week $2850

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•   Fabulous Northfork Getaway with All Amenities and Comforts 3BR+/2.5BA – Sleeps 6-8 – Southold #106308
  0
  From $400/nt - $3600/wk - $14,000/mo US Dollars only.

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•   One Block from the Beach!! 3BR+/3.5BA – Sleeps 6-8 – Southold #397434
  0
  $400 per night 14 night min stay

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•   Jazz on the Vine 2/9-3/17 2013 Wine Fest Weekend Rentals 3BR/1.5BA – Sleeps 6 – Southold #144002
  3
  $200.00/nt

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•   Lakefront Beach Cottage One Block from Long Island Sound 3BR/0BA – Sleeps 6 – Southold #3023095ha
  0
  $133 - $214 per night

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•   Jazz on the Vine 2/9/13-3/17/13 Weekend Rates Available 2BR/1.5BA – Sleeps 4 – Southold #445033
  0
  $1475.00/'wk

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•   Luxury Diamond by the Bay 5BR/3BA – Sleeps 8-10 – Southold #473330
  0
  $3850 - $4900 per week 7 night min stay

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•   Cottage Nestled on a Gentle Hilltop 3BR/1BA – Sleeps 2-6 – Southold #432350
  0
  $1800/wk

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•   North Fork Waterfront Home - Lots of Room - Luxurious Comfort 5BR+/3.5BA – Sleeps 10 – Southold #335825
  1
  From $2000/wk to $30,000 summer season

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•   Paradise on the Bay! 6BR/5BA – Sleeps 12 – Southold #410632
  0
  From $70,000

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•   September Special! Spacious Cape, 2 Master Suites, 'Man-Cave', Private Backyard 4BR/3BA – Sleeps 4-8 – Southold #457522
  0
  Save 15%

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•   Charming 1840 School House on 2 Acres of Meadows, Beaches! Vineyards! Farmstand Studio/0BA – Sleeps 4-5 – Southold #476262
  0
  $200 per night 3-7 night min stay

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