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Vacation Rentals in Southold, New York

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about Southold

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Southold, New York vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Southold are added and updated every week!

Compared to hotels, Southold vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Southold, New York Vacation Rentals and Tourism

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Weekly rate:

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$2,000
$4,000+

Bedrooms: Min 0, Max 5

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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

North Fork Beach House
Southold House Rental Picture
  • bedrooms 3
  • community Southold Shores
  • rental type House
  • sleeps 7
  • baths 2
  • rates (USD) $170 - $315 /nt
    $500 - $2,200 /wk
 
 
 
 
 

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Luxury Wine Country Beach House for less than a Hotel Room
Southold House Rental Picture
  • bedrooms 3
  • community Southold Shores
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths 2
  • rates (USD) $228 - $350 /nt
    $1,600 - $2,400 /wk
 
 
 
 
 

57 reviews write a review

North Fork Lake House
Southold House Rental Picture
  • bedrooms 3
  • community
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $2,800 - $3,200 /wk
    $11,200 - $12,800 /mth
 
 
 
 
 

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Southold Soundfront Private Beach
Southold House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $400 - $475 /nt
    $3,300 /wk
    $12,750 /mth
 
 
 
 
 

6 reviews write a review

Charming 2BR in Heart of North Fork. Walk to Sandy Bay Beach
Southold House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $325 - $350 /nt
    $2,100 - $2,400 /wk
 
 
 
 
 

13 reviews write a review

Waterfront, pool, golf much more! August CANCELATION BOOK NOW!
Southold House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 12
  • baths
  • rates (USD) $250 - $1,500 /nt
    $9,000 /wk
 
 
 
 
 

127 reviews write a review

Fully Furnished Home, Heart Of Long Island Wine Country, Walk To Many Spots!
Southold House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 13
  • baths 3
  • rates (USD) $385 - $400 /nt
    $2,700 /wk
 
 
 
 
 

2 reviews write a review

Secluded Cottage on Lake - Walk to Sound Beach
Southold Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $200 - $250 /nt
    $1,500 /wk
 
 
 
 
 

38 reviews write a review

Town Harbor Lane, Founders Landing Beach, Southold, North Fork, LI, NY
Southold House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 5
  • baths 1
  • rates (USD) $228 - $315 /nt
    $1,599 - $2,200 /wk
    $6,000 /mth
 
 
 
 
 

1 reviews write a review

Beach Front in Southold; newly renovated/baths/kitchen/2nd floor family room!
Southold House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 2
  • rates (USD) $499 - $750 /nt
    $3,497 - $4,375 /wk
    $9,348 /mth
 
 
 
 
 

3 reviews write a review

Location Location, Charming Cottage, a block from beach, Town, close to Vineyars
Southold Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $257 - $600 /nt
    $6,500 - $12,000 /mth
 
 
 
 
 

9 reviews write a review

Lighthouse Inspired Lakefront Beach House, Overlooking LI Sound
Southold House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $257 - $350 /nt
    $1,800 /wk
    $6,000 /mth
 
 
 
 
 

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Waterfront Home/ Private Beachcommunity/ Heart of Wine Country
Southold House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 8
  • baths 2
  • rates (USD) $642 - $3,500 /wk
    $2,750 - $13,000 /mth
 
 
 
 
 

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Beach house in wine country; huge sun room, all new renovation,designer interior
Southold Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $295 - $475 /nt
    $1,800 - $3,200 /wk
 
 
 
 
 

6 reviews write a review

Sunny 4 Bed / 2 Bath Summer Home Steps from Private Beach
Southold House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $2,700 - $3,500 /wk
 
 
 
 
 

12 reviews write a review

Walk barefoot to the beach...
Southold Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • sleeps 8
  • baths 2
  • rates (USD) $150 - $800 /nt
    $1,800 /wk
    $5,000 - $12,000 /mth
 
 
 
 
 

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