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Holiday Lettings
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> Houses and condos in Southold

Houses in Southold and Condos - Holiday Lettings - Holiday Rentals Southold

Price per night

£1 £750 -

Bedrooms

Property rating (out of 5)
  • 5
  • 4 and above
  • 3 and above
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Filtered properties are rated either by Tripadvisor Vacation Rentals users, or by Vrbo users. Both rating systems are separate, and are depicted differently as shown in the key above. Tripadvisor performs checks on its reviews. Holiday Lettings and companies under Tripadvisor Group do not check Vrbo reviews.
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Under 5s
Pets allowed

Great rentals within 20 miles that match your search

Home rental in Sag Harbor

Sag Harbor house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

from £915 / night

£6,400 / week

1 / 7

Great rentals within 20 miles that match your search

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Holiday home in Greenport

Greenport house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Pets allowed

from £327 / night

£2,286 / week

1 / 18

Great rentals within 20 miles that match your search

Holiday home letting

Southold house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Pets allowed

4 reviews

from £343 / night

£2,286 / week

1 / 17

Great rentals within 20 miles that match your search

Holiday apartment in Greenport

Greenport apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Pets allowed

from £366 / night

£2,560 / week

1 / 14

Great rentals within 20 miles that match your search

Holiday home in Greenport

Greenport house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Under 5s

from £305 / night

£2,134 / week

1 / 16

Great rentals within 20 miles that match your search

Shelter Island holiday home rental

Shelter Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

from £849 / night

£5,943 / week

1 / 19

Great rentals within 20 miles that match your search

Holiday home in Greenport

Greenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Pets allowed

from £422 / night

£2,951 / week

1 / 13

Great rentals within 20 miles that match your search

Noyack holiday home rental

Noyack house

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 10

1 filter does not match: Pets allowed

from £1,219 / night

£8,534 / week

1 / 10

Great rentals within 20 miles that match your search

Home rental in Southold

Southold house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

1 filter does not match: Pets allowed

from £342 / night

£1,756 / week

1 / 21

Great rentals within 20 miles that match your search

Holiday home in Greenport

Greenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 filter does not match: Pets allowed

from £543 / night

£3,800 / week

1 / 33

Great rentals within 20 miles that match your search

Greenport holiday home rental

Greenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

from £730 / night

£5,109 / week

1 / 22

Great rentals within 20 miles that match your search

Peconic holiday cottage rental

Peconic cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 filter does not match: Pets allowed

from £235 / night

£1,424 - £3,341 / week

1 / 63

Great rentals within 20 miles that match your search

Holiday home in Southold

Southold house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 filter does not match: Pets allowed

from £239 / night

£1,457 - £3,215 / week

1 / 49

Great rentals within 20 miles that match your search

Holiday home in Southold

Southold house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Pets allowed

from £271 / night

£1,651 - £4,308 / week

1 / 46

Great rentals within 20 miles that match your search

Southold holiday home rental

Southold house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Pets allowed

from £179 / night

£1,252 - £4,903 / week

1 / 31

Great rentals within 20 miles that match your search

Holiday home in Southold

Southold house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Pets allowed

from £316 / night

£1,901 - £5,014 / week

1 / 33

Great rentals within 20 miles that match your search

Holiday home in Southold

Southold house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

1 filter does not match: Pets allowed

from £1,968 / night

£4,700 - £8,295 / week

1 / 36

Great rentals within 20 miles that match your search

Holiday home in Shelter Island Heights

Shelter Island Heights house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Pets allowed

from £479 / night

£3,354 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday cottage in Southold

Southold cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Pets allowed

from £268 / night

£1,873 / week

1 / 30

Great rentals within 20 miles that match your search

Ski cottage to rent in Greenport

Greenport cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Pets allowed

from £270 / night

£1,890 / week

1 / 30

Great rentals within 20 miles that match your search

Ski home to rent in Sag Harbor

Sag Harbor house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

1 filter does not match: Pets allowed

from £823 / night

£5,757 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday home in Greenport

Greenport house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Pets allowed

from £223 / night

£1,560 / week

1 / 24

Great rentals within 20 miles that match your search

Cottage rental in Peconic

Peconic cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Pets allowed

from £396 / night

£2,767 / week

1 / 30

Great rentals within 20 miles that match your search

Holiday home in Shelter Island Heights

Shelter Island Heights house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Pets allowed

from £463 / night

£3,237 / week

1 / 24

Great rentals within 20 miles that match your search

Ski cottage to rent in Peconic

Peconic cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

1 filter does not match: Pets allowed

from £220 / night

£1,537 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday apartment in Greenport

Greenport apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Pets allowed

from £304 / night

£2,124 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday home in Greenport

Greenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: Pets allowed

from £418 / night

£2,924 / week

1 / 30

Great rentals within 20 miles that match your search

Cottage accommodation in Southold

Southold cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 filter does not match: Pets allowed

from £1,649 / night

£11,542 / week

1 / 30

Great rentals within 20 miles that match your search

Sag Harbor ski home to rent.

Sag Harbor house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 filter does not match: Pets allowed

from £456 / night

£3,186 / week

1 / 16

Great rentals within 20 miles that match your search

Greenport holiday home rental

Greenport house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Pets allowed

from £707 / night

£4,947 / week

1 / 19

Great rentals within 20 miles that match your search

Holiday home in Greenport

Greenport house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

1 filter does not match: Pets allowed

from £991 / night

£6,931 / week

1 / 30

Great rentals within 20 miles that match your search

Southold ski home to rent.

Southold house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Pets allowed

from £306 / night

£2,141 / week

1 / 16

Great rentals within 20 miles that match your search

Holiday cottage in Greenport

Greenport cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

from £559 / night

£3,913 / week

1 / 30

Great rentals within 20 miles that match your search

Ski home to rent in Southold

Southold house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

from £719 / night

£5,031 / week

1 / 30

Great rentals within 20 miles that match your search

Southold ski home to rent.

Southold house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 filter does not match: Pets allowed

from £400 / night

£2,795 / week

1 / 29

Great rentals within 20 miles that match your search

Home rental in Greenport

Greenport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Pets allowed

from £773 / night

£5,405 / week

1 / 30

Great rentals within 20 miles that match your search

Shelter Island Heights holiday home rental

Shelter Island Heights house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Pets allowed

from £360 / night

£2,516 / week

1 / 21

Great rentals within 20 miles that match your search

Holiday cottage in Cutchogue

Cutchogue cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Pets allowed

from £228 / night

£1,593 / week

1 / 18

Great rentals within 20 miles that match your search

Greenport ski apartment to rent.

Greenport apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Pets allowed

from £320 / night

£2,236 / week

1 / 24

Great rentals within 20 miles that match your search

Home rental in Cutchogue

Cutchogue house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

from £368 / night

£2,572 / week

1 / 10

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