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

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124 Holiday homes

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Holiday home in Southold

Southold house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

from £509 / night

£3,560 / week

1 / 9

Ski home to rent in Southold

Southold house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £893 / night

£6,250 / week

1 / 30

Southold ski cottage to rent.

Southold cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £317 / night

£2,216 / week

1 / 22

Southold holiday home rental

Southold house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £840 / night

£5,877 / week

1 / 21

Southold ski cottage to rent.

Southold cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £368 / night

£2,575 / week

1 / 25

Southold holiday home rental

Southold house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

from £156 / night

£1,090 / week

1 / 15

Southold holiday cottage rental

Southold cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 3

from £139 / night

£971 / week

1 / 25

Holiday home in Southold

Southold house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from £363 / night

£2,541 / week

1 / 27

Holiday home rental

Southold house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £201 / night

£1,406 / week

1 / 15

Southold ski home to rent.

Southold house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £282 / night

£1,971 / week

1 / 16

Holiday cottage in Southold

Southold cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £226 / night

£1,581 / week

1 / 23

Holiday home in Southold

Southold house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £342 / night

£2,394 / week

1 / 21

Holiday home in Southold

Southold house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £380 / night

£2,659 / week

1 / 13

Holiday home in Southold

Southold house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £451 / night

£3,156 / week

1 / 30

Holiday home accommodation

Southold house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £242 / night

£1,693 / week

1 / 21

Southold holiday home rental

Southold house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £112 / night

£782 / week

1 / 7

Holiday home in Southold

Southold house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £493 / night

£3,450 / week

1 / 19

Southold holiday home let

Southold house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £319 / night

£2,230 / week

1 / 17

Southold holiday home rental

Southold house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

from £434 / night

£3,038 / week

1 / 30

Southold ski home to rent.

Southold house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

from £436 / night

£3,049 / week

1 / 28

Holiday home rental

Southold house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £445 / night

£3,111 / week

1 / 30

Holiday home in Southold

Southold house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £508 / night

£3,551 / week

1 / 22

Holiday cottage in Southold

Southold cottage

  • 4 bedrooms
  • 1 bathroom
  • sleeps 10

from £1,015 / night

£7,102 / week

1 / 18

Holiday home in Southold

Southold house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £319 / night

£2,230 / week

1 / 17

Holiday cottage rental

Southold cottage

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from £758 / night

£5,301 / week

1 / 30

Holiday home in Southold

Southold house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

from £516 / night

£3,608 / week

1 / 20

Southold ski home to rent.

Southold house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from £807 / night

£5,646 / week

1 / 20

Ski home to rent in Southold

Southold house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

from £371 / night

£2,592 / week

1 / 21

Southold holiday home rental

Southold house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £321 / night

£2,247 / week

1 / 30

Southold holiday home rental

Southold house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £297 / night

£2,078 / week

1 / 14

Holiday home in Southold

Southold house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £686 / night

£4,799 / week

1 / 30

Southold holiday home rental

Southold house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 8

from £596 / night

£4,167 / week

1 / 30

Southold holiday home rental

Southold house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

from £1,347 / night

£9,428 / week

1 / 30

Holiday home in Southold

Southold house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £556 / night

£3,890 / week

1 / 30

Southold ski home to rent.

Southold house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £441 / night

£3,088 / week

1 / 30

Holiday home in Southold

Southold house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £403 / night

£2,818 / week

1 / 30

Southold ski home to rent.

Southold house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £657 / night

£4,596 / week

1 / 11

Ski home to rent in Southold

Southold house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £503 / night

£3,518 / week

1 / 24

Holiday home in Southold

Southold house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £283 / night

£1,976 / week

1 / 14

Holiday home in Southold

Southold house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from £565 / night

£3,952 / week

1 / 30

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