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> Houses and condos in Southold

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

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£1 £750 -

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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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Great rentals within 20 miles that match your search

Home rental in Westhampton Beach

Westhampton Beach house

  • 8 bedrooms
  • 7 bathrooms
  • sleeps 18
3 reviews

from £1,602 / night

£11,209 / week

1 / 45

Great rentals within 20 miles that match your search

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Holiday villa in Southampton

Southampton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Pets allowed

from £818 / night

£5,725 / week

1 / 22

Great rentals within 20 miles that match your search

Westhampton Beach holiday home rental

Westhampton Beach house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

1 filter does not match: Pets allowed

4 reviews

from £1,100 / night

£7,695 / week

1 / 45

Great rentals within 20 miles that match your search

Holiday home in Southampton

Southampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

from £916 / night

£3,664 / week

1 / 5

Great rentals within 20 miles that match your search

Holiday home rental

Southampton house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

7 reviews

from £916 / night

£6,412 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday home in New London

New London house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 9

1 filter does not match: Pets allowed

1 review

from £265 / night

£2,107 - £2,474 / week

1 / 28

Great rentals within 20 miles that match your search

Holiday condo in Southampton

Southampton condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Pets allowed

from £393 / night

£2,748 / week

1 / 21

Great rentals within 20 miles that match your search

Bridgehampton holiday home rental

Bridgehampton house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Golf within 30mins drive

from £393 / night

£2,748 / week

1 / 4

Great rentals within 20 miles that match your search

Holiday home in Montauk

Montauk house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Pets allowed

from £825 / night

£5,771 / week

1 / 19

Great rentals within 20 miles that match your search

Holiday home with swimming pool in East Hampton

East Hampton house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

from £458 / night

£3,206 / week

1 / 13

Great rentals within 20 miles that match your search

Holiday home with golf nearby in East Hampton

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Golf within 30mins drive

from £2,016 / night

£11,450 / week

1 / 26

Great rentals within 20 miles that match your search

Holiday home in Southampton

Southampton house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

1 filter does not match: Pets allowed

from £1,374 / night

£9,618 / week

1 / 83

Great rentals within 20 miles that match your search

Holiday townhouse in Southampton

Southampton townhouse

  • 4 bedrooms
  • 10 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

from £118 / night

£823 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday home in Southampton

Southampton house

  • 4 bedrooms
  • 11 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

from £1,636 / night

£11,450 / week

1 / 18

Great rentals within 20 miles that match your search

Holiday manor house in Amagansett

Amagansett manor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

from £1,100 / night

£7,695 / week

1 / 24

Great rentals within 20 miles that match your search

Amagansett holiday home rental

Amagansett house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

from £1,047 / night

£7,328 / week

1 / 11

Great rentals within 20 miles that match your search

Home rental in Southampton

Southampton house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

1 filter does not match: Pets allowed

from £2,617 / night

£18,320 / week

1 / 16

Great rentals within 20 miles that match your search

East Hampton holiday home rental

East Hampton house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Pets allowed

1 review

from £786 / night

£5,496 / week

1 / 13

Great rentals within 20 miles that match your search

Home rental in Baiting Hollow

Baiting Hollow house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Golf within 30mins drive

1 review

from £641 / night

£4,482 / week

1 / 51

Great rentals within 20 miles that match your search

Montauk holiday manor house rental

Montauk manor house

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 10

1 filter does not match: Pets allowed

from £13,740 / night

£96,177 / week

1 / 30

Great rentals within 20 miles that match your search

Home rental in Hampton Bays

Hampton Bays house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 20

1 filter does not match: Pets allowed

from £975 / night

£6,824 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday farmhouse in East Hampton

East Hampton farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

from £871 / night

£6,092 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday home in Southold

Southold house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 filter does not match: Pets allowed

3 reviews

from £732 / night

£3,847 / week

1 / 32

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: Golf within 30mins drive

from £306 / night

£2,138 / week

1 / 16

Great rentals within 20 miles that match your search

Home rental in Sag Harbor

Sag Harbor house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

1 filter does not match: Golf within 30mins drive

from £916 / night

£6,412 / week

1 / 7

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 £344 / night

£2,290 / week

1 / 17

Great rentals within 20 miles that match your search

New Haven holiday home rental

New Haven house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Pets allowed

11 reviews

from £164 / night

£1,145 / week

1 / 19

Great rentals within 20 miles that match your search

Holiday home in Remsenburg

Remsenburg house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Golf within 30mins drive

5 reviews

from £642 / night

£2,886 / week

1 / 20

Great rentals within 20 miles that match your search

Hampton Bays holiday home rental

Hampton Bays house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Pets allowed

9 reviews

from £367 / night

£1,834 / week

1 / 17

Great rentals within 20 miles that match your search

Holiday home in Water Mill

Water Mill house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 13

1 filter does not match: Golf within 30mins drive

from £1,375 / night

£9,626 / week

1 / 14

Great rentals within 20 miles that match your search

Holiday home in Water Mill

Water Mill house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Pets allowed

1 review

from £623 / night

£4,580 / week

1 / 10

Great rentals within 20 miles that match your search

Holiday home in Westhampton Beach

Westhampton Beach house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 14

1 filter does not match: Pets allowed

1 review

from £1,200 / night

£8,400 / week

1 / 50

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 £367 / night

£2,565 / week

1 / 14

Great rentals within 20 miles that match your search

Holiday home in Westhampton

Westhampton house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 16

1 filter does not match: Pets allowed

1 review

from £916 / night

£6,412 / week

1 / 13

Great rentals within 20 miles that match your search

Holiday home with golf nearby in Baiting Hollow

Baiting Hollow house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

1 filter does not match: Golf within 30mins drive

5 reviews

from £229 / night

£1,466 / week

1 / 10

Great rentals within 20 miles that match your search

Holiday home in Hampton Bays

Hampton Bays house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 filter does not match: Pets allowed

5 reviews

from £1,100 / night

£7,328 - £8,610 / week

1 / 71

Great rentals within 20 miles that match your search

Holiday villa in Water Mill

Water Mill villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 10

1 filter does not match: Golf within 30mins drive

from £5,496 / night

£38,471 - £57,706 / week

1 / 20

Great rentals within 20 miles that match your search

Holiday home in East Hampton

East Hampton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Pets allowed

from £1,145 / night

£8,015 / week

1 / 12

Great rentals within 20 miles that match your search

East Quogue holiday home rental

East Quogue house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 filter does not match: Pets allowed

from £321 / night

£2,245 / week

1 / 12

Great rentals within 20 miles that match your search

Holiday home in Southampton

Southampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 filter does not match: Pets allowed

from £432 / night

£3,023 / week

1 / 17

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