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Best Florida Keys Vacation rentals on Holiday Lettings - House rentals

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6,648 Vacation rentals

Vacation condo in Key West

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $320 / night

$1,987 - $3,046 / week

1 / 20

Home rental in Marathon Shores

Marathon Shores house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $258 / night

$1,804 / week

1 / 13

Vacation boathouse with shared pool in Tavernier

Tavernier boathouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $252 / night

$1,489 - $2,691 / week

1 / 31

Vacation apartment in Key Largo

Key Largo apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $458 / night

$2,976 / week

1 / 11

Vacation home in Key West

Key West house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from $343 / night

$2,400 - $4,900 / week

1 / 32

Key Largo Vacation home accommodation

Key Largo house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $344 / night

$2,233 - $2,863 / week

1 / 22

Key West Vacation apartment rental

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $287 / night

$2,004 / week

1 / 69

Vacation condo in Key Largo

Key Largo condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $315 / night

$1,712 - $2,748 / week

1 / 31

Little Torch Key Vacation home rental

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $172 / night

$1,203 / week

1 / 13

Ramrod Key Vacation home rental

Ramrod Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $268 / night

$1,874 / week

1 / 19

Key West Vacation apartment accommodation

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $745 / night

$5,153 / week

1 / 50

Vacation apartment in Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $321 / night

$2,245 / week

1 / 24

Home rental in Cudjoe Key

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

from $621 / night

$5,267 - $6,870 / week

1 / 35

Vacation condo in Marathon

Marathon condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $153 / night

$1,068 / week

1 / 17

Key Largo Vacation home rental

Key Largo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $275 / night

$1,924 / week

1 / 29

Vacation caravan/mobile home in Key Largo

Key Largo caravan/mobile home

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $130 / night

$909 / week

1 / 6

Vacation home in Cudjoe Key

Cudjoe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $117 / night

$817 / week

1 / 15

Vacation condo with swimming pool in Key West

Key West condo

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from $315 / night

$2,205 / week

1 / 25

Vacation home in Ramrod Key

Ramrod Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $120 / night

$840 / week

1 / 11

Vacation home in Little Torch Key

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $150 / night

$1,050 / week

1 / 18

Vacation home in Cudjoe Key

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $144 / night

$1,004 / week

1 / 14

Vacation home rental

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $414 / night

$2,894 / week

1 / 23

Vacation home in Sugarloaf

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $204 / night

$1,424 / week

1 / 19

Vacation home in Sugarloaf

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $257 / night

$1,797 / week

1 / 19

Home rental in Little Torch Key

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $194 / night

$1,354 / week

1 / 16

Vacation home in Summerland Key

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $317 / night

$2,217 / week

1 / 12

Vacation home in Summerland Key

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $164 / night

$1,144 / week

1 / 18

Little Torch Key Vacation home rental

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $744 / night

$5,202 / week

1 / 25

Vacation home in Ramrod Key

Ramrod Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $217 / night

$1,517 / week

1 / 12

Vacation home in Cudjoe Key

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $160 / night

$1,120 / week

1 / 8

Vacation home in Little Torch Key

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $160 / night

$1,120 / week

1 / 15

Vacation apartment in Key West

Key West apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $573 / night

$4,008 / week

1 / 53

Vacation home in Tavernier

Tavernier house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

from $247 / night

$1,724 / week

1 / 41

Vacation home in Little Torch Key

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $189 / night

$1,319 / week

1 / 12

Vacation apartment in Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $382 / night

$2,672 / week

1 / 35

Vacation home in Sugarloaf

Sugarloaf house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $230 / night

$1,610 / week

1 / 17

Vacation home in Big Pine Key

Big Pine Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $140 / night

$980 / week

1 / 16

Vacation home in Big Pine Key

Big Pine Key house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from $147 / night

$1,027 / week

1 / 17

Vacation home in Summerland Key

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $197 / night

$1,377 / week

1 / 14

Vacation home in Little Torch Key

Little Torch Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $150 / night

$1,050 / week

1 / 8

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