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Best Florida Keys Vacation rentals on Holiday Lettings - House rentals

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549 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

Vacation villa rental

Marathon Shores villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $258 / night

$1,804 / week

1 / 13

Little Torch Key Vacation home rental

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $172 / night

$1,203 / week

1 / 13

Little Torch Key Vacation home rental

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $686 / night

$4,801 / week

1 / 25

Home rental in Marathon Shores

Marathon Shores house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $258 / night

$1,804 / week

1 / 13

Ramrod Key Vacation home rental

Ramrod Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $257 / night

$1,797 / week

1 / 19

Key West Vacation apartment accommodation

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $745 / night

$5,153 / week

1 / 43

Vacation home rental

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $384 / night

$2,684 / week

1 / 23

Home rental in Little Torch Key

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $172 / night

$1,202 / week

1 / 16

Cudjoe Key Vacation home rental

Cudjoe Key house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

from $790 / night

$5,531 - $7,134 / week

1 / 26

Vacation condo in Marathon

Marathon condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $153 / night

$1,068 / week

1 / 17

Vacation home in Summerland Key

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $297 / night

$2,077 / week

1 / 12

Vacation home in Little Torch Key

Little Torch Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $110 / night

$770 / week

1 / 12

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 Big Pine Key

Big Pine Key house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

from $129 / night

$899 / week

1 / 17

Vacation home in Ramrod Key

Ramrod Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $107 / night

$747 / week

1 / 11

Vacation home in Sugarloaf

Sugarloaf house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $177 / night

$1,237 / week

1 / 17

Vacation home in Summerland Key

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $160 / night

$1,120 / week

1 / 14

Vacation home in Sugarloaf

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $175 / night

$1,225 / week

1 / 19

Vacation home in Sugarloaf

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $234 / night

$1,634 / week

1 / 19

Vacation home in Summerland Key

Summerland Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $334 / night

$2,334 / week

1 / 18

Vacation home in Summerland Key

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $140 / night

$980 / week

1 / 18

Vacation apartment in Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $321 / night

$2,245 / week

1 / 24

Condo rental in Tavernier

Tavernier condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $171 / night

$1,140 - $1,712 / week

1 / 55

Vacation home in Ramrod Key

Ramrod Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $184 / night

$1,284 / week

1 / 12

Vacation home in Little Torch Key

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $207 / night

$1,447 / week

1 / 17

Vacation home in Cudjoe Key

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $140 / night

$980 / week

1 / 8

Little Torch Key Vacation home rental

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $159 / night

$1,109 / week

1 / 16

Vacation home in Little Torch Key

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $144 / night

$1,004 / week

1 / 15

Vacation home in Little Torch Key

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $160 / night

$1,120 / week

1 / 12

Vacation home in Cudjoe Key

Cudjoe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $100 / night

$700 / week

1 / 15

Vacation home rental

Key Colony Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

from $413 / night

$2,886 / week

1 / 21

Vacation home in Key Largo

Key Largo house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $573 / night

$4,008 - $4,809 / week

1 / 30

Vacation home in Key Colony Beach

Key Colony Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $1,145 / night

$8,015 - $11,450 / week

1 / 33

Vacation home in Ramrod Key

Ramrod Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $154 / night

$1,074 / week

1 / 15

Vacation home in Key West

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $339 / night

$2,373 / week

1 / 13

Vacation home in Big Pine Key

Big Pine Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $125 / night

$875 / week

1 / 16

Vacation home in Cudjoe Key

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $120 / night

$840 / week

1 / 14

Key Largo Vacation home rental

Key Largo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $275 / night

$1,924 / week

1 / 29

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

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