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Best Florida Keys Vacation rentals on Holiday Lettings - House rentals

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524 Vacation rentals

Vacation condo in Key West

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $331 / night

$2,004 - $3,046 / week

1 / 20

Key Largo Vacation private room rental

Key Largo private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $172 / night

$1,031 - $1,074 / week

1 / 57

Vacation home in Key West

Key West house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from $343 / night

$2,400 - $4,900 / week

1 / 26

Vacation home in Sugarloaf

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $189 / night

$1,323 / week

1 / 23

Key West Vacation apartment rental

Key West apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $166 / night

$1,163 / week

1 / 15

Vacation apartment in Key Largo

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $228 / night

$1,425 - $1,718 / week

1 / 49

Vacation apartment in Key West

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $130 / night

$910 / week

1 / 16

Summerland Key Vacation home rental

Summerland Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $556 / night

$3,888 / week

1 / 25

Vacation home in Key Largo

Key Largo house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $630 / night

$3,607 / week

1 / 30

Little Torch Key Vacation home rental

Little Torch Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from $401 / night

$2,806 / week

1 / 55

Vacation home in Key West

Key West house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 12

from $2,119 / night

$14,828 / week

1 / 58

Key West Vacation apartment rental

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $296 / night

$2,068 / week

1 / 69

Vacation apartment in Key Largo

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $418 / night

$2,518 / week

1 / 12

Little Torch Key Vacation home rental

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $172 / night

$1,203 / week

1 / 13

Vacation home in Big Pine Key

Big Pine Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

from $258 / night

$1,804 - $2,806 / week

1 / 47

Vacation home in Big Pine Key

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from $218 / night

$1,523 / week

1 / 12

Vacation villa in Big Pine Key

Big Pine Key villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $344 / night

$2,405 / week

1 / 7

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 villa in Key Largo

Key Largo villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $229 / night

$1,603 - $2,205 / week

1 / 18

Vacation home in Cudjoe Key

Cudjoe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $100 / night

$700 / week

1 / 15

Vacation home in Big Pine Key

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

from $446 / night

$3,118 / week

1 / 41

Islamorada Vacation home rental

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from $982 / night

$5,725 / week

1 / 21

Vacation home in Little Torch Key

Little Torch Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $110 / night

$770 / week

1 / 12

Vacation home accommodation

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from $344 / night

$2,405 / week

1 / 25

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 condo in Key Largo

Key Largo condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $337 / night

$2,355 / week

1 / 22

Home rental in Little Torch Key

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $172 / night

$1,202 / week

1 / 16

Vacation townhouse with shared pool in Islamorada

Islamorada townhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from $602 / night

$2,233 / week

1 / 31

Vacation home in Cudjoe Key

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $140 / night

$980 / week

1 / 8

Key West Vacation condo rental

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $343 / night

$2,004 / week

1 / 13

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 Summerland Key

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $256 / night

$1,791 / week

1 / 13

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 Ramrod Key

Ramrod Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $107 / night

$747 / week

1 / 11

Vacation home in Little Torch Key

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $207 / night

$1,447 / week

1 / 17

Condo rental in Key West with shared pool

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $338 / night

$2,004 / week

1 / 13

Vacation home in Key Colony Beach

Key Colony Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $982 / night

$6,870 / week

1 / 33

Vacation apartment in Key Largo

Key Largo apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $458 / night

$2,976 / week

1 / 11

Vacation apartment in Key Largo

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $338 / night

$1,890 / week

1 / 21

Vacation home in Cudjoe Key

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $120 / night

$840 / week

1 / 14

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