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Best Florida Keys Vacation rentals on Holiday Lettings - House rentals

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473 Vacation rentals

Vacation apartment in Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $434 / night

$3,038 / week

1 / 17

Duck Key Vacation condo rental

Duck Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $327 / night

$2,285 / week

1 / 24

Vacation apartment in Key Largo

Key Largo apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $441 / night

$2,862 / week

1 / 11

Vacation villa in Big Pine Key

Big Pine Key villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $229 / night

$1,603 / week

1 / 7

Vacation condo in Tavernier

Tavernier condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $338 / night

$2,365 / week

1 / 63

Marathon Shores Vacation home rental

Marathon Shores house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

from $401 / night

$2,748 - $3,550 / week

1 / 55

Key Largo Vacation private room rental

Key Largo private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $115 / night

$687 - $722 / week

1 / 54

Vacation home in Marathon

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $212 / night

$1,598 - $2,216 / week

1 / 35

Home rental in Cudjoe Key

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $476 / night

$3,327 / week

1 / 32

Vacation home with golf nearby in Marathon

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $659 / night

$4,609 / week

1 / 29

Islamorada Vacation home rental

Islamorada house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $630 / night

$3,378 / week

1 / 43

Vacation home in Big Pine Key

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

from $423 / night

$2,958 / week

1 / 42

Key West Vacation home rental

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $430 / night

$3,006 / 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

Islamorada Vacation apartment accommodation

Islamorada apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $124 / night

$864 / week

1 / 25

Vacation home in Big Pine Key

Big Pine Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from $252 / night

$1,764 / week

1 / 32

Islamorada Vacation home rental

Islamorada house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $207 / night

$1,447 / week

1 / 25

Vacation condo in Tavernier

Tavernier condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $310 / night

$2,004 / week

1 / 18

Vacation apartment rental

Islamorada apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $100 / night

$700 / week

1 / 25

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

Cudjoe Key Vacation home rental

Cudjoe Key house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

from $687 / night

$4,809 - $6,092 / week

1 / 27

Home rental in Summerland Key

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $161 / night

$1,123 / week

1 / 15

Vacation home in Marathon Shores

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $458 / night

$3,206 / week

1 / 40

Islamorada Vacation villa rental

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $429 / night

$3,000 / week

1 / 23

Islamorada Vacation villa rental

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $429 / night

$3,000 / week

1 / 24

Vacation apartment with shared pool in Islamorada

Islamorada apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $94 / night

$654 / week

1 / 24

Islamorada Vacation villa rental

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $429 / night

$3,000 / week

1 / 25

Vacation apartment rental

Islamorada apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $134 / night

$934 / week

1 / 25

Home rental in Tavernier

Tavernier house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $201 / night

$1,403 / week

1 / 20

Vacation apartment in Islamorada

Islamorada apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $134 / night

$934 / week

1 / 25

Vacation apartment rental

Islamorada apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $110 / night

$770 / week

1 / 25

Vacation apartment in Islamorada

Islamorada apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $124 / night

$864 / week

1 / 21

Vacation home in Tavernier

Tavernier house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $250 / night

$1,750 / week

1 / 25

Apartment rental in Key West with shared pool

Key West apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $477 / night

$3,340 / week

1 / 38

Home rental in Islamorada

Islamorada house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $458 / night

$3,206 / week

1 / 15

Marathon Shores Vacation home rental

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $2,045 / night

$14,313 - $22,442 / week

1 / 75

Vacation condo in Marathon

Marathon condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from $271 / night

$1,894 - $7,150 / week

1 / 32

Vacation home with swimming pool in Tavernier

Tavernier house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $417 / night

$2,917 / week

1 / 25

Vacation apartment in Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $191 / night

$1,336 / week

1 / 35

Vacation apartment in Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $229 / night

$1,603 / week

1 / 41

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