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Best Florida Keys Vacation rentals on Holiday Lettings - House rentals

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518 Vacation rentals

Marathon Shores Vacation home rental

Marathon Shores house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

from $287 / night

$1,718 - $4,809 / week

1 / 47

Vacation home in Big Pine Key

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 12

from $487 / night

$3,407 / week

1 / 40

Vacation apartment in Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $320 / night

$2,233 / 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

Ski home to rent in Marathon

Marathon house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $1,546 / night

$10,821 / week

1 / 42

Vacation apartment in Key Largo

Key Largo apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $401 / night

$2,404 / week

1 / 11

Islamorada Vacation home rental

Islamorada house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 14

from $516 / night

$3,607 / week

1 / 67

Vacation apartment in Key Largo

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $166 / night

$997 / week

1 / 48

Vacation villa rental

Marathon Shores villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $493 / night

$3,435 / week

1 / 14

Key Largo Vacation private room rental

Key Largo private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $115 / night

$687 / week

1 / 57

Marathon Shores Vacation home rental

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $2,045 / night

$14,313 - $22,442 / week

1 / 50

Vacation home in Marathon

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $216 / night

$1,507 / week

1 / 37

Vacation cottage in Key Largo

Key Largo cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from $373 / night

$2,233 - $2,682 / week

1 / 75

Vacation home with golf nearby in Marathon

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $659 / night

$4,609 / week

1 / 29

Key West Vacation condo rental

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $343 / night

$2,176 / week

1 / 13

Islamorada Vacation home rental

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from $982 / night

$5,725 - $8,015 / week

1 / 21

Vacation home in Key West

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from $1,144 / night

$8,007 / week

1 / 21

Vacation home in Marathon Shores

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $687 / night

$4,809 / week

1 / 25

Key Largo Vacation apartment rental

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $321 / night

$2,245 / week

1 / 30

Key West Vacation townhouse rental

Key West townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $393 / night

$2,748 / week

1 / 12

Townhouse rental in Key Largo

Key Largo townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from $745 / night

$5,210 / week

1 / 57

Apartment rental in Islamorada

Islamorada apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $287 / night

$1,775 / week

1 / 20

Key West Vacation apartment rental

Key West apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $172 / night

$1,203 / week

1 / 15

Vacation condo in Key Largo

Key Largo condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $330 / night

$2,309 / week

1 / 22

Tavernier Vacation apartment rental

Tavernier apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $298 / night

$2,084 / week

1 / 17

Vacation apartment in Key Largo

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $321 / night

$2,245 / week

1 / 30

Studio rental in Marathon

Marathon studio

  • Studio
  • 1 bathroom
  • sleeps 3

from $238 / night

$1,661 / week

1 / 9

Vacation condo in Marathon

Marathon condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from $303 / night

$2,119 / week

1 / 13

Villa rental in Islamorada

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $315 / night

$1,884 - $2,557 / week

1 / 44

Vacation townhouse in Key West

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $246 / night

$1,718 / week

1 / 9

Villa rental in Duck Key

Duck Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $338 / night

$2,365 / week

1 / 16

Vacation home in Summerland Key

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $332 / night

$2,325 / week

1 / 22

Vacation condo in Tavernier

Tavernier condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $252 / night

$1,764 / week

1 / 11

Vacation apartment rental

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $544 / night

$6,298 / week

1 / 49

Vacation apartment in Key Largo

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

from $258 / night

$1,712 - $8,800 / week

1 / 48

Vacation home with golf nearby in Grassy Key

Grassy Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $802 / night

$5,611 / week

1 / 33

Cottage rental in Key Largo

Key Largo cottage

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 4

from $252 / night

$1,764 / week

1 / 20

Vacation apartment in Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $343 / night

$2,397 / week

1 / 24

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 Sugarloaf

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $175 / night

$1,225 / week

1 / 19

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