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Best Florida Keys Vacation rentals on Holiday Lettings - House rentals

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715 Vacation rentals

Vacation home in Big Pine Key

Big Pine Key house

3 bedrooms • 2 bathrooms • sleeps 13

from $457 / night

$3,198 / week

1 / 30

Islamorada Vacation home rental

Islamorada house

4 bedrooms • 4 bathrooms • sleeps 10

from $573 / night

$4,580 / week

1 / 21

Vacation apartment in Key Largo

Key Largo apartment

2 bedrooms • 1 bathroom • sleeps 6

from $401 / night

$2,404 / week

1 / 11

Marathon Shores Vacation home rental

Marathon Shores house

2 bedrooms • 2 bathrooms • sleeps 7

from $315 / night

$2,205 / week

1 / 29

Vacation home in Marathon

Marathon house

2 bedrooms • 2 bathrooms • sleeps 6

from $114 / night

$794 - $2,519 / week

1 / 35

Villa rental in Islamorada

Islamorada villa

2 bedrooms • 2 bathrooms • sleeps 6

from $304 / night

$1,884 - $2,477 / week

1 / 44

Apartment rental in Key West

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 6

from $308 / night

$2,156 / week

1 / 22

Apartment rental in Key West

Key West apartment

1 bedroom • 1 bathroom • sleeps 6

from $343 / night

$2,397 / week

1 / 17

Marathon Shores Vacation home rental

Marathon Shores house

3 bedrooms • 2 bathrooms • sleeps 8

from $1,718 / night

$12,023 - $23,816 / week

1 / 50

Vacation apartment rental

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 6

from $516 / night

$3,246 / week

1 / 50

Vacation apartment in Key West

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 6

from $320 / night

$2,233 / week

1 / 17

Vacation apartment in Key Largo

Key Largo apartment

1 bedroom • 1 bathroom • sleeps 3

from $281 / night

$1,684 - $1,740 / week

1 / 66

Vacation home in Key West

Key West house

5 bedrooms • 4 bathrooms • sleeps 12

from $1,947 / night

$13,626 - $14,427 / week

1 / 58

Vacation yacht with shared pool in Key West

Key West yacht

3 bedrooms • 3 bathrooms • sleeps 7

from $1,946 / night

$12,590 / week

1 / 16

Vacation condo in Islamorada

Islamorada condo

2 bedrooms • 2 bathrooms • sleeps 4

from $229 / night

$1,603 / week

1 / 17

Islamorada Vacation home rental

Islamorada house

4 bedrooms • 4 bathrooms • sleeps 10

from $1,227 / night

$8,015 - $9,733 / week

1 / 32

Home rental in Islamorada

Islamorada house

3 bedrooms • 2 bathrooms • sleeps 8

from $458 / night

$3,206 / week

1 / 15

Home rental in Tavernier

Tavernier house

2 bedrooms • 2 bathrooms • sleeps 6

from $172 / night

$1,203 / week

1 / 28

Ski home to rent in Marathon

Marathon house

3 bedrooms • 2 bathrooms • sleeps 6

from $516 / night

$3,607 / week

1 / 42

Vacation home in Marathon Shores

Marathon Shores house

3 bedrooms • 2 bathrooms • sleeps 8

from $344 / night

$2,405 / week

1 / 42

Vacation condo rental

Islamorada condo

3 bedrooms • 2 bathrooms • sleeps 6

from $164 / night

$1,145 - $1,832 / week

1 / 35

Vacation apartment rental

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 6

from $516 / night

$3,607 / week

1 / 38

Vacation apartment in Key West

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 6

from $524 / night

$3,663 / week

1 / 25

Key West Vacation condo rental

Key West condo

1 bedroom • 1 bathroom • sleeps 2

from $172 / night

$1,203 / week

1 / 18

Matecumbe Key Vacation home rental

Matecumbe Key house

2 bedrooms • 2 bathrooms • sleeps 4

from $247 / night

$1,661 - $2,519 / week

1 / 19

Key West Vacation townhouse rental

Key West townhouse

2 bedrooms • 2 bathrooms • sleeps 4

from $393 / night

$2,748 / week

1 / 12

Home rental in Key Colony Beach with golf nearby

Key Colony Beach house

2 bedrooms • 2 bathrooms • sleeps 4

from $269 / night

$1,884 / week

1 / 86

Studio rental in Marathon

Marathon studio

Studio • 1 bathroom • sleeps 3

from $197 / night

$1,374 / week

1 / 9

Vacation home in Big Pine Key

Big Pine Key house

3 bedrooms • 3 bathrooms • sleeps 6

from $161 / night

$1,123 / week

1 / 17

Key Largo Vacation private room rental

Key Largo private room

1 bedroom • 1 bathroom • sleeps 2

from $121 / night

$722 / week

1 / 57

Key West Vacation apartment rental

Key West apartment

1 bedroom • 1 bathroom • sleeps 4

from $229 / night

$1,546 / week

1 / 69

Vacation villa with shared pool in Marathon

Marathon villa

3 bedrooms • 3 bathrooms • sleeps 8

from $424 / night

$2,966 / week

1 / 78

Vacation home in Cudjoe Key

Cudjoe Key house

3 bedrooms • 2 bathrooms • sleeps 6

from $140 / night

$980 / week

1 / 8

Vacation home in Little Torch Key

Little Torch Key house

2 bedrooms • 1 bathroom • sleeps 4

from $104 / night

$724 / week

1 / 12

Vacation apartment in Key Largo

Key Largo apartment

1 bedroom • 1 bathroom • sleeps 4

from $138 / night

$962 / week

1 / 22

Vacation home in Little Torch Key

Little Torch Key house

3 bedrooms • 2 bathrooms • sleeps 6

from $160 / night

$1,120 / week

1 / 8

Home rental in Summerland Key

Summerland Key house

2 bedrooms • 2 bathrooms • sleeps 6

from $161 / night

$1,123 / week

1 / 14

Vacation home with golf nearby in Marathon

Marathon house

4 bedrooms • 3 bathrooms • sleeps 10

from $745 / night

$5,210 / week

1 / 29

Vacation home in Big Pine Key

Big Pine Key house

2 bedrooms • 1 bathroom • sleeps 4

from $119 / night

$829 / week

1 / 16

Vacation condo in Marathon

Marathon condo

1 bedroom • 2 bathrooms • sleeps 4

from $270 / night

$1,890 / week

1 / 13

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