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50 Best Florida Keys Vacation rentals on Holiday Lettings - House rentals

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725 Vacation rentals

Vacation condo in Key Largo

Key Largo condo

2 bedrooms • 2 bathrooms • sleeps 6

14 reviews

from $276 / night

$1,598 / week

1 / 17

Vacation apartment in Islamorada

Islamorada apartment

3 bedrooms • 2 bathrooms • sleeps 6

3 reviews

from $270 / night

$1,890 - $2,691 / week

1 / 32

Vacation yacht in Key West

Key West yacht

3 bedrooms • 3 bathrooms • sleeps 6

7 reviews

from $2,977 / night

$14,828 - $21,240 / week

1 / 70

Vacation apartment in Marathon

Marathon apartment

2 bedrooms • 2 bathrooms • sleeps 6

19 reviews

from $278 / night

$1,941 - $2,743 / week

1 / 37

Islamorada Vacation home rental

Islamorada house

4 bedrooms • 4 bathrooms • sleeps 10

13 reviews

from $1,227 / night

$8,015 - $9,733 / week

1 / 32

Vacation home in Islamorada

Islamorada house

3 bedrooms • 3 bathrooms • sleeps 8

3 reviews

from $1,718 / night

$12,023 / week

1 / 21

Marathon Shores Vacation home rental

Marathon Shores house

2 bedrooms • 2 bathrooms • sleeps 6

3 reviews

from $287 / night

$2,004 / week

1 / 27

Apartment rental in Islamorada

Islamorada apartment

2 bedrooms • 2 bathrooms • sleeps 4

from $287 / night

$1,775 / week

1 / 20

Vacation home in Marathon

Marathon house

2 bedrooms • 2 bathrooms • sleeps 6

3 reviews

from $310 / night

$2,164 / week

1 / 27

Townhouse rental in Key Largo

Key Largo townhouse

4 bedrooms • 4 bathrooms • sleeps 10

4 reviews

from $716 / night

$5,010 / week

1 / 57

Vacation condo in Marathon

Marathon condo

3 bedrooms • 2 bathrooms • sleeps 6

1 review

from $201 / night

$1,145 - $1,512 / week

1 / 40

Vacation home in Marathon

Marathon house

4 bedrooms • 3 bathrooms • sleeps 10

1 review

from $327 / night

$2,285 / week

1 / 49

Key West Vacation townhouse rental

Key West townhouse

2 bedrooms • 3 bathrooms • sleeps 6

1 review

from $572 / night

$4,000 / week

1 / 19

Vacation condo in Key West

Key West condo

2 bedrooms • 2 bathrooms • sleeps 6

4 reviews

from $458 / night

$3,149 - $3,206 / week

1 / 48

Vacation apartment in Islamorada

Islamorada apartment

1 bedroom • 1 bathroom • sleeps 4

3 reviews

from $201 / night

$1,403 / week

1 / 10

Islamorada Vacation home rental

Islamorada house

4 bedrooms • 3 bathrooms • sleeps 8

5 reviews

from $328 / night

$2,863 - $3,149 / week

1 / 35

Vacation home rental

Long Key house

3 bedrooms • 3 bathrooms • sleeps 8

from $328 / night

$2,290 - $3,149 / week

1 / 26

Vacation apartment rental

Key Largo apartment

2 bedrooms • 2 bathrooms • sleeps 4

38 reviews

from $331 / night

$2,170 / week

1 / 37

Vacation home in Duck Key

Duck Key house

3 bedrooms • 2 bathrooms • sleeps 9

4 reviews

from $602 / night

$4,208 / week

1 / 27

Islamorada Vacation home rental

Islamorada house

3 bedrooms • 2 bathrooms • sleeps 8

from $401 / night

$2,806 / week

1 / 43

Vacation cottage in Cudjoe Key

Cudjoe Key cottage

2 bedrooms • 2 bathrooms • sleeps 6

1 review

from $184 / night

$1,219 / week

1 / 11

Islamorada Vacation condo rental

Islamorada condo

2 bedrooms • 2 bathrooms • sleeps 6

7 reviews

from $207 / night

$1,523 / week

1 / 17

Cottage rental in Key Largo

Key Largo cottage

2 bedrooms • 4 bathrooms • sleeps 4

51 reviews

from $178 / night

$1,243 / week

1 / 20

Vacation home in Key Largo

Key Largo house

1 bedroom • 1 bathroom • sleeps 3

4 reviews

from $144 / night

$859 / week

1 / 11

Vacation apartment in Conch Key

Conch Key apartment

1 bedroom • 1 bathroom • sleeps 3

14 reviews

from $189 / night

$1,117 / week

1 / 19

Vacation apartment rental

Key West apartment

2 bedrooms • 2 bathrooms • sleeps 6

43 reviews

from $487 / night

$3,407 / week

1 / 38

Vacation studio in Marathon

Marathon studio

Studio • 1 bathroom • sleeps 2

2 reviews

from $229 / night

$1,203 - $1,374 / week

1 / 31

Vacation home with shared pool in Islamorada

Islamorada house

4 bedrooms • 4 bathrooms • sleeps 8

from $430 / night

$3,006 / week

1 / 65

Vacation condo in Tavernier

Tavernier condo

2 bedrooms • 2 bathrooms • sleeps 6

39 reviews

from $252 / night

$1,764 / week

1 / 11

Home rental in Key Largo

Key Largo house

4 bedrooms • 4 bathrooms • sleeps 10

from $573 / night

$4,008 / week

1 / 38

Marathon Vacation apartment rental

Marathon apartment

2 bedrooms • 2 bathrooms • sleeps 5

11 reviews

from $287 / night

$2,004 - $2,405 / week

1 / 24

Vacation home in Cudjoe Key

Cudjoe Key house

3 bedrooms • 3 bathrooms • sleeps 6

from $196 / night

$1,375 / week

1 / 13

Vacation apartment in Key West

Key West apartment

1 bedroom • 1 bathroom • sleeps 2

2 reviews

from $331 / night

$2,317 / week

1 / 16

Matecumbe Key Vacation home rental

Matecumbe Key house

2 bedrooms • 2 bathrooms • sleeps 4

7 reviews

from $247 / night

$1,661 - $2,519 / week

1 / 19

Key West Vacation home rental

Key West house

2 bedrooms • 2 bathrooms • sleeps 6

from $480 / night

$3,359 / week

1 / 14

Vacation apartment in Islamorada

Islamorada apartment

2 bedrooms • 2 bathrooms • sleeps 4

6 reviews

from $124 / night

$864 / week

1 / 21

Marathon Vacation home accommodation

Marathon house

4 bedrooms • 3 bathrooms • sleeps 10

23 reviews

from $866 / night

$4,918 - $7,323 / week

1 / 45

Islamorada Vacation home rental

Islamorada house

2 bedrooms • 2 bathrooms • sleeps 4

from $156 / night

$1,088 - $1,718 / week

1 / 13

Vacation villa in Marathon

Marathon villa

3 bedrooms • 3 bathrooms • sleeps 8

7 reviews

from $1,145 / night

$8,015 / week

1 / 42

Vacation apartment in Marathon

Marathon apartment

3 bedrooms • 2 bathrooms • sleeps 8

9 reviews

from $373 / night

$2,233 / week

1 / 33

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