50 Best Key West Vacation rentals on Holiday Lettings - House rentals

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348 Vacation rentals

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33

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

 …see more

from $268 / night

$1876 - $4186 / week

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from $268 / night

20

Florida Keys / Key West

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

 …see more

from $128 / night

$896 - $1807 / week

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from $128 / night

(13) Excellent 

17

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Car not necessary
  • Air conditioning

 …see more

from $279 / night

$1953 / week

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from $279 / night

22

Florida Keys / Key West

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

 …see more

from $138 / night

$967 - $2226 / week

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from $138 / night

25

Florida Keys / Key West

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $168 / night

$1177 - $2506 / week

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from $168 / night

34

Florida Keys / Key West

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

 …see more

from $239 / night

$1667 - $3836 / week

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from $239 / night

(13) Excellent 

36

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $418 / night

$2927 - $5096 / week

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from $418 / night

(1) Very Good 

28

Florida Keys / Key West

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $148 / night

$1036 - $2437 / week

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from $148 / night

33

Florida Keys / Key West

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

 …see more

from $209 / night

$1457 - $3486 / week

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from $209 / night

(29) Very Good 

32

Florida Keys / Key West

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

 …see more

from $219 / night

$1526 - $3136 / week

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from $219 / night

(2) Excellent 

31

Florida Keys / Key West

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

 …see more

from $168 / night

$1177 - $2647 / week

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from $168 / night

28

Florida Keys / Key West

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

 …see more

from $178 / night

$1246 - $2577 / week

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from $178 / night

(23) Excellent 

14

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary

 …see more

from $249 / night

$1743 / week

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from $249 / night

(42) Very Good 

28

Florida Keys / Key West

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

 …see more

from $168 / night

$1177 - $2577 / week

Book View

from $168 / night

(25) Very Good 

33

Florida Keys / Key West

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning

 …see more

from $189 / night

$1317 - $2716 / week

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from $189 / night

29

Florida Keys / Key West

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $148 / night

$1036 - $2437 / week

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from $148 / night

(4) Excellent 

15

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $270 / night

$1875 / week

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from $270 / night

(4) Excellent 

25

Florida Keys / Key West

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Pet friendly

 …see more

from $479 / night

$3346 - $6147 / week

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from $479 / night

(33) Very Good 

14

Florida Keys / Key West

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary

 …see more

from $330 / night

$2304 / week

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from $330 / night

(1) Excellent 

28

Florida Keys / Key West

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning

 …see more

from $219 / night

$1526 - $3136 / week

Book View

from $219 / night

30

Florida Keys / Key West

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

 …see more

from $189 / night

$1317 - $2927 / week

Book View

from $189 / night

25

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

 …see more

from $219 / night

$1526 - $2787 / week

Book View

from $219 / night

31

Florida Keys / Key West

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $158 / night

$1107 - $2437 / week

Book View

from $158 / night

(2) Very Good 

28

Florida Keys / Key West

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

 …see more

from $168 / night

$1177 - $2226 / week

Book View

from $168 / night

(25) Very Good 

27

Florida Keys / Key West

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $199 / night

$1386 - $2927 / week

Book View

from $199 / night

(2) Very Good 

36

Florida Keys / Key West

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Pet friendly

 …see more

from $258 / night

$1807 - $3486 / week

Book View

from $258 / night

37

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

 …see more

from $219 / night

$1526 - $2787 / week

Book View

from $219 / night

27

Florida Keys / Key West

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

 …see more

from $128 / night

$896 - $1807 / week

Book View

from $128 / night

25

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $219 / night

$1526 - $2787 / week

Book View

from $219 / night

(30) Very Good 

33

Florida Keys / Key West

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $199 / night

$1386 - $2927 / week

Book View

from $199 / night

30

Florida Keys / Key West

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $199 / night

$1386 - $2787 / week

Book View

from $199 / night

(30) Very Good 

17

Florida Keys / Key West

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Car not necessary

 …see more

from $259 / night

$1813 / week

Book View

from $259 / night

26

Florida Keys / Key West

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Pet friendly

 …see more

from $168 / night

$1177 - $2647 / week

Book View

from $168 / night

28

Florida Keys / Key West

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $528 / night

$3696 - $6987 / week

Book View

from $528 / night

(1) Excellent 

29

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $219 / night

$1526 - $2787 / week

Book View

from $219 / night

(32) Very Good 

27

Florida Keys / Key West

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

 …see more

from $209 / night

$1457 - $3417 / week

Book View

from $209 / night

25

Florida Keys / Key West

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $178 / night

$1246 - $2437 / week

Book View

from $178 / night

(8) Very Good 

29

Florida Keys / Key West

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $178 / night

$1246 - $2787 / week

Book View

from $178 / night

(1) Very Good 

26

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning

 …see more

from $288 / night

$2016 - $4186 / week

Book View

from $288 / night

(2) Excellent 

32

Florida Keys / Key West

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from $321 / night

$2451 / week

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from $321 / night