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

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366 Vacation rentals

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(4) Excellent 

21

Key West Vacation houseboat rental

Florida Keys / Key West

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Ocean view yacht with beautiful sunsets and sunrises. Underwater windows in the forward cabins makes this yacht unbelievable. Located in the finest most elegant first class member only marinas. Guests have access to private pool, tiki bar, fine dining restaurant and fre  …see more

from $405 / night

$2500 - $6650 / week

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from $405 / night

(37) 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 $329 / night

$2303 / week

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from $329 / night

(36) Excellent 

39

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

 …see more

from $340 / night

$2143 - $3800 / week

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from $340 / night

(33) 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

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from $259 / night

33

Florida Keys / Key West

Studio 6 Min stay varies

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

 …see more

from $228 / night

$1876 - $3836 / week

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from $228 / night

(4) Excellent 

53

Florida Keys / Key West

Studio 6 3 nights min

  • Studio
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $350 / night

$2250 - $2993 / week

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from $350 / night

(15) 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

26

Florida Keys / Key West

Studio 6 Min stay varies

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

 …see more

from $268 / night

$1876 - $3836 / week

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from $268 / night

(16) Very Good 

13

Florida Keys / Key West

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $169 / night

$1000 - $2500 / week

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from $169 / night

(4) Very Good 

20

Florida Keys / Key West

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly

 …see more

from $240 / night

$1600 / week

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from $240 / night

26

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 $108 / night

$896 - $1806 / week

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from $108 / night

(10) Very Good 

39

Florida Keys / Key West

Studio 8 Min stay varies

  • Studio
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

 …see more

from $348 / night

$2996 - $5586 / week

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from $348 / 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 $118 / night

$966 - $2226 / week

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from $118 / night

(14) Excellent 

52

Florida Keys / Key West

Studio 16 Min stay varies

  • Studio
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $798 / night

$5586 - $9716 / week

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from $798 / night

(3) Excellent 

30

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

$1176 - $2646 / week

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from $168 / 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

33

Florida Keys / Key West

Studio 6 Min stay varies

  • Studio
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Pet friendly

 …see more

from $398 / night

$2786 - $5586 / week

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from $398 / night

(4) Excellent 

25

Florida Keys / Key West

Studio 10 Min stay varies

  • Studio
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Pet friendly

 …see more

from $438 / night

$3346 - $5936 / week

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from $438 / night

34

Florida Keys / Key West

Studio 6 Min stay varies

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

 …see more

from $168 / night

$1526 - $2786 / week

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from $168 / night

(29) Very Good 

32

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 $208 / night

$1526 - $3136 / week

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from $208 / night

(25) 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

(1) Very Good 

10

Florida Keys / Key West

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Air conditioning
  • Private garden

 …see more

from $400 / night

$2800 / week

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from $400 / night

(4) Very Good 

33

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

$1176 - $2646 / week

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from $168 / night

(25) Very Good 

33

Florida Keys / Key West

Studio 4 Min stay varies

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

 …see more

from $188 / night

$1316 - $2716 / week

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from $188 / night

(2) Very Good 

31

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 $148 / night

$1176 - $2226 / week

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from $148 / night

(24) Very Good 

33

Florida Keys / Key West

Studio 6 Min stay varies

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

 …see more

from $228 / night

$1596 - $3136 / week

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from $228 / night

(22) Very Good 

23

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 $188 / night

$1526 - $2926 / week

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from $188 / night

(1) Excellent 

24

Florida Keys / Key West

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from $680 / night

$4760 / week

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from $680 / night

23

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

$1176 - $2506 / week

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from $148 / night

(3) Excellent 

22

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $275 / night

$1900 - $2400 / week

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from $275 / night

(2) Excellent 

29

Florida Keys / Key West

Studio 6 Min stay varies

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

 …see more

from $168 / night

$1526 - $2786 / week

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from $168 / night

(49) Very Good 

30

Florida Keys / Key West

Studio 8 Min stay varies

  • Studio
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

 …see more

from $398 / night

$2926 - $6286 / week

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from $398 / night

(79) Very Good 

15

Florida Keys / Key West

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $222 / night

$1485 - $2960 / week

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from $222 / night

(2) Very Good 

28

Florida Keys / Key West

Studio 6 Min stay varies

  • Studio
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning

 …see more

from $168 / night

$1526 - $2786 / week

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from $168 / night

(1) Very Good 

30

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 $198 / night

$1386 - $2786 / week

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from $198 / night

(48) Very Good 

27

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 $228 / night

$1666 - $3276 / week

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from $228 / night

27

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 - $2436 / week

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from $148 / night

28

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 $178 / night

$1246 - $2576 / week

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from $178 / night

26

Florida Keys / Key West

Studio 6 Min stay varies

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

 …see more

from $168 / night

$1526 - $2786 / week

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from $168 / night

37

Florida Keys / Key West

Studio 6 Min stay varies

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

 …see more

from $168 / night

$1526 - $2786 / week

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from $168 / night

1