Key West apartment or villa with a private pool area | Holiday Lettings

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50 Holiday homes

Filters applied: Private pool (51)

Travellers going to Key West are booking December dates now. Secure your holiday home today and have the perfect trip.

(1) Very Good 

24

Luxury house rental Key West - Key West house sleeps 8

Florida Keys / Key West

3 8 30 nights min

  • 3 bedrooms
  • Sleeps 8
  • 30 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
28 DAY MINIMUM STAY IS MANDATED BY COUNTY LAW. PLEASE DO NOT SEND ENQUIRIES FOR SHORTER PERIODS!! Charted back in the 1800's, Shark Key was named by early explorers for its shark-like shape. This exclusive island boasts more than 2 miles of pristine shoreline, lush  …see more

from £216 / night

£1509 / week

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from £216 / night

(22) Very Good 

27

Florida Keys / Key West

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £177 / night

£1097 - £2493 / week

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from £177 / night

(26) Very Good 

22

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £139 / night

£808 - £1755 / week

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from £139 / night

24

Florida Keys / Key West

5 18 14 nights min

  • 5 bedrooms
  • Sleeps 18
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £731 / night

£5116 / week

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from £731 / night

44

Florida Keys / Key West

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Swimming pool

 …see more

from £539 / night

£3770 / week

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from £539 / night

(3) Excellent 

30

Florida Keys / Key West

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £604 / night

£4077 - £8795 / week

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from £604 / night

(25) Very Good 

28

Florida Keys / Key West

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £481 / night

£3204 - £6441 / week

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from £481 / night

(2) Excellent 

24

Florida Keys / Key West

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £511 / night

£3577 - £8143 / week

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from £511 / night

(27) Very Good 

32

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £174 / night

£1116 - £2426 / week

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from £174 / night

(35) Very Good 

23

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £204 / night

£1212 - £2437 / week

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from £204 / night

(84) Very Good 

24

Florida Keys / Key West

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £358 / night

£2385 - £4924 / week

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from £358 / night

(25) Very Good 

31

Florida Keys / Key West

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £227 / night

£1539 - £3987 / week

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from £227 / night

(11) Very Good 

29

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £174 / night

£1039 - £2314 / week

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from £174 / night

24

Florida Keys / Key West

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £170 / night

£1050 - £2140 / week

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from £170 / night

(25) Very Good 

28

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £158 / night

£950 - £2175 / week

Enquire View

from £158 / night

(10) Excellent 

25

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £204 / night

£1212 - £2437 / week

Enquire View

from £204 / night

(27) Very Good 

24

Florida Keys / Key West

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £166 / night

£943 - £2002 / week

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from £166 / night

(11) Very Good 

32

Florida Keys / Key West

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £170 / night

£1050 - £2140 / week

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from £170 / night

(34) Very Good 

25

Florida Keys / Key West

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £200 / night

£1250 - £2827 / week

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from £200 / night

(52) Excellent 

27

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £147 / night

£1077 - £2314 / week

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from £147 / night

(36) Very Good 

20

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £204 / night

£1212 - £2437 / week

Enquire View

from £204 / night

(28) Very Good 

24

Florida Keys / Key West

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £124 / night

£720 - £1779 / week

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from £124 / night

(54) Very Good 

25

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £262 / night

£1697 - £3798 / week

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from £262 / night

(6) Very Good 

33

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £289 / night

£1731 - £3039 / week

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from £289 / night

(11) Very Good 

27

Florida Keys / Key West

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £235 / night

£1462 - £2984 / week

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from £235 / night

(15) Very Good 

27

Florida Keys / Key West

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £216 / night

£1404 - £3067 / week

Enquire View

from £216 / night

(24) Very Good 

29

Florida Keys / Key West

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £481 / night

£3204 - £6441 / week

Enquire View

from £481 / night

(23) Very Good 

29

Florida Keys / Key West

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £174 / night

£1039 - £2314 / week

Enquire View

from £174 / night

(32) Very Good 

23

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £158 / night

£950 - £2175 / week

Enquire View

from £158 / night

14

Florida Keys / Key West

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+

 …see more

from £90 / night

£629 / week

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from £90 / night

(55) Very Good 

21

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £262 / night

£1697 - £3798 / week

Enquire View

from £262 / night

(29) Very Good 

39

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £170 / night

£1020 - £2097 / week

Enquire View

from £170 / night

(22) Very Good 

24

Florida Keys / Key West

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £200 / night

£1250 - £2827 / week

Enquire View

from £200 / night

(31) Very Good 

34

Florida Keys / Key West

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £208 / night

£1270 - £3000 / week

Enquire View

from £208 / night

(27) Very Good 

26

Florida Keys / Key West

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £227 / night

£1454 - £3168 / week

Enquire View

from £227 / night

(2) Excellent 

27

Florida Keys / Key West

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £139 / night

£808 - £2008 / week

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from £139 / night

(13) Very Good 

27

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £139 / night

£808 - £1755 / week

Enquire View

from £139 / night

(26) Very Good 

29

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £158 / night

£950 - £2175 / week

Enquire View

from £158 / night

(3) Very Good 

13

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £158 / night

£950 - £2175 / week

Enquire View

from £158 / night

(29) Very Good 

24

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £170 / night

£1020 - £2097 / week

Enquire View

from £170 / night

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