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

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89 Holiday homes

Filters applied: Private pool (90)

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

(1) Very Good 

24

USA East Coast holiday home rental

Florida Keys / Key West

3 8 30 nights min

  • 3 bedrooms
  • Sleeps 8
  • 30 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Luxury house 10 minutes from Duval Street, pool, dock, pool bar, hot tub. Home owner association tennis courts and private beach on exclusive gated community island.  …see more

from £214 / night

£1496 / week

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from £214 / night

(2) Excellent 

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 £196 / night

£1104 - £2225 / week

Enquire View

from £196 / 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 £532 / night

£3720 - £8468 / week

Enquire View

from £532 / night

(27) Very Good 

24

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 £200 / night

£1172 - £2523 / week

Enquire View

from £200 / night

(25) Very Good 

24

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 £260 / night

£1616 - £4147 / week

Enquire View

from £260 / night

(6) 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 £300 / night

£1800 - £3160 / week

Enquire View

from £300 / night

(22) Very Good 

24

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 £184 / night

£1140 - £2592 / week

Enquire View

from £184 / night

(10) Excellent 

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 £220 / night

£1280 - £2535 / week

Enquire View

from £220 / night

(27) Very Good 

23

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 £156 / night

£852 - £1825 / week

Enquire View

from £156 / night

(36) 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 £220 / night

£1280 - £2535 / week

Enquire View

from £220 / night

(32) Very Good 

24

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 £164 / night

£988 - £2262 / week

Enquire View

from £164 / night

(2) Excellent 

24

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 £152 / night

£860 - £2088 / week

Enquire View

from £152 / night

(52) Excellent 

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 £152 / night

£1120 - £2407 / week

Enquire View

from £152 / night

(9) Excellent 

23

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 £264 / night

£1620 - £3248 / week

Enquire View

from £264 / night

(4) Excellent 

24

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 £644 / night

£4280 - £9147 / week

Enquire View

from £644 / night

(55) Very Good 

23

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 £276 / night

£1820 - £3950 / week

Enquire View

from £276 / night

(84) Very Good 

25

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 £392 / night

£2520 - £5121 / week

Enquire View

from £392 / night

(29) Very Good 

23

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 £184 / night

£1112 - £2180 / week

Enquire View

from £184 / night

(23) Very Good 

24

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 £188 / night

£1092 - £2407 / week

Enquire View

from £188 / night

(54) 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 £276 / night

£1820 - £3950 / week

Enquire View

from £276 / night

(24) Very Good 

24

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 £500 / night

£3332 - £6699 / week

Enquire View

from £500 / night

(2) Excellent 

26

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 £686 / night

£4800 - £9860 / week

Enquire View

from £686 / 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 £220 / night

£1312 - £2940 / week

Enquire View

from £220 / 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 £107 / night

£747 / week

Book View

from £107 / 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 £172 / night

£984 - £2082 / week

Enquire View

from £172 / night

(13) Very Good 

23

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 £156 / night

£852 - £1825 / week

Enquire View

from £156 / night

(26) Very Good 

24

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 £164 / night

£988 - £2262 / week

Enquire View

from £164 / night

(1) Excellent 

25

Florida Keys / Key West

3 8 7 nights min

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

 …see more

from £458 / night

£3200 - £7064 / week

Enquire View

from £458 / night

(27) Very Good 

24

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 £252 / night

£1528 - £3295 / week

Enquire View

from £252 / night

(25) Very Good 

24

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 £164 / night

£988 - £2262 / week

Enquire View

from £164 / 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 £132 / night

£756 - £1850 / week

Enquire View

from £132 / 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 £184 / night

£1112 - £2180 / week

Enquire View

from £184 / 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 £188 / night

£1092 - £1995 / week

Enquire View

from £188 / 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 £560 / night

£3920 / week

Book View

from £560 / night

(11) Very Good 

24

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 £188 / night

£1092 - £2407 / week

Enquire View

from £188 / night

(5) Excellent 

33

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £159 / night

£1112 - £1508 / week

Book View

from £159 / night

(31) 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 £224 / night

£1340 - £3120 / week

Enquire View

from £224 / night

(25) Very Good 

24

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 £500 / night

£3332 - £6699 / week

Enquire View

from £500 / night

20

Florida Keys / Key West

4 8 30 nights min

  • 4 bedrooms
  • Sleeps 8
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £160 / night

£1120 / week

Book View

from £160 / night

(11) 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 £196 / night

£1104 - £2225 / week

Enquire View

from £196 / night

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