Villas with a pool Key West | Apartments to rent with swimming facilities | Holiday Lettings

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139 Holiday homes

Filters applied: Swimming pool (140)

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

(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 km
  • Swimming pool

 …see more

from £256 / night

£1654 - £2993 / week

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from £256 / night

(27) 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 £204 / night

£1428 / week

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from £204 / night

(32) 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 £260 / night

£1814 / week

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from £260 / night

(2) Excellent 

21

USA East Coast holiday 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 £319 / night

£1969 - £3839 / week

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from £319 / night

(22) 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 £197 / night

£1373 / week

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from £197 / night

(8) Very Good 

14

Florida Keys / Key West

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £315 / night

£2205 / week

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from £315 / night

6

Florida Keys / Key West

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £178 / night

£1241 / week

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from £178 / 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 £220 / night

£1538 / week

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from £220 / night

(1) Excellent 

22

Florida Keys / Key West

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £197 / night

£1260 - £1969 / week

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from £197 / night

(9) Excellent 

14

Florida Keys / Key West

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 2 km
  • Swimming pool
  • Child friendly

 …see more

from £134 / night

£945 - £2200 / week

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from £134 / 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 £524 / night

£3662 - £8335 / week

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from £524 / night

16

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 £178 / night

£945 - £1339 / week

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from £178 / 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 £213 / night

£1477 / week

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from £213 / night

(15) 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 £157 / night

£788 - £1969 / week

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from £157 / night

6

Florida Keys / Key West

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from £169 / night

£1182 / week

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from £169 / 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 £193 / night

£1087 - £2190 / week

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from £193 / 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 £217 / night

£1260 - £2495 / week

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from £217 / night

15

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 £236 / night

£1654 - £2530 / week

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from £236 / night

(48) 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 £189 / night

£1091 - £2483 / week

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from £189 / night

(3) Very Good 

6

Florida Keys / Key West

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £233 / night

£1626 / week

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from £233 / night

(4) Very Good 

20

Florida Keys / Key West

2 6 3 nights min

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

 …see more

from £189 / night

£1260 - £1418 / week

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from £189 / 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 £150 / night

£847 - £2056 / week

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from £150 / 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 £154 / night

£839 - £1797 / week

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from £154 / 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 £217 / night

£1260 - £2495 / week

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from £217 / 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 £162 / night

£973 - £2226 / week

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from £162 / 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 £197 / night

£1154 - £2483 / week

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from £197 / 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 £130 / night

£745 - £1821 / week

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from £130 / 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 £296 / night

£1772 - £3111 / week

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from £296 / 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 £634 / night

£4213 - £9003 / week

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from £634 / 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 £182 / night

£1095 - £2146 / week

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from £182 / 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 £170 / night

£969 - £2049 / week

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from £170 / 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 £260 / night

£1595 - £3197 / week

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from £260 / 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 £150 / night

£1103 - £2369 / week

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from £150 / night

13

Florida Keys / Key West

1 3 5 nights min

  • 1 bedroom
  • Sleeps 3
  • 5 nights min
  • Nearest beach 2 km
  • Swimming pool
  • Car not necessary

 …see more

from £178 / night

£1182 / week

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from £178 / 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 £182 / night

£1095 - £2146 / week

Enquire View

from £182 / 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 £256 / night

£1591 - £4082 / week

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from £256 / 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 £221 / night

£1319 - £3071 / week

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from £221 / 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 £154 / night

£839 - £1797 / week

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from £154 / 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 £162 / night

£973 - £2226 / week

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from £162 / 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 £182 / night

£1123 - £2552 / week

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from £182 / night