Villas with a pool Florida Keys | Apartments to rent with swimming facilities | Holiday Lettings

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Location

  • United States
  • Florida
  • Florida Keys

Location

  • All locations
  • Big Pine Key (1)
  • Conch Key (1)
  • Cudjoe Key (4)
  • Duck Key (3)
  • Islamorada (51)
  • Key Colony Beach (8)
  • Key Largo (58)
  • Key West (98)
  • Long Key (3)
  • Lower Keys (4)
  • Marathon (40)
  • Matecumbe Key (1)

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Also consider

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Estates Marathon
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Holiday rentals Islamorada
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Big Pine Key
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Key Colony Beach
15 properties
Cudjoe Key
7 properties
Lower Keys
5 properties
Villas Duck Key
5 properties
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272 Holiday homes

Filters applied: Swimming pool (272)

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

(25) Very Good 

1 / 14

Florida / Florida Keys / Key West

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Not suitable for children;
 …see more

from £252 / night

£1759 - £1919 / week

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from £252 / night

(2) Excellent 

1 / 9

Florida / Florida Keys / Key Largo

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car not necessary;
 …see more

from £153 / night

£993 - £1451 / week

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from £153 / night

1 / 25

Florida / Florida Keys / Cudjoe Key

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 23 km; Swimming pool;
 …see more

from £107 / night

£680 - £1069 / week

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from £107 / night

(14) Excellent 

1 / 17

Florida / Florida Keys / Key Largo / Tavernier

2 bedroomsSleeps 63 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £153 / night

£917 - £1069 / week

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from £153 / night

(22) Excellent 

1 / 17

Florida / Florida Keys / Key West

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Not suitable for children;
 …see more

from £191 / night

£0 / week

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from £191 / night

1 / 16

Florida / Florida Keys / Key Colony Beach

2 bedroomsSleeps 614 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 14 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £104 / night

£726 - £1069 / week

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from £104 / night

(9) Very Good 

1 / 15

Florida / Florida Keys / Duck Key

2 bedroomsSleeps 61 night min stay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £152 / night

£962 - £1336 / week

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from £152 / night

1 / 22

Florida / Florida Keys / Key Colony Beach

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £115 / night

£802 - £1069 / week

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from £115 / night

1 / 5

Florida / Florida Keys / Islamorada

1 bedroomSleeps 31 night min stay

  • 1 bedroom
  • Sleeps 3
  • 1 night min stay
Key info: Beach / lakeside relaxation; Swimming pool; Suitable for children age 5+;
 …see more

from £107 / night

£1010 - £1117 / week

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from £107 / night

(8) Excellent 

1 / 14

Florida / Florida Keys / Key West

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 2 km; Swimming pool; Great for children of all ages ;
 …see more

from £130 / night

£840 - £2133 / week

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from £130 / night

1 / 25

Florida / Florida Keys / Islamorada

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £213 / night

£1336 - £1680 / week

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from £213 / night

1 / 25

Florida / Florida Keys / Islamorada

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 0 km; Swimming pool;
 …see more

from £1527 / night

£1604 - £5726 / week

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from £1527 / night

(12) Excellent 

1 / 17

Florida / Florida Keys / Key West

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Not suitable for children; Car not necessary;
 …see more

from £213 / night

£0 / week

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from £213 / night

(9) Very Good 

1 / 36

Florida / Florida Keys / Key Largo

2 bedroomsSleeps 47 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 2 km; Swimming pool;
 …see more

from £153 / night

£1069 - £1336 / week

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from £153 / night

1 / 24

Florida / Florida Keys / Key Largo

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Ask owner if suitable for children; Air conditioning;
 …see more

from £126 / night

£878 - £2546 / week

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from £126 / night

(3) Very Good 

1 / 14

Florida / Florida Keys / Key Largo

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £134 / night

£878 - £1069 / week

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from £134 / night

(3) Excellent 

1 / 9

Florida / Florida Keys / Islamorada

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £84 / night

£690 / week

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from £84 / night

(19) Excellent 

1 / 14

Florida / Florida Keys / Key West

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Not suitable for children;
 …see more

from £183 / night

£0 / week

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from £183 / night

(11) Very Good 

1 / 13

Florida / Florida Keys / Key West

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £130 / night

£764 - £1909 / week

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from £130 / night

1 / 29

Florida / Florida Keys / Key Largo

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 8 km; Swimming pool;
 …see more

from £115 / night

£688 - £1146 / week

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from £115 / night

1 / 7

Florida / Florida Keys / Marathon / Marathon Shores

2 bedroomsSleeps 64 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £153 / night

£840 / week

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from £153 / night

(7) Very Good 

1 / 17

Florida / Florida Keys / Marathon

3 bedroomsSleeps 83 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 6 km; Swimming pool;
 …see more

from £172 / night

£1069 / week

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from £172 / night

(7) Excellent 

1 / 96

Florida / Florida Keys / Key Colony Beach

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 2 km; Swimming pool;
 …see more

from £152 / night

£763 - £1481 / week

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from £152 / night

(8) Excellent 

1 / 15

Florida / Florida Keys / Marathon

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £184 / night

£1222 - £1375 / week

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from £184 / night

1 / 43

Florida / Florida Keys / Key Largo / Tavernier

4 bedroomsSleeps 9Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Car essential;
 …see more

from £229 / night

£0 / week

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from £229 / night

1 / 7

Florida / Florida Keys / Islamorada

1 bedroomSleeps 21 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Beach / lakeside relaxation; Swimming pool; Not suitable for children;
 …see more

from £68 / night

£476 / week

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from £68 / night

1 / 11

Florida / Florida Keys / Duck Key

3 bedroomsSleeps 10Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £535 / night

£3207 - £4123 / week

Book Book View

from £535 / night

(3) Excellent 

1 / 21

Florida / Florida Keys / Key Largo / Tavernier

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £115 / night

£745 - £1279 / week

Book Book View

from £115 / night

1 / 17

Florida / Florida Keys / Marathon

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £210 / night

£0 / week

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from £210 / night

1 / 13

Florida / Florida Keys / Lower Keys / Summerland Key

5 bedroomsSleeps 830 nights min stay

  • 5 bedrooms
  • Sleeps 8
  • 30 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £140 / night

£0 / week

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from £140 / night

1 / 12

Florida / Florida Keys / Key Largo

1 bedroomSleeps 37 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 7 nights min stay
Key info: Swimming pool; Not suitable for children; Air conditioning;
 …see more

from £66 / night

£459 / week

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from £66 / night

(8) Very Good 

1 / 14

Florida / Florida Keys / Key West

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
 …see more

from £344 / night

£2405 - £3512 / week

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from £344 / night

1 / 14

Florida / Florida Keys / Duck Key

3 bedroomsSleeps 104 nights min stay

  • 3 bedrooms
  • Sleeps 10
  • 4 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £535 / night

£3207 - £4581 / week

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from £535 / night

(10) Very Good 

1 / 19

Florida / Florida Keys / Marathon

1 bedroomSleeps 4Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 2 km; Swimming pool;
 …see more

from £77 / night

£459 - £611 / week

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from £77 / night

1 / 15

Florida / Florida Keys / Key West

2 bedroomsSleeps 53 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £172 / night

£917 - £1298 / week

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from £172 / night

(10) Very Good 

1 / 48

Florida / Florida Keys / Matecumbe Key

4 bedroomsSleeps 87 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 0 km; Swimming pool;
 …see more

from £382 / night

£2672 - £2806 / week

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from £382 / night

(3) Excellent 

1 / 19

Florida / Florida Keys / Islamorada

1 bedroomSleeps 430 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 30 nights min stay
Key info: Nearest beach 0 km; Swimming pool; Great for children of all ages ;
 …see more

from £90 / night

£630 - £745 / week

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from £90 / night

1 / 14

Florida / Florida Keys / Marathon

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £130 / night

£840 - £993 / week

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from £130 / night

1 / 25

Florida / Florida Keys / Islamorada

2 bedroomsSleeps 67 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Swimming pool; Great for children of all ages ; Air conditioning;
 …see more

from £109 / night

£764 / week

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from £109 / night

1 / 27

Florida / Florida Keys / Marathon

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 9 km; Swimming pool;
 …see more

from £251 / night

£1752 - £2210 / week

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from £251 / night

Top Destination reviews

Captain Rons Tropical Vacation Hideaway
THE place to stay in the keys if you like peace and quiet!

Captain Rons Tropical Vacation Hideaway is only 30 miles to Key West, but worlds away from the crowds. The home is very clean and comfortable. Captain Ron made the whole process simple and painless. I would without hesitation stay here again and rec … see more

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