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

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399 properties
Villas Key Largo
181 properties
Holiday rentals Islamorada
95 properties
Estates Marathon
80 properties
Big Pine Key
23 properties
Key Colony Beach
15 properties
Little Torch Key
14 properties
Long Key
8 properties
Lower Keys
8 properties
Cudjoe Key
6 properties

Florida Keys

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445 Holiday homes

Filters applied: Swimming pool (447)

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

(2) Excellent 

41

Holiday apartment in Islamorada

Florida Keys / Islamorada

3 6 14 nights min

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
lettings restrictions apply. Contact the owner for more information. An additional fee is payable if pets stay with you.  …see more

from £165 / night

£1155 - £1738 / week

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from £165 / night

(12) Very Good 

14

Holiday condo in Key Largo

Florida Keys / Key Largo

2 7 3 nights min

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
“Just perfect” We have had a wonderful holiday in Moon Bay. Condo was larger than we were expecting. Both bedrooms large and clean. Lovely patio to sit out on. The complex itself had everythine we could need and kids loved the fishing and snorkling  …see more

from £163 / night

£821 / week

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from £163 / night

(12) Excellent 

55

Key Largo / Tavernier

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool

 …see more

from £167 / night

£1167 / week

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from £167 / night

(4) Excellent 

23

Key Largo / Tavernier

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £150 / night

£1050 / week

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from £150 / 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 £225 / night

£1563 / week

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from £225 / night

(33) 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 £270 / night

£1888 / week

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from £270 / night

(30) 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 £213 / night

£1487 / week

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from £213 / night

29

Florida Keys / Key Largo

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 8 km
  • Swimming pool

 …see more

from £155 / night

£959 - £1250 / week

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from £155 / night

(7) Very Good 

25

Florida Keys / Islamorada

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children

 …see more

from £176 / night

£1230 - £1558 / week

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from £176 / night

29

Florida Keys / Key West

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £122 / night

£850 - £1997 / week

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from £122 / night

(3) Average 

36

Florida Keys / Key West

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £409 / night

£2858 - £5038 / week

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from £409 / night

(23) 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 £208 / night

£1453 / week

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from £208 / 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 £229 / night

£1601 / week

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from £229 / night

(4) Excellent 

21

Key Largo / Tavernier

2 6 Min stay varies

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

 …see more

from £123 / night

£800 - £1373 / week

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from £123 / night

25

Florida Keys / Key West

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £138 / night

£964 - £2055 / week

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from £138 / night

(4) Very Good 

28

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 £141 / night

£984 - £2296 / week

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from £141 / night

29

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £179 / night

£1251 - £2284 / week

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from £179 / night

23

Florida Keys / Key West

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £146 / night

£1022 - £1997 / week

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from £146 / night

(25) Very Good 

27

Florida Keys / Key West

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £163 / night

£1137 - £2399 / week

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from £163 / night

(1) Excellent 

29

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £179 / night

£1251 - £2284 / week

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from £179 / 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 km
  • Swimming pool

 …see more

from £284 / night

£1786 - £3167 / week

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from £284 / night

9

Florida Keys / Marathon

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

 …see more

from £542 / night

£3792 - £6755 / week

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from £542 / night

(1) Excellent 

31

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £204 / night

£1423 - £2571 / week

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from £204 / night

(48) Very Good 

27

Florida Keys / Key West

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £196 / night

£1366 - £2686 / week

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from £196 / night

(10) Excellent 

96

Florida Keys / Key Colony Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool

 …see more

from £119 / night

£833 - £1534 / week

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from £119 / night

(4) Excellent 

9

Florida Keys / Key Largo

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

 …see more

from £167 / night

£1084 - £1346 / week

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from £167 / night

(1) Excellent 

25

Florida Keys / Islamorada

2 6 Min stay varies

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

 …see more

from £155 / night

£1021 - £2667 / week

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from £155 / night

25

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £179 / night

£1251 - £2284 / week

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from £179 / night

31

Florida Keys / Key West

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £130 / night

£907 - £1997 / week

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from £130 / night

25

Florida Keys / Key West

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £146 / night

£1022 - £1997 / week

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from £146 / night

30

Florida Keys / Key West

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £163 / night

£1137 - £2284 / week

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from £163 / night

(1) Average 

28

Florida Keys / Key West

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £105 / night

£735 - £1538 / week

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from £105 / night

8

Florida Keys / Big Pine Key

3 11 1 night min

  • 3 bedrooms
  • Sleeps 11
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £375 / night

£2625 / week

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from £375 / night

30

Florida Keys / Key West

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £122 / night

£850 - £1997 / week

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from £122 / night

28

Florida Keys / Key West

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £433 / night

£3030 - £5727 / week

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from £433 / night

(3) Average 

24

Florida Keys / Key Colony Beach

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £129 / night

£902 - £1107 / week

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from £129 / night

(4) Very Good 

9

Florida Keys / Islamorada

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £91 / night

£753 / week

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from £91 / 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 £169 / night

£1013 - £2318 / week

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from £169 / 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 £334 / night

£2334 / week

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from £334 / night

38

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £246 / night

£1550 - £2066 / week

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from £246 / night