50 Best Florida Keys villas on Holiday Lettings - Holiday rentals

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Location

  • United States
  • Florida
  • Florida Keys

Location

  • All locations
  • Big Pine Key (21)
  • Conch Key (2)
  • Cudjoe Key (19)
  • Duck Key (4)
  • Islamorada (74)
  • Key Colony Beach (11)
  • Key Largo (133)
  • Key West (123)
  • Little Torch Key (14)
  • Long Key (6)
  • Lower Keys (3)
  • Marathon (68)
  • Matecumbe Key (2)
  • Ramrod Key (10)

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Also consider

Villas Key Largo
132 properties
Villas Key West
123 properties
Holiday rentals Islamorada
74 properties
Estates Marathon
68 properties
Big Pine Key
21 properties
Cudjoe Key
19 properties
Little Torch Key
14 properties
Key Colony Beach
11 properties
Ramrod Key
10 properties
Long Key
6 properties
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491 Holiday homes

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

(21) Very Good 

1 / 14

Apartment rental in Key West

Florida Keys / Key West

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from £198 / night

£1578 - £1722 / week

Book Book View

from £198 / night

(12) Excellent 

1 / 16

Holiday apartment in Key West

Florida Keys / Key West

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from £185 / night

£1290 / week

Book Book View

from £185 / night

(7) Excellent 

1 / 20

Cottage rental in Key Largo

Florida Keys / Key Largo

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min stay

from £134 / night

£857 - £908 / week

Book Book View

from £134 / night

(14) Excellent 

1 / 24

Holiday home in Tavernier

Key Largo / Tavernier

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from £120 / night

£720 / week

Book Book View

from £120 / night

(9) Very Good 

1 / 13

Holiday apartment in Key West

Florida Keys / Key West

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies

from £116 / night

£685 - £1713 / week

Book Book View

from £116 / night

(3) Very Good 

1 / 27

Holiday home in Islamorada

Florida Keys / Islamorada

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min stay

from £309 / night

£1918 / week

Book Book View

from £309 / night

(1) Excellent 

1 / 42

Home rental in Tavernier

Key Largo / Tavernier

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay

from £89 / night

£583 - £856 / week

Book Book View

from £89 / night

(2) Excellent 

1 / 9

Holiday apartment in Key Largo

Florida Keys / Key Largo

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from £137 / night

£891 - £1302 / week

Book Book View

from £137 / night

(3) Very Good 

1 / 6

Holiday apartment with shared pool in Key West

Florida Keys / Key West

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay

from £182 / night

£1233 - £1415 / week

Book Book View

from £182 / night

(7) Excellent 

1 / 10

Holiday home in Big Pine Key

Florida Keys / Big Pine Key

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from £96 / night

£668 - £1627 / week

Book Book View

from £96 / night

(4) Very Good 

1 / 20

Holiday apartment in Key West

Florida Keys / Key West

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min stay

from £165 / night

£1096 - £1233 / week

Book Book View

from £165 / night

1 / 16

Key Largo holiday home rental

Florida Keys / Key Largo

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from £240 / night

£1610 - £1970 / week

Book Book View

from £240 / night

(5) Excellent 

1 / 40

Holiday home rental

Florida Keys / Islamorada

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from £177 / night

£1233 / week

Book Book View

from £177 / night

(8) Excellent 

1 / 15

Holiday apartment in Key West

Florida Keys / Key West

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from £116 / night

£754 - £1914 / week

Book Book View

from £116 / night

(12) Very Good 

1 / 22

Holiday villa in Islamorada

Florida Keys / Islamorada

  • 1 bedroom
  • Sleeps 3
  • 30 nights min stay

from £86 / night

£600 / week

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from £86 / night

(2) Excellent 

1 / 14

Apartment rental in Key West

Florida Keys / Key West

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay

from £189 / night

£1370 - £1610 / week

Book Book View

from £189 / night

(6) Excellent 

1 / 36

Holiday villa rental

Florida Keys / Marathon

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies

from £158 / night

£1096 - £1603 / week

Book Book View

from £158 / night

(2) Excellent 

1 / 9

Islamorada holiday b&b rental

Florida Keys / Islamorada

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay

from £89 / night

£619 / week

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from £89 / night

1 / 27

Holiday cottage in Key Largo

Florida Keys / Key Largo

  • 1 bedroom
  • Sleeps 6
  • Min stay varies

from £117 / night

£788 - £1120 / week

Book Book View

from £117 / night

(2) Very Good 

1 / 10

Home rental in Key Largo

Florida Keys / Key Largo

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay

from £226 / night

£1576 - £1987 / week

Book Book View

from £226 / night

(4) Excellent 

1 / 12

Holiday villa in Marathon

Florida Keys / Marathon

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from £245 / night

£1713 - £2569 / week

Book Book View

from £245 / night

(1) Excellent 

1 / 23

Little Torch Key holiday home rental

Florida Keys / Little Torch Key

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from £170 / night

£1185 - £1237 / week

Book Book View

from £170 / night

(6) Excellent 

1 / 96

Holiday home with golf nearby in Key Colony Beach

Florida Keys / Key Colony Beach

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £137 / night

£685 - £1466 / week

Book Book View

from £137 / night

(9) Excellent 

1 / 17

Holiday home in Big Pine Key

Florida Keys / Big Pine Key

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £137 / night

£959 - £1233 / week

Book Book View

from £137 / night

(1) Very Good 

1 / 29

Key Largo holiday home rental

Florida Keys / Key Largo

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £206 / night

£925 - £1336 / week

Book Book View

from £206 / night

(2) Excellent 

1 / 19

Condo rental in Islamorada

Florida Keys / Islamorada

  • 1 bedroom
  • Sleeps 4
  • 7 nights min stay

from £81 / night

£566 - £668 / week

Book Book View

from £81 / night

(1) Excellent 

1 / 12

Holiday home in Key Largo

Florida Keys / Key Largo

  • 3 bedrooms
  • Sleeps 10
  • 7 nights min stay

from £206 / night

£1439 / week

Book Book View

from £206 / night

(2) Excellent 

1 / 20

Islamorada holiday condo rental

Florida Keys / Islamorada

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay

from £172 / night

£959 - £2398 / week

Book Book View

from £172 / night

(5) Very Good 

1 / 15

Holiday condo in Tavernier

Key Largo / Tavernier

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay

from £96 / night

£651 / week

Book Book View

from £96 / night

(3) Excellent 

1 / 37

Holiday home with swimming pool in Key Largo

Florida Keys / Key Largo

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min stay

from £822 / night

£5137 - £5480 / week

Book Book View

from £822 / night

(2) Excellent 

1 / 26

Tavernier holiday home rental

Key Largo / Tavernier

  • 3 bedrooms
  • Sleeps 8
  • 30 nights min stay

from £137 / night

£1233 - £3151 / week

Book Book View

from £137 / night

(1) Excellent 

1 / 54

Holiday condo in Tavernier

Key Largo / Tavernier

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from £137 / night

£959 / week

Book Book View

from £137 / night

(1) Very Good 

1 / 24

Holiday home rental

Florida Keys / Key Largo

  • 3 bedrooms
  • Sleeps 8
  • 30 nights min stay

from £103 / night

£720 / week

Book Book View

from £103 / night

(6) Excellent 

1 / 19

Villa rental in Islamorada

Florida Keys / Islamorada

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £177 / night

£1233 - £1713 / week

Book Book View

from £177 / night

(1) Excellent 

1 / 12

Holiday houseboat in Tavernier

Key Largo / Tavernier

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from £110 / night

£1028 / week

Book Book View

from £110 / night

(1) Excellent 

1 / 15

Home rental in Marathon

Florida Keys / Marathon

  • 4 bedrooms
  • Sleeps 12
  • 7 nights min stay

from £196 / night

£1367 - £2227 / week

Book Book View

from £196 / night

(1) Excellent 

1 / 12

Villa rental in Duck Key

Florida Keys / Duck Key

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from £155 / night

£1415 - £1679 / week

Book Book View

from £155 / night

(2) Excellent 

1 / 4

Holiday cottage in Marathon

Florida Keys / Marathon

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from £250 / night

£1575 - £2508 / week

Book Book View

from £250 / night

(8) Very Good 

1 / 36

Key Largo holiday apartment rental

Florida Keys / Key Largo

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay

from £137 / night

£959 - £1199 / week

Book Book View

from £137 / night

1 / 15

Holiday condo with shared pool in Tavernier

Key Largo / Tavernier

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from £100 / night

£696 / week

Book Book View

from £100 / night

(14) Very Good 

1 / 69

Key Largo holiday cottage rental

Florida Keys / Key Largo

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay

from £96 / night

£672 / week

Book Book View

from £96 / night

1 / 4

Islamorada holiday b&b let

Florida Keys / Islamorada

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay

from £130 / night

£907 / week

Book Book View

from £130 / night

1 / 6

Tavernier holiday boathouse rental

Key Largo / Tavernier

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from £137 / night

£959 / week

Book Book View

from £137 / night

(8) Excellent 

1 / 15

Holiday apartment with tennis court in Marathon

Florida Keys / Marathon

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from £165 / night

£1096 - £1233 / week

Book Book View

from £165 / night

(4) Excellent 

1 / 15

Apartment rental in Key West

Florida Keys / Key West

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay

from £185 / night

£1285 / week

Book Book View

from £185 / night

(5) Very Good 

1 / 19

Holiday apartment in Key West

Florida Keys / Key West

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay

from £136 / night

£857 - £1679 / week

Book Book View

from £136 / night

(4) Very Good 

1 / 5

Key West holiday apartment rental

Florida Keys / Key West

  • 1 bedroom
  • Sleeps 2
  • Min stay varies

from £83 / night

£548 - £792 / week

Book Book View

from £83 / night

1 / 29

Holiday home in Marathon

Florida Keys / Marathon

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from £68 / night

£475 - £1394 / week

Book Book View

from £68 / night

(6) Very Good 

1 / 7

Holiday home in Key Largo

Florida Keys / Key Largo

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min stay

from £172 / night

£754 / week

Book Book View

from £172 / night

(2) Excellent 

1 / 18

Holiday home in Marathon

Florida Keys / Marathon

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £133 / night

£925 / week

Book Book View

from £133 / night

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