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

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  • United States
  • Florida
  • Florida Keys

Location

  • All locations
  • Conch Key (1)
  • Cudjoe Key (4)
  • Duck Key (2)
  • Islamorada (48)
  • Key Colony Beach (7)
  • Key Largo (43)
  • Key West (90)
  • Long Key (3)
  • Marathon (31)
  • Matecumbe Key (1)

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Also consider

Villas Key Largo
132 properties
Villas Key West
122 properties
Holiday rentals Islamorada
73 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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231 Holiday homes

Filters applied: Swimming pool (231)

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

(18) Excellent 

1 / 17

Key West holiday apartment let

Florida Keys / Key West

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies

from £171 / night

£1194 / week

Book Book View

from £171 / 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

(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 / 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

(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

(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

(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

(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) Very Good 

1 / 14

Holiday apartment in Key West

Florida Keys / Key West

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from £309 / night

£2158 - £3151 / week

Book Book View

from £309 / 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

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from £96 / 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

Book Book View

from £89 / 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

(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

(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

(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

(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

(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

(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

(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

(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 / 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 / 7

Marathon Shores holiday condo rental

Marathon / Marathon Shores

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min stay

from £137 / night

£685 / week

Book Book View

from £137 / 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

(3) Very Good 

1 / 6

Home rental in Key Largo with shared pool

Florida Keys / Key Largo

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from £144 / night

£1044 / week

Book Book View

from £144 / night

1 / 22

Holiday condo in Key West

Florida Keys / Key West

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from £155 / night

£1096 - £1713 / week

Book Book View

from £155 / night

(2) Very Good 

1 / 25

Holiday apartment in Islamorada

Florida Keys / Islamorada

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay

from £172 / night

£1062 / week

Book Book View

from £172 / night

(1) Very Good 

1 / 9

Key Largo holiday townhouse rental

Florida Keys / Key Largo

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £79 / night

£548 - £778 / week

Book Book View

from £79 / night

(2) Poor 

1 / 31

Holiday condo in Tavernier

Key Largo / Tavernier

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £185 / night

£1290 / week

Book Book View

from £185 / night

1 / 14

Holiday home in Islamorada

Florida Keys / Islamorada

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £157 / night

£1096 - £2055 / week

Book Book View

from £157 / night

1 / 28

Holiday home in Key West

Florida Keys / Key West

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min stay

from £205 / night

£1434 / week

Book Book View

from £205 / 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

1 / 25

Condo rental in Islamorada

Florida Keys / Islamorada

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £98 / night

£685 / week

Book Book View

from £98 / night

(44) Very Good 

1 / 24

Holiday cottage with shared pool in Key West

Florida Keys / Key West

  • 1 bedroom
  • Sleeps 2
  • Min stay varies

from £103 / night

£566 - £1495 / week

Enquire Enquire View

from £103 / night

(2) Excellent 

1 / 30

Holiday condo in Key West

Florida Keys / Key West

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies

from £278 / night

£1542 - £2227 / week

Book Book View

from £278 / night

(9) Very Good 

1 / 15

Holiday villa in Duck Key

Florida Keys / Duck Key

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay

from £137 / night

£864 - £1199 / week

Book Book View

from £137 / night

(10) Very Good 

1 / 48

Home rental in Matecumbe Key with swimming pool

Florida Keys / Matecumbe Key

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay

from £343 / night

£2398 - £2518 / week

Book Book View

from £343 / night

(2) Very Good 

1 / 32

Holiday apartment in Key Largo

Florida Keys / Key Largo

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £134 / night

£935 / week

Book Book View

from £134 / night

1 / 25

Holiday apartment rental

Florida Keys / Key Largo

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min stay

from £172 / night

£994 / week

Book Book View

from £172 / night

1 / 25

Villa rental in Islamorada

Florida Keys / Islamorada

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £192 / night

£1199 - £1507 / week

Book Book View

from £192 / night

(2) Excellent 

1 / 41

Holiday apartment in Florida Keys

Florida / Florida Keys

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay

from £136 / night

£949 / week

Book Book View

from £136 / night

1 / 25

Holiday cottage in Cudjoe Key

Florida Keys / Cudjoe Key

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from £96 / night

£610 - £959 / week

Book Book View

from £96 / 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

(11) Very Good 

1 / 19

Marathon holiday apartment rental

Florida Keys / Marathon

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from £69 / night

£411 - £548 / week

Book Book View

from £69 / night

1 / 9

Holiday hotel apartment with shared pool in Key West

Florida Keys / Key West

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £319 / night

£2227 / week

Book Book View

from £319 / night

1 / 18

Condo rental in Key Colony Beach with golf nearby

Florida Keys / Key Colony Beach

  • 2 bedrooms
  • Sleeps 4
  • 14 nights min stay

from £137 / night

£959 / week

Book Book View

from £137 / night

(3) Excellent 

1 / 21

Holiday condo in Tavernier

Key Largo / Tavernier

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £96 / night

£668 - £1148 / week

Book Book View

from £96 / night

1 / 25

Holiday home accommodation

Florida Keys / Islamorada

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from £1370 / night

£1370 - £5137 / week

Book Book View

from £1370 / night

1 / 24

Holiday townhouse in Key West

Florida Keys / Key West

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from £117 / night

£816 - £990 / week

Book Book View

from £117 / night

(7) Very Good 

1 / 17

Holiday apartment in Marathon

Florida Keys / Marathon

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min stay

from £155 / night

£959 / week

Book Book View

from £155 / night

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