Air conditioned apartments and villas to rent in Florida Keys

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Location

  • United States
  • Florida
  • Florida Keys

Location

  • All locations
  • Big Pine Key (16)
  • Conch Key (2)
  • Cudjoe Key (7)
  • Duck Key (5)
  • Islamorada (45)
  • Key Colony Beach (12)
  • Key Largo (134)
  • Key West (75)
  • Little Torch Key (1)
  • Long Key (4)
  • Lower Keys (5)
  • Marathon (65)
  • Matecumbe Key (2)
  • Ramrod Key (1)

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Also consider

Villas Key Largo
165 properties
Villas Key West
87 properties
Holiday rentals Islamorada
80 properties
Estates Marathon
76 properties
Big Pine Key
16 properties
Key Colony Beach
15 properties
Cudjoe Key
7 properties
Long Key
6 properties
Lower Keys
6 properties
Villas Duck Key
5 properties
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374 Holiday homes

Filters applied: Air conditioning (374)

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

(22) Excellent 

1 / 17

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 / 19

Florida Keys / Big Pine Key

2 bedroomsSleeps 6Min stay varies

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

from £165 / night

£1107 / week

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from £165 / night

1 / 37

Florida Keys / Key Largo

1 bedroomSleeps 62 nights min stay

  • 1 bedroom
  • Sleeps 6
  • 2 nights min stay
Key info: Ask owner if suitable for children; Car advised; Air conditioning;
 …see more

from £130 / night

£878 - £1249 / week

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from £130 / night

(9) Very Good 

1 / 15

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

(2) Excellent 

1 / 41

Ocean Harbour Apartment, Islamorada, Florida Keys

Florida Keys / Islamorada

2 bedroomsSleeps 430 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
Located in Islamorada, Florida Keys, Ocean Harbour is our beautiful and luxurious home away from home surrounded by the tropical beauty of the Florida Keys. The location is in the perfect proximity for visiting Key West & Miami. With its exceptional location and gated  …see more

from £152 / night

£1058 / week

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from £152 / night

(2) Excellent 

1 / 9

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

(19) Excellent 

1 / 14

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

1 / 22

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

(14) Excellent 

1 / 17

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

1 / 14

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

(2) Excellent 

1 / 12

Florida Keys / Duck Key

2 bedroomsSleeps 6Min stay varies

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

from £153 / night

£1577 / week

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from £153 / night

1 / 25

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

(37) Excellent 

1 / 27

Florida Keys / Marathon

1 bedroomSleeps 42 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Not suitable for children; Car advised;
 …see more

from £96 / night

£668 / week

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from £96 / night

(11) Very Good 

1 / 14

Tropical Island Getaway-Keys - Key Largo condo sleeps 7

Florida Keys / Key Largo

2 bedroomsSleeps 73 nights min stay

  • 2 bedrooms
  • Sleeps 7
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 0.2 km; Swimming pool;
A view of the pool off your patio and the Florida Bay sunset glows at your front door. Tropical breezes and gardens grace the gated condo community. Yes, laptops do work in the apartment!At Moon Bay condominium you will have the opportunity to relax in the heated pool,  …see more

from £149 / night

£752 / week

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from £149 / night

(2) Excellent 

1 / 24

Marathon / Grassy Key

Sleeps 25 nights min stay

  • Sleeps 2
  • 5 nights min stay
Key info: Not suitable for children; Car not necessary; Air conditioning;
 …see more

from £100 / night

£611 - £688 / week

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from £100 / night

1 / 43

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 / 25

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

(4) Excellent 

1 / 23

Key Largo / Tavernier

2 bedroomsSleeps 64 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 0 km; Great for children of all ages ;
 …see more

from £115 / night

£0 / week

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from £115 / night

1 / 18

Marathon / Marathon Shores

6 bedroomsSleeps 127 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Not suitable for children; Air conditioning; Some pets are welcome - please contact the owner;
 …see more

from £375 / night

£2619 - £4730 / week

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from £375 / night

1 / 39

Florida Keys / Big Pine Key

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Great for children of all ages ; Air conditioning; No pets allowed;
 …see more

from £210 / night

£1390 - £2100 / week

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from £210 / night

(9) Excellent 

1 / 17

Florida Keys / Big Pine Key

3 bedroomsSleeps 67 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Great for children of all ages ; Car not necessary;
 …see more

from £153 / night

£1069 - £1375 / week

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from £153 / night

(1) Very Good 

1 / 24

Luxury house rental Key West - Key West house sleeps 8

Florida Keys / Key West

3 bedroomsSleeps 830 nights min stay

  • 3 bedrooms
  • Sleeps 8
  • 30 nights min stay
Key info: Beach / lakeside relaxation; Swimming pool; Great for children of all ages ;
28 DAY MINIMUM STAY IS MANDATED BY COUNTY LAW. PLEASE DO NOT SEND ENQUIRIES FOR SHORTER PERIODS!! Charted back in the 1800's, Shark Key was named by early explorers for its shark-like shape. This exclusive island boasts more than 2 miles of pristine shoreline, lush  …see more

from £211 / night

£0 / week

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from £211 / night

1 / 26

Florida Keys / Little Torch Key

3 bedroomsSleeps 7Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
Key info: Beach / lakeside relaxation; Suitable for children age 5+; Air conditioning;
 …see more

from £191 / night

£1331 - £2004 / week

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from £191 / night

1 / 25

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 / 29

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

(8) Excellent 

1 / 14

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

(13) Excellent 

1 / 17

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

(8) Excellent 

1 / 15

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 / 11

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

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from £535 / night

(1) Terrible 

1 / 30

Florida Keys / Key Largo

3 bedroomsSleeps 123 nights min stay

  • 3 bedrooms
  • Sleeps 12
  • 3 nights min stay
Key info: Swimming pool; Great for children of all ages ; Car essential;
 …see more

from £229 / night

£1756 / week

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from £229 / night

1 / 7

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

1 / 54

Florida Keys / Cudjoe Key

3 bedroomsSleeps 614 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min stay
Key info: Great for children of all ages ; Car not necessary; Air conditioning;
 …see more

from £120 / night

£840 / week

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from £120 / night

1 / 16

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

1 / 24

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

(9) Very Good 

1 / 36

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 / 25

Florida Keys / Key Largo

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 £191 / night

£1107 / week

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from £191 / night

1 / 24

Private Oceanview Estate 20 Minutes to Key West

Florida Keys / Key West

6 bedroomsSleeps 14Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
Key info: Nearest beach 10 km; Swimming pool; Great for children of all ages ;
Great for large groups - 6 bdrms, 3 bathrms, sleeps up to 14 adults, just 20 minutes drive from Key West. Our home is away from the hustle of Key West activities but close enough to the excitement when you want it and the Atlantic Ocean’s spectacular sunrises, sunset  …see more

from £317 / night

£2214 - £3271 / week

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from £317 / night

1 / 25

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

(3) Excellent 

1 / 19

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

(3) Excellent 

1 / 9

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

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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