50 Best Florida Keys Vacation rentals on Holiday Lettings - House rentals

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Vacation rentals Key West
417 properties
Vacation rentals Key Largo
201 properties
Vacation rentals Islamorada
105 properties
Vacation rentals Marathon
89 properties
Vacation rentals Big Pine Key
22 properties
Vacation rentals Key Colony Beach
16 properties
Cottages Little Torch Key
14 properties
Long Key
8 properties
Lower Keys
8 properties
Vacation rentals Cudjoe Key
8 properties

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854 Vacation rentals

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27

Marathon Shores Vacation home rental

Marathon / Marathon Shores

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning
Beautifully decorated, extra clean, new furniture, fully equipped kitchen brand new hot tub, along with everything you will need to make your stay comfortable. Walking distance to one of the most beautiful beaches in the Florida Keys. Only minutes away from the 7 mile  …see more

from $158 / night

$1101 - $1550 / week

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from $158 / night

(3) Excellent 

21

Key West Vacation houseboat rental

Florida Keys / Key West

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Ocean view yacht with beautiful sunsets and sunrises. Underwater windows in the forward cabins makes this yacht unbelievable. Located in the finest most elegant first class member only marinas. Guests have access to private pool, tiki bar, fine dining restaurant and fre  …see more

from $406 / night

$2500 - $6650 / week

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from $406 / night

80

Key Largo Vacation home rental

Florida Keys / Key Largo

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
Our Key Largo Holiday Vacation Rental home is fully air conditioned and all on one level with Tiled floors for hygiene throughout. We have a Queen size bed in the master bedroom, 2 x full size doubles in the second bedroom. All beds have quality posture-pedic mattresses  …see more

from $13 / night

$868 - $1538 / week

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from $13 / night

(2) Excellent 

41

Vacation 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
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 g  …see more

from $198 / night

$1385 - $2086 / week

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from $198 / night

(12) Very Good 

14

Vacation 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 mi
  • 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 t  …see more

from $195 / night

$986 / week

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from $195 / night

24

Apartment rental in Tavernier

Key Largo / Tavernier

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
Ocean view, private beach and marina, free parking, tennis courts, swimming pool Travelling with your family or friends and want to stay all together? Prefer to cook by yourself while on the vacation? Or maybe you just want to feel yourself like home, not like in a hot  …see more

from $999 / night

$6993 / week

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from $999 / night

24

Vacation apartment in Tavernier

Key Largo / Tavernier

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
Ocean view, private beach and marina, free parking, tennis courts, swimming pool Travelling with your family or friends and want to stay all together? Prefer to cook by yourself while on the vacation? Or maybe you just want to feel yourself like home, not like in a hot  …see more

from $999 / night

$6993 / week

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from $999 / night

(14) Excellent 

55

Key Largo / Tavernier

2 4 Min stay varies

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

 …see more

from $200 / night

$1400 / week

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from $200 / night

21

Florida Keys / Duck Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly

 …see more

from $306 / night

$2500 / week

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from $306 / night

6

Florida Keys / Key West

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $215 / night

$1500 / week

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from $215 / 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 mi
  • Swimming pool

 …see more

from $341 / night

$2144 - $3800 / week

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from $341 / 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 $175 / night

$1075 - $1675 / week

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from $175 / night

(7) Very Good 

25

Florida Keys / Islamorada

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children

 …see more

from $226 / night

$1575 - $1996 / week

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from $226 / night

(1) Very Good 

9

Florida Keys / Key Largo

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool

 …see more

from $129 / night

$900 - $1201 / week

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from $129 / night

(24) Very Good 

33

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

 …see more

from $229 / night

$1597 - $3136 / week

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from $229 / night

(35) 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 $330 / night

$2304 / week

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from $330 / night

(2) Very Good 

16

Key Largo / Tavernier

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly

 …see more

from $200 / night

$1201 / week

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from $200 / night

(16) Very Good 

13

Florida Keys / Key West

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $169 / night

$1001 - $2500 / week

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from $169 / night

(31) 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 $260 / night

$1814 / week

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from $260 / 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 mi
  • Swimming pool

 …see more

from $143 / night

$999 - $1841 / week

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from $143 / 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 $200 / night

$1400 / week

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from $200 / night

(14) 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 $279 / night

$1953 / week

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from $279 / night

6

Key Largo / Tavernier

3 12 6 nights min

  • 3 bedrooms
  • Sleeps 12
  • 6 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $401 / night

$2801 / week

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from $401 / night

(5) Excellent 

14

Florida Keys / Key West

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Air conditioning

 …see more

from $180 / night

$1500 - $4850 / week

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from $180 / night

(2) Excellent 

32

Florida Keys / Key Largo

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning

 …see more

from $178 / night

$1205 - $1635 / week

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from $178 / night

(7) Excellent 

18

Florida Keys / Islamorada

2 6 30 nights min

  • 2 bedrooms
  • Sleeps 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $127 / night

$887 / week

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from $127 / night

(9) Excellent 

17

Florida Keys / Big Pine Key

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

 …see more

from $200 / night

$1400 - $1601 / week

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from $200 / 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 $271 / night

$1876 / week

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from $271 / night

(40) Excellent 

26

Florida Keys / Marathon

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Air conditioning

 …see more

from $125 / night

$875 / week

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from $125 / night

(24) 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 $249 / night

$1743 / week

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from $249 / night

(1) Excellent 

24

Florida Keys / Key Largo

3 7 30 nights min

  • 3 bedrooms
  • Sleeps 7
  • 30 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $174 / night

$1214 / week

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from $174 / night

15

Marathon / Marathon Shores

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from $342 / night

$2500 - $4250 / week

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from $342 / night

(29) Very Good 

32

Florida Keys / Key West

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

 …see more

from $218 / night

$1526 - $3136 / week

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from $218 / night

(13) Excellent 

36

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $419 / night

$2926 - $5096 / week

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from $419 / night

(15) Excellent 

17

Key Largo / Tavernier

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $200 / night

$1201 - $1500 / week

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from $200 / night

(1) Excellent 

29

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $218 / night

$1526 - $2786 / week

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from $218 / night

33

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly

 …see more

from $268 / night

$1876 - $3836 / week

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from $268 / night

(2) Excellent 

12

Florida Keys / Duck Key

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $251 / night

$2066 / week

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from $251 / night

(4) Excellent 

30

Florida Keys / Key Largo

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $143 / night

$999 / week

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from $143 / night

24

Florida Keys / Long Key

2 5 30 nights min

  • 2 bedrooms
  • Sleeps 5
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $179 / night

$1250 / week

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from $179 / night