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

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Vacation rentals Key West
186 properties
Vacation rentals Key Largo
179 properties
Vacation rentals Islamorada
91 properties
Vacation rentals Marathon
73 properties
Vacation rentals Big Pine Key
30 properties
Lower Keys
19 properties
Vacation rentals Cudjoe Key
19 properties
Cottages Little Torch Key
14 properties
Vacation rentals Key Colony Beach
13 properties
Ramrod Key
12 properties
Long Key
7 properties
Sugarloaf
5 properties

Florida Keys

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654 Vacation rentals

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(27) 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 $262 / night

$1828 / week

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from $262 / night

(22) 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 $251 / night

$1757 / week

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from $251 / night

(3) 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 $202 / night

$1311 - $1628 / week

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from $202 / night

(31) 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 $332 / night

$2322 / week

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from $332 / 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 $126 / night

$882 / week

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from $126 / night

18

Marathon / Marathon Shores

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Air conditioning
  • Ask about pets

 …see more

from $494 / night

$3458 - $6245 / week

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from $494 / 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 $202 / night

$1210 - $1412 / week

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from $202 / night

(2) Excellent 

40

Vacation apartment in USA East Coast

Florida Keys / Islamorada

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 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 gated  …see more

from $200 / night

$1397 / week

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from $200 / night

(1) Excellent 

21

USA East Coast Vacation houseboat rental

Florida Keys / Key West

4 9 2 nights min

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min
  • 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 $409 / night

$2520 - $4410 / week

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from $409 / night

(1) Very Good 

24

USA East Coast Vacation home rental

Florida Keys / Key West

3 8 30 nights min

  • 3 bedrooms
  • Sleeps 8
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
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 $267 / night

$1869 / week

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from $267 / 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 $202 / night

$1412 - $1613 / week

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from $202 / night

(8) Excellent 

15

Florida Keys / Marathon

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $242 / night

$1613 - $2016 / week

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from $242 / night

(1) Excellent 

6

Key Largo / Tavernier

2 6 Min stay varies

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

 …see more

from $353 / night

$2470 / week

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from $353 / night

21

Key Largo / Tavernier

2 6 3 nights min

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

 …see more

from $176 / night

$1101 - $1300 / week

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from $176 / night

(7) Excellent 

36

Florida Keys / Marathon

3 8 Min stay varies

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

 …see more

from $303 / night

$1764 - $2601 / week

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from $303 / night

80

USA East Coast 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 $109 / night

$882 - $1449 / week

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from $109 / night

(3) Excellent 

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 $110 / night

$911 / week

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from $110 / night

(18) Excellent 

20

Florida Keys / Key Largo

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $191 / night

$1134 - $1336 / week

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from $191 / night

25

Florida Keys / Cudjoe Key

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 23 mi
  • Swimming pool

 …see more

from $142 / night

$898 - $1109 / week

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from $142 / 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 $201 / night

$2082 / week

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from $201 / night

14

Florida Keys / Islamorada

2 6 7 nights min

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

 …see more

from $231 / night

$1612 - $3023 / week

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from $231 / 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 $200 / night

$1396 - $1901 / week

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from $200 / night

43

Florida Keys / Islamorada

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $1153 / night

$8064 - $12096 / week

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from $1153 / night

5

Florida Keys / Marathon

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about pets

 …see more

from $227 / night

$1429 - $2096 / week

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from $227 / 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 $280 / night

$1954 / week

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from $280 / night

6

Marathon / Marathon Shores

1 4 14 nights min

  • 1 bedroom
  • Sleeps 4
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $197 / night

$1376 / week

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from $197 / night

20

Key Largo / Tavernier

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

 …see more

from $433 / night

$3024 / week

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from $433 / night

19

Florida Keys / Ramrod Key

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $257 / night

$1795 - $1961 / week

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from $257 / night

(5) Excellent 

11

Florida Keys / Marathon

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Ask about pets

 …see more

from $288 / night

$1810 - $3366 / week

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from $288 / night

22

Florida Keys / Key Colony Beach

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $152 / night

$1059 - $1412 / week

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from $152 / night

(12) Very Good 

14

Vacation condo in USA East Coast

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 $196 / night

$985 / week

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from $196 / night

(5) Excellent 

12

Florida Keys / Marathon

3 6 Min stay varies

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

 …see more

from $404 / night

$2823 - $3780 / week

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from $404 / 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 $130 / night

$908 - $1210 / week

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from $130 / night

(1) Excellent 

15

Florida Keys / Little Torch Key

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $411 / night

$2873 - $3024 / week

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from $411 / night

(2) Very Good 

14

Florida Keys / Marathon

2 6 Min stay varies

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

 …see more

from $152 / night

$958 - $1311 / week

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from $152 / night

(6) Excellent 

19

Florida Keys / Islamorada

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Ask about children
  • Pet friendly

 …see more

from $149 / night

$1041 - $1300 / week

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from $149 / night

17

Florida Keys / Marathon

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $302 / night

$2110 / week

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from $302 / night

(2) Excellent 

24

Florida Keys / Key Largo

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Child friendly

 …see more

from $252 / night

$1512 / week

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from $252 / night

(2) Excellent 

4

Florida Keys / Marathon

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

 …see more

from $368 / night

$2318 - $3691 / week

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from $368 / night

(2) Excellent 

15

Florida Keys / Key Largo

2 6 7 nights min

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

 …see more

from $142 / night

$990 - $1150 / week

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from $142 / night

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