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

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Vacation rentals Key West
399 properties
Vacation rentals Key Largo
181 properties
Vacation rentals Islamorada
95 properties
Vacation rentals Marathon
80 properties
Vacation rentals Big Pine Key
23 properties
Vacation rentals Key Colony Beach
15 properties
Cottages Little Torch Key
14 properties
Long Key
8 properties
Lower Keys
8 properties
Vacation rentals Cudjoe Key
6 properties

Florida Keys

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821 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 - $1551 / week

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from $158 / 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

$1386 - $2085 / 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

$985 / week

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from $195 / 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 $104 / night

$840 - $1380 / week

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from $104 / night

(42) Very Good 

28

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 $168 / night

$1176 - $2577 / week

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from $168 / 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 $201 / night

$1401 - $1600 / week

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from $201 / night

(1) Excellent 

18

Marathon / Marathon Shores

6 12 7 nights min

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

 …see more

from $490 / night

$3430 - $6195 / week

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from $490 / night

(3) Excellent 

30

Florida Keys / Key West

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Pet friendly

 …see more

from $168 / night

$1176 - $2646 / week

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from $168 / night

(12) 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 $201 / night

$1401 / week

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from $201 / 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 $180 / night

$1260 / week

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from $180 / 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 $270 / night

$1875 / week

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from $270 / night

33

Florida Keys / Key West

1 6 Min stay varies

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

 …see more

from $208 / night

$1456 - $3486 / week

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from $208 / night

(33) 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

20

Florida Keys / Key Largo

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Suitable for children age 5+

 …see more

from $265 / night

$1600 - $2635 / week

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from $265 / night

(30) 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 $259 / night

$1813 / week

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from $259 / night

29

Florida Keys / Key Largo

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Swimming pool

 …see more

from $186 / night

$1150 - $1500 / week

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from $186 / night

20

Florida Keys / Key West

Studio 2 Min stay varies

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

 …see more

from $129 / night

$897 - $1806 / week

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from $129 / 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 $215 / night

$1500 - $1900 / week

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from $215 / 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 - $4186 / week

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from $268 / 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 $158 / night

$1101 - $1300 / week

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from $158 / night

29

Florida Keys / Key West

Studio 2 Min stay varies

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

 …see more

from $148 / night

$1036 - $2436 / week

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from $148 / night

(3) Good 

36

Florida Keys / Key West

3 6 Min stay varies

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

 …see more

from $498 / night

$3486 - $6147 / week

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from $498 / night

(23) 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

(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 $279 / night

$1953 / week

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from $279 / 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 $150 / night

$975 - $1675 / week

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from $150 / night

25

Florida Keys / Key West

Studio 2 Min stay varies

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

 …see more

from $168 / night

$1176 - $2506 / week

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from $168 / night

(21) Very Good 

23

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 $219 / night

$1527 - $2926 / week

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from $219 / night

(4) Very Good 

28

Florida Keys / Key West

2 4 7 nights min

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

 …see more

from $172 / night

$1200 - $2800 / week

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from $172 / night

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 $219 / night

$1527 - $2787 / week

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from $219 / night

(2) Excellent 

39

Florida Keys / Key Largo

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly

 …see more

from $175 / night

$1150 - $1251 / week

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from $175 / night

23

Florida Keys / Key West

Studio 2 Min stay varies

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

 …see more

from $178 / night

$1246 - $2436 / week

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from $178 / night

(25) Very Good 

27

Florida Keys / Key West

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $198 / night

$1386 - $2926 / week

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from $198 / 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 $219 / night

$1527 - $2787 / week

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from $219 / night

30

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 $189 / night

$1317 - $2926 / week

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from $189 / 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 $340 / night

$2143 - $3801 / week

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from $340 / night

(2) Excellent 

31

Florida Keys / Key West

Studio 4 Min stay varies

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

 …see more

from $168 / night

$1176 - $2646 / week

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from $168 / night

27

Florida Keys / Key Colony Beach

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly

 …see more

from $193 / night

$1350 - $2350 / week

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from $193 / night

9

Florida Keys / Marathon

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning

 …see more

from $651 / night

$4551 - $8106 / week

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from $651 / night

22

Florida Keys / Key West

Studio 2 Min stay varies

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

 …see more

from $138 / night

$966 - $2226 / week

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from $138 / night

(1) Excellent 

31

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 $249 / night

$1737 - $3136 / week

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from $249 / night