50 Best Islamorada Vacation rentals on Holiday Lettings - House rentals

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103 Vacation rentals

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(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 - $2085 / week

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from $198 / 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 $179 / night

$1253 / week

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from $179 / night

(1) Excellent 

21

Florida Keys / Islamorada

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Child friendly

 …see more

from $175 / night

$1000 - $1300 / week

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from $175 / night

(3) Excellent 

19

Florida Keys / Islamorada

1 4 30 nights min

  • 1 bedroom
  • Sleeps 4
  • 30 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

 …see more

from $114 / night

$795 - $1025 / week

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from $114 / night

(2) Good 

11

Florida Keys / Islamorada

Studio 10 Min stay varies

  • Studio
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from $575 / night

$2828 - $5054 / week

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from $575 / night

23

Florida Keys / Islamorada

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool

 …see more

from $229 / night

$1599 - $2395 / week

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from $229 / night

20

Florida Keys / Islamorada

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Car not necessary

 …see more

from $250 / night

$1550 / week

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from $250 / night

(4) Very Good 

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 $109 / night

$903 / week

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from $109 / night

6

Florida Keys / Islamorada

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly

 …see more

from $286 / night

$2000 - $2300 / week

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from $286 / night

(13) Very Good 

22

Florida Keys / Islamorada

1 3 30 nights min

  • 1 bedroom
  • Sleeps 3
  • 30 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $125 / night

$875 / week

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from $125 / night

25

Florida Keys / Islamorada

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

 …see more

from $300 / night

$2100 / week

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from $300 / night

15

Florida Keys / Islamorada

5 16 7 nights min

  • 5 bedrooms
  • Sleeps 16
  • 7 nights min
  • Child friendly
  • Pet friendly

 …see more

from $572 / night

$4000 - $15400 / week

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from $572 / night

(6) Excellent 

19

Florida Keys / Islamorada

Studio 3 Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
  • Ask about children
  • Pet friendly

 …see more

from $158 / night

$1100 - $1300 / week

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from $158 / night

(3) Excellent 

1

Florida Keys / Islamorada

Studio 8 28 nights min

  • Studio
  • Sleeps 8
  • 28 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $100 / night

$903 / week

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from $100 / night

(3) Excellent 

8

Florida Keys / Islamorada

Studio 8 7 nights min

  • Studio
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $350 / night

$2296 - $2653 / week

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from $350 / night

(8) Excellent 

25

Florida Keys / Islamorada

Studio 6 7 nights min

  • Studio
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children

 …see more

from $225 / night

$1575 - $1995 / week

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from $225 / night

14

Florida Keys / Islamorada

2 4 7 nights min

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

 …see more

from $158 / night

$1100 - $1400 / week

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from $158 / night

7

Florida Keys / Islamorada

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning

 …see more

from $89 / night

$623 / week

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from $89 / night

(1) Excellent 

21

Florida Keys / Islamorada

2 6 7 nights min

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

 …see more

from $142 / night

$994 - $1500 / week

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from $142 / night

26

Florida Keys / Islamorada

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Air conditioning

 …see more

from $243 / night

$1700 - $2350 / week

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from $243 / night

(4) Excellent 

20

Florida Keys / Islamorada

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $286 / night

$2000 - $2500 / week

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from $286 / night

(1) Excellent 

25

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 $279 / night

$1995 - $2000 / week

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from $279 / night

15

Florida Keys / Islamorada

1 5 30 nights min

  • 1 bedroom
  • Sleeps 5
  • 30 nights min
  • Beach/lakeside relaxation
  • Child friendly

 …see more

from $129 / night

$903 / week

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from $129 / night

(1) Excellent 

25

Florida Keys / Islamorada

2 6 7 nights min

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

 …see more

from $175 / night

$995 - $1925 / week

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from $175 / night

(1) Excellent 

15

Florida Keys / Islamorada

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children

 …see more

from $67 / night

$469 / week

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from $67 / night

20

Florida Keys / Islamorada

2 6 7 nights min

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

 …see more

from $150 / night

$1050 - $1598 / week

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from $150 / 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

26

Florida Keys / Islamorada

2 6 28 nights min

  • 2 bedrooms
  • Sleeps 6
  • 28 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

 …see more

from $289 / night

$2023 - $2443 / week

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from $289 / night

18

Florida Keys / Islamorada

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Air conditioning
  • Pet friendly

 …see more

from $358 / night

$2500 / week

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from $358 / night

17

Florida Keys / Islamorada

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children

 …see more

from $147 / night

$1029 / week

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from $147 / night

24

Florida Keys / Islamorada

Studio 10 Min stay varies

  • Studio
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Pet friendly

 …see more

from $217 / night

$1519 / week

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from $217 / night

17

Florida Keys / Islamorada

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Pet friendly

 …see more

from $320 / night

$2350 - $2950 / week

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from $320 / night

15

Florida Keys / Islamorada

4 11 5 nights min

  • 4 bedrooms
  • Sleeps 11
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $395 / night

$2765 / week

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from $395 / night

(5) Very Good 

29

Florida Keys / Islamorada

2 6 30 nights min

  • 2 bedrooms
  • Sleeps 6
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly

 …see more

from $450 / night

$3150 / week

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from $450 / night

(23) Excellent 

29

Florida Keys / Islamorada

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $322 / night

$2250 / week

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from $322 / night

34

Florida Keys / Islamorada

4 10 30 nights min

  • 4 bedrooms
  • Sleeps 10
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $834 / night

$5834 / week

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from $834 / night

27

Florida Keys / Islamorada

4 10 7 nights min

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

 …see more

from $1643 / night

$11500 / week

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from $1643 / night

4

Florida Keys / Islamorada

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning

 …see more

from $199 / night

$1393 / week

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from $199 / night

23

Florida Keys / Islamorada

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Ask about children

 …see more

from $107 / night

$749 / week

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from $107 / night

26

Florida Keys / Islamorada

2 6 30 nights min

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

 …see more

from $215 / night

$1500 / week

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from $215 / night

1