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

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Vacation rentals Key West
367 properties
Vacation rentals Key Largo
220 properties
Vacation rentals Islamorada
102 properties
Vacation rentals Marathon
88 properties
Vacation rentals Big Pine Key
31 properties
Vacation rentals Cudjoe Key
24 properties
Lower Keys
22 properties
Vacation rentals Key Colony Beach
17 properties
Cottages Little Torch Key
14 properties
Ramrod Key
13 properties
Long Key
8 properties
Sugarloaf
6 properties

Florida Keys

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849 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 $159 / night

$1109 - $1563 / week

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from $159 / 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 $200 / night

$1397 - $2102 / week

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from $200 / night

26

Vacation apartment rental

Florida Keys / Key Largo

6 18 Min stay varies

  • 6 bedrooms
  • Sleeps 18
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
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 hotel. If you have many people in your party, or big family, or want to have some pri  …see more

from $485 / night

$3395 / week

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from $485 / night

(4) 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 $405 / night

$2500 - $6650 / week

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from $405 / 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 $197 / night

$993 / week

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from $197 / night

24

Apartment rental in Tavernier

Key Largo / Tavernier

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • 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 $159 / night

$1113 / week

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from $159 / night

23

Vacation apartment in Tavernier

Key Largo / Tavernier

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Ocean view, private beach and marina, free parking, tennis courts, swimming pool This beautiful 1 bedroom apartment is located in an Oceanfront hotel style building in the heart of Key Largo, which is halfway between Miami and Key West. 60 acres in the Florida Keys ar  …see more

from $149 / night

$1043 / week

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from $149 / night

26

Tavernier Vacation apartment rental

Key Largo / Tavernier

6 18 Min stay varies

  • 6 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Island 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 ho  …see more

from $449 / night

$3143 / week

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from $449 / night

26

Vacation apartment in Tavernier

Key Largo / Tavernier

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
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 $325 / night

$2275 / week

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from $325 / night

29

Marathon Shores Vacation home rental

Marathon / Marathon Shores

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 8 mi
  • Child friendly
  • Air conditioning
The "Mermaid House" sits directly on the ocean with the unobstructed views, gorgeous sunrises and some of the best boating access in the Marathon area. House offers 4 Queen Bedrooms and 2 full bathrooms. 3 bedrooms and a bathroom are located on the ground leve  …see more

from $434 / night

$3025 - $4033 / week

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from $434 / night

23

Home rental in Tavernier with swimming pool

Key Largo / Tavernier

2 6 6 nights min

  • 2 bedrooms
  • Sleeps 6
  • 6 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Charming doesn't even begin to describe this modern, tastefully appointed waterfront 2 bedroom 2 bathroom house. Plush bedding, upgraded kitchen and bath, and a breezy terrace perfect for bbq's and relaxing. This home features a private pool, and dock and di  …see more

from $379 / night

$2659 / week

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from $379 / night

24

Vacation apartment in Tavernier

Key Largo / Tavernier

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • 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 $162 / night

$1134 / week

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from $162 / night

(37) 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 $329 / night

$2303 / week

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from $329 / night

(33) 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

9

Florida Keys / Key Colony Beach

2 6 Min stay varies

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

 …see more

from $142 / night

$908 - $1210 / week

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from $142 / night

27

Florida Keys / Key Colony Beach

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly

 …see more

from $195 / night

$1361 - $2369 / week

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from $195 / 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 $115 / night

$802 - $1034 / week

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from $115 / night

(25) 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

(23) 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

$1334 / week

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from $191 / night

33

Florida Keys / Key West

Studio 6 Min stay varies

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

 …see more

from $228 / night

$1876 - $3836 / week

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from $228 / 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

(10) 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

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 $308 / night

$2521 / week

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from $308 / night

(5) 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 - $1629 / week

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from $202 / night

(16) 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 $202 / night

$1412 / week

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from $202 / night

(22) Very Good 

23

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 $188 / night

$1526 - $2926 / week

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from $188 / 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 $193 / night

$1351 / week

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from $193 / 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 $343 / night

$2161 - $3831 / week

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from $343 / night

(1) Excellent 

18

Marathon / Marathon Shores

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from $494 / night

$3458 - $6245 / week

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from $494 / night

(11) Very Good 

12

Florida Keys / Key Largo

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from $130 / night

$807 - $1059 / week

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from $130 / night

(5) Good 

42

Key Largo / Tavernier

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Ask about children
  • Air conditioning

 …see more

from $131 / night

$911 / week

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from $131 / 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

Marathon / Marathon Shores

2 7 7 nights min

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

 …see more

from $345 / night

$2520 - $4285 / week

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from $345 / night

(25) Very Good 

33

Florida Keys / Key West

Studio 4 Min stay varies

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

 …see more

from $188 / night

$1316 - $2716 / week

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from $188 / night

(3) Very Good 

30

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 $188 / night

$1316 - $2926 / week

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from $188 / night

(5) 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 $177 / night

$1084 - $1689 / week

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from $177 / 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 $127 / night

$883 - $1165 / week

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from $127 / night

26

Key Largo / Tavernier

3 6 Min stay varies

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

 …see more

from $298 / night

$2117 / week

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from $298 / night

(42) Very Good 

26

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 - $2576 / week

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from $168 / 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 $202 / night

$1412 / week

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from $202 / night

1