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

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Vacation rentals Key West
419 properties
Vacation rentals Key Largo
226 properties
Vacation rentals Islamorada
125 properties
Vacation rentals Marathon
87 properties
Vacation rentals Big Pine Key
21 properties
Vacation rentals Key Colony Beach
17 properties
Long Key
13 properties
Cottages Little Torch Key
13 properties
Vacation rentals Cudjoe Key
10 properties
Lower Keys
9 properties
Matecumbe Key
5 properties

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973 Vacation rentals

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 level. Upstair …see more

from $430 / night

$3000 - $4000 / week

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from $430 / 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

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

(6) 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

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

$1100 - $1550 / 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 gated …see more

from $198 / night

$1385 - $2085 / week

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from $198 / 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

(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

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

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

15

Houseboat rental in Key West

Florida Keys / Key West

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Pet friendly
Rosie is at anchor in harbor just off the bustling downtown life of Key West. She has a very comfortable queen size V berth bed, a cozy saloon (living room) great for curling up, amazing sunset views, and in a very friendly neighborhood of boats! Rosie is a 33ft Pears …see more

from $169 / night

$999 - $1349 / week

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from $169 / 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 direct canal …see more

from $350 / night

$2659 / week

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from $350 / night

4

Key West Vacation boathouse rental

Florida Keys / Key West

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
2 private bedrooms, plus pullout bed. Immaculate cabin interior. Approximately 100 yards off shore is where your adventure begins! Enjoy key west sunshine on your own private sundeck with comfortable upholstered seating & outdoor table for drinks/snacks. After you've wo …see more

from $225 / night

$1575 / week

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from $225 / 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

from $270 / night

$1875 / week

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from $270 / night

(32) 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

from $259 / night

$1813 / week

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from $259 / night

21

Florida Keys / Duck Key

2 6 4 nights min

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

from $305 / night

$2135 / week

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from $305 / 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

from $340 / night

$2143 - $3800 / week

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from $340 / 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

from $228 / night

$1876 - $3836 / week

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from $228 / night

(38) 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

from $329 / night

$2303 / week

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from $329 / night

(3) Very Good 

16

Key Largo / Tavernier

2 6 3 nights min

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

from $200 / night

$1200 / week

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from $200 / night

(1) Very Good 

43

Florida Keys / Key Largo

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Air conditioning

from $158 / night

$925 - $1155 / week

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from $158 / night

(26) 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

from $249 / night

$1743 / week

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from $249 / night

(3) Excellent 

22

Florida Keys / Key West

2 6 3 nights min

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

from $275 / night

$1700 - $2400 / week

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from $275 / night

13

Florida Keys / Key West

2 6 Min stay varies

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

from $299 / night

$1400 - $2500 / week

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from $299 / night

(3) Excellent 

30

Florida Keys / Key West

Studio 4 Min stay varies

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

from $168 / night

$1176 - $2646 / week

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from $168 / night

(16) 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

from $279 / night

$1953 / week

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from $279 / night

(24) 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

from $189 / night

$1323 / week

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from $189 / night

(19) 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

from $200 / night

$1400 / week

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from $200 / night

(2) Very Good 

9

Florida Keys / Marathon

Studio 3 7 nights min

  • Studio
  • Sleeps 3
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $143 / night

$1000 - $1200 / week

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from $143 / 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

from $229 / night

$1600 - $2500 / week

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from $229 / night

(2) Excellent 

13

Florida Keys / Key Largo

3 8 7 nights min

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

from $200 / night

$1400 - $2400 / week

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from $200 / night

(7) Excellent 

30

Florida Keys / Marathon

3 8 Min stay varies

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

from $250 / night

$1450 - $2100 / week

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from $250 / night

(40) Excellent 

26

Florida Keys / Marathon

1 4 2 nights min

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

from $125 / night

$875 - $1155 / week

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from $125 / 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

from $127 / night

$887 / week

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from $127 / night

(16) Very Good 

24

Florida Keys / Islamorada

2 4 7 nights min

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

from $214 / night

$1500 - $1650 / week

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from $214 / night

35

Florida Keys / Key West

2 4 7 nights min

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

from $208 / night

$1450 - $2800 / week

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from $208 / night

(1) Excellent 

23

Florida Keys / Key West

Studio 2 Min stay varies

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

from $138 / night

$966 - $2016 / week

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from $138 / night

19

Florida Keys / Sugarloaf

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

from $189 / night

$1319 / week

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from $189 / night

14

Florida Keys / Ramrod Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

from $100 / night

$700 / week

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from $100 / night

1