Florida Keys Vacation Rentals - Wimdu base64Hash Florida Keys Vacation Rentals - Wimdu

Florida Keys Vacation Rentals

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Choose from 18,724 vacation rentals and homes for your trip!

Best-rated vacation rentals in the Florida Keys

Discover vacation rentals with top-notch guest ratings

House Cudjoe Key
from $800 per night
House ∙ 14 guests ∙ 5 bedrooms

214 m² House

4.7
Excellent(90 ratings)
Cudjoe Key, Monroe County, Florida, United States
Vrbo
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House Sugarloaf Shores
from $504 per night
10 guests ∙ 4 bedrooms

House

4.9
Outstanding(62 ratings)
Sugarloaf Shores, Monroe County, Florida, United States
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House Islamorada
from $765 per night
House ∙ 8 guests ∙ 4 bedrooms

314 m² House

5.0
Outstanding(51 ratings)
Islamorada, Monroe County, Florida, United States
Vrbo
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Pet-friendly rentals in the Florida Keys

Explore best dog-friendly accommodation offers and enjoy vacation with your pet

House Key West
from $281 per night
House ∙ 8 guests ∙ 4 bedrooms

195 m² House

4.7
Excellent(25 ratings)
Key West, Monroe County, Florida, United States
Pet-friendly
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House Marathon
from $2,388 per night
22 guests ∙ 11 bedrooms

House

5.0
Outstanding(38 ratings)
Marathon, Monroe County, Florida, United States
Pet-friendly
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House Key Colony Beach
from $518 per night
House ∙ 8 guests ∙ 4 bedrooms

162 m² House

5.0
Outstanding
Key Colony Beach, Monroe County, Florida, United States
Pet-friendly
Vacasa
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Vacation rentals with pool in the Florida Keys

Discover best cabin and house rentals with pool in the Florida Keys

Maisonette Key Colony Beach
-10%
$554
from $497 per night
Maisonette ∙ 17 guests ∙ 7 bedrooms

300 m² Maisonette

4.2
Very good(49 ratings)
Key Colony Beach, Monroe County, Florida, United States
Pool
Vacasa
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House Islamorada
from $643 per night
6 guests ∙ 3 bedrooms

House

4.4
Very good(24 ratings)
Islamorada, Monroe County, Florida, United States
Pool
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House Marathon
from $742 per night
House ∙ 10 guests ∙ 5 bedrooms

316 m² House

4.9
Outstanding(35 ratings)
Marathon, Monroe County, Florida, United States
Pool
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Best vacation rental offers in the Florida Keys

House Marathon
from $1,029 per night
House ∙ 12 guests ∙ 6 bedrooms

307 m² House

5.0
Outstanding(51 ratings)
Marathon, Monroe County, Florida, United States
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House Marathon
from $520 per night
8 guests ∙ 3 bedrooms

House

4.0
Very good(2 ratings)
Marathon, Monroe County, Florida, United States
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House Marathon
from $730 per night
House ∙ 10 guests ∙ 4 bedrooms

186 m² House

5.0
Outstanding(8 ratings)
Marathon, Monroe County, Florida, United States
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House Marathon
from $861 per night
House ∙ 12 guests ∙ 5 bedrooms

242 m² House

5.0
Outstanding(2 ratings)
Marathon, Monroe County, Florida, United States
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House Marathon
from $887 per night
House ∙ 10 guests ∙ 5 bedrooms

316 m² House

5.0
Outstanding(18 ratings)
Marathon, Monroe County, Florida, United States
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House Marathon
from $441 per night
8 guests ∙ 3 bedrooms

House

5.0
Outstanding(4 ratings)
Marathon, Monroe County, Florida, United States
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House Islamorada
from $438 per night
House ∙ 9 guests ∙ 4 bedrooms

130 m² House

4.9
Outstanding(24 ratings)
Islamorada, Monroe County, Florida, United States
Vrbo
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House Marathon
from $1,027 per night
16 guests ∙ 6 bedrooms

House

5.0
Outstanding(37 ratings)
Marathon, Monroe County, Florida, United States
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House Marathon
from $1,107 per night
16 guests ∙ 7 bedrooms

House

4.9
Outstanding(32 ratings)
Marathon, Monroe County, Florida, United States
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House Marathon
from $320 per night
6 guests ∙ 4 bedrooms

House

4.8
Outstanding(158 ratings)
Marathon, Monroe County, Florida, United States
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House Marathon
from $391 per night
House ∙ 8 guests ∙ 4 bedrooms

135 m² House

4.5
Excellent(65 ratings)
Marathon, Monroe County, Florida, United States
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House Big Pine Key
from $582 per night
House ∙ 12 guests ∙ 6 bedrooms

223 m² House

Big Pine Key, Monroe County, Florida, United States
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House Islamorada
from $701 per night
House ∙ 12 guests ∙ 5 bedrooms

332 m² House

4.9
Outstanding(16 ratings)
Islamorada, Monroe County, Florida, United States
Vrbo
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House Marathon
from $425 per night
House ∙ 10 guests ∙ 4 bedrooms

232 m² House

4.9
Outstanding(56 ratings)
Marathon, Monroe County, Florida, United States
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House Marathon
from $505 per night
12 guests ∙ 6 bedrooms

House

4.8
Outstanding(45 ratings)
Marathon, Monroe County, Florida, United States
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House Marathon
from $653 per night
12 guests ∙ 6 bedrooms

House

4.9
Outstanding(49 ratings)
Marathon, Monroe County, Florida, United States
Vrbo
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House Key Colony Beach
from $400 per night
House ∙ 10 guests ∙ 5 bedrooms

232 m² House

4.5
Excellent(90 ratings)
Key Colony Beach, Monroe County, Florida, United States
Vrbo
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House Marathon
from $585 per night
10 guests ∙ 4 bedrooms

House

5.0
Outstanding(16 ratings)
Marathon, Monroe County, Florida, United States
Vrbo
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House Marathon
from $678 per night
House ∙ 10 guests ∙ 4 bedrooms

127 m² House

4.8
Outstanding(86 ratings)
Marathon, Monroe County, Florida, United States
Vacasa
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House Marathon
from $716 per night
House ∙ 8 guests ∙ 4 bedrooms

281 m² House

4.6
Excellent(32 ratings)
Marathon, Monroe County, Florida, United States
Vrbo
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House Key Colony Beach
from $1,229 per night
House ∙ 12 guests ∙ 6 bedrooms

325 m² House

5.0
Outstanding(92 ratings)
Key Colony Beach, Monroe County, Florida, United States
Vrbo
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House Marathon
from $262 per night
House ∙ 8 guests ∙ 4 bedrooms

204 m² House

4.7
Excellent(165 ratings)
Marathon, Monroe County, Florida, United States
Vrbo
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House Marathon
from $530 per night
House ∙ 8 guests ∙ 5 bedrooms

174 m² House

4.7
Excellent(16 ratings)
Marathon, Monroe County, Florida, United States
Vrbo
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House Summerland Key
from $479 per night
8 guests ∙ 5 bedrooms

House

5.0
Outstanding(27 ratings)
Summerland Key, Monroe County, Florida, United States
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House Summerland Key
from $374 per night
House ∙ 8 guests ∙ 4 bedrooms

130 m² House

5.0
Outstanding(10 ratings)
Summerland Key, Monroe County, Florida, United States
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House Marathon
from $732 per night
10 guests ∙ 4 bedrooms

House

5.0
Outstanding(47 ratings)
Marathon, Monroe County, Florida, United States
Vrbo
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House Islamorada
from $419 per night
6 guests ∙ 4 bedrooms

House

5.0
Outstanding(2 ratings)
Islamorada, Monroe County, Florida, United States
Vrbo
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House Islamorada
from $763 per night
10 guests ∙ 4 bedrooms

House

4.8
Outstanding(109 ratings)
Islamorada, Monroe County, Florida, United States
Vrbo
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Villa Marathon
from $520 per night
10 guests ∙ 5 bedrooms

Villa

4.9
Outstanding(36 ratings)
Marathon, Monroe County, Florida, United States
Vrbo
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House Islamorada
from $974 per night
House ∙ 10 guests ∙ 5 bedrooms

465 m² House

5.0
Outstanding(82 ratings)
Islamorada, Monroe County, Florida, United States
Vrbo
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Show all 17783 apartments in Florida Keys

Price and Availability Index in Florida Keys

Click on any bar to see price and availability information

Vacation Rental Price Information in the Florida Keys

The graph above shows the average prices of vacation rentals in the Florida Keys throughout the year. December and the period of 12/27 – 1/3 are the most expensive in the year. Typical accommodation prices amount to $632 per night. September is the cheapest month to book your vacation rental getaway, so make sure to consider it when planning your next trip.

Rental availability information in the Florida Keys

Here, you can see how busy Florida Keys will be at different times of year. The busiest time of year in the Florida Keys is May. On the other hand, only 43% of vacation rentals in the Florida Keys have been booked in September, so this is a good time to look for deals.

Vacation rental on Florida Keys - for active people and connoisseurs

Many holiday accommodations on the Florida Keys are typical American houses with wooden verandas and picturesque columns. There is also a choice of modern villas with private gardens and studios in multi-storey apartment buildings.

2,916,635 reviews
2,916,635 travelers who stayed in the Florida Keys rated their vacation home 4.5/5 stars on average.
  • Culinary specialties on Florida Keys

    Fresh fish and seafood are ingredients for many delicacies. Legendary dishes include Key West pink shrimp and conch. During the crab season from October to May, innkeepers like to serve crab cakes.

    Those with a sweet tooth sweeten their holiday with Key Lime Pie, which bakers make from limes grown only in Florida Keys. A sweet and sour cream made from fruit juice and condensed milk sits on the base made from crumbled biscuits.

And we love our apartments

307 m² House
House
186 m² House
242 m² House
316 m² House
Show all 17783 apartments in Florida Keys

Features of Florida Keys vacation rentals

💳 Discounts up to 10%
⭐ Popular amenities Air conditioning, Pool and Internet
🏊  Vacation rentals with a pool 12,996 rentals
🌙 Minimum price starting at $156
🐾 Pet friendly vacation homes 5,880 rentals
🏡 Rentals available 18,724 rentals

Beautiful regions abroad to consider for next trip

Beautiful regions near to consider for next trip

Get inspired for your vacation in the Florida Keys

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