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Florida Keys Vacation Rentals

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Florida Keys
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$100 - $199
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Enjoy Festivities and Nature From a Florida Keys Vacation Home

The Florida Keys have long been a celebrated vacation destination for couples, families, and those who have a love of the sea and underwater life. Florida Keys vacation rentals are typically beautiful and breezy beachside houses, ranging from cosy, romantic cottages for two, to larger houses with their own pool, perfect for a family or large group.

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Best Vacation Home Deals in Florida Keys

Save up to 38%

House Key Colony Beach
Sept 2 - Sept 9
-38%
$842
$522 per night
House ∙ 6 guests ∙ 2 bedrooms
Beautiful Vacation Home in Key Colony Beach with Large Pool + Water Views
4.9
"Excellent" (132 ratings)
Key Colony Beach, Monroe County, Florida, United States
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House Marathon
Sept 2 - Sept 9
-33%
$1,753
$1,176 per night
House ∙ 8 guests ∙ 4 bedrooms
House in Marathon with Yard, Grill & Pool + Glorious View
5.0
"Excellent" (1 rating)
Marathon, Monroe County, Florida, United States
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Condo Islamorada
Aug 12 - Aug 19
-36%
$564
$362 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Rental Condo in Islamorada with Outdoor Pool + Spectacular Views
4.8
"Excellent" (141 ratings)
Islamorada, Monroe County, Florida, United States
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12,222 welcoming vacation rentals from 16 vacation rental websites are available in Florida Keys, with prices starting at $235 a night. Each of the properties from our partner websites are directly compared by our algorithm so you can save up to 38%.

Top-Rated Offers and Accommodations in Florida Keys

Book Vacation Rentals with the Highest User Rating

House Marathon
Jun 29 - Jul 6
$797 per night
House ∙ 6 guests ∙ 3 bedrooms
Entire Vacation Home in Marathon with Gunite Pool
5.0
"Excellent" (183 ratings)
Marathon, Monroe County, Florida, United States
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Condo Key Colony Beach
Jul 29 - Aug 5
-39%
$694
$421 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Condo in Key Colony Beach with Pool, Grill & Yard
4.9
"Excellent" (122 ratings)
Key Colony Beach, Monroe County, Florida, United States
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House Marathon
Oct 7 - Oct 14
-40%
$1,550
$929 per night
House ∙ 12 guests ∙ 5 bedrooms
House in Marathon with Pool & Grill
5.0
"Excellent" (110 ratings)
Marathon, Monroe County, Florida, United States
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Recommended Vacation Rentals in Florida Keys

Find your perfect vacation rental in Florida Keys: from $231 per night

House Key Colony Beach
Sept 9 - Sept 16
$474 per night
House ∙ 4 guests ∙ 2 bedrooms
Wonderful House in Key Colony Beach with Large Pool
4.9
"Excellent" (60 ratings)
Key Colony Beach, Monroe County, Florida, United States
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House Cudjoe Key
Jan 6 - Jan 13
$1,296 per night
House ∙ 12 guests ∙ 5 bedrooms
Vacation Home in Cudjoe Key with Huge Pool + Ocean View
4.9
"Excellent" (75 ratings)
Cudjoe Key, Monroe County, Florida, United States
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House Marathon
Sept 2 - Sept 9
-38%
$1,906
$1,176 per night
House ∙ 8 guests ∙ 4 bedrooms
House in Marathon with Yard, Grill & Pool + Glorious View
5.0
"Excellent" (1 rating)
Marathon, Monroe County, Florida, United States
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House Cudjoe Key
Jun 29 - Jul 6
$382 per night
House ∙ 6 guests ∙ 2 bedrooms
Vacation Home in Cudjoe Key with Overnight Parking
4.9
"Excellent" (212 ratings)
Cudjoe Key, Monroe County, Florida, United States
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Condo Islamorada
Aug 26 - Sept 2
-35%
$564
$368 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Rental Condo in Islamorada with Outdoor Pool + Spectacular Views
4.8
"Excellent" (141 ratings)
Islamorada, Monroe County, Florida, United States
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House Marathon
Oct 7 - Oct 14
$706 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Marathon with Deep Pool
5.0
"Excellent" (56 ratings)
Marathon, Monroe County, Florida, United States
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House Key Colony Beach
Oct 21 - Oct 28
$364 per night
House ∙ 4 guests ∙ 2 bedrooms
House in Key Colony Beach with Pool, Yard & Grill
4.9
"Excellent" (136 ratings)
Key Colony Beach, Monroe County, Florida, United States
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House Marathon
Nov 4 - Nov 11
$1,385 per night
House ∙ 14 guests ∙ 6 bedrooms
House in Marathon with Private Pool + Front Views
4.9
"Excellent" (41 ratings)
Marathon, Monroe County, Florida, United States
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House Key Colony Beach
Sept 2 - Sept 9
$818 per night
House ∙ 8 guests ∙ 4 bedrooms
Vacation Home in Key Colony Beach with Private Pool
5.0
"Excellent" (72 ratings)
Key Colony Beach, Monroe County, Florida, United States
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Budget-friendly Rentals in Florida Keys

Find Fantastic yet Inexpensive Rentals

House Marathon
Oct 7 - Oct 14
-31%
$855
$586 per night
House ∙ 6 guests ∙ 2 bedrooms
Lovely Vacation Home in Marathon with Private Pool
5.0
"Excellent" (3 ratings)
Marathon, Monroe County, Florida, United States
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House Marathon
Sept 30 - Oct 7
-55%
$1,316
$594 per night
House ∙ 8 guests ∙ 3 bedrooms
House in Marathon with In-Ground Pool
5.0
"Excellent" (41 ratings)
Marathon, Monroe County, Florida, United States
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Cottage Marathon
Oct 14 - Oct 21
$292 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Cottage in Marathon with Grill & Pool
5.0
"Excellent" (85 ratings)
Marathon, Monroe County, Florida, United States
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Vacation rentals and apartments with air conditioning

Keep cool during your trip to Florida Keys and book a vacation rental with air conditioning.

House Air conditioning Marathon
Sept 1 - Sept 8
$707 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Marathon with Private Pool
5.0
"Excellent" (105 ratings)
Marathon, Monroe County, Florida, United States
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Condo Air conditioning Key Colony Beach
Aug 26 - Sept 2
-40%
$696
$419 per night
Condo ∙ 4 guests ∙ 2 bedrooms
Condo in Key Colony Beach with Pool & Grill + Beautiful View
4.9
"Excellent" (131 ratings)
Key Colony Beach, Monroe County, Florida, United States
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Condo Air conditioning Marathon
Jun 29 - Jul 6
-17%
$432
$358 per night
Condo ∙ 6 guests ∙ 2 bedrooms
Pleasant Condo in Marathon with Grill, Yard & Pool + Pool Views
4.8
"Excellent" (107 ratings)
Marathon, Monroe County, Florida, United States
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Vacation homes and cottages with a garden

Looking for vacation homes with a little extra outdoor space? Check out these accommodations in Florida Keys with private yards.

House Yard Marathon
Sept 9 - Sept 16
-40%
$1,218
$732 per night
House ∙ 8 guests ∙ 3 bedrooms
Vacation Home in Marathon with Private Pool + Ocean View
4.9
"Excellent" (150 ratings)
Marathon, Monroe County, Florida, United States
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House Yard Key Colony Beach
Sept 2 - Sept 9
-38%
$842
$522 per night
House ∙ 6 guests ∙ 2 bedrooms
Beautiful Vacation Home in Key Colony Beach with Large Pool + Water Views
4.9
"Excellent" (132 ratings)
Key Colony Beach, Monroe County, Florida, United States
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House Yard Key Colony Beach
Aug 26 - Sept 2
$620 per night
House ∙ 5 guests ∙ 2 bedrooms
House in Key Colony Beach with Private Pool
4.9
"Excellent" (110 ratings)
Key Colony Beach, Monroe County, Florida, United States
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Cabins with a sauna

Relax and enjoy yourself in one of these Florida Keys vacation rentals with saunas.

Condo Sauna Key West
Sept 23 - Sept 30
-31%
$609
$422 per night
Condo ∙ 7 guests ∙ 3 bedrooms
Condo in Key West with Grill, Pool & Sauna + Next to Beach
4.8
"Excellent" (108 ratings)
Key West, Florida Keys, Florida, United States
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Condo Sauna Key West
Aug 26 - Sept 2
-22%
$706
$554 per night
Condo ∙ 4 guests ∙ 1 bedroom
Condo in Key West with Grill, Yard & Sauna, Close to West Martello Tower
4.9
"Excellent" (266 ratings)
Key West, Florida Keys, Florida, United States
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House Sauna Marathon
Oct 14 - Oct 21
-54%
$2,632
$1,214 per night
House ∙ 10 guests ∙ 4 bedrooms
House in Marathon with Expansive Pool
4.9
"Excellent" (22 ratings)
Marathon, Monroe County, Florida, United States
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Popular Rental Amenities in Florida Keys

  • Pool (9,689)
  • WiFi (11,693)
  • Air conditioning (11,699)
  • Pet-friendly (2,622)
  • Kitchen (9,301)
  • Parking (431)
  • Washing machine (7,492)
  • TV (11,277)
  • Balcony/patio (3,131)
  • Dishwasher (6,415)
  • Grill (6,551)
  • Fishing (6,414)

You will have a large selection of accommodations to choose from if you are looking for a rental offering a pool in Florida Keys. Also, vacation rentals with pools in Florida Keys have an average price of $993 a night. Most of the listed properties with pools are hotel room. You can also find and book a vacation rental with a pool near the water, which is the case for more than two-thirds of the rentals in this destination.

Price and Availability Index in Florida Keys

Click on any bar to see price and availability information

Vacation Rental Price Information in Florida Keys

In the above graph, you will find information on average prices of the vacation homes & apartments in Florida Keys. Prices in a week of February (2/17 - 2/24) go up to $1,018 per night, which is the highest average price in the next 12 months. Conversely, the cheapest average prices are in a week of September (9/23 - 9/30).

Rental availability information in Florida Keys

Check out the graph above to find out how many accommodations are available in Florida Keys(in %). It is harder to find an accommodation during a week of August (8/31 - 9/7), as 78% of the rentals are booked. October (10/28 - 11/4) has got the highest percentage of available rentals.

The Weather in Florida Keys

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27°
21°
7 days 7
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26°
20°
6 days 6
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27°
21°
7 days 7
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30°
24°
6 days 6
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31°
25°
9 days 9
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32°
26°
12 days 12
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33°
27°
13 days 13
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33°
27°
14 days 14
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32°
26°
16 days 16
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30°
24°
11 days 11
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27°
22°
9 days 9
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26°
21°
9 days 9
Jan.
Feb.
Mar.
Apr.
May
June
July
Aug.
Sep.
Oct.
Nov.
Dec.
- Rainy days

This is the climate diagram in Florida Keys. July is the warmest month of the year in Florida Keys with temperatures reaching a maximum average of 33°. On the contrary, the coolest month is February. Bring your umbrella in September, the rainiest month of the year!

7-Day Weather Forecast in Florida Keys

Sat., 23 Sep.
28°
27°

15%

1 h

21 km/h

Sun., 24 Sep.
28°
27°

15%

1 h

15 km/h

Mon., 25 Sep.
29°
28°

10%

8 h

12 km/h

Tue., 26 Sep.
29°
28°

10%

10 h

12 km/h

Wed., 27 Sep.
29°
28°

15%

5 h

15 km/h

Thu., 28 Sep.
29°
28°

15%

4 h

20 km/h

Fri., 29 Sep.
29°
28°

15%

4 h

27 km/h

What are the best activities for families in Florida Keys?

Family fun in the Florida Keys: dolphins, sea lions, and history

For a great family activity, take the kids to see the dolphins at Island Dolphin Care or Theater of the Sea, which also offers sea lion shows. You can also introduce your family to the Keys' history at the Ernest Hemingway Home and Museum in Key West, where you can see the famous author's magnificent house and gardens.

What are the best nightlife spots in Florida Keys?

Enjoying the lively nightlife in Key West

The city of Key West is located at the southern tip of the Florida Keys and is the centre of nightlife on these islands. Key West has a number of lively bars and restaurants, which are largely focused around busy Duval Street. The city also hosts festivities on the waterfront at Mallory Square, every night at sunset: Typical entertainment includes live music, street performers, performance artists, and local vendors selling handicrafts and souvenirs.

Where are the unique attractions in Florida Keys?

Explore the underwater world with stunning coral reefs

The Florida Keys are well-known as a destination for snorkellers, scuba divers, and marine life enthusiasts. From Key West, as well as other islands, you can explore the area's beautiful coral reefs and diverse marine life. Particularly stunning spots include John Pennekamp Coral Reef State Park, popular not only for snorkelling but also glass-bottom boat tours, and Molasses Reef, where divers can enjoy the colourful underwater landscape. Nature lovers can also hike through Key Largo Hammock Botanical State Park for a chance to spot crocodiles.

Information about vacation rentals in Florida Keys

🏡 Vacation rentals available 12,222 homes
💳 Possible discounts up to 38%
🌙 Nightly prices starting at $235
⭐ Popular amenities Pool, Internet and Air conditioning
🐾 Pet friendly homes 2,615 homes
🏊 Vacation rentals with pools 9,711 homes

Frequently Asked Questions

What is the typical price of a vacation home in Florida Keys?

Accommodation prices in Florida Keys start at $235 per night.

What is the typical availability of House rental in Florida Keys?

November has the highest availability of House rental in Florida Keys, so you can expect plenty of selection, even for last-minute bookings.

What are the most popular vacation home amenities in Florida Keys?

When looking to book a vacation home in Florida Keys, the most requested amenities include Pool, Internet, and Air conditioning.

How many House rental and Apartment rental can I find in Florida Keys?

Florida Keys has 12,222 House rental and Apartment rental available to book.

Are there pet-friendly vacation rentals in Florida Keys?

Finding a vacation rental in Florida Keys that allows dogs is definitely possible, with 2,615 pet-friendly homes on offfer.

What's the best month to visit Florida Keys?

When booking accommodation in Florida Keys, remember that the rainiest months are usually September and August, with February often being the sunniest.

What are the popular vacation destinations in Florida Keys?

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