Holiday lettings in Florida Keys - Wimdu base64Hash Holiday lettings in Florida Keys - Wimdu

Holiday lettings in Florida Keys

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Choose from 15,023 holiday lettings and homes for your trip!

Best-rated holiday lettings in Florida Keys

Discover holiday rentals with top-notch guest ratings

House Key Colony Beach
from £146 per night
House ∙ 10 guests ∙ 3 bedrooms

Holiday home with pool, terrace & garden | Nature view

5.0
Outstanding(9 ratings)
Key Colony Beach, Monroe County, Florida, United States
View deal
House Marathon
from £199 per night
House ∙ 8 guests ∙ 3 bedrooms

Children-friendly holiday home with heated pool, barbeque & terrace | Pets allowed

4.7
Excellent(125 ratings)
Marathon, Monroe County, Florida, United States
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Villa Marathon
from £1,294 per night
Villa ∙ 20 guests ∙ 8 bedrooms

Family-oriented villa with garden, barbeque & terrace | Perfect for remote work

4.9
Outstanding(114 ratings)
Marathon, Monroe County, Florida, United States
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Pet-friendly rentals in Florida Keys

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

House Key West
from £234 per night
House ∙ 12 guests ∙ 6 bedrooms

House with garden, BBQ & private pool | Next to West Martello Tower

Key West, Monroe County, Florida, United States
Pet-friendly
View deal
House Islamorada
from £439 per night
House ∙ 8 guests ∙ 4 bedrooms

House with terrace, garden & barbeque | Nature view | Good for workation

4.0
Very good(1 rating)
Islamorada, Monroe County, Florida, United States
Pet-friendly
View deal
House Key Largo
from £146 per night
House ∙ 9 guests ∙ 4 bedrooms

Family-oriented spacious holiday home with terrace, sauna & garden | Perfect for remote work | Pets are welcome

4.3
Very good(4 ratings)
Key Largo, Monroe County, Florida, United States
Pet-friendly
View deal
See all pet-friendly offers

Holiday cottages with pool in Florida Keys

Discover best holiday homes and cottages with pool in Florida Keys

House Key West
from £783 per night
House ∙ 16 guests ∙ 6 bedrooms

Fully equipped holiday home with barbecue, garden & private pool | Near Duval Street | Nature view | Perfect for remote work | Pet-friendly

Key West, Monroe County, Florida, United States
Pool
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House Key Largo
from £280 per night
House ∙ 8 guests ∙ 4 bedrooms

Holiday home with garden, terrace & heated pool | Nature view

4.9
Outstanding(116 ratings)
Key Largo, Monroe County, Florida, United States
Pool
View deal
House Islamorada
from £408 per night
House ∙ 8 guests ∙ 4 bedrooms

House with terrace, barbeque & heated pool | Nature view | Perfect for remote work

5.0
Outstanding(57 ratings)
Islamorada, Monroe County, Florida, United States
Pool
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See all offers with pool

Best holiday rental offers in Florida Keys

House Cudjoe Key
from £187 per night
House ∙ 4 guests ∙ 2 bedrooms

House with pool

Cudjoe Key, Monroe County, Florida, United States
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House Big Pine Key
from £222 per night
House ∙ 8 guests ∙ 3 bedrooms

House with 3 bedrooms for 8 persons

Big Pine Key, Monroe County, Florida, United States
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House Big Pine Key
from £169 per night
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped holiday home with BBQ | Pets allowed

5.0
Outstanding(1 rating)
Big Pine Key, Monroe County, Florida, United States
View deal
House Marathon
from £280 per night
House ∙ 12 guests ∙ 4 bedrooms

Fully equipped holiday home with barbecue & terrace | Nature view | Pets are welcome

4.8
Outstanding(52 ratings)
Marathon, Monroe County, Florida, United States
View deal
House Marathon
from £437 per night
House ∙ 8 guests ∙ 3 bedrooms

House with private pool, barbeque & terrace

4.4
Very good(3 ratings)
Marathon, Monroe County, Florida, United States
View deal
House Islamorada
from £415 per night
House ∙ 8 guests ∙ 3 bedrooms

Holiday home with pool

3.0
(2 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Marathon
from £362 per night
House ∙ 10 guests ∙ 4 bedrooms

Fully equipped house with terrace, private pool & barbecue | Nature view | Pets are welcome

4.4
Very good(13 ratings)
Marathon, Monroe County, Florida, United States
View deal
House Marathon
from £630 per night
House ∙ 14 guests ∙ 6 bedrooms

Child-friendly lovely house with pool, barbeque & hot tub | Dogs allowed

5.0
Outstanding(42 ratings)
Marathon, Monroe County, Florida, United States
View deal
House Key Largo
from £627 per night
House ∙ 10 guests ∙ 5 bedrooms

Holiday home with barbecue, private pool & terrace | City view

4.8
Outstanding(40 ratings)
Key Largo, Monroe County, Florida, United States
View deal
House Marathon
from £608 per night
House ∙ 10 guests ∙ 4 bedrooms

Fully equipped holiday home with jacuzzi, BBQ & private pool | Suitable for remote work

4.9
Outstanding(58 ratings)
Marathon, Monroe County, Florida, United States
View deal
House Key West
from £311 per night
House ∙ 14 guests ∙ 5 bedrooms

Fully equipped spacious house with garden, private pool & BBQ | Nature view | Good for workation | Pets are welcome

4.9
Outstanding(14 ratings)
Key West, Monroe County, Florida, United States
View deal
House Islamorada
from £181 per night
House ∙ 12 guests ∙ 3 bedrooms

House with barbeque, terrace & garden

4.7
Excellent(6 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Marathon
from £616 per night
House ∙ 16 guests ∙ 7 bedrooms

Fully equipped spacious holiday home with BBQ, garden & private pool | Pet-friendly

5.0
Outstanding(93 ratings)
Marathon, Monroe County, Florida, United States
View deal
House Layton
from £65 per night
House ∙ 8 guests ∙ 2 bedrooms

House with pool, hot tub & BBQ | Nature view

3.7
Good(16 ratings)
Layton, Monroe County, Florida, United States
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House Marathon
from £399 per night
House ∙ 10 guests ∙ 5 bedrooms

House with barbeque, terrace & private pool

4.9
Outstanding(45 ratings)
Marathon, Monroe County, Florida, United States
View deal
House Marathon
from £406 per night
House ∙ 8 guests ∙ 3 bedrooms

Holiday home with BBQ & pool

Marathon, Monroe County, Florida, United States
View deal
House Key West
from £207 per night
House ∙ 6 guests ∙ 2 bedrooms

Fully equipped charming house with BBQ, jacuzzi & terrace | Perfect for remote work | Pets allowed

4.5
Excellent(98 ratings)
Key West, Monroe County, Florida, United States
View deal
House Key West
from £139 per night
House ∙ 6 guests ∙ 3 bedrooms

Spacious holiday home with private pool | Close to Duval Street

4.9
Outstanding(8 ratings)
Key West, Monroe County, Florida, United States
View deal
House Key West
from £1,332 per night
House ∙ 21 guests ∙ 8 bedrooms

House with heated pool, terrace & garden | Near West Martello Tower | City view

Key West, Monroe County, Florida, United States
View deal
House Islamorada
from £310 per night
House ∙ 10 guests ∙ 4 bedrooms

House with private pool, BBQ & jacuzzi | Suitable for remote work

5.0
Outstanding(3 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Marathon
from £244 per night
House ∙ 8 guests ∙ 3 bedrooms

Holiday home with heated pool, barbeque & terrace

4.8
Outstanding(66 ratings)
Marathon, Monroe County, Florida, United States
View deal
House Key Largo
from £89 per night
House ∙ 6 guests ∙ 3 bedrooms

Beautiful house with garden, barbeque & terrace | Nature view

4.5
Excellent(21 ratings)
Key Largo, Monroe County, Florida, United States
View deal
House Islamorada
from £316 per night
House ∙ 14 guests ∙ 3 bedrooms

Holiday home with barbeque, garden & pool

5.0
Outstanding(3 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Duck Key
from £501 per night
House ∙ 12 guests ∙ 4 bedrooms

House | Nature view

4.0
Very good(26 ratings)
Duck Key, Monroe County, Florida, United States
View deal
House Key Haven
from £328 per night
House ∙ 8 guests ∙ 4 bedrooms

Holiday home with private pool, BBQ & garden

Key Haven, Monroe County, Florida, United States
View deal
House Islamorada
from £180 per night
House ∙ 10 guests ∙ 4 bedrooms

Holiday home with pool & terrace

Islamorada, Monroe County, Florida, United States
View deal
House Key Largo
from £114 per night
House ∙ 6 guests ∙ 2 bedrooms

Fully equipped beautiful holiday home with terrace & pool | Nature view | Pets are welcome

4.8
Outstanding(8 ratings)
Key Largo, Monroe County, Florida, United States
View deal
House Marathon
from £526 per night
House ∙ 12 guests ∙ 5 bedrooms

Holiday home with terrace, BBQ & private pool

5.0
Outstanding(1 rating)
Marathon, Monroe County, Florida, United States
View deal
House Islamorada
from £236 per night
House ∙ 6 guests ∙ 3 bedrooms

Holiday home with barbeque

Islamorada, Monroe County, Florida, United States
View deal
House Monroe County
from £197 per night
House ∙ 9 guests ∙ 3 bedrooms

Children-friendly lovely holiday home with hot tub, terrace & garden | Perfect for remote work | Pets allowed

4.9
Outstanding(13 ratings)
Monroe County, Florida, United States
View deal
Show more in Florida Keys

Price and Availability Index for Florida Keys

Click on any bar to see price and availability information

Holiday Letting Price Information in Florida Keys

Check the graph above to find out what's the best time to travel and find accommodation in Florida Keys. If you plan to book your accommodation in December, remember it's the most expensive period, with average prices of £720. The average accommodation price reaches its minimum in September (12/09 – 19/09), at £481 per night.

Rental availability information in Florida Keys

Above, you can see what percentage of the holiday rentals in Florida Keys are available at different times of year. The busiest week of the year is in May (29/05 – 05/06). The week with the highest availability is in July (11/07 – 18/07) - 79 of the holiday rentals are still available.

647 reviews
Travellers who stayed in Florida Keys rated their holiday home 4.1/5 on average, based on 647 reviews.

And we love our apartments

House with pool
House with 3 bedrooms for 8 persons
Fully equipped holiday home with BBQ | Pets allowed
Fully equipped holiday home with barbecue & terrace | Nature view | Pets are welcome
House with private pool, barbeque & terrace
Show more in Florida Keys

Features of Florida Keys holiday rentals

💳 Discounts up to 10%
⭐ Popular amenities Air conditioning, Pool and Internet
🏊  Holiday rentals with a pool 11,507 rentals
🌙 Minimum price starting at £65
🐾 Pet friendly holiday homes 5,283 rentals
🏡 Rentals available 15,023 rentals

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