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

Holiday lettings in Florida Keys

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Choose from 14,932 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 £575 per night
House ∙ 10 guests ∙ 4 bedrooms

Holiday home with heated pool | Pets allowed

5.0
Outstanding(65 ratings)
Key Colony Beach, Monroe County, Florida, United States
View deal
Villa Islamorada
from £265 per night
Villa ∙ 6 guests ∙ 3 bedrooms

Villa with barbeque, garden & heated pool | Nature view | Suitable for remote work

4.7
Excellent(28 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Key Colony Beach
from £147 per night
House ∙ 8 guests ∙ 3 bedrooms

Holiday home with pool, terrace & jacuzzi | Nature view

5.0
Outstanding(11 ratings)
Key Colony Beach, Monroe County, Florida, United States
View deal

Pet-friendly rentals in Florida Keys

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

House Key West
from £614 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
Pet-friendly
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House Key West
from £325 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
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House Big Pine Key
from £127 per night
House ∙ 7 guests ∙ 3 bedrooms

Holiday home with private pool, barbecue & garden

Big Pine Key, 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 £205 per night
House ∙ 8 guests ∙ 4 bedrooms

Holiday home with barbeque, garden & private pool | Close to West Martello Tower | Good for workation

4.0
Very good(2 ratings)
Key West, Monroe County, Florida, United States
Pool
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House Marathon
from £155 per night
House ∙ 8 guests ∙ 3 bedrooms

Holiday home with heated pool, barbeque & terrace

4.7
Excellent(69 ratings)
Marathon, Monroe County, Florida, United States
Pool
View deal
House Marathon
from £360 per night
House ∙ 8 guests ∙ 4 bedrooms

Holiday home with pool, BBQ & terrace

5.0
Outstanding(18 ratings)
Marathon, Monroe County, Florida, United States
Pool
View deal
See all offers with pool

Best holiday rental offers in Florida Keys

House Marathon
from £259 per night
House ∙ 8 guests ∙ 4 bedrooms

Holiday home with terrace & garden | Suitable for remote work

Marathon, Monroe County, Florida, United States
View deal
House Marathon
from £230 per night
House ∙ 6 guests ∙ 2 bedrooms

Fully equipped holiday home with barbecue, terrace & private pool | Pets are welcome

4.0
Very good(1 rating)
Marathon, Monroe County, Florida, United States
View deal
House Big Pine Key
from £673 per night
House ∙ 9 guests ∙ 4 bedrooms

Family-friendly beautiful holiday home with barbeque & private pool | Nature view

5.0
Outstanding(75 ratings)
Big Pine Key, Monroe County, Florida, United States
View deal
House Marathon
from £354 per night
House ∙ 12 guests ∙ 5 bedrooms

Holiday home with garden, barbecue & private pool

4.7
Excellent(99 ratings)
Marathon, Monroe County, Florida, United States
View deal
House Islamorada
from £419 per night
House ∙ 10 guests ∙ 4 bedrooms

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

5.0
Outstanding(9 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Key Largo
from £108 per night
House ∙ 8 guests ∙ 3 bedrooms

House with barbeque, terrace & private pool

4.9
Outstanding(14 ratings)
Key Largo, Monroe County, Florida, United States
View deal
Apartment Key Largo
from £68 per night
Apartment ∙ 2 guests ∙ 1 bedroom

Flat with barbecue

Key Largo, Monroe County, Florida, United States
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House Key Largo
from £97 per night
House ∙ 5 guests ∙ 2 bedrooms

Child-friendly pleasant house with barbecue

4.8
Outstanding(7 ratings)
Key Largo, Monroe County, Florida, United States
View deal
House Marathon
from £312 per night
House ∙ 10 guests ∙ 4 bedrooms

House with terrace, barbecue & pool | Nature view

4.9
Outstanding(66 ratings)
Marathon, Monroe County, Florida, United States
View deal
Villa Marathon
from £1,273 per night
Villa ∙ 20 guests ∙ 8 bedrooms

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

4.9
Outstanding(119 ratings)
Marathon, Monroe County, Florida, United States
View deal
Cottage Key Largo
from £90 per night
Cottage ∙ 4 guests ∙ 2 bedrooms

Cottage with barbecue | Nature view

5.0
Outstanding(10 ratings)
Key Largo, Monroe County, Florida, United States
View deal
House Key Haven
from £475 per night
House ∙ 12 guests ∙ 5 bedrooms

Fully equipped wonderful holiday home with barbeque, jacuzzi & private pool | Perfect for remote work | Pets are welcome

5.0
Outstanding(3 ratings)
Key Haven, Monroe County, Florida, United States
View deal
House Key Largo
from £268 per night
House ∙ 8 guests ∙ 4 bedrooms

Holiday home with garden, terrace & heated pool

4.9
Outstanding(118 ratings)
Key Largo, Monroe County, Florida, United States
View deal
House Marathon
from £289 per night
House ∙ 8 guests ∙ 3 bedrooms

House with garden, private pool & terrace

4.5
Excellent(26 ratings)
Marathon, Monroe County, Florida, United States
View deal
House Key West
from £192 per night
House ∙ 8 guests ∙ 4 bedrooms

House with terrace, BBQ & jacuzzi | Nature view | Suitable for remote work

5.0
Outstanding(25 ratings)
Key West, Monroe County, Florida, United States
View deal
House Cudjoe Key
from £374 per night
House ∙ 10 guests ∙ 4 bedrooms

House with terrace, barbeque & hot tub

3.9
Good(133 ratings)
Cudjoe Key, Monroe County, Florida, United States
View deal
House Marathon
from £396 per night
House ∙ 10 guests ∙ 5 bedrooms

House with barbeque, terrace & private pool

4.8
Outstanding(48 ratings)
Marathon, Monroe County, Florida, United States
View deal
House Marathon
from £607 per night
House ∙ 16 guests ∙ 7 bedrooms

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

5.0
Outstanding(99 ratings)
Marathon, Monroe County, Florida, United States
View deal
House Marathon
from £341 per night
House ∙ 8 guests ∙ 4 bedrooms

Family-oriented beautiful holiday home with garden, private pool & BBQ | Nature view | Perfect for remote work | Pets allowed

4.4
Very good(40 ratings)
Marathon, Monroe County, Florida, United States
View deal
House Islamorada
from £174 per night
House ∙ 4 guests ∙ 2 bedrooms

Holiday home with terrace, garden & barbeque

5.0
Outstanding(14 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Marathon
from £484 per night
House ∙ 8 guests ∙ 3 bedrooms

Fully equipped lovely house with terrace, garden & private pool | Perfect for remote work | Pets allowed

4.8
Outstanding(7 ratings)
Marathon, Monroe County, Florida, United States
View deal
House Key Largo
from £217 per night
House ∙ 6 guests ∙ 2 bedrooms

Children-friendly holiday home with hot tub, garden & BBQ | Perfect for remote work | Dogs allowed

Key Largo, Monroe County, Florida, United States
View deal
House Marathon
from £294 per night
House ∙ 12 guests ∙ 4 bedrooms

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

4.8
Outstanding(53 ratings)
Marathon, Monroe County, Florida, United States
View deal
House Marathon
from £178 per night
House ∙ 8 guests ∙ 3 bedrooms

House with barbecue, garden & jacuzzi

4.7
Excellent(51 ratings)
Marathon, Monroe County, Florida, United States
View deal
House Marathon
from £422 per night
House ∙ 8 guests ∙ 3 bedrooms

Family-oriented spacious house with terrace, garden & private pool | Dogs allowed

4.8
Outstanding(20 ratings)
Marathon, Monroe County, Florida, United States
View deal
House Islamorada
from £395 per night
House ∙ 8 guests ∙ 4 bedrooms

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

5.0
Outstanding(63 ratings)
Islamorada, Monroe County, Florida, United States
View deal
House Big Pine Key
from £145 per night
House ∙ 6 guests ∙ 3 bedrooms

House | Pets allowed

5.0
Outstanding(4 ratings)
Big Pine Key, Monroe County, Florida, United States
View deal
House Marathon
from £719 per night
House ∙ 14 guests ∙ 6 bedrooms

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

5.0
Outstanding(60 ratings)
Marathon, Monroe County, Florida, United States
View deal
House Key Haven
from £570 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 £351 per night
House ∙ 10 guests ∙ 4 bedrooms

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

5.0
Outstanding(4 ratings)
Islamorada, 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 £693. The average accommodation price reaches its minimum in September (19/09 – 26/09), at £517 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 September (04/09 – 11/09). The week with the highest availability is in October (31/10 – 07/11) - 86 of the holiday rentals are still available.

591 reviews
Travellers who stayed in Florida Keys rated their holiday home 4.1/5 on average, based on 591 reviews.

And we love our apartments

Holiday home with terrace & garden | Suitable for remote work
Fully equipped holiday home with barbecue, terrace & private pool | Pets are welcome
Family-friendly beautiful holiday home with barbeque & private pool | Nature view
Holiday home with garden, barbecue & private pool
Holiday home with terrace, private pool & garden | Nature view
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 11,443 rentals
🌙 Minimum price starting at £68
🐾 Pet friendly holiday homes 5,310 rentals
🏡 Rentals available 14,932 rentals

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