Villas in Florida Keys and Holiday rentals - Holiday Lettings - Holiday Rentals Florida Keys

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North America Holidays
172843 properties
United States Holidays
128205 properties
Florida Holidays
39567 properties
Villas Key Largo
229 properties
Villas Key West
150 properties
Holiday rentals Islamorada
138 properties
Estates Marathon
92 properties
Big Pine Key
29 properties
Cudjoe Key
25 properties
Lower Keys
21 properties
Long Key
18 properties
Key Colony Beach
18 properties
Ramrod Key
15 properties
Little Torch Key
14 properties
Cottages Sugarloaf
5 properties
Matecumbe Key
5 properties

Florida Keys

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761 Holiday homes

29

Marathon Shores holiday home rental

Marathon / Marathon Shores

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Nearest beach 8 km
  • Child friendly
  • Air conditioning

from £331 / night

£2308 - £3077 / week

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Responds fast!
avg. 2 hours 0 minutes

from £331 / night

27

Marathon Shores holiday home rental

Marathon / Marathon Shores

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 2 km
  • Child friendly
  • Air conditioning

from £121 / night

£847 - £1193 / week

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Responds fast!
avg. 1 hour 38 minutes

from £121 / 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

from £123 / night

£857 / week

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Responds fast!
avg. 37 minutes

from £123 / night

(7) Excellent 

21

Key West holiday houseboat rental

Florida Keys / Key West

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Great location and boat!” First time for us renting a boat and previous reviews proved accurate. Location in marina at end of pier was nice. Arranged for a captain to take us out for one day (at additional fee) which was a great way to spend a day enj
…see more

from £312 / night

£1924 - £5116 / week

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Responds fast!
avg. 1 hour 5 minutes

from £312 / night

26

Tavernier holiday apartment rental

Key Largo / Tavernier

6 18 Min stay varies

  • 6 bedrooms
  • Sleeps 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £346 / night

£2418 / week

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Responds fast!
avg. 37 minutes

from £346 / night

26

Holiday 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

from £374 / night

£2612 / week

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Responds fast!
avg. 37 minutes

from £374 / night

(2) Excellent 

41

Holiday 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

from £153 / night

£1066 - £1604 / week

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Responds fast!
avg. 2 hours 48 minutes

from £153 / night

26

Holiday apartment in Tavernier

Key Largo / Tavernier

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £250 / night

£1750 / week

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Responds fast!
avg. 37 minutes

from £250 / night

(12) Very Good 

14

Holiday 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 km
  • Swimming pool
“We've stayed here 4 times so far and have booked again for Spring 2017.” Great location, less than an hour away from Miami Airport. Shops and restaurants within walking distance and plenty more choice if you fancy travelling a little further. Great da
…see more

from £150 / night

£758 / week

Enquire View

from £150 / night

24

Holiday 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

from £125 / night

£873 / week

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Responds fast!
avg. 37 minutes

from £125 / 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

from £250 / night

£2046 / week

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Responds fast!
avg. 3 hours 1 minutes

from £250 / night

(1)  

15

Houseboat rental in Key West

Florida Keys / Key West

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Pet friendly

from £130 / night

£769 - £1038 / week

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from £130 / night

23

Holiday apartment in Tavernier

Key Largo / Tavernier

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £115 / night

£803 / week

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Responds fast!
avg. 37 minutes

from £115 / night

4

Key West holiday boathouse rental

Florida Keys / Key West

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning

from £174 / night

£1212 / week

Book View

from £174 / night

(39) Very Good 

Certificate of Excellence

14

Apartment rental in Key West

Florida Keys / Key West

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Car not necessary

Certificate of Excellence

from £254 / night

£1772 / week

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Responds fast!
avg. 1 hour 33 minutes

from £254 / night

15

Holiday home letting

Florida Keys / Key West

2 6 30 nights min

  • 2 bedrooms
  • Sleeps 6
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £72 / night

£503 / week

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Responds fast!
avg. 33 minutes

from £72 / night

21

Holiday villa in Duck Key

Florida Keys / Duck Key

2 6 4 nights min

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

from £235 / night

£1643 / week

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from £235 / night

29

Key Largo holiday villa rental

Florida Keys / Key Largo

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 8 km
  • Swimming pool

from £116 / night

£693 - £1154 / week

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Responds fast!
avg. 2 hours 54 minutes

from £116 / night

18

Holiday home in Little Torch Key

Florida Keys / Little Torch Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask owner if suitable for children
  • Air conditioning
  • Ask about pets

from £75 / night

£521 / week

Enquire View

from £75 / night

(32) Very Good 

Certificate of Excellence

17

Key West holiday apartment let

Florida Keys / Key West

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Car not necessary

Certificate of Excellence

from £200 / night

£1395 / week

Book View

Responds fast!
avg. 1 hour 33 minutes

from £200 / night

19

Holiday home in Sugarloaf

Florida Keys / Sugarloaf

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask owner if suitable for children
  • Air conditioning
  • Ask about pets

from £145 / night

£1015 / week

Enquire View

from £145 / night

15

Holiday home in Ramrod Key

Florida Keys / Ramrod Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask owner if suitable for children
  • Air conditioning
  • Ask about pets

from £139 / night

£970 / week

Enquire View

from £139 / night

19

Holiday home rental

Florida Keys / Ramrod Key

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Ask owner if suitable for children
  • Air conditioning
  • Ask about pets

from £46 / night

£321 / week

Enquire View

from £46 / night

13

Key West holiday condo rental

Florida Keys / Key West

2 6 Min stay varies

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

from £230 / night

£1077 - £1924 / week

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Responds fast!
avg. 3 hours 44 minutes

from £230 / night

(42) Excellent 

26

Holiday cottage rental

Florida Keys / Marathon

1 4 2 nights min

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

from £97 / night

£674 - £889 / week

Book View

Responds fast!
avg. 2 hours 19 minutes

from £97 / night

(5) Excellent 

16

Holiday condo in Tavernier

Key Largo / Tavernier

2 6 3 nights min

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

from £154 / night

£924 / week

Book View

from £154 / night

(5) Average 

42

Home rental in Tavernier

Key Largo / Tavernier

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Ask owner if suitable for children
  • Air conditioning

from £100 / night

£695 / week

Book View

from £100 / night

(37) Excellent 

Certificate of Excellence

39

Holiday apartment rental

Florida Keys / Key West

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool

Certificate of Excellence

from £262 / night

£1649 - £2924 / week

Book View

Responds fast!
avg. 1 hour 30 minutes

from £262 / night

11

Holiday home in Ramrod Key

Florida Keys / Ramrod Key

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Ask owner if suitable for children
  • Air conditioning
  • Ask about pets

from £69 / night

£481 / week

Enquire View

from £69 / night

7

Key West holiday hotel apartment rental

Florida Keys / Key West

2 6 7 nights min

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

from £385 / night

£2693 / week

Book View

Responds fast!
avg. 2 hours 57 minutes

from £385 / night

(19) Excellent 

Certificate of Excellence

55

Holiday condo in Tavernier

Key Largo / Tavernier

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool

Certificate of Excellence

from £154 / night

£1077 / week

Book View

Responds fast!
avg. 1 hour 31 minutes

from £154 / night

(4) Very Good 

20

Holiday apartment in Key West

Florida Keys / Key West

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 3 km
  • Swimming pool
  • Child friendly

from £185 / night

£1231 / week

Book View

Responds fast!
avg. 3 hours 1 minutes

from £185 / night

(11) Excellent 

23

Holiday home in Big Pine Key

Florida Keys / Big Pine Key

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
“THE place to stay in the keys if you like peace and quiet!” Captain Rons Tropical Vacation Hideaway is only 30 miles to Key West, but worlds away from the crowds. The home is very clean and comfortable. Captain Ron made the whole process simple and p
…see more

from £70 / night

£750 / week

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from £70 / night

12

Holiday home in Summerland Key

Lower Keys / Summerland Key

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Ask owner if suitable for children
  • Air conditioning
  • Ask about pets

from £65 / night

£449 / week

Enquire View

from £65 / night

6

Holiday hotel apartment in Key West

Florida Keys / Key West

2 6 7 nights min

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

from £366 / night

£2558 / week

Book View

Responds fast!
avg. 2 hours 57 minutes

from £366 / night

18

Holiday condo in Tavernier

Key Largo / Tavernier

2 6 3 nights min

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

from £174 / night

£1212 / week

Book View

Responds fast!
avg. 1 hour 46 minutes

from £174 / night

15

Holiday home in Summerland Key

Lower Keys / Summerland Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask owner if suitable for children
  • Air conditioning
  • Ask about pets

from £90 / night

£629 / week

Enquire View

from £90 / night

(1) Very Good 

43

Holiday apartment in Key Largo

Florida Keys / Key Largo

1 3 Min stay varies

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

from £122 / night

£712 - £739 / week

Book View

Responds fast!
avg. 1 hour 55 minutes

from £122 / night

11

Ramrod Key holiday home rental

Florida Keys / Ramrod Key

3 6 30 nights min

  • 3 bedrooms
  • Sleeps 6
  • 30 nights min
  • Ask owner if suitable for children
  • Air conditioning
  • Ask about pets

from £86 / night

£602 / week

Enquire View

from £86 / night

21

Holiday condo in Tavernier

Key Largo / Tavernier

2 6 3 nights min

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

from £154 / night

£924 - £1154 / week

Book View

from £154 / night

Top Destination reviews

OCEANFRONT CONDO WITH ALL AMMENITIES!
Great place

We had 5 days at Ocean Pointe in the apartment which had great views of the ocean. Apartment was clean, comfortable, well equipped and a good size. Ideally situated for exploring the keys. Amenities on site were good. Recommendations on food establis … see more
Luxurious 3bd/3bth Villa - Your Keys Escape
Marathon memories

We had a great stay at the property we rented in Marathon. It was extremely well equipped with everything we needed for our week. My sister and I were most impressed with the amount of Tupperware, which is always a must with 4 children! The house had … see more
LAST MINUTE DISCOUNT! 48' 4 Bed 4 Bath Yacht
Great location and boat!

First time for us renting a boat and previous reviews proved accurate. Location in marina at end of pier was nice. Arranged for a captain to take us out for one day (at additional fee) which was a great way to spend a day enjoying the ocean and sun. … see more
Captain Rons Tropical Vacation Hideaway
THE place to stay in the keys if you like peace and quiet!

Captain Rons Tropical Vacation Hideaway is only 30 miles to Key West, but worlds away from the crowds. The home is very clean and comfortable. Captain Ron made the whole process simple and painless. I would without hesitation stay here again and rec … see more
Tropical Island Getaway-Keys
We've stayed here 4 times so far and have booked again for Spring 2017.

Great location, less than an hour away from Miami Airport. Shops and restaurants within walking distance and plenty more choice if you fancy travelling a little further. Great days out on the Keys or Everglades NP. The condo isn't fancy but it's clea … see more
THIS IS IT! Magnificent Oceanfront Paradise!
A great view

Great flat. The photos of the balcony do not do it justice. Ideal situation for seeing the Keys. The apartment was comfortable and well equipped. … see more
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