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Holiday Lettings
> North America
> United States
> Florida
> Florida Keys
> Villas and holiday rentals in Key West

Villas in Key West and Holiday rentals - Holiday Lettings - Holiday Rentals Key West

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£1 £750 -

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  • 3 and above
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Filtered properties are rated either by Tripadvisor Vacation Rentals users, or by Vrbo users. Both rating systems are separate, and are depicted differently as shown in the key above. Tripadvisor performs checks on its reviews. Holiday Lettings and companies under Tripadvisor Group do not check Vrbo reviews.
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Swimming pool

Great rentals within 20 miles that match your search

Islamorada holiday home rental

Islamorada house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £1,174 / night

£8,220 / week

1 / 20

Great rentals within 20 miles that match your search

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Holiday home in Islamorada

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Fireplace

from £300 / night

£2,101 / week

1 / 13

Great rentals within 20 miles that match your search

Holiday condo in Marathon

Marathon condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Fireplace

6 reviews

from £274 / night

£1,914 / week

1 / 18

Great rentals within 20 miles that match your search

Holiday studio in Marathon

Marathon studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 filter does not match: Fireplace

from £165 / night

£914 / week

1 / 31

Great rentals within 20 miles that match your search

Villa rental in Islamorada

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Fireplace

from £163 / night

£1,142 - £3,106 / week

1 / 6

Great rentals within 20 miles that match your search

Holiday home in Islamorada

Islamorada house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 filter does not match: Fireplace

from £640 / night

£4,476 / week

1 / 22

Great rentals within 20 miles that match your search

Tavernier holiday home rental

Tavernier house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: Fireplace

from £64 / night

£448 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday villa in Islamorada

Islamorada villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Fireplace

from £457 / night

£2,284 / week

1 / 26

Great rentals within 20 miles that match your search

Holiday apartment in Marathon

Marathon apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Fireplace

19 reviews

from £274 / night

£1,914 / week

1 / 37

Great rentals within 20 miles that match your search

Cudjoe Key holiday home rental

Cudjoe Key house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

1 filter does not match: Fireplace

16 reviews

from £631 / night

£4,412 - £5,690 / week

1 / 26

Great rentals within 20 miles that match your search

Home rental in Cudjoe Key

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

1 filter does not match: Fireplace

12 reviews

from £495 / night

£4,202 - £5,480 / week

1 / 35

Great rentals within 20 miles that match your search

Key West holiday apartment rental

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Fireplace

17 reviews

from £389 / night

£2,649 / week

1 / 19

Great rentals within 20 miles that match your search

Holiday apartment in Grassy Key

Grassy Key apartment

  • 1 bathroom
  • sleeps 2

1 filter does not match: Fireplace

4 reviews

from £201 / night

£1,096 / week

1 / 37

Great rentals within 20 miles that match your search

Holiday home in Marathon

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Fireplace

15 reviews

from £319 / night

£2,234 / week

1 / 50

Great rentals within 20 miles that match your search

Holiday condo rental

Islamorada condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Fireplace

18 reviews

from £203 / night

£1,416 / week

1 / 35

Great rentals within 20 miles that match your search

Holiday home accommodation

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Fireplace

from £274 / night

£1,918 / week

1 / 25

Great rentals within 20 miles that match your search

Marathon holiday home let

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 filter does not match: Fireplace

14 reviews

from £398 / night

£2,786 / week

1 / 17

Great rentals within 20 miles that match your search

Holiday home in Marathon

Marathon house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Fireplace

36 reviews

from £1,827 / night

£12,787 / week

1 / 36

Great rentals within 20 miles that match your search

Holiday condo in Key West

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Fireplace

102 reviews

from £255 / night

£1,585 - £1,859 / week

1 / 20

Great rentals within 20 miles that match your search

Villa rental in Islamorada

Islamorada villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Fireplace

1 review

from £284 / night

£1,982 / week

1 / 25

Great rentals within 20 miles that match your search

Marathon holiday home accommodation

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 filter does not match: Fireplace

23 reviews

from £914 / night

£6,394 / week

1 / 45

Great rentals within 20 miles that match your search

Holiday condo in Key West

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Fireplace

4 reviews

from £389 / night

£2,649 - £2,877 / week

1 / 48

Great rentals within 20 miles that match your search

Marathon Shores holiday home rental

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Fireplace

5 reviews

from £1,762 / night

£12,330 - £14,157 / week

1 / 75

Great rentals within 20 miles that match your search

Holiday home in Islamorada

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Fireplace

3 reviews

from £365 / night

£2,551 / week

1 / 2

Great rentals within 20 miles that match your search

Condo rental in Islamorada

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Fireplace

4 reviews

from £126 / night

£880 / week

1 / 19

Great rentals within 20 miles that match your search

Holiday condo in Marathon

Marathon condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

1 filter does not match: Fireplace

2 reviews

from £281 / night

£1,964 / week

1 / 13

Great rentals within 20 miles that match your search

Studio rental in Marathon

Marathon studio

  • Studio
  • 1 bathroom
  • sleeps 3

1 filter does not match: Fireplace

4 reviews

from £255 / night

£1,781 / week

1 / 9

Great rentals within 20 miles that match your search

Home rental in Key West

Key West house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Fireplace

from £274 / night

£1,918 / week

1 / 20

Great rentals within 20 miles that match your search

Islamorada holiday condo let

Islamorada condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Fireplace

8 reviews

from £274 / night

£1,279 - £1,918 / week

1 / 23

Great rentals within 20 miles that match your search

Holiday yacht with shared pool in Key West

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 filter does not match: Fireplace

from £1,552 / night

£10,043 / week

1 / 16

Great rentals within 20 miles that match your search

Holiday home with golf nearby in Key Colony Beach

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Fireplace

from £210 / night

£1,471 / week

1 / 24

Great rentals within 20 miles that match your search

Holiday home in Duck Key

Duck Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

1 filter does not match: Fireplace

4 reviews

from £526 / night

£3,677 / week

1 / 26

Great rentals within 20 miles that match your search

Holiday home in Marathon Shores

Marathon Shores house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 filter does not match: Fireplace

10 reviews

from £783 / night

£5,480 / week

1 / 45

Great rentals within 20 miles that match your search

Lower Matecumbe Key holiday home rental

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Fireplace

from £617 / night

£4,316 / week

1 / 47

Great rentals within 20 miles that match your search

Little Torch Key holiday home rental

Little Torch Key house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

1 filter does not match: Fireplace

from £639 / night

£4,469 / week

1 / 49

Great rentals within 20 miles that match your search

Holiday home letting

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Fireplace

3 reviews

from £457 / night

£3,197 / week

1 / 34

Great rentals within 20 miles that match your search

Home rental in Little Torch Key

Little Torch Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 filter does not match: Fireplace

1 review

from £245 / night

£1,714 / week

1 / 27

Great rentals within 20 miles that match your search

Key West holiday home rental

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Fireplace

from £384 / night

£2,686 / week

1 / 29

Great rentals within 20 miles that match your search

Holiday home in Islamorada

Islamorada house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

1 filter does not match: Fireplace

5 reviews

from £914 / night

£6,394 - £10,960 / week

1 / 34

Great rentals within 20 miles that match your search

Holiday home in Islamorada

Islamorada house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Fireplace

1 review

from £1,697 / night

£11,874 / week

1 / 36

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