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Family Friendly Holidays in Key West - Holiday Lettings

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106 family friendly properties

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Holiday apartment in Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £261 / night

£1,824 / week

1 / 17

Condo rental in Key West with shared pool

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £276 / night

£1,637 / week

1 / 13

Key West holiday condo rental

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £280 / night

£1,777 / week

1 / 13

Holiday home in Key West

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £935 / night

£6,541 / week

1 / 21

Key West holiday townhouse rental

Key West townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £321 / night

£2,245 / week

1 / 12

Holiday townhouse in Key West

Key West townhouse

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £201 / night

£1,403 / week

1 / 9

Holiday apartment rental

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £445 / night

£5,145 / week

1 / 49

Holiday apartment in Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Great place! Great Price!” The host was very helpful with everything. Good location close to Smathers beach. Everything was as described. Would stay again if ever in Key West.

from £280 / night

£1,958 / week

1 / 24

Apartment rental in Key West

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from £936 / night

£6,548 / week

1 / 17

Holiday apartment in Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £655 / night

£4,677 / week

1 / 49

Holiday condo in Key West

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £398 / night

£2,713 / week

1 / 48

Holiday townhouse in Key West

Key West townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £280 / night

£1,958 / week

1 / 12

Holiday condo with shared pool in Key West

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £88 / night

£611 / week

1 / 17

Key West holiday apartment rental

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from £933 / night

£6,530 / week

1 / 17

Apartment letting in Key West with shared pool

Key West apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £281 / night

£1,965 / week

1 / 38

Key West holiday apartment accommodation

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“penthouse and paradise” We had the times of our lives here in Key West, made special by the wonderfull condos we had at Henry's Penthouse and Henry's Piece of Paradise. 10 of us stayed for the Christmas holiday, and have already become repeat stayers...booked again to go this Christmas. Absolutely loved it!

from £351 / night

£1,679 - £1,876 / week

1 / 21

Holiday apartment rental

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £234 / night

£1,637 / week

1 / 39

Key West holiday townhouse rental

Key West townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £748 / night

£5,232 / week

1 / 19

Key West holiday home rental

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £351 / night

£2,456 / week

1 / 29

Holiday apartment in Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £156 / night

£1,092 / week

1 / 35

Holiday apartment in Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £141 / night

£982 / week

1 / 41

Key West holiday apartment rental

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £156 / night

£1,092 / week

1 / 39

Home rental in Key West with shared pool

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £585 / night

£4,677 / week

1 / 32

Holiday apartment in Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £141 / night

£982 / week

1 / 64

Holiday yacht with shared pool in Key West

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

from £1,589 / night

£10,284 / week

1 / 16

Holiday apartment in Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £125 / night

£873 / week

1 / 35

Holiday home rental

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £150 / night

£1,048 / week

1 / 22

Holiday apartment with shared pool in Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £390 / night

£2,728 / week

1 / 36

Holiday home in Key West

Key West house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from £155 / night

£1,081 / week

1 / 13

Holiday apartment in Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £172 / night

£1,201 / week

1 / 59

Key West holiday apartment rental

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £278 / night

£2,239 / week

1 / 69

Holiday condo in Key West

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £468 / night

£3,274 / week

1 / 17

Key West holiday apartment rental

Key West apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £702 / night

£9,821 / week

1 / 47

Holiday apartment rental

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £110 / night

£764 / week

1 / 42

Holiday apartment in Key West

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £314 / night

£2,194 / week

1 / 11

Key West holiday apartment rental

Key West apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“Simply - Perfect” The Condo was just perfect for a family vacation. It is located in a secure gated community just outside Key west offering some peace and quiet with easy access to everything. Key west is a short drive or bike ride away. The extras are awesome, everything one would need for a carefree Key west vacation like free bikes, beach chairs, pool floats e.t.c. The owner was also very helpful recommending fun things to do in Key west. We will definitely stay here again on our next visit.

from £258 / night

£1,801 / week

1 / 30

Holiday home in Key West

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £277 / night

£1,938 / week

1 / 13

Holiday apartment in Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £725 / night

£4,911 - £8,184 / week

1 / 41

Holiday home in Key West

Key West house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 12

“We had a wonderful stay” Whata great and comfortable house. I felt it was a privilege to be able to rent such a nice place. Excellent location. All in all great. The kids loved the pool and so did we.

from £1,731 / night

£12,113 / week

1 / 58

Home rental in Key West

Key West house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £281 / night

£1,965 / week

1 / 20

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