Updating

Tell us your dates, and we will find the most accurate rates and availability for you

Updating

Best Vacation Rentals in Windley Key - Holiday Lettings - Cabins

All filters

Filters

87 Vacation rentals

Revenue impacts this sort order. Learn more

Vacation home in Windley Key

Windley Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from $553 / night

$3,871 / week

1 / 30

Vacation home in Windley Key

Windley Key house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 10

from $287 / night

$2,009 / week

1 / 30

Home rental in Windley Key

Windley Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $438 / night

$3,066 / week

1 / 29

Windley Key ski apartment to rent.

Windley Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $506 / night

$3,542 / week

1 / 30

Vacation home in Windley Key

Windley Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

from $437 / night

$3,059 / week

1 / 30

Ski apartment to rent in Windley Key

Windley Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from $807 / night

$5,649 / week

1 / 28

Vacation home in Windley Key

Windley Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from $208 / night

$1,456 / week

1 / 22

Vacation home in Windley Key

Windley Key house

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 10

from $784 / night

$5,488 / week

1 / 30

Ski home to rent in Windley Key

Windley Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $221 / night

$1,547 / week

1 / 30

Condo rental in Windley Key

Windley Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $170 / night

$1,190 / week

1 / 14

Windley Key ski home to rent.

Windley Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $393 / night

$2,751 / week

1 / 30

Home rental in Windley Key

Windley Key house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from $755 / night

$5,285 / week

1 / 23

Windley Key Vacation home rental

Windley Key house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

from $206 / night

$1,442 / week

1 / 20

Windley Key Vacation home rental

Windley Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $225 / night

$1,575 / week

1 / 30

Home rental in Windley Key

Windley Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $231 / night

$1,617 / week

1 / 23

Vacation home in Windley Key

Windley Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $270 / night

$1,890 / week

1 / 25

Windley Key Vacation home rental

Windley Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $300 / night

$2,100 / week

1 / 19

Vacation home in Windley Key

Windley Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $269 / night

$1,883 / week

1 / 30

Vacation home in Windley Key

Windley Key house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 14

from $722 / night

$5,054 / week

1 / 30

Ski home to rent in Windley Key

Windley Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $149 / night

$1,043 / week

1 / 30

Vacation home rental

Windley Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from $230 / night

$1,610 / week

1 / 19

Home rental in Windley Key

Windley Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $659 / night

$4,613 / week

1 / 30

Home rental in Windley Key

Windley Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $379 / night

$2,653 / week

1 / 30

Ski apartment to rent in Windley Key

Windley Key apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 16

from $1,571 / night

$10,997 / week

1 / 28

Windley Key ski home to rent.

Windley Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from $452 / night

$3,164 / week

1 / 30

Windley Key ski apartment to rent.

Windley Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $406 / night

$2,842 / week

1 / 27

Vacation home rental

Windley Key house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from $546 / night

$3,822 / week

1 / 30

Vacation apartment in Windley Key

Windley Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $145 / night

$1,015 / week

1 / 30

Ski home to rent in Windley Key

Windley Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $1,161 / night

$8,127 / week

1 / 30

Windley Key Vacation home rental

Windley Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $368 / night

$2,576 / week

1 / 30

Ski home to rent in Windley Key

Windley Key house

  • 6 bedrooms
  • 9 bathrooms
  • sleeps 14

from $3,054 / night

$21,378 / week

1 / 30

Home rental in Windley Key

Windley Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

from $508 / night

$3,556 / week

1 / 30

Windley Key ski condo to rent.

Windley Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $330 / night

$2,310 / week

1 / 22

Vacation home in Windley Key

Windley Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $255 / night

$1,785 / week

1 / 30

Home rental in Windley Key

Windley Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $329 / night

$2,303 / week

1 / 30

Vacation home rental

Windley Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $337 / night

$2,359 / week

1 / 30

Vacation home in Windley Key

Windley Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $378 / night

$2,646 / week

1 / 30

Vacation home in Windley Key

Windley Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

from $694 / night

$4,858 / week

1 / 27

Home accommodation in Windley Key

Windley Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

from $686 / night

$4,802 / week

1 / 13

Home rental in Windley Key

Windley Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

from $279 / night

$1,953 / week

1 / 30