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Best Siesta Key Beach rentals on Holiday Lettings - Vacation rentals

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418 Vacation rentals

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $264 / night

$1,843 - $3,441 / week

1 / 59

Vacation townhouse in Siesta Key

Siesta Key townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $338 / night

$2,365 / week

1 / 24

Vacation condo in Siesta Key

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $247 / night

$1,947 / week

1 / 12

Siesta Key Vacation home rental

Siesta Key house

  • 7 bedrooms
  • 3 bathrooms
  • sleeps 15

from $2,285 / night

$15,990 / week

1 / 64

Cottage rental in Siesta Key

Siesta Key cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $224 / night

$1,563 / week

1 / 24

Siesta Key Vacation condo rental

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $355 / night

$2,170 - $2,963 / week

1 / 24

Vacation condo in Siesta Key

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $229 / night

$3,206 / week

1 / 21

Vacation apartment in Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $193 / night

$1,350 - $2,655 / week

1 / 38

Vacation townhouse in Siesta Key

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $302 / night

$2,108 / week

1 / 16

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $167 / night

$1,170 - $2,310 / week

1 / 34

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $167 / night

$1,170 - $2,310 / week

1 / 35

Apartment rental in Siesta Key with swimming pool

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $167 / night

$1,170 - $2,310 / week

1 / 26

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $171 / night

$1,200 - $2,455 / week

1 / 19

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $290 / night

$2,030 - $3,530 / week

1 / 23

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $171 / night

$1,200 - $2,455 / week

1 / 32

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $264 / night

$1,845 - $3,200 / week

1 / 15

Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $249 / night

$1,740 - $2,900 / week

1 / 16

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $290 / night

$2,030 - $3,530 / week

1 / 38

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $290 / night

$2,030 - $3,530 / week

1 / 26

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $249 / night

$1,740 - $2,900 / week

1 / 24

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $142 / night

$995 - $2,045 / week

1 / 19

Apartment rental in Siesta Key with swimming pool

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $264 / night

$1,845 - $3,200 / week

1 / 26

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $142 / night

$995 - $2,045 / week

1 / 21

Vacation apartment in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $249 / night

$1,740 - $2,900 / week

1 / 20

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $167 / night

$1,170 - $2,310 / week

1 / 31

Vacation apartment in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $264 / night

$1,845 - $3,200 / week

1 / 36

Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $142 / night

$995 - $2,045 / week

1 / 21

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $264 / night

$1,845 - $3,200 / week

1 / 23

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $249 / night

$1,740 - $2,900 / week

1 / 33

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $171 / night

$1,200 - $2,455 / week

1 / 18

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $264 / night

$1,845 - $3,200 / week

1 / 42

Apartment rental in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $263 / night

$1,839 - $3,556 / week

1 / 29

Siesta Key Vacation home rental

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $264 / night

$1,844 - $2,245 / week

1 / 35

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $137 / night

$960 - $1,795 / week

1 / 15

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $629 / night

$4,400 - $7,200 / week

1 / 62

Vacation apartment accommodation

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $290 / night

$2,030 - $3,530 / week

1 / 37

Apartment rental in Siesta Key with shared pool

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $245 / night

$999 - $2,289 / week

1 / 39

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $142 / night

$995 - $2,045 / week

1 / 17

Vacation apartment in Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $290 / night

$2,030 - $3,530 / week

1 / 32

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $290 / night

$2,030 - $3,530 / week

1 / 28