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Best Siesta Key Beach rentals on Holiday Lettings - Vacation rentals

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1,197 Vacation rentals

Condo rental in Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from $355 / night

$2,056 - $2,628 / week

1 / 18

Vacation condo rental

Siesta Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $1,008 / night

$7,054 / week

1 / 9

Vacation condo in Siesta Key

Siesta Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $229 / night

$3,206 / week

1 / 21

Apartment rental in Siesta Key with shared pool

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $327 / night

$2,290 - $4,008 / week

1 / 22

Vacation studio in Siesta Key

Siesta Key studio

  • Studio
  • 1 bathroom
  • sleeps 2

from $126 / night

$882 / week

1 / 28

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $263 / night

$1,839 - $3,086 / week

1 / 59

Siesta Key Vacation condo rental

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $355 / night

$2,170 - $3,086 / week

1 / 24

Vacation condo with swimming pool in Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $126 / night

$882 / week

1 / 40

Vacation home rental

Siesta Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $630 / night

$4,409 / week

1 / 35

Vacation apartment in Siesta Key

Siesta Key apartment

  • 1 bathroom
  • sleeps 2

from $148 / night

$1,034 / week

1 / 25

Vacation condo rental

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $178 / night

$1,145 / week

1 / 20

Siesta Key Vacation home rental

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $172 / night

$1,203 / week

1 / 13

Siesta Key Vacation villa rental

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $233 / night

$1,626 / week

1 / 25

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 / 26

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $125 / night

$874 / week

1 / 38

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $500 / night

$3,500 - $7,200 / week

1 / 47

Siesta Key Vacation townhouse rental

Siesta Key townhouse

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from $228 / night

$1,595 / week

1 / 13

Vacation apartment in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $249 / night

$1,740 - $2,900 / week

1 / 24

Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $264 / night

$1,845 - $3,200 / 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

Apartment rental in Siesta Key with swimming pool

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $171 / night

$1,200 - $2,455 / week

1 / 22

Vacation townhouse in Siesta Key

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $264 / night

$1,844 / week

1 / 16

Ski home to rent in Siesta Key

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from $544 / night

$3,808 / week

1 / 22

Vacation home with swimming pool in Siesta Key

Siesta Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

from $2,846 / night

$19,918 / week

1 / 49

Home rental in Siesta Key with swimming pool

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $194 / night

$1,357 / week

1 / 24

Vacation apartment in Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $193 / night

$1,350 - $2,655 / week

1 / 38

Siesta Key Vacation condo rental

Siesta Key condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

from $340 / night

$2,381 / week

1 / 25

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $264 / night

$1,845 - $3,200 / week

1 / 27

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $249 / night

$1,740 - $2,900 / week

1 / 17

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 / 23

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $167 / night

$1,170 - $2,310 / week

1 / 32

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

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 $137 / night

$960 - $1,795 / week

1 / 20

Siesta Key Vacation apartment accommodation

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $142 / night

$995 - $2,045 / week

1 / 28

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 / 31

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $236 / night

$1,655 - $2,615 / week

1 / 20

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $287 / night

$2,004 / week

1 / 20

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