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Best Siesta Key Beach rentals on Holiday Lettings - Vacation rentals

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391 Vacation rentals

Siesta Key Vacation condo rental

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $172 / night

$1,031 - $2,290 / week

1 / 22

Vacation condo rental

Siesta Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $178 / night

$1,145 / week

1 / 20

Vacation townhouse in Siesta Key

Siesta Key townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $377 / night

$2,637 / week

1 / 23

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 / 28

Apartment rental in Siesta Key with shared pool

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $409 / night

$2,863 / week

1 / 22

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 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

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $137 / night

$960 - $1,795 / week

1 / 30

Apartment rental in Siesta Key with swimming pool

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $249 / night

$1,740 - $2,900 / week

1 / 22

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 $249 / night

$1,740 - $2,900 / week

1 / 33

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $249 / night

$1,740 - $2,900 / week

1 / 17

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 rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $264 / night

$1,845 - $3,200 / 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 / 29

Vacation apartment in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $167 / night

$1,170 - $2,310 / week

1 / 26

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $167 / night

$1,170 - $2,310 / week

1 / 31

Siesta Key Vacation villa rental

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $233 / night

$1,626 - $2,622 / week

1 / 25

Vacation apartment in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $263 / night

$1,839 - $3,556 / week

1 / 38

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from $315 / night

$2,061 / week

1 / 23

Apartment rental in Siesta Key with shared pool

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $145 / night

$927 - $2,289 / week

1 / 39

Vacation condo in Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $401 / night

$2,806 / week

1 / 27

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 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

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $205 / night

$1,435 - $2,810 / week

1 / 44

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

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $290 / night

$2,030 - $3,530 / week

1 / 26

Apartment rental in Siesta Key with swimming pool

Siesta Key apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $290 / night

$2,030 - $3,530 / week

1 / 31

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 $205 / night

$1,435 - $2,810 / week

1 / 27

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 home rental

Siesta Key house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 15

from $974 / night

$6,813 / week

1 / 126

Siesta Key Vacation condo rental

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $355 / night

$2,722 - $2,963 / 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

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 / 26

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

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from $142 / night

$995 - $2,045 / week

1 / 18