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Best Siesta Key Beach rentals on Holiday Lettings - Vacation rentals

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1,254 Vacation rentals

Vacation townhouse in Siesta Key

Siesta Key townhouse

1 bedroom • 1 bathroom • sleeps 4

from $327 / night

$2,285 / week

1 / 24

Vacation condo rental

Siesta Key condo

3 bedrooms • 3 bathrooms • sleeps 6

from $1,008 / night

$7,054 / week

1 / 9

Vacation villa in Siesta Key

Siesta Key villa

3 bedrooms • 2 bathrooms • sleeps 6

from $229 / night

$1,603 / 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

Ski home to rent in Siesta Key

Siesta Key house

3 bedrooms • 2 bathrooms • sleeps 4

from $430 / night

$3,006 / week

1 / 22

Condo rental in Siesta Key

Siesta Key condo

2 bedrooms • 2 bathrooms • sleeps 8

from $355 / night

$2,485 / week

1 / 18

Cottage rental in Siesta Key

Siesta Key cottage

2 bedrooms • 2 bathrooms • sleeps 6

from $276 / night

$1,932 / week

1 / 24

Vacation apartment in Siesta Key

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

from $102 / night

$714 - $1,195 / week

1 / 42

Siesta Key Vacation apartment rental

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

from $245 / night

$1,712 - $3,035 / week

1 / 59

Apartment rental in Siesta Key with shared pool

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 4

from $409 / night

$2,863 - $3,206 / week

1 / 22

Vacation apartment in Siesta Key

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

from $261 / night

$1,839 - $3,390 / week

1 / 35

Siesta Key Vacation home rental

Siesta Key house

3 bedrooms • 3 bathrooms • sleeps 6

from $390 / night

$2,726 / week

1 / 15

Vacation condo in Siesta Key

Siesta Key condo

2 bedrooms • 2 bathrooms • sleeps 6

from $321 / night

$2,245 / week

1 / 27

Vacation townhouse in Siesta Key

Siesta Key townhouse

3 bedrooms • 3 bathrooms • sleeps 6

from $264 / night

$1,844 / week

1 / 16

Vacation apartment in Siesta Key

Siesta Key apartment

• 1 bathroom • sleeps 2

from $125 / night

$874 / week

1 / 25

Vacation condo in Siesta Key

Siesta Key condo

2 bedrooms • 2 bathrooms • sleeps 6

from $182 / night

$1,275 / week

1 / 13

Vacation apartment rental

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

from $331 / night

$2,317 / week

1 / 26

Siesta Key Vacation apartment accommodation

Siesta Key apartment

2 bedrooms • 1 bathroom • sleeps 6

from $136 / night

$950 - $1,955 / week

1 / 28

Siesta Key Vacation apartment rental

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

from $239 / night

$1,670 - $2,630 / week

1 / 23

Apartment rental in Siesta Key with swimming pool

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

from $159 / night

$1,115 - $2,100 / week

1 / 26

Siesta Key Vacation apartment rental

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

from $239 / night

$1,670 - $2,630 / week

1 / 30

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 4

from $236 / night

$1,655 - $2,645 / week

1 / 14

Vacation apartment in Siesta Key

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

from $288 / night

$2,012 / week

1 / 16

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

4 bedrooms • 3 bathrooms • sleeps 8

from $437 / night

$3,060 - $5,800 / week

1 / 28

Vacation home in Siesta Key

Siesta Key house

6 bedrooms • 5 bathrooms • sleeps 14

from $999 / night

$6,989 / week

1 / 23

Vacation home rental

Siesta Key house

4 bedrooms • 3 bathrooms • sleeps 10

from $630 / night

$4,409 / week

1 / 35

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

3 bedrooms • 2 bathrooms • sleeps 6

from $255 / night

$1,785 - $3,410 / 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 / 28

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

3 bedrooms • 2 bathrooms • sleeps 6

from $194 / night

$1,355 - $2,400 / week

1 / 44

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

3 bedrooms • 2 bathrooms • sleeps 6

from $255 / night

$1,785 - $3,410 / week

1 / 23

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

3 bedrooms • 2 bathrooms • sleeps 6

from $255 / night

$1,785 - $3,410 / week

1 / 26

Apartment rental in Siesta Key with swimming pool

Siesta Key apartment

3 bedrooms • 2 bathrooms • sleeps 6

from $255 / night

$1,785 - $3,410 / week

1 / 31

Siesta Key Vacation apartment rental

Siesta Key apartment

3 bedrooms • 2 bathrooms • sleeps 6

from $255 / night

$1,785 - $3,410 / week

1 / 38

Siesta Key Vacation apartment rental

Siesta Key apartment

3 bedrooms • 2 bathrooms • sleeps 6

from $194 / night

$1,355 - $2,400 / week

1 / 27

Siesta Key Vacation apartment rental

Siesta Key apartment

3 bedrooms • 2 bathrooms • sleeps 6

from $255 / night

$1,785 - $3,410 / week

1 / 26

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 • 2 bathrooms • sleeps 6

from $245 / night

$1,712 - $1,953 / week

1 / 24

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 4

from $296 / night

$2,070 - $3,600 / week

1 / 37

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

2 bedrooms • 1 bathroom • sleeps 6

from $136 / night

$950 - $1,955 / week

1 / 19

Vacation apartment with swimming pool in Siesta Key

Siesta Key apartment

2 bedrooms • 1 bathroom • sleeps 4

from $131 / night

$915 - $1,715 / week

1 / 15