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50 Best Siesta Key Beach rentals on Holiday Lettings - Vacation rentals

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1,320 Vacation rentals

Siesta Key Vacation condo rental

Siesta Key condo

2 bedrooms • 2 bathrooms • sleeps 5

38 reviews

from $303 / night

$2,119 - $3,264 / week

1 / 28

Home rental in Siesta Key with swimming pool

Siesta Key house

3 bedrooms • 2 bathrooms • sleeps 6

1 review

from $292 / night

$2,044 / week

1 / 24

Vacation villa in Siesta Key

Siesta Key villa

4 bedrooms • 2 bathrooms • sleeps 8

2 reviews

from $490 / night

$2,451 / week

1 / 26

Vacation townhouse in Siesta Key

Siesta Key townhouse

2 bedrooms • 4 bathrooms • sleeps 6

1 review

from $269 / night

$1,718 / week

1 / 38

Vacation condo in Siesta Key

Siesta Key condo

2 bedrooms • 2 bathrooms • sleeps 6

from $321 / night

$2,245 / week

1 / 27

Condo rental in Siesta Key

Siesta Key condo

2 bedrooms • 2 bathrooms • sleeps 8

from $355 / night

$2,485 / week

1 / 18

Vacation home with swimming pool in Siesta Key

Siesta Key house

4 bedrooms • 3 bathrooms • sleeps 8

from $290 / night

$3,550 / week

1 / 43

Siesta Key Vacation condo rental

Siesta Key condo

2 bedrooms • 2 bathrooms • sleeps 6

6 reviews

from $114 / night

$796 / week

1 / 58

Vacation condo in Siesta Key

Siesta Key condo

2 bedrooms • 2 bathrooms • sleeps 6

3 reviews

from $147 / night

$1,031 / week

1 / 10

Siesta Key Vacation home rental

Siesta Key house

1 bedroom • 1 bathroom • sleeps 2

5 reviews

from $160 / night

$1,114 / week

1 / 12

Vacation condo with swimming pool in Siesta Key

Siesta Key condo

2 bedrooms • 2 bathrooms • sleeps 5

5 reviews

from $126 / night

$882 / week

1 / 40

Siesta Key Vacation apartment rental

Siesta Key apartment

2 bedrooms • 1 bathroom • sleeps 5

24 reviews

from $201 / night

$1,403 - $1,718 / week

1 / 16

Siesta Key Vacation apartment rental

Siesta Key apartment

3 bedrooms • 2 bathrooms • sleeps 7

16 reviews

from $286 / night

$1,993 - $2,519 / week

1 / 23

Vacation villa rental

Siesta Key villa

2 bedrooms • 2 bathrooms • sleeps 6

9 reviews

from $295 / night

$2,060 / week

1 / 54

Siesta Key Vacation condo rental

Siesta Key condo

2 bedrooms • 2 bathrooms • sleeps 5

from $165 / night

$1,127 - $3,203 / week

1 / 43

Vacation condo with shared pool in Siesta Key

Siesta Key condo

2 bedrooms • 1 bathroom • sleeps 6

from $110 / night

$806 - $919 / week

1 / 52

Siesta Key Vacation apartment rental

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

17 reviews

from $218 / night

$1,443 - $3,035 / week

1 / 59

Apartment rental in Siesta Key with shared pool

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

1 review

from $154 / night

$959 - $3,347 / week

1 / 43

Vacation townhouse in Siesta Key

Siesta Key townhouse

1 bedroom • 1 bathroom • sleeps 4

23 reviews

from $327 / night

$2,285 / week

1 / 24

Vacation apartment in Siesta Key

Siesta Key apartment

3 bedrooms • 2 bathrooms • sleeps 8

from $502 / night

$3,511 / week

1 / 19

Vacation apartment in Siesta Key

Siesta Key apartment

1 bedroom • 1 bathroom • sleeps 4

37 reviews

from $103 / night

$745 - $1,088 / week

1 / 30

Vacation apartment in Siesta Key

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

4 reviews

from $288 / night

$2,012 / week

1 / 16

Siesta Key Vacation apartment rental

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 4

from $149 / night

$738 - $1,796 / week

1 / 46

Siesta Key Vacation condo rental

Siesta Key condo

2 bedrooms • 2 bathrooms • sleeps 6

10 reviews

from $245 / night

$1,712 - $2,411 / week

1 / 24

Vacation apartment in Siesta Key

Siesta Key apartment

2 bedrooms • 1 bathroom • sleeps 6

from $123 / night

$722 - $2,357 / week

1 / 41

Vacation home with swimming pool in Siesta Key

Siesta Key house

4 bedrooms • 3 bathrooms • sleeps 6

2 reviews

from $277 / night

$1,969 - $2,963 / week

1 / 37

Siesta Key Vacation home rental

Siesta Key house

2 bedrooms • 2 bathrooms • sleeps 6

1 review

from $180 / night

$1,108 - $1,623 / week

1 / 18

Siesta Key Vacation home rental

Siesta Key house

3 bedrooms • 2 bathrooms • sleeps 8

1 review

from $342 / night

$1,147 - $2,894 / week

1 / 39

Vacation villa in Siesta Key

Siesta Key villa

2 bedrooms • 2 bathrooms • sleeps 6

from $549 / night

$3,840 / week

1 / 16

Apartment rental in Siesta Key with shared pool

Siesta Key apartment

3 bedrooms • 3 bathrooms • sleeps 8

1 review

from $263 / night

$1,103 - $2,594 / week

1 / 61

Apartment rental in Siesta Key with shared pool

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 4

from $155 / night

$774 - $1,969 / week

1 / 37

Siesta Key Vacation villa rental

Siesta Key villa

2 bedrooms • 2 bathrooms • sleeps 6

from $541 / night

$3,783 / week

1 / 40

Siesta Key Vacation apartment rental

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 4

1 review

from $122 / night

$916 - $1,031 / week

1 / 34

Siesta Key Vacation condo rental

Siesta Key condo

1 bedroom • 1 bathroom • sleeps 4

from $136 / night

$895 - $2,377 / week

1 / 37

Siesta Key Vacation hotel apartment rental

Siesta Key hotel apartment

3 bedrooms • 1 bathroom • sleeps 6

1 review

from $138 / night

$962 / week

1 / 14

Siesta Key Vacation condo accommodation

Siesta Key condo

2 bedrooms • 1 bathroom • sleeps 5

1 review

from $91 / night

$634 / week

1 / 41

Vacation apartment in Siesta Key

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

3 reviews

from $212 / night

$1,483 - $2,445 / week

1 / 32

Vacation condo with shared pool in Siesta Key

Siesta Key condo

2 bedrooms • 2 bathrooms • sleeps 6

from $103 / night

$758 - $2,658 / week

1 / 45

Vacation apartment rental

Siesta Key apartment

2 bedrooms • 2 bathrooms • sleeps 6

20 reviews

from $189 / night

$1,323 / week

1 / 36