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

2,319 Vacation rentals

Siesta Key Vacation condo rental

Siesta Key condo

32

  • Beach/lakeside relaxation
  • •  Nearest beach 0.01 mi
  • •  Swimming pool
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $409 / night

$2,863 / week

Home rental in Siesta Key with swimming pool

Siesta Key house

1

  • Beach/lakeside relaxation
  • •  Nearest beach 0.8 mi
  • •  Swimming pool
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $255 / night

$1,783 / week

Vacation villa in Siesta Key

Siesta Key villa

2

  • Beach/lakeside relaxation
  • •  Swimming pool
  • •  Child friendly
  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from $232 / night

$1,157 - $2,697 / week

Vacation condo in Siesta Key

Siesta Key condo

  • Beach/lakeside relaxation
  • •  Nearest beach 1 mi
  • •  Swimming pool
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $131 / night

$916 / week

Vacation home rental

Siesta Key house

  • Child friendly
  • •  Air conditioning
  • •  Pet friendly
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $328 / night

$2,290 / week

Home rental in Siesta Key

Siesta Key house

  • Nearest beach 0.5 mi
  • •  Swimming pool
  • •  Child friendly
  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $262 / night

$1,832 - $2,290 / week

Home accommodation in Siesta Key

Siesta Key house

  • Nearest beach 0.6 mi
  • •  Swimming pool
  • •  Child friendly
  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $344 / night

$2,405 - $2,863 / week

Siesta Key Vacation home rental

Siesta Key house

  • Nearest beach 1 mi
  • •  Swimming pool
  • •  Child friendly
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

from $278 / night

$1,947 - $2,290 / week

Vacation townhouse in Siesta Key

Siesta Key townhouse

1

  • Beach/lakeside relaxation
  • •  Nearest beach 0.1 mi
  • •  Swimming pool
  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

from $269 / night

$1,718 - $2,863 / week

Vacation home in Siesta Key

Siesta Key house

  • Child friendly
  • •  Air conditioning
  • •  Pet friendly
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $201 / night

$1,403 / week

Siesta Key Vacation apartment rental

Siesta Key apartment

16

  • Beach/lakeside relaxation
  • •  Nearest beach 1 mi
  • •  Child friendly
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

from $228 / night

$1,518 - $2,405 / week

Siesta Key Vacation home rental

Siesta Key house

5

  • Nearest beach 0.32 mi
  • •  Child friendly
  • •  Air conditioning
  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $110 / night

$770 / week

Siesta Key Vacation apartment rental

Siesta Key apartment

24

  • Beach/lakeside relaxation
  • •  Nearest beach 1 mi
  • •  Child friendly
  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from $178 / night

$1,145 - $1,941 / week

Vacation cottage in Siesta Key

Siesta Key cottage

  • Child friendly
  • •  Pet friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $171 / night

$1,195 / week

Vacation condo with swimming pool in Siesta Key

Siesta Key condo

5

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $114 / night

$794 / week

Vacation townhouse in Siesta Key

Siesta Key townhouse

  • Child friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $240 / night

$1,676 / week

Vacation condo in Siesta Key

Siesta Key condo

3

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $147 / night

$1,031 / week

Home rental in Siesta Key

Siesta Key house

23

  • Beach/lakeside relaxation
  • •  Nearest beach 0 mi
  • •  Swimming pool
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $344 / night

$2,061 - $2,748 / week

Siesta Key Vacation apartment rental

Siesta Key apartment

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $217 / night

$874 - $1,684 / week

Siesta Key Vacation condo rental

Siesta Key condo

5

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $107 / night

$745 - $1,489 / week

Vacation home with swimming pool in Siesta Key

Siesta Key house

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $287 / night

$2,004 / week

Vacation condo with shared pool in Siesta Key

Siesta Key condo

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $92 / night

$859 - $1,095 / week

Siesta Key Vacation apartment rental

Siesta Key apartment

1

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $124 / night

$916 - $2,028 / week

Apartment rental in Siesta Key with shared pool

Siesta Key apartment

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $162 / night

$863 - $2,305 / week

Vacation apartment in Siesta Key

Siesta Key apartment

4

  • Beach/lakeside relaxation
  • •  Swimming pool
  • •  Child friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $288 / night

$2,012 / week

Vacation villa in Siesta Key

Siesta Key villa

  • Child friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $228 / night

$1,595 / week

Vacation apartment in Siesta Key

Siesta Key apartment

36

  • Beach/lakeside relaxation
  • •  Swimming pool
  • •  Child friendly
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $103 / night

$687 - $1,088 / week

Vacation apartment in Siesta Key

Siesta Key apartment

  • Swimming pool
  • •  Child friendly
  • •  Car not necessary
  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from $205 / night

$1,435 / week

Apartment rental in Siesta Key with shared pool

Siesta Key apartment

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $148 / night

$694 - $1,744 / week

Siesta Key Vacation condo rental

Siesta Key condo

10

  • Beach/lakeside relaxation
  • •  Swimming pool
  • •  Child friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $245 / night

$1,712 - $2,640 / week

Siesta Key Vacation apartment rental

Siesta Key apartment

17

  • Beach/lakeside relaxation
  • •  Swimming pool
  • •  Child friendly
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $166 / night

$1,163 - $2,731 / week

Vacation villa rental

Siesta Key villa

6

  • Beach/lakeside relaxation
  • •  Nearest beach 0.1 mi
  • •  Swimming pool
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $194 / night

$1,355 / week

Siesta Key Vacation apartment rental

Siesta Key apartment

2

  • Child friendly
  • •  Air conditioning
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $91 / night

$634 / week

Siesta Key Vacation apartment rental

Siesta Key apartment

5

  • Beach/lakeside relaxation
  • •  Nearest beach 0.2 mi
  • •  Swimming pool
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $115 / night

$802 - $1,489 / week

Siesta Key Vacation condo rental

Siesta Key condo

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $122 / night

$790 - $1,343 / week

Vacation apartment in Siesta Key

Siesta Key apartment

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from $123 / night

$618 - $1,676 / week

Siesta Key Vacation condo rental

Siesta Key condo

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $253 / night

$943 - $2,570 / week

Siesta Key Vacation condo accommodation

Siesta Key condo

1

  • Child friendly
  • •  Air conditioning
  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from $91 / night

$634 / week

Siesta Key Vacation apartment rental

Siesta Key apartment

1

  • Swimming pool
  • •  Child friendly
  • •  Air conditioning
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from $182 / night

$1,275 / week

Siesta Key Vacation villa rental

Siesta Key villa

8

  • Beach/lakeside relaxation
  • •  Nearest beach 0.2 mi
  • •  Swimming pool
  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $184 / night

$1,603 - $2,164 / week