Siesta Key apartment or villa with a private pool area | Holiday Lettings

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153 Holiday homes

Filters applied: Private pool (153)

Travellers going to Siesta Key are booking May dates now. Secure your holiday home today and have the perfect trip.

(1) Poor 

1 / 19

Holiday condo rental

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 6
  • 14 nights min stay

from £137 / night

£959 / week

Book Book View

from £137 / night

1 / 28

Siesta Key holiday home rental

Florida / Siesta Key

  • 6 bedrooms
  • Sleeps 12
  • 3 nights min stay

from £343 / night

£2261 - £4898 / week

Book Book View

from £343 / night

(3) Poor 

1 / 16

Siesta Key holiday home rental

Florida / Siesta Key

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay

from £294 / night

£2055 / week

Book Book View

from £294 / night

(9) Very Good 

1 / 27

Apartment rental in Siesta Key

Florida / Siesta Key

  • 1 bedroom
  • Sleeps 4
  • Min stay varies

from £83 / night

£480 - £651 / week

Book Book View

from £83 / night

(1) Excellent 

1 / 24

Home rental in Siesta Key with swimming pool

Florida / Siesta Key

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min stay

from £133 / night

£925 - £959 / week

Book Book View

from £133 / night

(3) Very Good 

1 / 24

Siesta Key holiday condo rental

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from £79 / night

£548 - £651 / week

Enquire Enquire View

from £79 / night

1 / 24

Holiday home with swimming pool in Siesta Key

Florida / Siesta Key

  • 4 bedrooms
  • Sleeps 12
  • 7 nights min stay

from £196 / night

£1370 - £1850 / week

Book Book View

from £196 / night

1 / 24

Holiday condo with swimming pool in Siesta Key

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 5
  • 6 nights min stay

from £66 / night

£456 / week

Book Book View

from £66 / night

1 / 45

Siesta Key holiday apartment rental

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £101 / night

£706 - £1233 / week

Enquire Enquire View

from £101 / night

1 / 22

Apartment rental in Siesta Key with shared pool

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £83 / night

£579 - £1014 / week

Enquire Enquire View

from £83 / night

(4) Good 

1 / 14

Siesta Key holiday apartment rental

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from £69 / night

£446 - £891 / week

Book Book View

from £69 / night

1 / 22

Holiday home in Siesta Key

Florida / Siesta Key

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min stay

from £192 / night

£1131 - £1199 / week

Book Book View

from £192 / night

(2) Very Good 

1 / 15

Holiday villa with shared pool in Siesta Key

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from £96 / night

£667 - £1036 / week

Enquire Enquire View

from £96 / night

(6) Very Good 

1 / 14

Siesta Key holiday apartment rental

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from £146 / night

£1022 - £1549 / week

Enquire Enquire View

from £146 / night

1 / 24

Holiday home with swimming pool in Siesta Key

Florida / Siesta Key

  • 6 bedrooms
  • Sleeps 16
  • 6 nights min stay

from £445 / night

£2733 / week

Book Book View

from £445 / night

1 / 37

Holiday home in Siesta Key

Florida / Siesta Key

  • 3 bedrooms
  • Sleeps 6
  • 14 nights min stay

from £133 / night

£925 / week

Book Book View

from £133 / night

1 / 24

Home rental in Siesta Key

Florida / Siesta Key

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £182 / night

£1268 / week

Book Book View

from £182 / night

1 / 18

Holiday apartment with shared pool in Siesta Key

Florida / Siesta Key

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £111 / night

£778 - £1278 / week

Enquire Enquire View

from £111 / night

1 / 14

Holiday apartment rental

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from £86 / night

£600 - £1090 / week

Enquire Enquire View

from £86 / night

1 / 17

Holiday apartment with shared pool in Siesta Key

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £83 / night

£579 - £1014 / week

Enquire Enquire View

from £83 / night

1 / 35

Holiday apartment with shared pool in Siesta Key

Florida / Siesta Key

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £122 / night

£857 - £1343 / week

Enquire Enquire View

from £122 / night

(1) Excellent 

1 / 19

Siesta Key holiday apartment rental

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £104 / night

£727 - £1233 / week

Enquire Enquire View

from £104 / night

1 / 15

Holiday apartment with shared pool in Siesta Key

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay

from £150 / night

£1048 - £1548 / week

Enquire Enquire View

from £150 / night

1 / 17

Holiday apartment with shared pool in Siesta Key

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £93 / night

£648 - £1120 / week

Enquire Enquire View

from £93 / night

1 / 17

Holiday apartment with shared pool in Siesta Key

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay

from £86 / night

£600 - £1090 / week

Enquire Enquire View

from £86 / night

1 / 36

Siesta Key holiday apartment rental

Florida / Siesta Key

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £161 / night

£1131 - £1908 / week

Enquire Enquire View

from £161 / night

1 / 25

Holiday apartment in Siesta Key

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £101 / night

£706 - £1233 / week

Enquire Enquire View

from £101 / night

1 / 40

Holiday apartment rental

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £101 / night

£706 - £1233 / week

Enquire Enquire View

from £101 / night

1 / 23

Holiday apartment with shared pool in Siesta Key

Florida / Siesta Key

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £161 / night

£1131 - £1908 / week

Enquire Enquire View

from £161 / night

1 / 17

Holiday apartment rental

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay

from £150 / night

£1048 - £1548 / week

Enquire Enquire View

from £150 / night

1 / 23

Siesta Key holiday apartment rental

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £83 / night

£579 - £1014 / week

Enquire Enquire View

from £83 / night

1 / 31

Holiday apartment with shared pool in Siesta Key

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £104 / night

£727 - £1233 / week

Enquire Enquire View

from £104 / night

1 / 25

Holiday apartment with shared pool in Siesta Key

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £86 / night

£600 - £1090 / week

Enquire Enquire View

from £86 / night

1 / 15

Siesta Key holiday apartment rental

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay

from £150 / night

£1048 - £1548 / week

Enquire Enquire View

from £150 / night

1 / 16

Siesta Key holiday apartment rental

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £146 / night

£1024 - £1459 / week

Enquire Enquire View

from £146 / night

1 / 30

Apartment rental in Siesta Key with shared pool

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from £104 / night

£727 - £1233 / week

Enquire Enquire View

from £104 / night

1 / 18

Siesta Key holiday apartment rental

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay

from £150 / night

£1048 - £1548 / week

Enquire Enquire View

from £150 / night

1 / 14

Holiday apartment with shared pool in Siesta Key

Florida / Siesta Key

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £122 / night

£857 - £1343 / week

Enquire Enquire View

from £122 / night

1 / 15

Holiday apartment rental

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay

from £150 / night

£1048 - £1548 / week

Enquire Enquire View

from £150 / night

1 / 28

Siesta Key holiday apartment rental

Florida / Siesta Key

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £122 / night

£857 - £1343 / week

Enquire Enquire View

from £122 / night

1 / 38

Holiday apartment in Siesta Key

Florida / Siesta Key

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £117 / night

£816 - £1319 / week

Enquire Enquire View

from £117 / night

1 / 25

Holiday home in Siesta Key

Florida / Siesta Key

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay

from £309 / night

£1884 - £4795 / week

Book Book View

from £309 / night

1 / 38

Holiday apartment accommodation

Florida / Siesta Key

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £161 / night

£1131 - £1908 / week

Enquire Enquire View

from £161 / night

1 / 28

Holiday apartment with shared pool in Siesta Key

Florida / Siesta Key

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from £161 / night

£1131 - £1908 / week

Enquire Enquire View

from £161 / night

1 / 22

Holiday apartment with shared pool in Siesta Key

Florida / Siesta Key

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min stay

from £264 / night

£1846 - £3295 / week

Enquire Enquire View

from £264 / night

1 / 14

Apartment rental in Siesta Key with shared pool

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £162 / night

£1134 - £1641 / week

Enquire Enquire View

from £162 / night

1 / 26

Siesta Key holiday apartment accommodation

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay

from £86 / night

£600 - £1090 / week

Enquire Enquire View

from £86 / night

(11) Very Good 

1 / 17

Siesta Key holiday villa rental

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from £114 / night

£792 - £1190 / week

Enquire Enquire View

from £114 / night

(5) Very Good 

1 / 16

Villa rental in Siesta Key

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from £114 / night

£792 - £1190 / week

Enquire Enquire View

from £114 / night

(2) Excellent 

1 / 18

Villa rental in Siesta Key

Florida / Siesta Key

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from £114 / night

£792 - £1190 / week

Enquire Enquire View

from £114 / night

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