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Vacation homes - vacation rentals

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Home rental in Osprey

Osprey house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $654 / night

$4,575 / week

1 / 15

Osprey Vacation home rental

Osprey house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $149 / night

$1,042 / week

1 / 24

Osprey Vacation condo rental

Osprey condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $161 / night

$1,123 / week

1 / 9

Villa accommodation in Osprey with golf nearby

Osprey villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $161 / night

$1,123 / week

1 / 41

Osprey Vacation cottage rental

Osprey cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

from $132 / night

$922 / week

1 / 24

Great rentals within 20 miles that match your search

Vacation apartment rental

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $68 / night

$447 - $676 / week

1 / 27

Vacation home in Sarasota

Sarasota house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $315 / night

$2,205 / week

1 / 11

Sarasota Vacation apartment rental

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $295 / night

$2,061 / week

1 / 10

Vacation condo in Siesta Key

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $332 / night

$2,325 / week

1 / 24

Vacation condo in Sarasota

Sarasota condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

from $573 / night

$4,008 / week

1 / 30

Vacation condo in Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $300 / night

$2,100 / week

1 / 16

Vacation home accommodation

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $212 / night

$1,603 - $2,084 / week

1 / 35

Vacation condo in Siesta Key

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $344 / night

$2,405 / week

1 / 27

Vacation condo rental

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $272 / night

$1,900 - $3,200 / week

1 / 31

Vacation home in Siesta Key

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

from $999 / night

$6,989 / week

1 / 23

Vacation condo with shared pool in Sarasota

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $115 / night

$802 / week

1 / 24

Vacation home in Venice

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from $155 / night

$974 / week

1 / 32

Vacation apartment in Bradenton

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $401 / night

$2,806 / week

1 / 59

Vacation townhouse in Siesta Key

Siesta Key townhouse

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

from $430 / night

$2,977 - $3,092 / week

1 / 38

Bradenton Vacation villa rental

Bradenton villa

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $195 / night

$1,363 / week

1 / 30

Vacation cottage with swimming pool in Sarasota

Sarasota cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $532 / night

$3,722 / week

1 / 32

Vacation home in North Port

North Port house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $138 / night

$962 - $1,283 / week

1 / 30

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from $310 / night

$2,061 - $2,691 / week

1 / 16

Vacation villa in Siesta Key

Siesta Key villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $802 / night

$5,611 / week

1 / 27

Venice Vacation apartment rental

Venice apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $138 / night

$962 / week

1 / 31

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $205 / night

$1,435 / week

1 / 80

Vacation apartment rental

Venice apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from $241 / night

$1,684 / week

1 / 34

Vacation apartment in Sarasota

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $258 / night

$1,718 / week

1 / 19

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

Home rental in Venice

Venice house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from $138 / night

$859 - $2,061 / week

1 / 31

Vacation townhouse in Siesta Key

Siesta Key townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from $272 / night

$3,300 / week

1 / 50

Vacation home in Siesta Key

Siesta Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

from $550 / night

$3,850 - $7,000 / week

1 / 35

Vacation apartment in Siesta Key

Siesta Key apartment

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from $486 / night

$3,400 - $7,650 / week

1 / 24

Vacation caravan/mobile home in Sarasota

Sarasota caravan/mobile home

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from $115 / night

$802 / week

1 / 8

Vacation apartment in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $315 / night

$2,200 - $3,300 / week

1 / 27

Siesta Key Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from $272 / night

$1,900 - $3,400 / week

1 / 36

Vacation condo rental

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from $269 / night

$1,718 - $2,084 / week

1 / 27

Vacation home in Sarasota

Sarasota house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $121 / night

$847 - $995 / week

1 / 35

Vacation apartment in Siesta Key

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $430 / night

$3,006 / week

1 / 39

Vacation apartment rental

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from $189 / night

$1,323 / week

1 / 36