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5 Best Osprey Apartments on Holiday Lettings - Villas

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1,020 Vacation rentals

Osprey Vacation home rental

Osprey house

3 bedrooms • 2 bathrooms • sleeps 6

from $149 / night

$1,042 / week

1 / 27

Villa accommodation in Osprey with golf nearby

Osprey villa

2 bedrooms • 2 bathrooms • sleeps 6

from $287 / night

$2,004 / week

1 / 29

Vacation condo with golf nearby in Osprey

Osprey condo

2 bedrooms • 2 bathrooms • sleeps 4

2 reviews

from $69 / night

$481 / week

1 / 59

Osprey Vacation cottage rental

Osprey cottage

2 bedrooms • 1 bathroom • sleeps 2

from $98 / night

$682 / week

1 / 18

Home rental in Osprey

Osprey house

3 bedrooms • 2 bathrooms • sleeps 5

from $97 / night

$674 / week

1 / 28

Osprey Vacation condo rental

Osprey condo

2 bedrooms • 2 bathrooms • sleeps 6

from $153 / night

$1,069 / week

1 / 9

Vacation home with swimming pool in Osprey

Osprey house

3 bedrooms • 4 bathrooms • sleeps 9

from $185 / night

$1,289 - $3,319 / week

1 / 58

Great rentals within 20 miles that match your search

Vacation condo with shared pool in Sarasota

Sarasota condo

2 bedrooms • 2 bathrooms • sleeps 4

from $100 / night

$745 / week

1 / 5

Vacation condo in North Port

North Port condo

2 bedrooms • 2 bathrooms • sleeps 4

from $107 / night

$748 / week

1 / 10

Venice Vacation home rental

Venice house

1 bedroom • 1 bathroom • sleeps 3

from $121 / night

$722 / week

1 / 37

Vacation apartment with golf nearby in Sarasota

Sarasota apartment

1 bedroom • 1 bathroom • sleeps 4

from $123 / night

$859 - $1,374 / week

1 / 7

Vacation home with swimming pool in Sarasota

Sarasota house

3 bedrooms • 3 bathrooms • sleeps 6

from $210 / night

$1,470 / week

1 / 33

Studio rental in Sarasota

Sarasota studio

Studio • 1 bathroom • sleeps 3

from $114 / night

$796 - $1,913 / week

1 / 19

Vacation condo with golf nearby in Longboat Key

Longboat Key condo

2 bedrooms • 2 bathrooms • sleeps 6

from $332 / night

$2,325 / week

1 / 22

Villa rental in Nokomis

Nokomis villa

2 bedrooms • 1 bathroom • sleeps 6

1 review

from $194 / night

$1,258 - $1,418 / week

1 / 25

Vacation condo in Sarasota

Sarasota condo

2 bedrooms • 1 bathroom • sleeps 3

from $573 / night

$4,008 / week

1 / 30

Sarasota Vacation apartment rental

Sarasota apartment

1 bedroom • 1 bathroom • sleeps 3

1 review

from $131 / night

$916 - $1,872 / week

1 / 17

Vacation condo in Sarasota

Sarasota condo

1 bedroom • 1 bathroom • sleeps 2

from $98 / night

$682 / week

1 / 29

Cottage rental in Longboat Key with shared pool, golf nearby

Longboat Key cottage

3 bedrooms • 2 bathrooms • sleeps 8

from $687 / night

$4,809 / week

1 / 12

Sarasota Vacation apartment rental

Sarasota apartment

2 bedrooms • 2 bathrooms • sleeps 4

from $295 / night

$2,061 / week

1 / 10

Venice Vacation condo rental

Venice condo

2 bedrooms • 2 bathrooms • sleeps 3

from $115 / night

$802 / week

1 / 20

Vacation condo in Sarasota

Sarasota condo

2 bedrooms • 3 bathrooms • sleeps 6

from $96 / night

$668 / week

1 / 8

Apartment rental in Sarasota

Sarasota apartment

1 bedroom • 1 bathroom • sleeps 3

2 reviews

from $131 / night

$916 - $2,050 / week

1 / 18

Vacation home in Fruitville

Fruitville house

2 bedrooms • 2 bathrooms • sleeps 6

from $344 / night

$2,405 / week

1 / 8

Vacation home rental

Nokomis house

3 bedrooms • 2 bathrooms • sleeps 8

from $109 / night

$762 / week

1 / 24

Vacation apartment accommodation

Longboat Key apartment

2 bedrooms • 2 bathrooms • sleeps 5

from $168 / night

$1,176 / week

1 / 6

Vacation home in South Venice

South Venice house

2 bedrooms • 2 bathrooms • sleeps 4

from $126 / night

$504 / week

1 / 16

Casey Key Vacation villa rental

Casey Key villa

3 bedrooms • 2 bathrooms • sleeps 6

from $224 / night

$1,432 / week

1 / 19

Vacation home in Sarasota

Sarasota house

4 bedrooms • 3 bathrooms • sleeps 9

5 reviews

from $355 / night

$2,434 - $2,834 / week

1 / 23

Vacation home in Siesta Key

Siesta Key house

6 bedrooms • 5 bathrooms • sleeps 14

1 review

from $999 / night

$6,989 / week

1 / 23

Vacation condo with shared pool in Siesta Key

Siesta Key condo

1 bedroom • 2 bathrooms • sleeps 4

from $138 / night

$962 / week

1 / 12

Vacation apartment rental

Venice apartment

2 bedrooms • 2 bathrooms • sleeps 5

1 review

from $187 / night

$1,310 / week

1 / 34

Vacation home in Sarasota

Sarasota house

2 bedrooms • 1 bathroom • sleeps 6

3 reviews

from $228 / night

$1,595 / week

1 / 18

Sarasota Vacation apartment rental

Sarasota apartment

2 bedrooms • 1 bathroom • sleeps 6

from $228 / night

$1,595 / week

1 / 17

Vacation apartment in Sarasota

Sarasota apartment

2 bedrooms • 1 bathroom • sleeps 6

from $228 / night

$1,595 / week

1 / 22

Vacation apartment in Sarasota

Sarasota apartment

2 bedrooms • 1 bathroom • sleeps 6

from $228 / night

$1,595 / week

1 / 14

Vacation apartment in Sarasota

Sarasota apartment

2 bedrooms • 1 bathroom • sleeps 6

from $228 / night

$1,595 / week

1 / 19

Vacation apartment rental

Sarasota apartment

2 bedrooms • 1 bathroom • sleeps 6

from $228 / night

$1,595 / week

1 / 18