Villas in Osprey and Apartments - Holiday Lettings - Holiday Rentals Osprey

Close

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

1,478 Holiday homes

(1) Excellent 

17

Holiday home in Osprey

Florida / Osprey

3 8 90 nights min

  • 3 bedrooms
  • sleeps 8
  • 90 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool

from £134 / night

£933 / week

Book View

from £134 / night

24

Holiday condo in Osprey

Florida / Osprey

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £86 / night

£600 / week

Book View

Responds fast!
avg. 28 minutes

from £86 / night

24

Holiday apartment in Osprey

Florida / Osprey

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £111 / night

£774 / week

Book View

Responds fast!
avg. 10 minutes

from £111 / night

(2) Very Good 

17

Holiday home in Osprey

Florida / Osprey

3 5 3 nights min

  • 3 bedrooms
  • sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £137 / night

£857 / week

Book View

from £137 / night

24

Osprey holiday condo rental

Florida / Osprey

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

from £220 / night

£1,874 / week

Book View

from £220 / night

14

Holiday apartment with shared pool in Osprey

Florida / Osprey

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

from £113 / night

£731 - £1,053 / week

Book View

Responds fast!
avg. 1 hour 51 minutes

from £113 / night

29

Villa accommodation in Osprey with golf nearby

Florida / Osprey

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Nearest beach 7 km
  • Swimming pool
  • Child friendly

from £78 / night

£510 - £619 / week

Book View

from £78 / night

33

Holiday home in Osprey

Florida / Osprey

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly

from £103 / night

£720 / week

Book View

from £103 / night

33

Holiday condo with shared pool in Osprey

Florida / Osprey

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £50 / night

£351 / week

Book View

Responds fast!
avg. 2 minutes

from £50 / night

26

Condo rental in Osprey

Florida / Osprey

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly

from £47 / night

£327 / week

Book View

from £47 / night

16

Holiday home in Osprey

Florida / Osprey

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £59 / night

£410 / week

Book View

from £59 / night

25

Holiday condo in Osprey

Florida / Osprey

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly

from £74 / night

£518 / week

Book View

from £74 / night

18

Holiday condo in Osprey

Florida / Osprey

1 4 30 nights min

  • 1 bedroom
  • sleeps 4
  • 30 nights min
  • Child friendly

from £53 / night

£370 / week

Book View

from £53 / night

(2) Excellent 

15

Holiday condo with golf nearby in Osprey

Florida / Osprey

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £47 / night

£328 / week

Book View

from £47 / night

Great rentals within 20 miles that match your search

Distance approx 2.03 miles from Osprey Show on Map

(29) Excellent 

28

Siesta Key holiday condo rental

Florida / Siesta Key

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.01 km
  • Swimming pool

from £278 / night

£1,944 / week

Book View

Responds fast!
avg. 32 minutes

from £278 / night

Distance approx 11.75 miles from Osprey

12

Apartment rental in Sarasota

Southwest Gulf Coast / Sarasota

2 1 30 nights min

  • 2 bedrooms
  • sleeps 1
  • 30 nights min
  • Ask owner if suitable for children
  • Air conditioning

from £86 / night

£583 / week

Enquire View

from £86 / night

Distance approx 7.48 miles from Osprey

(1) Excellent 

16

Holiday home with swimming pool, golf nearby in Sarasota

Southwest Gulf Coast / Sarasota

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 13 km
  • Swimming pool

from £78 / night

£547 - £1,257 / week

Book View

Responds fast!
avg. 40 minutes

from £78 / night

Distance approx 16.41 miles from Osprey

(1) Excellent 

28

Apartment rental in Longboat Key

Florida / Longboat Key

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly

from £279 / night

£1,951 / week

Book View

Responds fast!
avg. 2 hours 56 minutes

from £279 / night

Distance approx 9.81 miles from Osprey

(7) Very Good 

9

Holiday apartment in Sarasota

Southwest Gulf Coast / Sarasota

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

from £97 / night

£674 / week

Book View

from £97 / night

Distance approx 4.82 miles from Osprey Show on Map

(9) Excellent 

Certificate of Excellence

24

Holiday condo rental

Florida / Siesta Key

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £139 / night

£972 - £1,322 / week

Book View

Responds fast!
avg. 54 minutes

from £139 / night

Distance approx 4.98 miles from Osprey Show on Map

(12) Excellent 

58

Sarasota holiday apartment rental

Southwest Gulf Coast / Sarasota

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £175 / night

£1,222 - £1,755 / week

Book View

Responds fast!
avg. 3 hours 31 minutes

from £175 / night

Distance approx 6.88 miles from Osprey

(2) Very Good 

30

Holiday villa with golf nearby in Venice

Southwest Gulf Coast / Venice

2 4 29 nights min

  • 2 bedrooms
  • sleeps 4
  • 29 nights min
  • Nearest beach 3 km
  • Swimming pool
  • Air conditioning

from £53 / night

£391 - £527 / week

Book View

from £53 / night

Distance approx 5.28 miles from Osprey Show on Map

53

Sarasota holiday condo rental

Southwest Gulf Coast / Sarasota

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £135 / night

£945 / week

Book View

from £135 / night

Distance approx 6.95 miles from Osprey

10

Holiday home in Venice

Southwest Gulf Coast / Venice

2 6 1 night min

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

from £55 / night

£383 / week

Book View

Responds fast!
avg. 34 minutes

from £55 / night

Distance approx 19.39 miles from Osprey

(1) Very Good 

38

Holiday condo in Bradenton

Southwest Gulf Coast / Bradenton

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 10 km
  • Swimming pool
  • Child friendly

from £94 / night

£626 - £871 / week

Book View

Responds fast!
avg. 44 minutes

from £94 / night

Distance approx 5.36 miles from Osprey Show on Map

(1) Excellent 

12

Holiday villa in Siesta Key

Florida / Siesta Key

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £141 / night

£937 / week

Book View

from £141 / night

Distance approx 7.21 miles from Osprey

19

Holiday condo in Siesta Key

Florida / Siesta Key

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child friendly

from £108 / night

£757 / week

Book View

from £108 / night

Distance approx 14.85 miles from Osprey

(2) Very Good 

17

Home rental in Englewood

Southwest Gulf Coast / Englewood

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £145 / night

£1,011 - £1,229 / week

Book View

from £145 / night

Distance approx 8.19 miles from Osprey

(1) Excellent 

15

Holiday home in Venice

Southwest Gulf Coast / Venice

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 8 km
  • Swimming pool

from £102 / night

£984 / week

Book View

Responds fast!
avg. 2 hours 36 minutes

from £102 / night

Distance approx 4.15 miles from Osprey Show on Map

(1) Excellent 

26

Siesta Key holiday condo rental

Florida / Siesta Key

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child friendly
  • Air conditioning

from £117 / night

£1,678 / week

Book View

from £117 / night

Distance approx 12.59 miles from Osprey

(1) Average 

24

Condo rental in Venice

Southwest Gulf Coast / Venice

2 6 6 nights min

  • 2 bedrooms
  • sleeps 6
  • 6 nights min
  • Child friendly

from £67 / night

£465 / week

Book View

from £67 / night

Distance approx 4.47 miles from Osprey Show on Map

(1)  

4

Condo rental in Sarasota

Southwest Gulf Coast / Sarasota

1 4 30 nights min

  • 1 bedroom
  • sleeps 4
  • 30 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £65 / night

£456 / week

Book View

from £65 / night

Distance approx 4.93 miles from Osprey

24

Holiday home rental

Florida / Nokomis

3 8 14 nights min

  • 3 bedrooms
  • sleeps 8
  • 14 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £74 / night

£517 / week

Book View

from £74 / night

Distance approx 17.84 miles from Osprey

11

Longboat Key holiday condo rental

Florida / Longboat Key

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £200 / night

£1,400 / week

Book View

from £200 / night

Distance approx 19.41 miles from Osprey

48

Bradenton holiday apartment rental

Southwest Gulf Coast / Bradenton

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 8 km
  • Swimming pool
  • Child friendly

from £94 / night

£629 - £874 / week

Book View

Responds fast!
avg. 44 minutes

from £94 / night

Distance approx 6.03 miles from Osprey

20

Holiday condo with shared pool in Siesta Key

Florida / Siesta Key

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

from £155 / night

£1,082 - £1,584 / week

Book View

Responds fast!
avg. 2 hours 54 minutes

from £155 / night

Distance approx 4.46 miles from Osprey Show on Map

17

Siesta Key holiday villa rental

Florida / Siesta Key

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly

from £109 / night

£760 / week

Book View

from £109 / night

Distance approx 8.71 miles from Osprey

20

Holiday home in Sarasota

Southwest Gulf Coast / Sarasota

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £98 / night

£681 / week

Book View

from £98 / night

Distance approx 6.64 miles from Osprey

18

Home rental in Siesta Key

Florida / Siesta Key

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child friendly
  • Air conditioning

from £78 / night

£547 / week

Book View

from £78 / night

Distance approx 18.06 miles from Osprey

11

Apartment rental in Bradenton with swimming pool

Southwest Gulf Coast / Bradenton

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £81 / night

£566 - £664 / week

Book View

from £81 / night

Also consider