Vacation rentals in Osprey, United States

Carefully selected & verified rentals in Osprey, United States
Check-in
26Jun2025Select date
Check-out
27Jun2025Select date
Rooms and Guests2 Guests, 1 Room
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Windsor Lodge Unit 5 Close To The Beaches Siesta Key Osprey
Map1200 yd from City Centre500 yd from Historic Spanish Point
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Windsor Lodge Unit #19, Studio Close To Beaches Osprey
Map1200 yd from City Centre500 yd from Historic Spanish Point
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Windsor Lodge Unit 3 Close To The Beaches Siesta Key
Map1200 yd from City Centre500 yd from Historic Spanish Point
FromUS$ 104 /nightSelect
Windsor Lodge Unit 20, Studio, 1Br 1Ba Close To The Beaches, Pool Access
Map1200 yd from City Centre500 yd from Historic Spanish Point
FromUS$ 185 /nightSelect
Bay Acres Bungalow - A
Map600 yd from City Centre1200 yd from Historic Spanish Point
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Flexible Price Range for Vacation Homes in Osprey

From cozy retreats to luxury villas – Find the ideal stay for every budget

⬆️ The highest price
US$ 185
⬇️ The lowest price
US$ 104
đź’¸ Average price for
Apartments
US$ 144

Top vacation homes in Osprey

Based on guest reviews from the past 12 months

Beachside Getaway:
Windsor Lodge Unit 3 Close To The Beaches Siesta Key
Charming Accommodation:
Bay Acres Bungalow - A
Studio Comfort Near Shore:
Windsor Lodge Unit #19, Studio Close To Beaches
Cozy Retreat Close to Sand:
Windsor Lodge Unit 5 Close To The Beaches Siesta Key

Vacation Rentals Overview in Osprey

This guide provides key information about vacation rentals in Osprey, evaluating four properties to help travelers make informed accommodation choices.

Typical nightly rates range from $150 to $400.

There are 4 notable vacation rental properties available.

Peak travel seasons are winter (December to February) and summer (June to August).

Local lodging tax is 12%, with a cleaning fee typically around $100.

Key attractions like Siesta Key Beach are about 4 miles away, and booking early ensures better rates.

Check-in
26Jun2025Select date
Check-out
27Jun2025Select date
Rooms and Guests2 Guests, 1 Room