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Vacation Rentals in Osprey, Florida

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about Osprey

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Osprey, Florida vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Osprey are added and updated every week!

Compared to hotels, Osprey vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Osprey, Florida Vacation Rentals and Tourism

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Weekly rate:

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$2,000
$4,000+

Bedrooms: Min 0, Max 5

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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

Siesta Key - Gulf Front Tranquility with boat dock
Osprey Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,045 - $1,745 /wk
 
 
 
 
 

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Siesta Key Condo, Modernized, New Appliances,Washer/Dryer, HD-TV, Comcast WIFI
Osprey Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $1,040 - $1,865 /wk
    $4,998 - $5,916 /mth
 
 
 
 
 

21 reviews write a review

Spacious Sarasota Water Front Pool Home W/ Dock
Osprey House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths 2
  • rates (USD) $1,750 - $2,000 /wk
    $3,500 - $7,680 /mth
 
 
 
 
 

1 reviews write a review

Siesta Key with Boat Dock
Osprey Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths
  • rates (USD) $125 - $157 /nt
    $750 - $1,100 /wk
    $2,550 - $3,750 /mth
 
 
 
 
 

14 reviews write a review

$59/Day $350/Wk/ $1400/Mo 2nd floor overlooking pool/wi fi
Osprey Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • sleeps 4
  • baths 1
  • rates (USD) $59 - $225 /nt
    $350 - $1,125 /wk
    $1,400 - $2,500 /mth
 
 
 
 
 

3 reviews write a review

3Br Condo 1st Floor Next To The Pool!!!!!!!
Osprey Condo Rental Picture
  • bedrooms 3
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $160 - $214 /nt
    $725 - $1,500 /wk
    $2,500 - $3,500 /mth
 
 
 
 
 

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Best Lux Villa Fr $ 575 / wk Nr Siesta: Wifi,Pool,HDTV,C.C
Osprey Villa Rental Picture
  • bedrooms 2
  • rental type Villa
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $99 - $197 /nt
    $575 - $1,380 /wk
    $2,222 - $4,997 /mth
 
 
 
 
 

22 reviews write a review

Secluded Sarasota Home minutes from Siesta & Venice Beaches.
Osprey House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $630 - $1,225 /wk
    $1,650 - $3,000 /mth
 
 
 
 
 

16 reviews write a review

55/Day $ 361/wk $ 1,422/mo Nr1 Siesta White Beach 1BR Suite/Pool/Lake-view/C.c.
Osprey Condo Rental Picture
  • bedrooms 1
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $55 - $153 /nt
    $361 - $1,069 /wk
    $1,422 - $3,177 /mth
 
 
 
 
 

14 reviews write a review

Newly Renovated Condo Overlooking The Bay And With Direct Access To The Beach
Osprey Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 4
  • baths 2
  • rates (USD) $129 - $143 /nt
    $4,200 /mth
 
 
 
 
 

7 reviews write a review

Enchanting Beachfront 'Toes in the Sand' Condo
Osprey Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $149 - $249 /nt
    $1,245 /wk
 
 
 
 
 

6 reviews write a review

Quiet and comfortable condo near Turtle Beach on Siesta Key
Osprey Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 5
  • baths 2
  • rates (USD) $85 - $135 /nt
    $630 - $945 /wk
    $2,400 - $3,950 /mth
 
 
 
 
 

21 reviews write a review

Awesome waterfront community on Siesta Key, beach and bay access. 2/2 condo
Osprey Condo Rental Picture
  • bedrooms 0
  • rental type Condo
  • sleeps 4
  • baths 0
  • rates (USD) $71 - $133 /nt
    $4,000 /mth
 
 
 
 
 

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Lagoon-Front Studio: 'The Sunset Cottage' Full Water Views! 40 inch LED HD TV
Osprey Cottage Rental Picture
  • bedrooms 0
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD)
 
 
 
 
 

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