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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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Osprey things to do

 

Siesta Key Beach

Most beautiful beach you'll see, travel the world & come back. You'll appreciate what I mean. The sand is the consistency of powder. It never feels hot to...read more

 

Lido Beach

Absolutely loved it here. What's not to love about the gulf?!!! What sets this beach apart from others in the area is that it has a concession stand...read more

 

Brohard Paw Park & Beach

We found this dog beach online, decided to drive an hour to get there. I must say it was well worthed. Not only is it a off leash dog park, but it's a...read more

 

Siesta Key Oyster Bar

SKOB is more of an atmosphere place for me. The food is good, not great, but if you're on Siesta Key, and you want to sit on a loud patio with local...read more

 

AMC Sarasota 12

Very nice movie theater, very very clean. You can actually use the Yelp app to see movie times and purchase tickets through Fandango. We paid $21 for...read more

 

A To Z Baby Beach & Bike Rentals

As I was previously employed by a competitor, I was hesitant to rent from another company, however, the convenient pick up location in Venice, the better...read more

 

Goodfellas Cafe & Winery

Thanks to the Yelp reviews, we stopped here for lunch on our way to Siesta Key and we were beyond satisfied. The other reviews are spot on. Fresh...read more

 

Sea Life Kayak Adventures

Sea Life Kayak Adventures in Sarasota. Tom was our guide. Highlight of our trip! We just returned from the wildlife exploration with Tom. We had a great...read more

 

Nokomis Public Beach

Lots and lots of shark teeth! So many shark teeth that we call this beach SHARK TOOTH BEACH!!! We live in Tampa and frequent the Gulf Beaches that are in...read more

 

Canoe Outpost-Peace River

My husband and I went canoe camping this winter on the Peace River from Canoe Outpost. We loooooved it! I saw a lot of complaints about the customer service...read more

 

Cool Breeze - Boat & Jet Ski Rental

This place was awful! If i could give it zero stars I would. My family rented it on our last day of vacation. First of all the boat didn't work, it stopped...read more

 

CaliFlorida Surf Shop & Rentals

Super chill with the best prices in Siesta Key (think $10-$15 cheaper than the place down the street). The shop has some great clothing items and...read more

 

Siesta Key Bike & Kayak LLC

I had a lot of fun on their paddle board my family and I spend a lot of time together the owners were really nice and were very helpful. My daughter wrote...read more

 

Oscar Scherer State Park

Florida has some wonderful State Parks and Oscar Scherer State Park, which consists of some two miles of parkland created by the generosity of Elsa Scherer...read more

 

Florida Underwater Sports

Today my wife and I went to Florida Underwater Sports to buy snorkel masks and snorkels. We received excellent service and were able to try on the masks to...read more

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Welcome to Sarasota's Best Kept Secret! Available Beginning May 31,2015
Osprey Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $550 - $1,125 /wk
 
 
 
 
 

26 reviews write a review

Welcome to Your Vacation in Paradise! Available Beginning June 28, 2015
Osprey Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $550 - $1,125 /wk
 
 
 
 
 

13 reviews write a review

Castaway Cove 3B, on lagoon near beach, pet friendly, Siesta Key
Osprey Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 5
  • baths 2
  • rates (USD) $595 - $1,595 /wk
    $1,802 - $2,500 /mth
 
 
 
 
 

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Siesta Key Bay Tree #106, 2 bedrooms, 2 heated pools, spa, wifi, beach access
Osprey Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • sleeps 6
  • baths 2
  • rates (USD) $1,802 - $1,995 /mth
 
 
 
 
 

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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
 
 
 
 
 

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) $79 - $135 /nt
    $630 - $945 /wk
    $2,400 - $3,950 /mth
 
 
 
 
 

21 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) $700 - $1,225 /wk
    $2,550 - $3,000 /mth
 
 
 
 
 

18 reviews write a review

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

1 Week Just Isn't Enough - Beach & Surf at Your Doorstep!
Osprey Condo Rental Picture
  • bedrooms 2
  • rental type Condo
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $1,045 - $1,745 /wk
 
 
 
 
 

23 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) $1,800 - $2,000 /wk
    $4,000 - $8,000 /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

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

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
 
 
 
 
 

15 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) $110 - $214 /nt
    $725 - $1,500 /wk
    $2,500 - $3,500 /mth
 
 
 
 
 

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$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

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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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

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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