Osprey vacation rentals

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Best Osprey vacation rentals

Most recommended vacation rentals in Osprey

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Charming cozy coastal houseminutes away from Venice beach - Osprey - Beach
Charming cozy coastal houseminutes away from Venice beach
Osprey, FL
Free Wi-Fi
$239+
Check availability
King Bed & Patio, Minutes to the Beach - Osprey - Living room
King Bed & Patio, Minutes to the Beach
Osprey, FL
7.3Good(2)
Parking
Free Wi-Fi
Pet friendly
$192+
Check availability
2BR/2BA 1st Floor Condo in Stoneybrook Golf & Country Club - Osprey - Living room
2BR/2BA 1st Floor Condo in Stoneybrook Golf & Country Club
Osprey, FL
Free Wi-Fi
Pool
Spa
$113+
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Windsor Lodge Unit 3 close to the Beaches Siesta Key - Osprey - Living room
Windsor Lodge Unit 3 close to the Beaches Siesta Key
Osprey, FL
9.0Wonderful(1)
Parking
Free Wi-Fi
Pool
$202+
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Cozy 2BR Florida Home Near the Shore - Osprey - Bedroom
Cozy 2BR Florida Home Near the Shore
Osprey, FL
6.5Okay(2)
Parking
Free Wi-Fi
Pet friendly
$226+
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Casey Key Paradise - Osprey - Beach
Casey Key Paradise
Osprey, FL
Free Wi-Fi
Pet friendly
$2,292+
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Pool, Hot tub, Close to Beaches, Shopping, More! - Osprey - Living room
Pool, Hot tub, Close to Beaches, Shopping, More!
Osprey, FL
Parking
Free Wi-Fi
Pet friendly
$286+
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Smart Home Sarasota Family Getaway - Osprey - Living room
Smart Home Sarasota Family Getaway
Osprey, FL
9.7Wonderful(18)
Parking
Free Wi-Fi
$443+
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Osprey Vacation Rental w/ Kayaks: 4 Mi to Beach! - Osprey - Living room
Osprey Vacation Rental w/ Kayaks: 4 Mi to Beach!
Osprey, FL
Free Wi-Fi
$249+
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2 bedroom condo in osprey - Osprey - Dining room
2 bedroom condo in osprey
Osprey, FL
Pool
$214+
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Welcome to Lime on Green! I also have a rental CAR listed/available on TURO.COM - Osprey - Living room
Welcome to Lime on Green! I also have a rental CAR listed/available on TURO.COM
Osprey, FL
Pet friendly
$277+
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Pirates Treasure - Osprey
Pirates Treasure
Osprey, FL
Free Wi-Fi
Pool
Pet friendly
$271+
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38-Foot Vessel, Casey Key, Known for Amazing Fishing & Privacy - Osprey
38-Foot Vessel, Casey Key, Known for Amazing Fishing & Privacy
Osprey, FL
Pool
Pet friendly
Spa
$314+
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Convenient Cottage Close To Beaches - Pet Friendly! - Osprey
Convenient Cottage Close To Beaches - Pet Friendly!
Osprey, FL
Pet friendly
$91+
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Comfy Cozy Place. Open Room With Kitchenette. Close To Beaches With 3 Miles - Osprey
Comfy Cozy Place. Open Room With Kitchenette. Close To Beaches With 3 Miles
Osprey, FL
$142+
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Renovated Waterfront Home - Osprey
Renovated Waterfront Home
Osprey, FL
Pet friendly
$188+
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Good to know

Low season

November

High season

March

Average price (weeknight)

$313

Average price (weekend night)

$235
Cheapest month to stay with an average 22% drop in price.
Most expensive month to stay with an average 29% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Osprey vacation rental deals

  • Vacation rentals in Osprey are around 53% more expensive than hotels on average. Search here to compare prices for all accommodation types in Osprey.
  • The best vacation rental property in Osprey is Comfy Cozy Place. Open Room With Kitchenette. Close To Beaches With 3 Miles (8.9, 40 reviews), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Osprey, you should consider visiting during the low season. The cheapest vacation homes in Osprey can be found in November and May.
  • The cheapest night for renting a vacation home in Osprey is Tuesday. In contrast, the most expensive is Thursday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Osprey for 3 days.

FAQs when booking a vacation home in Osprey

  • What types of vacation rentals are available in Osprey?

    There are loads of different property types that you can make your vacation home in Osprey. You’ll find apartments, condos, houses and villas.

  • Are there any pet-friendly vacation rentals in Osprey?

    There are a number of dog and pet-friendly Osprey vacation rentals, with around 44% allowing you to bring your pet along with you.

  • How can I find vacation rentals near me in Osprey?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Osprey?

Our map will help you find the perfect place to stay in Osprey by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Osprey

Osprey vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Osprey. Find cheap vacation homes to rent in Osprey. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Osprey that suits you best.

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