110+ Vacation Home Rentals in Osprey |
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  3. Sarasota
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Osprey Vacation Rentals & Ski-in/Ski-out Homes

About Osprey Vacation Rentals

Explore over 110 vacation rentals in Osprey with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Osprey for more space and value.

In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Osprey. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Osprey tailored to your preferences. On average, these rentals offer 735.31 ft² of space, and are priced at an average of US $257 per night.

SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Osprey at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.

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Top Types of Ski Accommodations in Osprey

Type Count
Vacation Homes 58
Holiday Apartments 23
Villas 2
Unique Vacation Rentals 1
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Osprey

★ Pro Tip: Discover Your Ideal Vacation Rental in Osprey with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.

Weather in Osprey, FL

View the weather forecast for Osprey before booking your Osprey Vacation Rentals to confirm your best time to go.

December - February
High 79°F       Low 51°F
March - May
High 91°F       Low 53°F
June - August
High 92°F       Low 72°F
September - November
High 90°F       Low 57°F

Top Attractions Around Osprey, FL

Sunski offers a large selection of top attractions around Osprey . Research things to do on your vacation before you visit Osprey.


Oscar Scherer State Park
Historic Spanish Point
The Oaks Club
Nancy's Consignments
Lido Beach
Venice Beach
Siesta Key Beach
St. Armands Circle
Englewood Beach
Turtle Beach
IMG Academy
Nokomis Beach
Sarasota Jungle Gardens
Mote Marine Laboratory & Aquarium
Sarasota Memorial Hospital
John and Mable Ringling Museum of Art
Manasota Beach
Crescent Beach
Caspersen Beach
Siesta Key Marina

Other Places to Stay in Osprey, FL


Historic Spanish Point 766 Properties
Nancy's Consignments 744 Properties
The Oaks Club 719 Properties
Sorrento Shores 464 Properties
Oscar Scherer State Park 446 Properties
Rivendell 319 Properties
Bay Acres 316 Properties
Osprey Village 48 Properties

Frequently Asked Questions About Osprey?

What are the top vacation rentals in Osprey?

When organizing your trip to Osprey, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Osprey. Peruse our collection of highly-rated properties and secure your reservation today.

How many vacation rentals have private pools in Osprey?

Uncover 8 vacation rentals boasting private pools near Osprey. Explore top-rated RBO homes offering access to a swimming pool:

Which vacation homes or resorts in Osprey are best for families?

Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Osprey. Enjoy great views, locations and save money with SunSki Resorts.™

How many SunSkiResorts vacation rentals or resorts are available in Osprey?

Discover the ideal vacation rental in Osprey with SunSki Resorts™. We provide an extensive selection of over 110 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Osprey.

Nearby Neighborhood (5) 
Neighborhood Property Count
Vamo Vacation Rentals in Sarasota, Florida 64
Palmer Ranch Vacation Rentals in Sarasota, Florida 38
Bay Acres Vacation Rentals in Sarasota, Florida 316
Sorrento Shores Vacation Rentals in Sarasota, Florida 464
Rivendell Vacation Rentals in Sarasota, Florida 319

People Also Ask

There are 110 Osprey, FL Vacation Rentals

Recently Booked Vacation Rentals in Osprey