Naramata Wineries - Vacation Rentals in Osprey

Bayside Escape-Condo w Dock Pool and Near Beach From US $450
         

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10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Florida Vacation Condo From US $60
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Manatee Key-Waterfront Minutes to Turtle Beach From US $423
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Cute 3/2 Siesta home steps from Siesta waters From US $383
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
5 Mi to Beach: Family Retreat in Sarasota! From US $214
         

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10.0 (1 Review)
House
  • Parking
  • Balcony/Terrace
  • Security/Safety
Sand Dollar Retreat From US $180
         

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10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • View
Sarasota - Dunmore 8730 From US $180
         

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10.0 (1 Review)
House
  • Pool
  • Security/Safety
  • Guest Services

Luxury Places to Stay in Osprey

Over 27+ Luxury Places to Stay in or Near Osprey
Stay & Play Sarasota From US $831
         

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New
House
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The Inn at Turtle Beach (Adults Only) From US $780
         

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8.3 (104 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Siesta Key Marvel Pool SPA Deeded Beach Access From US $674
         

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1.0 (1 Review)
House
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  • Parking
  • Pool
Bay Tree Beach Side From US $341
         

New
House
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Mova Poolside Escape From US $333
         

New
House
  • Air Conditioner
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  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Osprey

Over 9+ Top-Rated Vacation Rentals with a Pool in or Near Osprey
Casey Key Resorts - Mainland From US $114
         

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8.1 (552 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Island Reef Bayside With Private Beach From US $297
         

New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Sarasota Home With Pool From US $266
         

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New
House
  • Air Conditioner
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  • Pool
The Sea Side Villa From US $237
         

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New
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Windsor Lodge Unit #19, studio close to beaches From US $183
         

Nokomis Sunset Retreat Unit 11 OR Unit 13 OR BOTH From US $181
         

Large Vacation Homes & Villas in Osprey

Over 1+ Large Vacation Homes & Villas in or Near Osprey

Osprey Vacation Rentals and Airbnb Places to Stay Under $200

Over 2+ Osprey Vacation Rentals and Airbnb Places to Stay Under $200
Private house with loft From US $167
         

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New
House
  • Air Conditioner
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  • View
Perfect Family Beach Getaway Near Siesta Key From US $162
         

New
House
  • Air Conditioner
  • Parking
  • Security/Safety

About Osprey Vacation Rentals

With more than 36 Osprey vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Naramatawineries and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Osprey.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Naramatawineries Osprey, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Osprey. Places to stay near Osprey are 2108.6 ft² on average, with prices averaging US $378 a night.

Naramatawineries makes it easy and safe to find and compare vacation rentals in Osprey with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Osprey

Type Count
Vacation Homes 27
Holiday Apartments 6
Hotels 1
Others 1
Resorts 1

Use these Quick Filters to Find a Vacation Rental in Osprey

Pro Tip: Naramatawineries makes it easy to compare the best listings on Naramatawineries homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Naramatawineries homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Osprey.

Weather in Osprey

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

Osprey Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Osprey?
How many vacation rentals are available in Osprey?

Currently, the total number of properties listed in 2026 is over 36 in the Osprey area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Osprey.