Where to stay around Osprey, FL?

Our 2019 property listings offer a large selection of 4,291 vacation rentals near Osprey. From 2,042 Condos/Apartments to 1,404 Houses, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Osprey for a holiday or a weekend are on VRBO.

What is the best area to stay when traveling to Osprey?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Osprey:

  • The Oaks: 19 vacation rentals
  • Lido Key: 1,398 vacation rentals
  • Gulf Gate: 303 vacation rentals
  • Indian Beach Sapphire Shores: 84 vacation rentals
  • Whitfield Estates: 35 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

Can I rent Condos/Apartments in Osprey?

Yes, of course. VRBO has 2,042 Condos/Apartments in Osprey. Our other popular types of vacation rentals in Osprey include:

  • Houses: 1,404 rentals available
  • Studios: 359 rentals available
  • Hotels: 233 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Villas and more.

Can I find a vacation rental with pool in Osprey?

Yes, you can select your prefered vacation rental with pool among our 3,091 vacation rentals with pool available in Osprey. Please use our search bar to access the selection of vacation rentals available.

    Historic Osprey will entice you

    The area's history and live music are just a few of the reasons to vacation in Osprey. Well known for its beaches, bars and gardens, this welcoming city won't disappoint. Venice Beach and Siesta Key Public Beach are just a couple of the must-sees in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

    Sightseeing in and around Osprey

    Do you want to find attractions to visit while you're in the area? Venture out of your vacation home and experience everything that makes Osprey a fun place to get away. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

    • Mote Marine Aquarium (11.3 mi / 18.2 km)
    • Stoneybrook Golf & Country Club (2 mi / 3.3 km)
    • Gulf Gate Golf Club (4.5 mi / 7.3 km)
    • Serenoa Golf Club (5.1 mi / 8.2 km)
    • Evie's Golf Center (7.4 mi / 11.9 km)
    • Coconuts Family Entertainment Center (7.7 mi / 12.5 km)

    Seasonal weather in Osprey

    If you're planning a vacation around warm-weather activities, July, August, September and June are the hottest months to visit, when temperatures average 90°F.

    Exploring the beaches and other natural features in Osprey

    Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Osprey is a great place to get outside. Here are some of the area’s most eye-catching features, all within 30 miles (48.2 km) of the city center:

    • Venice Beach (7 mi / 11.2 km)
    • Siesta Key Public Beach (6.6 mi / 10.6 km)
    • Marie Selby Botanical Gardens (10 mi / 16 km)
    • Sarasota Jungle Gardens (12.8 mi / 20.6 km)
    • Oscar Scherer State Park (1.7 mi / 2.7 km)
    • Jim Neville Marine Preserve (1.8 mi / 2.9 km)

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