Destination guide

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.

Natural features

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)
How to get there

Transportation options to and around Osprey

Fly into Sarasota, FL (SRQ-Sarasota-Bradenton Intl.), the closest airport, located 14.1 mi (22.7 km) from the city center.

Where to stay around Osprey?

Our 2019 property listings offer a large selection of 4,421 vacation rentals near Osprey. From 1,498 Houses to 2,259 Condos/Apartments, 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 HomeAway.

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: 24 vacation rentals
  • Sorrento Shores: 21 vacation rentals
  • Bay Acres: 16 vacation rentals
  • Lido Key: 1,915 vacation rentals
  • Palm Island: 187 vacation rentals

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

What are the popular points of interest near where I can stay when traveling to Osprey?

HomeAway offers a large selection of vacation rentals near lovely places in Osprey. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Historic Spanish Point: 5,565 vacation rentals
  • Nancy's Consignments: 5,513 vacation rentals
  • St. Armands Circle: 8,325 vacation rentals
  • Point of Rocks: 6,603 vacation rentals
  • Riverwood Golf and Country Club: 2,791 vacation rentals

But there are many other points of interest around Osprey listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Osprey?

Yes, of course. HomeAway has 1,498 Houses in Osprey. Our other popular types of vacation rentals in Osprey include:

  • Condos/Apartments: 2,259 rentals available
  • Villas: 293 rentals available
  • Cottages: 126 rentals available

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

Can I find a vacation rental with pool in Osprey?

Yes, you can select your preferred vacation rental with pool among our 3,166 vacation rentals with pool available in Osprey. Please use our search bar to access the selection of vacation rentals available.

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