Discover a selection of 5,000 vacation rentals in Osprey, FL that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $100 per night, and houses and condos are popular options for a stay in Osprey. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Osprey
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.

How many vacation rentals are available around Osprey, FL?

Our 2022 property listings offer a large selection of 5,056 vacation rentals around Osprey. From 2,399 house rentals to 2,565 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Houses in Osprey?

Yes, of course. Vrbo has 2,399 Houses in Osprey. Our other popular types of vacation rentals in Osprey include:

  • Condos/Apartments: 2,565 rentals available
  • Villas: 305 rentals available
  • Cottages: 153 rentals available

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

Can I find a vacation rental with pool in Osprey?

Yes, you can select your preferred vacation rental with pool among our 3,589 vacation rentals with pool available in Osprey. Please use our search bar to access the selection of vacation rentals available.