Find the best place to stay — Osprey

Where to stay around Osprey?

Our 2018 property listings offer a large selection of 3,181 vacation rentals near Osprey. From 1,366 condos to 1,093 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 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: 23 vacation rentals
  • Osprey Village: 20 vacation rentals
  • Lido Key: 186 vacation rentals
  • Golden Beach: 102 vacation rentals
  • Palmer Ranch: 157 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:

  • Southbay Yacht and Racquet Club: 4,306 vacation rentals
  • Oscar Scherer State Park: 4,345 vacation rentals
  • Historic Spanish Point: 4,373 vacation rentals
  • Venice Beach: 4,379 vacation rentals
  • Siesta Key Public Beach: 5,950 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 condos in Osprey?

Yes, of course. HomeAway has 1,366 condos in Osprey. Our other popular types of vacation rentals in Osprey include:

  • Houses: 1,093 rentals available
  • Apartments: 235 rentals available
  • Villas: 160 rentals available

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

Can I rent golf rentals in Osprey?

Absolutely, HomeAway has 1,790 golf rentals in Osprey. You have also many other possibilities in Osprey area, including:

  • Near the ocean rentals: 1,271 rentals
  • Beach rentals: 760 rentals
  • Waterfront rentals: 656 rentals

Please use our search bar to access the selection of vacation rentals.

Can I find a vacation rental with pool in Osprey?

Yes, you can select your preferred vacation rental with pool among our 2,331 vacation rentals with pool available in Osprey. Please use our search bar to access the selection of vacation rentals available.

    Travel to Historical Osprey

    The beaches and gardens create a pretty picture of Osprey. Well-known for its pubs, restaurants and boating, this welcoming city won't disappoint. Top attractions in the area include Venice Beach, Siesta Key Public Beach and Marie Selby Botanical Gardens. A vacation rental can help make your stay complete—many rentals come with a kitchen and laundry facilities.

    Attractions In and Around Osprey

    First time in Osprey and looking for places to see? Visitors searching for nearby cultural experiences can take a trip to Historic Spanish Point and Venice Train Depot or spend an enlightening afternoon at John and Mable Ringling Museum of Art or Venice Theater. To appreciate the outdoor scene, make time for beaches like Venice Beach and Siesta Key Public Beach and green spaces such as Marie Selby Botanical Gardens and Sarasota Jungle Gardens. You can take a shopping trip to St. Armands Circle, Pelican Plaza and Westfield Sarasota Square. Activities around the area include Siesta Key Marina, Venice Fishing Pier and Marina Jack. Also while in town, consider a visit to Oscar Scherer State Park and Casey Key.