Discover a selection of 4,000 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 kitchens. Prices start at $69 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.
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 2020 property listings offer a large selection of 4,427 vacation rentals around Osprey. From 1,464 house rentals to 2,274 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 a seaside property in Osprey?

Oh I do like to be beside the seaside... said... absolutely everyone. Find the right home away from home for your crew and you'll be well on your way to some well-deserved beach bliss! There are 1,421 beachside vacation rentals to pick from. Open to other suggestions? Vrbo has tons of other property options to search through, including:

  • 1,145 beach vacation rentals.
  • 815 water-view vacation rentals.
  • 790 beachfront vacation rentals.

Can I rent a condo in Osprey?

Sharing is good. But sharing bunk beds and bathrooms with strangers can be a bit much. Make the most of the time you have with your loved ones in a condo. The space and convenience makes for a much more comfortable stay. In this destination, Vrbo has 1,976 to pick from. Book now and you could part with as little as $33 a night. Or perhaps you'd rather one of the area's other lodging types, like:

  • House: 1,560 vacation homes. Prices start from $49 per night.
  • Villa: 309 vacation homes. Prices start from $50 per night.
  • Apartment: 297 vacation homes. Prices start from $42 per night.

Can I stay in Osprey in a large group?

Vacations with family can be oodles of fun, particularly when you're sleeping under the same roof in a fantastic new place! If you're traveling with a big group, Vrbo can help you. Condo vacation homes are the favorite choice for large groups, with 864 featured here. The lodging options that are perfect for large numbers here include:

  • Are you on the hunt for vacation homes that can fit 6 people? We have 3,446 that will be perfect. Prices begin from just $40 per night.
  • After somewhere for 8 guests? We have 750 that will suit. Prices begin at just $51 per night.
  • Going away with 5 guests? We've got 488 vacation homes that will be perfect. Prices start from $50 a night.

So don't fear! When you book with us you'll be able to bring your mom, your brother and all your friends to Osprey.

Where are the cheapest rentals in Osprey?

Friends are the family we choose. Make new memories with those you hold dearest and organize a value-for-money vacation with Vrbo. When it comes to getting your hands on an amazing deal, your first stop should be Osprey Village. Here, Vrbo has 21 rentals at an average price of $82 per night. Tara Golf & Country Club is another good option. Vrbo has 35 rentals here, and the average price is around $103 a night.

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