Osprey cottages

We found 106 cottages — enter your dates for availability

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  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

How much does it cost to stay in a cottage rental in Osprey?
Upscale or budget, in a busy tourist area or off the beaten path, peak season or low season — these factors and more will determine how much your cottage rental in Osprey will cost. How long you plan to stay can also affect the overall price. Some holiday rentals offer discounts if you stay longer, so keep your eyes peeled for special deals.
When is the best time to rent a cottage in Osprey?
With temperatures ranging from 14ºC (57ºF) to 20ºC (68ºF), January is when most people book a cottage rental in Osprey. As it's the most popular month, try to secure your stay early. Alternatively, consider the off-season for a more relaxed Sarasota County escape.
Where can I rent an Osprey holiday cottage with great views?
Vrbo makes it easy to find the terrific views you're looking for in your accommodation. Use our "Location" filter to narrow down the type of area you prefer to be in, and the views you like to immerse yourself in, while browsing cottage rentals in Osprey.
Does Osprey have any lakeside cottages?
For a refreshing getaway, you can't beat our lakeside cottage rentals. Try our "Location" filter and then check the box marked "Lake" to see if you can find any comfy cottages that'll put you near the water in Osprey. Spend your days exploring or simply enjoy seeing beautiful sunrises and sunsets reflecting off the lake.
What are the top things to do in Osprey?
Siesta Key Beach is one of the well-known attractions in Osprey. Choose a cottage rental in this destination and make sure you have enough time to explore other highlights, such as Venice Beach and Mote Marine Laboratory & Aquarium. They're all family friendly!
Why should I book my holiday cottage with Vrbo?
Vrbo offers customer support from the instant you book until the end of your trip, so every aspect of your holiday is stress-free. Plus we think our cottage rentals are something pretty special — think amenity-packed stays ideal for families and charming options perfect for a romantic rendezvous. You can also take advantage of flexible cancellation policies and other benefits like payment and deposit protection. And when you sign up to our One Key™ rewards programme, you'll be able to collect OneKeyCash™* on eligible bookings on Vrbo. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Vrbo.