Osprey rentals with pool

Check out our 4,904 vacation rentals with a pool and start planning your Osprey trip. Whether you want to stay in Osprey Village, Bay Acres, Rivendell or another popular area, you’ll discover the ideal poolside escape on Vrbo.

It doesn’t get better than a vacation rental with a pool, and it doesn’t have to cost a fortune with Vrbo. While many factors will determine how much you’ll pay for your Osprey getaway, our filters will help you find the best deal. Choose your budget and take advantage of our “Discounts” filter to search for properties that come with savings for longer stays. With an inviting pool ready and waiting for you, you’ll probably want to stick around longer anyway!

If you want to enjoy Osprey at one of its busiest times, plan your escape for January. That’s when temperatures range from around 14ºC (57ºF) to 20ºC (68ºF), and when most Vrbo guests unwind in a vacation rental with a pool here. Of course, there are other great times to be in this part of Sarasota County, so do some homework into which season or month is the best fit for your plans.

Relaxing is effortless at Vrbo’s vacation rentals with a pool in Osprey. Go for a swim or simply admire the outlooks. Filter your options by “Recommended” or “Guest rating” to see the very best stays where you can lose yourself in the incredible scenery as your worries float away.

Choose a vacation rental with a private pool in Osprey and go for a morning swim or midnight dip — or whenever the mood strikes! You can keep your little ones easily occupied, and you won’t have to worry about sharing with other guests. Use our “Private pool” filter to discover your perfect stay.

Fun times in Osprey await for the family when you book a vacation home rental with a pool. On top of visiting major attractions like Siesta Key Beach, Venice Beach and Mote Marine Laboratory & Aquarium, you’ll be able to spend your downtime relaxing by the water.

When you stay in a Vrbo vacation rental with a pool, the only people you have to share your living space with are whoever you take with you. It’ll just be you and your loved ones with the entire property to yourselves having a splashing good time. Our flexible cancellation policies also mean you can book your rental house with peace of mind should your plans change.