Osprey Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Osprey vacation rentals

Living area

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very Good, (362 reviews)
"super clean and comfortable. we were 4 people and had a very comfortable and lovely stay. i felt super at home and the location is very centralized to everything "
United States
Adanna
The price is P5,257
P13,230 total
includes taxes & fees
Apr 27 - Apr 28
Tiny House Siesta
Exterior

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (17 reviews)
"Great place and location "
United States
Cathy
The price is P7,289
P23,161 total
includes taxes & fees
Apr 15 - Apr 16
Chadwick Cove Resort & Marina
Terrace/patio

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (269 reviews)
"Wonderful place! Super friendly host! Very clean, affordable! Great place!!"
United States
Carolyn
The price is P8,146
P9,205 total
includes taxes & fees
May 4 - May 5
Kon Tiki Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osprey Hotel Reviews

Tropical Beach Resorts

Tropical Beach Resorts

8/10 Good
"Easy parking next to room. Quick access to beach. Bathroom was cramped. Kitchen was updated with and had everything you needed. Overall great location and wonderful staff. "
Ryan 1-night trip
Posted 4 hours ago
Tropical Beach Resorts

Find out more about Osprey

Search for holiday rentals in Osprey on Expedia! You can easily find your home rentals, villas, holiday apartments in Osprey using one of the methods below:

  • View our selection of featured holiday rentals in Osprey
  • Use the map to find apartments and other holiday homes in the Osprey neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Osprey while they last

Look no further and take a look at our great range of rental properties in Osprey!

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Osprey?

Yes, we have vacation rentals in Osprey near Jim Neville Marine Preserve, or you can go with a more secluded option if you're looking for extra privacy while you relax. Visitors to Osprey speak positively about the popular beaches and lively bars in this destination. While you're in the area, you can also enjoy the top-notch restaurants and shops.

What are some of the best vacation rentals in Osprey?

Siesta Key Island Rentals: This vacation home rental near Osprey comes with free WiFi so you can feel at home during your trip. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Osprey?

With 17 Expedia vacation rentals, you're sure to find just the right place for your Osprey stay.

What’s there to see and do in Osprey?

Family-friendly attractions include Jim Neville Marine Preserve and Nancy's Consignments, whereas Turtle Beach and Nokomis Beach are a couple of great spots to enjoy the outdoors. While in the area, you can also visit popular places like Siesta Key Beach and Lido Beach.

What’s a vacation rental in Osprey like?

Vacation rentals are private properties you can stay in for a long or short time in Osprey. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for families.