114+ Luxury Vacation Rentals & Cabins in Osprey |
  1. USA
  2. Florida
  3. Sarasota
  4. Osprey

Osprey Cabin Rentals

About Osprey Vacation Rentals

There are more than 114 incredible getaway rentals that are available in Osprey. These choices include cabins, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Stay Close to Nature with Cabinns.com and uncover great stays in Osprey.

Cabinns.com features numerous last-minute deals on private villas, hotels, and cabin rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Cabinns.com in Osprey, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the Cabinns.com vacation rentals, resorts, and Airbnb-style properties in Osprey. Places to stay near Osprey are 732.6 ft² on average, with prices averaging US $280 a night.

Cabinns.com helps you find the ideal holiday rental to create a lifetime of travel memories in Osprey. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect cabin retreat today.

Show more
Show less

Top Cabin Rentals, Cottages, and Holiday Home Rentals in Osprey

Type Count
Vacation Homes 63
Holiday Apartments 22
Villas 2
Unique Vacation Rentals 1
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Osprey

★ Pro Tip: Cabinns.com is a cabin vacation rental website, pulling some of the top cabins, luxury resorts, and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible cabin resorts and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Osprey with Cabinns.com.

Weather in Osprey, FL

View the weather forecast for Osprey before booking your Osprey Vacation Rentals to confirm your best time to go.

December - February
High 79°F       Low 51°F
March - May
High 91°F       Low 53°F
June - August
High 92°F       Low 72°F
September - November
High 90°F       Low 57°F

Activities Osprey Guest Reviews Local Attractions

Cabins Provides a Large Selection of Cabins and Vacation Rentals in and Near Osprey. Discover Top Attractions For Your Next Outdoor Adventure.


Oscar Scherer State Park
Historic Spanish Point
The Oaks Club
Nancy's Consignments
Lido Beach
Venice Beach
Siesta Key Beach
St. Armands Circle
Englewood Beach
Turtle Beach
IMG Academy
Nokomis Beach
Sarasota Jungle Gardens
Mote Marine Laboratory & Aquarium
Sarasota Memorial Hospital
John and Mable Ringling Museum of Art
Manasota Beach
Crescent Beach
Caspersen Beach
Siesta Key Marina

Find Nearby Cabin Rentals in these Cities & Neighborhoods


Historic Spanish Point 831 Properties
Nancy's Consignments 811 Properties
The Oaks Club 763 Properties
Bay Acres 647 Properties
Sorrento Shores 555 Properties
Oscar Scherer State Park 524 Properties
Rivendell 380 Properties
Osprey Village 44 Properties

Frequently Asked Questions About Osprey?

What are the top cabins, lake houses & summer homes in Osprey?

We provide an array of great vacation destinations in Osprey. If you are looking to stay in or around the Osprey area, make sure to browse our options to find a premium cabin resort or rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Osprey:

How many cabin rentals and resorts have private pools in Osprey?

We have 7 cabins, luxury resorts, and holiday home rentals featuring a private pool in and near Osprey. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which cabin rental, resort, or holiday home in Osprey is best for families?

Searching for a family-friendly cabin in Osprey? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfectly fit families of all sizes.

How many hotels, resorts, or cabin rentals are available in Osprey?

Cabinns.com offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Cabinns.com in 2025 is over 114 in the Osprey area, and that number rises every day. By combining listings from multiple websites and travel providers, Cabinns.com can provide you with a diverse amount of choices of the best luxury stays in Osprey.

Nearby Neighborhood (5) 
Neighborhood Property Count
Vamo Rental Cabins and Private Getaways in Sarasota, Florida 57
Palmer Ranch Rental Cabins and Private Getaways in Sarasota, Florida 45
Bay Acres Rental Cabins and Private Getaways in Sarasota, Florida 647
Sorrento Shores Rental Cabins and Private Getaways in Sarasota, Florida 555
Rivendell Rental Cabins and Private Getaways in Sarasota, Florida 380

People Also Ask

There are 2 hotels in Osprey and 87 rentals

Recently Booked Private Villas, Cabin Resorts, and Rentals Osprey