
Luxury Homes for Rent in Osprey, FL (168 Rentals) Page 3 of 4
The most luxurious Homes in Osprey with high-end amenities, features, and finishes.


5274 Far Oak Cir

5274 Far Oak Cir

5518 Modena Pl

5518 Modena Pl

2323 Doud St

4270 Castle Bridge

5610 Rain Lily Ct

7860 Holiday Dr

5361 Eliseo St

7860 Holiday Dr

5361 Eliseo St

2024 Calusa Lakes Blvd

617 Indiana Ave

8369 Wingate Dr

8784 Pebble Creek Ln

2500 Bayshore Rd

2140 Pinehurst St

2140 Pinehurst St

1507 Clower Creek Dr

4146 Westbourne Cir

9122 Midnight Pass Rd

8911 Veranda Way

4640 Tower Hill Ln

9641 Castle Point Dr

9300 Clubside Cir

9480 High Gate Dr

11605 Garessio Ln

9330 Clubside Cir

6075 Sawgrass Lk Ct

4639 Chapel Hill Dr

9630 Club S Cir

8735 Olde Hickory Ave

9320 Clubside Cir

2908 Captiva Dr

1498 Ernesto Dr

3705 Torrey Pines Blvd

1511 Pelican Point Dr

1511 Pelican Point Dr

9611 Castle Point Dr

8735 Midnight Pass Rd

1899 Vamo Way

8901 Veranda Way

5620 Soft Skies Dr

8974 Grey Oaks Ave

9480 Forest Hills Cir

8635 Midnight Pass Rd

9062 Midnight Pass Rd

9058 Midnight Pass Rd

8870 Huntington Pointe Dr
Osprey, FL Local Guide

How much does it cost to rent a home in Osprey?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Osprey 2 Bedroom Homes for Rent | $3,295 | $1,199 | $10,000+ |
| Osprey 3 Bedroom Homes for Rent | $4,348 | $1,599 | $10,000+ |
| Osprey 4 Bedroom Homes for Rent | $7,212 | $2,900 | $10,000+ |
| Osprey 5 Bedroom Homes for Rent | $5,578 | $3,200 | $10,000+ |
Browse Top Homes for Rent in Osprey
Explore Osprey
Frequently Asked Questions about Osprey
What type of rentals are currently available in Osprey?
There are currently 40 Apartments for Rent in Osprey, FL with pricing that ranges from $1,399 to $9,757. There are also 278 Single Family Homes for rent, Condos, and Townhome rentals currently available in Osprey ranging from $1,199 to $28,000.
What is the current price range for Rental Homes in Osprey?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Osprey ranges from $1,199 to $28,000 with an average monthly rent of $4,508.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.

The Best Sarasota Neighborhoods for Renting: Culture, Beaches, and Affordable Apartments
Written by: J. Lang Wood
Hi, I’m Joyce, your ApartmentHomeLiving.com Expert for Sarasota, Florida. My husband and I moved to the Sarasota area more than 20 years ago, and since then, we’ve learned about the city’s many surprising and enjoyable features.

Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!

The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.