
Luxury Homes for Rent in Osprey, FL (109 Rentals)
The most luxurious Homes in Osprey with high-end amenities, features, and finishes.


531 Latitude Ln

2068 Preymore St

76 Bishopscourt Rd

152 Navigation Cir

956 Scherer Way

293 Hidden Bay Dr, Unit 203, Unit 203

260 Hidden Bay Dr

557 Crane Prairie Way

124 Turquoise Ln
The Best Sarasota Neighborhoods for Renting: Culture, Beaches, and Affordable Apartments
Find your perfect Sarasota apartment! Explore diverse areas like Arlington Park, Cherokee Park, and Downtown. See housing options for singles, families, and retirees in beautiful SW Florida.

5100 Jessie Harbor Dr

605 Crane Prairie Way

14041 Bellagio Way

854 Macewen Dr

1601 Pelican Point Dr, Unit 215, Unit 215

1510 Pelican Point Dr, Unit BA168, Unit BA168

1633 Boathouse Cir, Unit HA132, Unit HA132

1611 Clower Creek Dr, Unit HA237, Unit HA237

4178 Central Sarasota Pkwy, Unit 324, Unit 324

1520 Pelican Point Dr, Unit BA153, Unit BA153
The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.

9200 Midnight Pass Rd, Unit 10, Unit 10

8625 Midnight Pass Rd, Unit B508, Unit B508

12232 Marsh Pointe Rd

1601 Pelican Point Dr

4224 Central Sarasota Pkwy

4118 Central Sarasota Pkwy

8389 Wingate Dr

5753 Haven Ter

8735 Olde Hickory Ave

213 Giotto Dr
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

5825 Biscotti St

3625 Square W Ln

1601 Bayhouse Point Dr, Unit 206, Unit 206

4017 Crockers Lake Blvd, Unit 21, Unit 21

8900 Phyliss Ave

6212 Dry Tortugas Dr

4636 Deer Trail Blvd

4612 Deer Trail Blvd

4170 Central Sarasota Pkwy

9397 Midnight Pass Rd, Unit 603, Unit 603
Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

9393 Midnight Pass Rd

2301 Goya Dr

8350 Wingate Dr

3624 Peck St

133 1st Ave

5516 Cantucci St

5636 Cantucci St

9480 Forest Hills Cir

15013 Shady Palms Ln

2420 Valentine St
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 | $2,992 | $1,199 | $8,500 |
| Osprey 3 Bedroom Homes for Rent | $3,516 | $1,599 | $10,000+ |
| Osprey 4 Bedroom Homes for Rent | $8,692 | $2,900 | $10,000+ |
| Osprey 5 Bedroom Homes for Rent | $13,000 | $10,000 | $10,000+ |
Browse Top Homes for Rent in Osprey
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Osprey, FL Local Guide
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10 Hidden Costs of Renting You Should Budget for Before Signing a Lease
Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.
Read ArticleDon't Settle: How to Negotiate Your Apartment Lease and Save Money
Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.
Read ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
Read ArticleCash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
Read ArticleQuick Rent Budget Calculator
How much rent can you afford?
The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
Remember the 3 Rules of Real Estate:Location, Location, Location!
Explore Osprey, FL Rentals by Map
See the most popular apartments and homes in Osprey, FL
Frequently Asked Questions about Osprey
What type of rentals are currently available in Osprey?
There are currently 41 Apartments for Rent in Osprey, FL with pricing that ranges from $1,000 to $8,545. There are also 202 Single Family Homes for rent, Condos, and Townhome rentals currently available in Osprey ranging from $1,199 to $16,000.
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 $16,000 with an average monthly rent of $6,117.
Expert Rental Resources
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.
Articles, How-To's, and Tips

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.

Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
Written by: Lauren Harrington
This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.