
Luxury Homes for Rent in Osprey, FL (86 Rentals)
The most luxurious Homes in Osprey with high-end amenities, features, and finishes.


2068 Preymore St

Total Monthly Price
111 Tina Island Dr, Unit SI ID1591462P

293 Hidden Bay Dr, Unit 203

14041 Bellagio Way, Unit 214

7302 Jessie Harbor Dr

5100 Jessie Harbor Dr

521 Habitat Blvd, Unit SI ID1624235P

854 Macewen Dr

4640 Tower Hill 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.

4118 Central Sarasota Pkwy

4224 Central Sarasota Pkwy

1510 Pelican Point Dr, Unit BA168

1633 Boathouse Cir, Unit HA132

1611 Clower Creek Dr, Unit HA237

4178 Central Sarasota Pkwy, Unit 324

1520 Pelican Point Dr, Unit BA153

8389 Wingate Dr

12724 Lateral Root Dr

9470 High Gate Dr, Unit Stoneybrook Golf and Country Club
Exploring Rental Options: Apartments, Townhomes, and Lofts—Oh My!
Looking for the perfect rental? From apartments and condos to lofts and single family rentals, explore the unique pros and cons of each rental type to help you land in your perfect new place.

2319 Falcon Trace Ln

1774 Mova St

1601 Bayhouse Point Dr, Unit 206

12232 Marsh Pointe Rd

9397 Midnight Pass Rd, Unit 903S

14389 Eagle Branch Dr

14860 Misty Pond Lp

8776 Midnight Pass Rd

5796 Ivrea Dr

5506 Modena Pl
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

8004 Camminare Dr

5361 Eliseo St

5805 Biscotti St

Total Monthly Price
8977 Midnight Pass Rd, Unit SI ID1591468P

2420 Valentine St

4216 Central Sarasota Pky, Unit 1325

8544 Park Shore Ln

5249 Far Oak Cir

5668 Cantucci St

15360 Isla Palma Ln
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

56XX Cantucci St

12413 Osorio Ct

8911 Midnight Pass Rd

1720 Glenhouse Dr, Unit GL430

1716 Glenhouse Dr, Unit GL323

424 Bellini Cir

2130 Pinehurst St

12294 Myrtle Bay Ct

753 SORRENTO Inlt

11230 Sandhill Preserve Dr
Cash 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.
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 | $3,069 | $1,499 | $8,000 |
| Osprey 3 Bedroom Homes for Rent | $3,281 | $1,399 | $10,000+ |
| Osprey 4 Bedroom Homes for Rent | $8,417 | $2,595 | $10,000+ |
Browse Top Homes for Rent in Osprey
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Osprey, FL Local Guide
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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.
Read ArticleReal Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University
From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.
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 43 Apartments for Rent in Osprey, FL with pricing that ranges from $1,000 to $17,651. There are also 225 Single Family Homes for rent, Condos, and Townhome rentals currently available in Osprey ranging from $775 to $20,000.
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 $775 to $20,000 with an average monthly rent of $3,473.
How much are larger Three and Four Bedroom Rentals in Osprey?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Osprey range from $1,740 to $11,036, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,399 to $16,000. Four Bedroom Single-Family rentals are also available starting from $2,595 and Four Bedroom Apartments start at $4,990.
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.

Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!
Written by: Robin Stewart
Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.

Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.