2924 Whispering Trails Dr
Winter HavenFL33884
Cheap Homes for Rent in Osprey Pointe Neighborhood of Winter Haven, FL from $900 (20 Rentals)
Search the lowest-cost Homes available for rent right now in the Osprey Pointe area of Winter Haven.
1103 Cypress Gardens Blvd
Winter HavenFL33884
5651 Struthers Ct
Winter HavenFL33884
5649 Struthers Ct
Winter HavenFL33884
1210 Ave Z SE
Winter HavenFL33884
76 Stebbins Dr
Winter HavenFL33884
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.
44 Stebbins Dr
Winter HavenFL33884
66 Stebbins Dr
Winter HavenFL33884
845 Orchid Springs Dr
Winter HavenFL33884
817 Orchid Springs Dr
Winter HavenFL33884
1708 Eagle Pond Dr
Winter HavenFL33884
632 Pavare Ct
Winter HavenFL33884
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.
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$1,3002 Bedroom Apartments Available Feb 1
115 5th St NE
115 5th St NEWinter Haven, FL 33881
1702 Garden Lake Dr
Winter HavenFL33884
403 Laurel Cove Way
Winter HavenFL33884
1507 Eagle Pond Dr
Winter HavenFL33884
210 Sweet Cir
Winter HavenFL33884
1712 Garden Lake Dr
Winter HavenFL33884
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.
1102 Eagle Pond Dr
Winter HavenFL33884
1401 Eagle Pond Dr
Winter HavenFL33884
Showing Results 1-20, Page 1 of 1
Osprey Pointe, Winter Haven, FL Local Guide
Cypress Gardens in Winter Haven by Flickr User: hyku is licensed under CC BY 2.0
How much does it cost to rent a home in Osprey Pointe?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Osprey Pointe 2 Bedroom Homes for Rent | $1,483 | $1,195 | $2,100 |
| Osprey Pointe 3 Bedroom Homes for Rent | $1,896 | $1,505 | $2,600 |
| Osprey Pointe 4 Bedroom Homes for Rent | $2,177 | $1,745 | $3,475 |
| Osprey Pointe 5 Bedroom Homes for Rent | $2,350 | $2,250 | $2,400 |
| Osprey Pointe 6 Bedroom Homes for Rent | $3,245 | $3,245 | $3,245 |
Browse Homes for Rent in this Neighborhood
There are currently 20 rentals with your search options within a 3 mile radius of the Osprey Pointe Neighborhood of Winter Haven, FL.
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Osprey Pointe, Winter Haven, FL Local Guide
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Cheapest Available Osprey Pointe Apartments for Rent
The cheapest available apartment rental in the Osprey Pointe area of Lakeland, FL is a 1 Bed unit found at The Carlton at Lake Dexter priced from $1,257. Barrington Place At Winter Haven has the second lowest priced unit, which is a 2 Beds apartment currently listed from $1,275. Here are the most affordable Osprey Pointe apartments for rent in Lakeland, FL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| The Carlton at Lake Dexter | Berkeley | 1BR,1BA | $1,257 |
| Barrington Place At Winter Haven | B1 | 2BR,1BA | $1,275 |
| Prose Cypress Pointe | A1 | 1BR,1BA | $1,299 |
| Vista Lake Ned | 1x1 | 1BR,1BA | $1,361 |
| Della Vita Apartments | Two Bed 1 Bath | 2BR,1BA | $1,365 |
Best Value Apartments for Rent in Osprey Pointe, FL
As of January 28, 2026 the best value apartment in the Osprey Pointe area is the $1.29 price per square foot B1 Model at Barrington Place At Winter Haven in the in the Graydon Hills neighborhood starting from $1,275. The second greatest value Osprey Pointe apartment is the Berkeley Model at The Carlton at Lake Dexter starting at $1,257 with a $1.27 price per square foot in the Cypress Grove neighborhood. Here is today’s list of the best values for Osprey Pointe apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| Barrington Place At Winter Haven | B1 | 2BR,1.5BA | $1.29 |
| The Carlton at Lake Dexter | Berkeley | 1BR,1BA | $1.27 |
| Della Vita Apartments | Two Bed 1 Bath | 2BR,1BA | $1.56 |
| Prose Cypress Pointe | A1 | 1BR,1BA | $1.56 |
| Vista Lake Ned | 1x1 | 1BR,1BA | $1.79 |
| The Waverly at Winter Haven | A3 | 1BR,1BA | $2.32 |
| Alera at Hunters Glen | A1 | 1BR,1BA | $2.23 |
| 448 Avenue A NE, Unit Cozy Cottage | 448 Avenue A NE | 1BR,1BA | $2.29 |
Don'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 Article
The 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
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Best Local Schools in Osprey Pointe, Winter Haven, FL
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Frequently Asked Questions about Osprey Pointe
What type of rentals are currently available in Osprey Pointe?
There are currently 32 Apartments for Rent in Osprey Pointe, FL with pricing that ranges from $859 to $3,007. There are also 114 Single Family Homes for rent, Condos, and Townhome rentals currently available in Osprey Pointe ranging from $950 to $6,500.
What is the current price range for Rental Homes in Osprey Pointe?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Osprey Pointe ranges from $950 to $6,500 with an average monthly rent of $2,620.
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
18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.
A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.
Renting with Roommates: Realistic Expectations for Shared Lease
Written by: Christine Leonard, Esq.
Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.
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.