
Cheap Homes for Rent in Osprey Pointe Neighborhood of Winter Haven, FL from $1,000 (14 Rentals)
Search the lowest-cost Homes available for rent right now in the Osprey Pointe area of Winter Haven.


400 El Camino Dr

1103 Cypress Gardens Blvd

100 El Camino Dr

611 Ave G SE

8305 Waterview Way

513 Ave J SE
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.

5667 Struthers Ct

900 Ave Z SE

1101 Eagle Pond Dr

850 17th Terrace NE

1202 Eagle Pond Dr

23 Kinsmen Dr

508 Eagle Pond Dr
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.
Osprey Pointe, Winter Haven, FL Local Guide

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 | $1,542 | $1,299 | $2,000 |
| Osprey Pointe 3 Bedroom Homes for Rent | $2,056 | $1,595 | $4,500 |
| Osprey Pointe 4 Bedroom Homes for Rent | $3,996 | $1,800 | $10,000+ |
| Osprey Pointe 5 Bedroom Homes for Rent | $2,525 | $2,300 | $3,100 |
Browse Homes for Rent in this Neighborhood
There are currently 14 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 Studio unit found at 218 Florida Ave priced from $995. Della Vita Apartments has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,160. Here are the most affordable Osprey Pointe apartments for rent in Lakeland, FL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| 218 Florida Ave | 0 Beds, 1 Baths | Studio,1BA | $995 |
| Della Vita Apartments | 1 Bed 1 Bath | 1BR,1BA | $1,160 |
| Vista Lake Ned | 1x1 | 1BR,1BA | $1,259 |
| Barrington Place At Winter Haven | B1 | 2BR,1BA | $1,285 |
| Prose Cypress Pointe | A1 | 1BR,1BA | $1,299 |
Best Value Apartments for Rent in Osprey Pointe, FL
As of June 22, 2026 the best value apartment in the Osprey Pointe area is the $1.24 price per square foot 690 Avenue C SE Model at 690 Avenue C SE, Unit 690 in the in the Graydon Hills neighborhood starting from $1,750. The second greatest value Osprey Pointe apartment is the Three Bedrooms/Two Baths Model at The Arbours at Garden Grove starting at $1,816 with a $1.43 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. |
|---|---|---|---|
| 690 Avenue C SE, Unit 690 | 690 Avenue C SE | 3BR,2BA | $1.24 |
| The Arbours at Garden Grove | Three Bedrooms/Two Baths | 3BR,2BA | $1.43 |
| Carlton Arms Of Winter Haven | (C6-2) Upstairs | 2BR,2BA | $1.27 |
| 501 Avenue L NE | 501 Avenue L NE | 2BR,1BA | $1.19 |
| Barrington Place At Winter Haven | B1 | 2BR,1.5BA | $1.30 |
| The Carlton at Lake Dexter | Berkeley | 1BR,1BA | $1.41 |
| Alera at Hunters Glen | B1 | 2BR,2BA | $1.90 |
| Prose Cypress Pointe | A1 | 1BR,1BA | $1.56 |
| Vista Lake Ned | 1x1 | 1BR,1BA | $1.65 |
| Della Vita Apartments | 1 Bed 1 Bath | 1BR,1BA | $1.55 |
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 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.
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 37 Apartments for Rent in Osprey Pointe, FL with pricing that ranges from $959 to $2,849. There are also 89 Single Family Homes for rent, Condos, and Townhome rentals currently available in Osprey Pointe ranging from $1,175 to $50,000.
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 $1,175 to $50,000 with an average monthly rent of $2,267.
How much are larger Three and Four Bedroom Rentals in Osprey Pointe?
For those who are looking for larger living arrangements, Three Bedroom Apartments in Osprey Pointe range from $1,575 to $2,849, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,595 to $4,500. Four Bedroom Single-Family rentals are also available starting from $1,800 and Four Bedroom Apartments start at $2,050.
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

Apartment Occupancy Rates: Renter Attraction vs Renter Retention
Written by: Robin Stewart
There’s a tenet in marketing about client or customer attraction and retention. Studies and data have consistently shown it costs less to keep a current customer than to attract a new one.

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Written by: Robin Stewart
Evaluating rental properties for clients draws many parallels to house-hunting. Whether an apartment, loft, townhouse, or other rental, finding the right place means finding “home” for your client.

Pet-Friendly Renting: Everything You Need to Know Before You Move
Written by: Christine Leonard, Esq.
For so many of us, pets are the best companions and a big part of our lives. For this reason, a pet-friendly house or apartment is often a very important - and nonnegotiable - part of a move.

Creative Ways Developers Reimagine Retail Spaces as Residential Units
Written by: Robin Stewart
Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.