115 8th St SE
Winter HavenFL33880
Cheap Homes for Rent in Osprey Pointe Neighborhood of Winter Haven, FL from $900 (14 Rentals)
Search the lowest-cost Homes available for rent right now in the Osprey Pointe area of Winter Haven.
2924 Whispering Trails Dr
Winter HavenFL33884
20 Stebbins Dr
Winter HavenFL33884
117 5th St NE
Winter HavenFL33881
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44 Stebbins Dr
Winter HavenFL33884
1250 5th St NE
Winter HavenFL33881
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.
645 7th St NE
Winter HavenFL33881
1737 Ave C NE
Winter HavenFL33881
900 Ave Z SE
Winter HavenFL33880
1240 6th St NE
Winter HavenFL33881
810 Marcia Loop
Winter HavenFL33884
2212 Garden Lake Dr
Winter HavenFL33884
2212 Garden Lake Dr
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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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 | $1,569 | $1,220 | $2,400 |
| Osprey Pointe 3 Bedroom Homes for Rent | $1,891 | $1,395 | $3,200 |
| Osprey Pointe 4 Bedroom Homes for Rent | $2,129 | $1,655 | $3,250 |
| Osprey Pointe 5 Bedroom Homes for Rent | $2,532 | $2,100 | $3,400 |
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 1 Bed unit found at The Carlton at Lake Dexter priced from $1,097. The Arbours at Garden Grove has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,200. 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 | Essex | 1BR,1BA | $1,097 |
| The Arbours at Garden Grove | One Bedroom/One Bath Reno | 1BR,1BA | $1,200 |
| Alera at Hunters Glen | A1 | 1BR,1BA | $1,310 |
| The Waverly at Winter Haven | A2 | 1BR,1BA | $1,338 |
| Prose Cypress Pointe | A1 | 1BR,1BA | $1,349 |
Best Value Apartments for Rent in Osprey Pointe, FL
As of October 24, 2025 the best value apartment in the Osprey Pointe area is the $1.36 price per square foot One Bedroom/One Bath Reno Model at The Arbours at Garden Grove in the in the Cypress Grove neighborhood starting from $1,200. The second greatest value Osprey Pointe apartment is the Two Bed 1 Bath Model at Della Vita Apartments starting at $1,365 with a $1.56 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. |
|---|---|---|---|
| The Arbours at Garden Grove | One Bedroom/One Bath Reno | 1BR,1BA | $1.36 |
| Della Vita Apartments | Two Bed 1 Bath | 2BR,1BA | $1.56 |
| Prose Cypress Pointe | A1 | 1BR,1BA | $1.62 |
| Vista Lake Ned | 1x1 | 1BR,1BA | $1.79 |
| The Waverly at Winter Haven | A3 | 1BR,1BA | $2.32 |
| The Carlton at Lake Dexter | Essex | 1BR,1BA | $1.76 |
| Alera at Hunters Glen | A1 | 1BR,1BA | $2.11 |
Apartment Common Area Rules: What Renters Need to Know
From the lounge to the laundry room, understand your rights and responsibilities in shared apartment spaces. Get tips on pet rules, noise, and security.
Read Article
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 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 ArticleQuick Rent Budget Calculator
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Pet Friendly LifestyleOsprey Pointe, Winter Haven, FL
Ranked #10
Among cities in Florida for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
2.5Pet Friendly
Best Local Schools in Osprey Pointe, Winter Haven, FL
School data provided by Great Schools
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 $700 to $3,975. There are also 111 Single Family Homes for rent, Condos, and Townhome rentals currently available in Osprey Pointe ranging from $995 to $3,400.
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 $995 to $3,400 with an average monthly rent of $1,883.
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 $1,400 to $3,975, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,395 to $3,200. Four Bedroom Single-Family rentals are also available starting from $1,655 and Four Bedroom Apartments start at $1,895.
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.
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.
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.