1111 Cypress Gardens Blvd
Winter HavenFL33884
Cheap Homes for Rent in Osprey Pointe Neighborhood of Winter Haven, FL from $800 (13 Rentals)
Search the lowest-cost Homes available for rent right now in the Osprey Pointe area of Winter Haven.
83 Stebbins Dr
Winter HavenFL33884
close
View Me
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.
429 Ave B NE
Winter HavenFL33881
707 Eagle Pond Dr
Winter HavenFL33884
119 5th St NE
Winter HavenFL33881
706 Eagle Pond Dr
Winter HavenFL33884
645 7th St NE
Winter HavenFL33881
900 Ave Z SE
Winter HavenFL33880
2254 Firestone Pl
Winter HavenFL33884
630 Pavare Ct
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.
1003 Eagle Pond Dr
Winter HavenFL33884
1809 5th St SE
Winter HavenFL33880
Showing Results 1-13, 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 | $1,680 | $1,195 | $2,700 |
| Osprey Pointe 3 Bedroom Homes for Rent | $1,979 | $1,599 | $3,200 |
| Osprey Pointe 4 Bedroom Homes for Rent | $2,256 | $1,829 | $4,000 |
| Osprey Pointe 5 Bedroom Homes for Rent | $2,454 | $1,800 | $3,400 |
Browse Homes for Rent in this Neighborhood
There are currently 13 rentals with your search options within a 3 mile radius of the Osprey Pointe Neighborhood of Winter Haven, FL.
Explore Winter Haven
Osprey Pointe, Winter Haven, FL Local Guide
- Nearby Winter Haven neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
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 Della Vita Apartments priced from $1,099. The Carlton at Lake Dexter has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,387. Here are the most affordable Osprey Pointe apartments for rent in Lakeland, FL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Della Vita Apartments | One Bedroom | 1BR,1BA | $1,099 |
| The Carlton at Lake Dexter | Berkeley | 1BR,1BA | $1,387 |
| The Waverly at Winter Haven | A2 | 1BR,1BA | $1,480 |
| Prose Cypress Pointe | A1 | 1BR,1BA | $1,499 |
| The Arbours at Garden Grove | Three Bedrooms/Two Baths | 3BR,2BA | $1,733 |
Best Value Apartments for Rent in Osprey Pointe, FL
As of July 13, 2025 the best value apartment in the Osprey Pointe area is the $1.36 price per square foot Three Bedrooms/Two Baths Model at The Arbours at Garden Grove in the in the Cypress Grove neighborhood starting from $1,733. The second greatest value Osprey Pointe apartment is the Berkeley Model at The Carlton at Lake Dexter starting at $1,387 with a $1.40 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 | Three Bedrooms/Two Baths | 3BR,2BA | $1.36 |
| The Carlton at Lake Dexter | Berkeley | 1BR,1BA | $1.40 |
| Della Vita Apartments | Two Bedroom 2 Bath | 2BR,2BA | $1.50 |
| Prose Cypress Pointe | A1 | 1BR,1BA | $1.80 |
| The Waverly at Winter Haven | A3 | 1BR,1BA | $2.32 |
| 836 Lake Martha Dr NE, Unit B | 836 Lake Martha Dr NE | 1BR,1BA | $2.00 |
Quick 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.
Let everyone know!
Do you know the Osprey Pointe area?
If you’re an expert on all things Osprey Pointe, tell us what you love (and don't) by rating it and writing a review.
Write a Review
Frequently Asked Questions about Osprey Pointe
What type of rentals are currently available in Osprey Pointe?
There are currently 33 Apartments for Rent in Osprey Pointe, FL with pricing that ranges from $650 to $2,230. There are also 113 Single Family Homes for rent, Condos, and Townhome rentals currently available in Osprey Pointe ranging from $800 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 $800 to $6,500 with an average monthly rent of $2,686.
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.
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.
The Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.
Know Your Budget: Calculating What You Can Realistically Afford When Renting
Written by: Lauren Harrington
Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.
The Freedom of Short-Term Leases: Exploring the Advantages for Renters
Written by: Bobbi Jackson
If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.