Cheap Homes for Rent in Osprey Pointe Neighborhood of Winter Haven, FL from $800 (11 Rentals)

How Many Bedrooms?Done
Select your price rangeDone
to
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done

Search the lowest-cost Homes available for rent right now in the Osprey Pointe area of Winter Haven.

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.

Read Article
property at 3110 Gowan Dr

3110 Gowan 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.

Read Article
Showing Results 1-11, Page 1 of 1

Osprey Pointe, Winter Haven, FL Local Guide

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 1 Lamplight Ln priced from $950. The Carlton at Lake Dexter has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,257. Here are the most affordable Osprey Pointe apartments for rent in Lakeland, FL:

Apartment ListingModel NameBed/BathPriced From
1 Lamplight LnSunrise1BR,1BA$950
The Carlton at Lake DexterBerkeley1BR,1BA$1,257
Alera at Hunters GlenA11BR,1BA$1,260
Prose Cypress PointeA11BR,1BA$1,329
Della Vita ApartmentsTwo Bed 1 Bath2BR,1BA$1,365

Best Value Apartments for Rent in Osprey Pointe, FL

As of December 12, 2025 the best value apartment in the Osprey Pointe area is the $1.27 price per square foot Berkeley Model at The Carlton at Lake Dexter in the in the Cypress Grove neighborhood starting from $1,257. The second greatest value Osprey Pointe apartment is the 2x1 Model at Vista Lake Ned starting at $1,461 with a $1.50 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 ListingModel NameBed/BathPrice Per Sq.Ft.
The Carlton at Lake DexterBerkeley1BR,1BA$1.27
Vista Lake Ned2x12BR,1BA$1.50
Della Vita ApartmentsTwo Bed 1 Bath2BR,1BA$1.56
Prose Cypress PointeA11BR,1BA$1.59
1 Lamplight LnSunrise1BR,1BA$1.36
The Waverly at Winter HavenA31BR,1BA$2.32
Alera at Hunters GlenA11BR,1BA$2.03

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
Decorative image

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 Article
Decorative image

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.

decorative image of people with a giant lease agreement

Pet Friendly Lifestyle
Osprey Pointe, Winter Haven, FL

Ranked #8

Among cities in Florida for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

2.5
Pet Friendly

decorative image of woman handing cat to small boy

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 31 Apartments for Rent in Osprey Pointe, FL with pricing that ranges from $859 to $3,081. There are also 117 Single Family Homes for rent, Condos, and Townhome rentals currently available in Osprey Pointe ranging from $899 to $3,100.

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 $899 to $3,100 with an average monthly rent of $1,893.

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

decorative image for Renting with Roommates: Realistic Expectations for Shared Lease article

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.

decorative image for Apartment Common Area Rules: What Renters Need to Know article

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.

decorative image for How to Negotiate Your Apartment Lease and Save Money article

How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

decorative image for The Rental Move-In Inspection Checklist: A Guide for Renters article

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.