Apartments for Rent in the Osprey Pointe Neighborhood of Winter Haven, FL (141 Rentals)

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Prose Cypress Pointe
Rent Specials
$1,299 - $1,860
Total Monthly Price

Total Monthly Price

Base Rent
$1,299 - $1,860
Total Monthly Price
$1,299 - $1,860
1 to 2 Bedroom Apartments Available Now

Prose Cypress Pointe

3110 Gowan DrWinter Haven, FL 33884
Affordability
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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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property at 6224 Botticella Blvd

$2,350

Total Monthly Price

Total Monthly Price

Base Rent
$2,350
Total Monthly Price
$2,350

5 Bedroom, 2.5 Bath Home for Rent

Available Now

6224 Botticella Blvd

Winter HavenFL33884
property at 711 Avenue B NE

$1,825

Total Monthly Price

Total Monthly Price

Base Rent
$1,825
Total Monthly Price
$1,825

3 Bedroom, 2 Bath Home for Rent

Available Now

711 Avenue B NE

Winter HavenFL33881

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

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Neighborhood & Market Insights: How to Choose the Right Area to Rent

Master your search for the perfect apartment. Location is everything. Discover how to leverage community insights, public data, and personal visits to make a fully informed decision about where to rent.

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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.

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property at 513 Ave J SE

$1,269

2 Bedroom Rentals

Available Now

513 Ave J SE

Winter HavenFL33880

Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

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Showing Results 1-50, Page 1 of 3

Osprey Pointe, Winter Haven, FL Local Guide

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back

Learn the property manager's true secrets to a zero-deduction move-out. Use this step-by-step guide on documentation, cleaning, and lease-reading to reclaim your security deposit.

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18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property

Tour smarter and choose with confidence. Get the essential 18 questions that reveal the truth about a rental property's maintenance, utilities, and safety.

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Real 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.

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Quick Rent Budget Calculator

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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.

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Osprey Pointe, Winter Haven, FL

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Frequently Asked Questions about Osprey Pointe

What is the current pricing and availability for apartments for rent in the Osprey Pointe area of Winter Haven, FL?

As of today, July 27, 2026, there are currently 141 available Osprey Pointe apartments priced from $959 to $4,391, with an average monthly rent of $1,677.

What is the current price range for One Bedroom Osprey Pointe Apartments for rent?

Today's rental pricing for One Bedroom Apartments in Osprey Pointe ranges from $1,001 to $1,780 with an average monthly rent of $1,433.

What does renting a Two Bedroom Apartment in Osprey Pointe cost?

The monthly rent prices of Two Bedroom Apartments currently available in Osprey Pointe range from $1,150 to $2,040. Today's average rental price for Two Bedrooms here is $1,748.

How expensive are Osprey Pointe Three Bedroom Apartments?

There are currently 11 Three Bedroom Apartments listings available in Osprey Pointe on ApartmentHomeLiving.com. The pricing ranges from $1,575 to $3,047 - averaging $2,051 for the location.

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 Renters Insurance 101: What It Is, What It Covers, and Why You Need It article

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

Written by: Robin Stewart

Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.

decorative image for Apartment Occupancy Rates: Renter Attraction vs Renter Retention article

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.

decorative image for How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide article

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.

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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.