Apartments for Rent in the Osprey Pointe Neighborhood of Winter Haven, FL (49 Rentals)

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Prose Cypress Pointe
Rent Specials
$1,299 - $1,649

Total Monthly Price

Base Rent$1,299 - $1,649
Total Monthly Price$1,299 - $1,649
1 to 2 Bedroom Apartments Available Now

Prose Cypress Pointe

3110 Gowan DrWinter Haven, FL 33884
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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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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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property at 679 Lake Dexter Cir
$2,300

Total Monthly Price

Base Rent$2,300
Total Monthly Price$2,300
2 Bedroom, 2 Bath Home for Rent
Available Now
Luxury

679 Lake Dexter Cir

Winter HavenFL33884
property at 715 Magnolia Pl
$1,700

Total Monthly Price

Base Rent$1,700
Total Monthly Price$1,700
2 Bedroom, 2 Bath Condo for Rent
Available Now
Luxury

715 Magnolia Pl, Unit 715

715 Magnolia Pl
Winter HavenFL33884

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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property at 687 Lake Dexter Cir
$1,900

Total Monthly Price

Base Rent$1,900
Total Monthly Price$1,900
3 Bedroom, 3 Bath Home for Rent
Available Now
Luxury

687 Lake Dexter Cir

Winter HavenFL33884
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Cypress Harbor
Studio Apartments

Cypress Harbor

3400 Cypress Gardens RdWinter Haven, FL 33884
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3333 Sage Rd
Studio Apartments

3333 Sage Rd

3333 Sage RdWinter Haven, FL 33884

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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Tzadik Brandywyne
1 to 2 Bedroom Apartments

Tzadik Brandywyne

411 18th St SEWinter Haven, FL 33884
  • Utilities Included
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Halcyon Apartments
Studio to 3 Bedroom Apartments

Halcyon Apartments

2237 9th St SEWinter Haven, FL 33880
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700 Avenue Q SE
1 Bedroom Apartments

700 Avenue Q SE

700 Avenue Q SEWinter Haven, FL 33880
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605 Avenue Q SE
2 Bedroom Apartments

605 Avenue Q SE

605 Avenue Q SEWinter Haven, FL 33880
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605 Piedmont Dr
2 Bedroom Apartments

605 Piedmont Dr

605 Piedmont DrWinter Haven, FL 33880

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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230 6th St NE
1 Bedroom Apartments

230 6th St NE

230 6th St NEWinter Haven, FL 33881
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1 Lamplight Ln
1 Bedroom Apartments

1 Lamplight Ln

1 Lamplight LnWinter Haven, FL 33884
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218 Florida Ave
Studio Apartments

218 Florida Ave

218 Florida AveDundee, FL 33838
Showing Results 1-49, Page 1 of 1

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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Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

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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

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.

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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, September 11, 2026, there are currently 49 available Osprey Pointe apartments priced from $959 to $6,400, with an average monthly rent of $1,676.

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 $996 to $1,820 with an average monthly rent of $1,406.

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 $1,265 to $2,060. Today's average rental price for Two Bedrooms here is $1,733.

How expensive are Osprey Pointe Three Bedroom Apartments?

There are currently 9 Three Bedroom Apartments listings available in Osprey Pointe on ApartmentHomeLiving.com. The pricing ranges from $1,600 to $4,102 - averaging $2,045 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

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Exploring Rental Options: Apartments, Townhomes, and Lofts - Oh My!

Written by: Robin Stewart

Where do you see yourself? When you think of home, sweet home, are you in a 3/2 apartment? Dreaming of a tall townhome? Maybe an industrial loft heavy on cool vibes is on your visioning board.

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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Written by: Robin Stewart

Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

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First Apartment Regrets: Real Renters Share What They'd Do Differently

Written by: Robin Stewart

Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

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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.