
Homes for Rent in Osprey Pointe Neighborhood of Winter Haven, FL Under $2,000 (48 Rentals)


5624 Struthers Ct

7708 Waterview Way, Unit 7708 Waterview Way, Unit 7708 Waterview Way

4030 Cypress Landing E

3037 Country Club Cir

206 Kingshill Ct SE

2069 Whispering Trails Blvd

240 16th St NE

104 Lake Daisy Terrace

3005 Whispering Trails Dr
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.

2753 Whispering Trails Dr

137 Woodland Dr

4973 Kaia Ave

3889 Giorgio Dr

4458 Rapallo Ave

861 Terranova Rd

3050 Laurel Oak Ln

632 Vittorio Dr

855 Turner Ln

4643 Ostero St
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.

4981 Kaia Ave

810 Terranova Rd

1026 Corso Dr

1568 Hummingbird Rd

4819 Summerfield Cir

506 Eagle Landing Blvd

2893 Whispering Trails Dr

125 Pine Island Dr

1019 Mockingbird Cir

8307 Waterview Way

715 Magnolia Pl

7903 Waterview Way

2249 9th St SE

64 Stebbins Dr

100 El Camino Dr

1707 Eagle Pond Dr

1101 Eagle Pond Dr

609 Ave G SE

611 Ave G SE

900 Ave Z SE

76 Stebbins Dr

400 El Camino Dr

129 Alachua Dr

715 Magnolia Pl, Unit 715, Unit 715

7903 Waterview Way

610 Dundee Rd

217 Betty Ave

603 Citrus Ave
Osprey Pointe, Winter Haven, FL Local Guide

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 | $1,508 | $1,325 | $1,650 |
| Osprey Pointe 3 Bedroom Homes for Rent | $2,124 | $1,550 | $4,500 |
| Osprey Pointe 4 Bedroom Homes for Rent | $2,254 | $1,725 | $4,500 |
| Osprey Pointe 5 Bedroom Homes for Rent | $2,566 | $2,100 | $3,100 |
Browse Homes for Rent in this Neighborhood
There are currently 48 rentals with your search options within a 3 mile radius of the Osprey Pointe Neighborhood of Winter Haven, FL.
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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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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.
Best Local Schools in Osprey Pointe, Winter Haven, FL
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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 $800 to $6,385. There are also 88 Single Family Homes for rent, Condos, and Townhome rentals currently available in Osprey Pointe ranging from $990 to $4,500.
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 $990 to $4,500 with an average monthly rent of $1,959.
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 $1,575 to $2,846, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,550 to $4,500. Four Bedroom Single-Family rentals are also available starting from $1,725 and Four Bedroom Apartments start at $6,385.
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

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back
Written by: Lauren Harrington
I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.

Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts
Written by: Lauren Harrington
This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.

Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.