Homes for Rent in Winter Park, FL Under $2,000 (134 Rentals) Page 2 of 3

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property at 860 N Orange Ave

$1,850

Total Monthly Price

Total Monthly Price

Base Rent
$1,850
Total Monthly Price
$1,850

1 Bedroom, 1 Bath Condo for Rent

Available Aug 21

860 N Orange Ave, Unit 268

860 N Orange Ave
OrlandoFL32801

Orlando's Best Affordable Neighborhoods

Learn about Orlando and the best places to live with original content written by our Local Expert Darla Ferrara

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property at 2510 Boyd Ave

$1,800

1 To 2 Bedroom Rentals

Available Now

2510 Boyd Ave

OrlandoFL32803

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 1521 Legacy Club Dr

$1,700

Total Monthly Price

Total Monthly Price

Base Rent
$1,700
Total Monthly Price
$1,700

1 Bedroom, 1 Bath Townhome for Rent

Available Now

1521 Legacy Club Dr

MaitlandFL32751

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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property at 860 N Orange Ave

$1,625

Total Monthly Price

Total Monthly Price

Base Rent
$1,625
Total Monthly Price
$1,625

1 Bedroom, 1 Bath Condo for Rent

Available Aug 1

860 N Orange Ave, Unit 371

860 N Orange Ave
OrlandoFL32801
property at 2407 Branch Way

$1,500

Total Monthly Price

Total Monthly Price

Base Rent
$1,500
Total Monthly Price
$1,500

2 Bedroom, 1 Bath Condo for Rent

Available Now

2407 Branch Way, Unit 105

2407 Branch Way
MaitlandFL32751
property at 911 N Orange Ave

$1,495 - $2,150

1 To 2 Bedroom Rentals

Available Now

911 N Orange Ave

OrlandoFL32801
Showing Results 51-100, Page 2 of 3

Frequently Asked Questions about Winter Park

What type of rentals are currently available in Winter Park?

There are currently 310 Apartments for Rent in Winter Park, FL with pricing that ranges from $250 to $7,275. There are also 286 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $825 to $9,500.

What is the current price range for Rental Homes in Winter Park?

Today's rental pricing for Homes for Rent, Condos and Townhomes in Winter Park ranges from $825 to $9,500 with an average monthly rent of $2,677.

How much are larger Three and Four Bedroom Rentals in Winter Park?

For those who are looking for larger living arrangements, Three Bedroom Apartments in Winter Park range from $750 to $7,275, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,645 to $9,500. Four Bedroom Single-Family rentals are also available starting from $2,070 and Four Bedroom Apartments start at $1,844.

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.

Helpful Local Expert Guides

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Where Orlando Locals Actually Live: A Renter's Guide to the Surrounding Cities

Written by: Darla Ferrara

When people think of Orlando, FL, the iconic theme parks and buzz of downtown tend to steal the spotlight.

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The Soul of the City Beautiful: What Life in Orlando Is Really Like

Written by: Darla Ferrara

When people think of Orlando, Florida, they dream of theme parks and sunny weather, and rightfully so. It’s that energy that keeps this city a mainstay in the global tourist industry.

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Unlock Your Orlando Commute: An Expert Guide to Ideal Neighborhoods Near Major Local Employers

Written by: Darla Ferrara

When I first moved to Orlando, Florida, in the 1990s, one of the things that drew me here was the remarkably low unemployment rates. There was a job for everyone. Two decades later, that fundamental appeal remains.

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Your Guide to the Perfect Orlando Neighborhood for Student Renters

Written by: Darla Ferrara

There is never a dull moment in Orlando, Florida. Along with top-tier universities, technical schools, and local colleges, there are world-class entertainment venues, the ocean within driving distance, and lots of sunshine.

Articles, How-To's, and Tips

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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.

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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.