Homes for Rent in Winter Park, FL Under $2,000 (132 Rentals)

How Many Bedrooms?Done
Select your price rangeDone
to
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done

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.

Read Article
property at 7473 Belle River Ct

$1,750

Total Monthly Price

Total Monthly Price

Base Rent
$1,750
Total Monthly Price
$1,750

3 Bedroom, 3 Bath Townhome for Rent

Available Now

7473 Belle River Ct

Winter ParkFL32792
property at 625 Trinidad Ct

$1,650

Total Monthly Price

Total Monthly Price

Base Rent
$1,650
Total Monthly Price
$1,650

2 Bedroom, 2 Bath Condo for Rent

Available Now

625 Trinidad Ct, Unit 625

625 Trinidad Ct
Winter ParkFL32792
property at 700 Melrose Ave

$1,650

Total Monthly Price

Total Monthly Price

Base Rent
$1,650
Total Monthly Price
$1,650

1 Bedroom, 1 Bath Condo for Rent

Available Now

700 Melrose Ave

Winter ParkFL32789

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

Orlando is much more than theme parks. Uncover the city's rich history, diverse neighborhoods like Winter Park and Downtown, and its bustling cultural and culinary life.

Read Article

Top Neighborhoods Near Orlando Major Employers

Learn about the best places to live near major employers in Orlando with original content written by our Local Expert Darla Ferrara

Read Article
property at 2500 Lee Rd

$1,465

Total Monthly Price

Total Monthly Price

Base Rent
$1,465
Total Monthly Price
$1,465

1 Bedroom, 1 Bath Condo for Rent

Available Now

2500 Lee Rd, Unit 244

2500 Lee Rd
Winter ParkFL32789
property at 151 N Orlando Ave

$1,450 - $2,750

1 To 3 Bedroom Rentals

Available Now

151 N Orlando Ave

Winter ParkFL32789
property at 1695 Lee Rd

$1,175 - $1,595

1 To 2 Bedroom Rentals

Available Now

1695 Lee Rd

Winter ParkFL32789

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.

Read Article
property at 5058 Seminole Ave

$1,000

Total Monthly Price

Total Monthly Price

Base Rent
$1,000
Total Monthly Price
$1,000

1 Bedroom, 1 Bath Home for Rent

Available Jun 12

5058 Seminole Ave, Unit Seminole 1

5058 Seminole Ave
Winter ParkFL32792
property at 16 S Primrose Dr

$2,000

Total Monthly Price

Total Monthly Price

Base Rent
$2,000
Total Monthly Price
$2,000

2 Bedroom, 1 Bath Home for Rent

Available Now

16 S Primrose Dr

OrlandoFL32803

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.

Read Article
Showing Results 1-50, Page 1 of 3

Winter Park, FL Local Guide

Your Guide to the Perfect Orlando Neighborhood for Student Renters

Learn About the Best Neighborhoods to Rent Near College Campuses in Orlando, FL | Find Orlando Off-Campus Student Housing at ApartmentHomeLiving.com

Read Article
Decorative image

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.

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

Remember the 3 Rules of Real Estate:
Location, Location, Location!

Explore Winter Park, FL Rentals by Map

Decorative image of map

See the most popular apartments and homes in Winter Park, FL

View Map
Winter Park, FL Apartments Map
View Map
Winter Park, FL Rental Homes Map

Frequently Asked Questions about Winter Park

What type of rentals are currently available in Winter Park?

There are currently 301 Apartments for Rent in Winter Park, FL with pricing that ranges from $250 to $6,500. There are also 288 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $795 to $20,000.

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 $795 to $20,000 with an average monthly rent of $2,885.

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 $1,082 to $6,500, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,150 to $10,900. Four Bedroom Single-Family rentals are also available starting from $2,049 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

decorative image for An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent article

An Orlando Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent

Written by: Darla Ferrara

For many, Orlando is the place where you vacation, not live. However, this city, located in the central region of Florida, offers a vibrant tech community, plenty of outdoor activities, and some of the best schools in the country.

decorative image for Your Guide to the Perfect Orlando Neighborhood for Student Renters article

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.

decorative image for Unlock Your Orlando Commute: An Expert Guide to Ideal Neighborhoods Near Major Local Employers article

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.

decorative image for The Soul of the City Beautiful: What Life in Orlando Is Really Like article

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.

Articles, How-To's, and Tips

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.

decorative image for Pet-Friendly Renting: Everything You Need to Know Before You Move article

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.

decorative image for Creative Ways Developers Reimagine Retail Spaces as Residential Units article

Creative Ways Developers Reimagine Retail Spaces as Residential Units

Written by: Robin Stewart

Adaptive reuse is when a commercial property is converted and repurposed. The real estate industry has embraced a growing number of these projects.

decorative image for Neighborhood and Market Insights: How to Choose the Right Area to Rent article

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

Written by: Robin Stewart

Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.