
Homes for Rent in Winter Park, FL Under $2,000 (144 Rentals) Page 2 of 3


33 E Princeton St

1150 Carmel Cir

1817 Shadow View Cir

900 Northern Dancer Way, Unit 100

1007 N Thornton Ave

1007 N Thornton Ave

3162 Plaza Terrace Dr

737 Carlson Dr
Orlando's Best Affordable Neighborhoods
Learn about Orlando and the best places to live with original content written by our Local Expert Darla Ferrara

510 Brighton Way

1016 Arthur Ave

860 N Orange Ave, Unit 860 N Orange Ave UNIT 464

124 W Hazel St

320 Lakeview St, Unit 214

2864 Wareham Ct

2423 Branch Way

1510 Charlotte Ln

1411 Woodward St

1413 Woodward St

435 Eaton St

300 Campus View Dr

1212 Sasoon Ave

1036 Altaloma Ave

421 Kentia Rd

1627 E Concord St

860 N Orange Ave, Unit 130

5205 2nd St

2414 Formosa Ave

3801 Grant Blvd

1111 Hardy Ave

1427 Virginia Dr

1150 Lake Shadow Cir

1032 N Fern Creek Ave

604 Kenwick Cir

5306 Satel Dr

1618 E Livingston St

1149 Exceller Ct

518 Polaris Loop

129 Georgetown Dr

1024 Manor Dr

638 Kenwick Cir

320 Lakeview St

1225 Lake Shadow Cir

1024 Manor Dr

4499 Twinview Ln

600 W Princeton St

1165 Paseo De Las Flores Apt C

5309 Andrus Ave

4101 Fairview Vista Point

5454 Decatur St
Winter Park, FL Local Guide

How much does it cost to rent a home in Winter Park?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Winter Park 2 Bedroom Homes for Rent | $1,962 | $1,245 | $4,850 |
Winter Park 3 Bedroom Homes for Rent | $2,712 | $1,450 | $6,050 |
Winter Park 4 Bedroom Homes for Rent | $4,979 | $2,000 | $10,000+ |
Winter Park 5 Bedroom Homes for Rent | $10,550 | $3,550 | $10,000+ |
Winter Park 6 Bedroom Homes for Rent | $800 | $800 | $800 |
Browse Top Homes for Rent in Winter Park
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Frequently Asked Questions about Winter Park
What type of rentals are currently available in Winter Park?
There are currently 300 Apartments for Rent in Winter Park, FL with pricing that ranges from $720 to $6,050. There are also 323 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $720 to $25,000.
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 $720 to $25,000 with an average monthly rent of $5,386.
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 $1,099 to $6,050, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,450 to $6,050. Four Bedroom Single-Family rentals are also available starting from $2,000 and Four Bedroom Apartments start at $3,150.
Expert Rental Resources
Helpful Apartment Articles, How-To's and Tips
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.

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.

The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.

Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.

The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Written by: Christine Leonard, Esq.
Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.