
Homes for Rent in Winter Park, FL Under $2,000 (143 Rentals) Page 3 of 3


1112 Princewood Dr

550 Flemming Way

1919 Canton St

2821 Kilgore St

2406 Branch Way

5632 Pinerock Rd

911 N Orange Ave

440 Banyon Tree Cir

2531 Carver Ave

520 Gamewell Ave

5049 Old Cheney Hwy

1166 Paseo De Las Flores

5523 Lehigh Ave

825 N Primrose Dr

113 E Smith St

2521 Caper Ln

860 N Orange Ave

1125 Lake Shadow Cir

1125 Lake Shadow Cir

670 Kenwick Cir

633 N Summerlin Ave

511 Hillcrest St

2525 Caper Ln

452 Banyon Tree Cir

204 Georgetown Dr

499 Ruffel St

439 Ruffel St

200 S W St

1900 E Robinson St

656 Kenwick Cir

4328 Edgewater Dr, Unit E204

214 S W St

421 E Kennedy Blvd

662 Kenwick Cir, Unit Casselberry

1212 Jamajo Blvd

648 Kenwick Cir, Unit 102

2223 Amherst Ave

14 Bel Air St

1224 Moselle Ave
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 | $1,963 | $1,245 | $4,850 |
Winter Park 3 Bedroom Homes for Rent | $2,712 | $1,450 | $6,050 |
Winter Park 4 Bedroom Homes for Rent | $5,013 | $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
Explore Winter Park
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 327 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 $5,390.
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.