
Homes for Rent in Winter Park, FL Under $2,000 (97 Rentals)Page 2 of 2


483 Meadowood Blvd

3104 Harrison Ave

941 Pine Grove Ave

1100 Delaney Ave

1506 Mt Vernon St

100 Eaton St

3012 E Jefferson St

828 Shady Ln Dr

31 Deacon Jones Blvd

612 Kenwick Cir

42 E Princeton St

303 Dryberry Way

922 Eldridge St

2609 Marble Ave

2611 Marble Ave

2407 Branch Way

1523 Pickwood Ave

1823 Canton St

642 Kenwick Cir

654 Kenwick Cir

911 N Orange Ave

408 Banyon Tree Cir

2617 Marble Ave

5214 Josephine St

5519 Lehigh Ave

7200 Aloma Ave

5333 Davisson Ave

860 N Orange Ave

658 Kenwick Cir

1000 Lake of the Woods Blvd

1172 Calle Del Rey

35 E Winter Park St

5049 Old Cheney Hwy

550 Cascade Cir

5304 Satel Dr

631 Shady Ln Dr

1502 Silver Star Rd

1171 Calle Del Rey

416 Lime St

616 Eola Dr

555 Flemming Way

555 Fleming Way

216 Obrien Rd

312 Orange St

421 E Kennedy Blvd

837 Cathcart Terrace
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 | $1,889 | $1,200 | $4,500 |
Winter Park 3 Bedroom Homes for Rent | $2,698 | $1,300 | $5,800 |
Winter Park 4 Bedroom Homes for Rent | $3,938 | $2,000 | $9,800 |
Winter Park 5 Bedroom Homes for Rent | $4,334 | $2,602 | $6,900 |
Winter Park 6 Bedroom Homes for Rent | $3,647 | $2,795 | $4,500 |
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 303 Apartments for Rent in Winter Park, FL with pricing that ranges from $600 to $9,558. There are also 201 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $997 to $9,800.
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 $997 to $9,800 with an average monthly rent of $2,767.
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 $1,146 to $9,558, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,300 to $5,800. Four Bedroom Single-Family rentals are also available starting from $2,000 and Four Bedroom Apartments start at $2,355.
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.

Know Your Rights - How Discrimination Laws Impact Landlords and Tenants
Written by: Christine Leonard, Esq.
Everyone needs a place to live and to call home. For decades, the federal government has established protections to ensure that individuals and families can find housing free from discriminatory barriers.

Renting Smart: Lease Basics Every Renter Needs
Written by: Christine Leonard, Esq.
Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.

Battling the Butts: Your Guide to the Reality of Smoke-Free Renting
Written by: Andrea Lee Negroni, JD
While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.