
Luxury Homes for Rent in Winter Park Neighborhood of Orlando, FL (28 Rentals)
The most luxurious Homes in the Winter Park area of Orlando with high-end amenities, features, and finishes.


2916 Lake Shore Dr

5271 Baskin St

1419 Lake Baldwin Ln

1130 Hardy Ave

5401 Decatur St

833 N Fern Creek Ave

1600 Utah Blvd

1053 Executive Center Dr

914 N Thornton Ave

1461 Vía Tuscany
Orlando's Best Affordable Neighborhoods
Learn about Orlando and the best places to live with original content written by our Local Expert Darla F

851 Virginia Dr

1731 Windsor Dr

860 N Denning Dr

782 S Pennsylvania Ave

437 N Capen Ave

2919 De Brocy Way

1850 Whitehall Dr

853 W Lyman Ave

151 N Orlando Ave

1905 Summerfield Rd

1823 Dover Rd
Winter Park
Named as one of the Best Affordable Areas to rent in Orlando by our , Local Expert Darla F. See how it ranks!

2750 Scarlet Rd

1913 N Park Ave

350 Carolina Ave

1101 S Pennsylvania Ave

7042 Green Needle Dr

2710 Winter Park Rd
Winter Park, Orlando, 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 | $1,843 | $1,345 | $3,000 |
Winter Park 3 Bedroom Homes for Rent | $3,073 | $1,850 | $6,500 |
Winter Park 4 Bedroom Homes for Rent | $5,422 | $2,200 | $10,000+ |
Winter Park 5 Bedroom Homes for Rent | $45,000 | $10,000 | $10,000+ |
Browse Homes for Rent in this Neighborhood
There are currently 28 rentals with your search options within a 2 mile radius of the Winter Park Neighborhood of Orlando, FL.
Explore Orlando
Winter Park, Orlando, FL Local Guide
- Nearby Orlando neighborhoods
- Nearby Cities
- ZIP codes
- Local Counties
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.
Frequently Asked Questions about Winter Park
What type of rentals are currently available in Winter Park?
There are currently 127 Apartments for Rent in Winter Park, FL with pricing that ranges from $1,000 to $12,183. There are also 78 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $1,050 to $45,000.
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 $1,050 to $45,000 with an average monthly rent of $11,339.
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 $1,261 to $9,609, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,850 to $6,500. Four Bedroom Single-Family rentals are also available starting from $2,200 and Four Bedroom Apartments start at $3,644.
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 F
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.

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.

Understanding Amenity Fees: Know Where You Might Be Able to Save Money
Written by: Amber Kanuckel
With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.

How Your Move-In Inspection Can Protect Your Security Deposit
Written by: Christine Leonard, Esq.
If you’re anything like most people, housing costs represent a huge chunk of your monthly budget. On top of that, moving can be both a stressful and expensive affair.