
Luxury Homes for Rent in Winter Park, FL (129 Rentals) Page 2 of 3
The most luxurious Homes in Winter Park with high-end amenities, features, and finishes.


2007 Cornell Ave

2020 Venetian Way

1860 Vía Contessa

1253 Blessing St

1025 Hunter Ave

226 Harvard St

2132 Falkner Rd

8028 Birman St

612 Stetson St
Navigating the Rental Market: Tips for First-Time Renters
Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

612 Stetson St

1483 Glastonberry Rd

605 Woodridge Dr

1633 E Concord St

1633 E Concord St

776 Eldridge St

101 S Glenwood Ave

1141 W Smith St

530 Ventris Ct

2126 Tortoise Shell 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

539 W Yale St

2627 Taft Ave

1207 E Jefferson St

110 Zora Pl

1819 E Central Blvd

416 Hillcrest St

2467 Sunderland Rd

2110 Gerda Terrace

690 San Pablo Ave

348 Georgetown Dr

1504 Minnesota St

2707 Kilgore St

1704 N Shore Terrace, Unit 2

840 Bethune Dr

1435 Oxford Rd

827 Meridale Ave

2514 Illinois St

1704 Weltin St

606 Marigold Rd

1936 Durrand Ave

1120 Hunter Ave

226 W Spruce St

1115 Yates St

3707 Pelican Ln

1519 Lake Baldwin Ln

21 N Hampton Ave

1111 Eastern Way

224 Doverwood Rd

749 Altaloma 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 | $1,974 | $1,290 | $5,000 |
| Winter Park 3 Bedroom Homes for Rent | $2,686 | $1,445 | $6,050 |
| Winter Park 4 Bedroom Homes for Rent | $3,923 | $1,950 | $10,000+ |
| Winter Park 5 Bedroom Homes for Rent | $7,825 | $2,450 | $10,000+ |
| Winter Park 6 Bedroom Homes for Rent | $3,099 | $3,099 | $3,099 |
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 295 Apartments for Rent in Winter Park, FL with pricing that ranges from $900 to $6,772. There are also 360 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $750 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 $750 to $25,000 with an average monthly rent of $4,477.
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 $6,772, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,445 to $6,050. Four Bedroom Single-Family rentals are also available starting from $1,950 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.

Apartment Common Area Rules: What Renters Need to Know
Written by: Christine Leonard, Esq.
Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

How to Negotiate Your Apartment Lease and Save Money
Written by: Christine Leonard, Esq.
Everything is a negotiation in real estate!

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.
