525 S Lakemont Ave
Winter ParkFL32792
Cheap Homes for Rent in Winter Park Neighborhood of Orlando, FL from $1,000 (28 Rentals)
Search the lowest-cost Homes available for rent right now in the Winter Park area of Orlando.
5058 Seminole Ave, Unit Seminole Unit 4
5058 Seminole Ave
Winter ParkFL32792
2421 Passamonte Dr
Winter ParkFL32792
3065 George Mason Ave
Winter ParkFL32792
3069 Aaron Burr Ave
Winter ParkFL32792
261 Scottsdale Sq, Unit 261
261 Scottsdale Sq
Winter ParkFL32792
261 Scottsdale Square
Winter ParkFL32792
The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.
293 Scottsdale Square
Winter ParkFL32792
3035 George Mason Ave
Winter ParkFL32792
200 St Andrews Blvd
Winter ParkFL32792
3019 Antique Oaks Cir
Winter ParkFL32792
3032 Antique Oaks Cir
Winter ParkFL32792
151 N Orlando Ave
Winter ParkFL32789
1000 S Semoran Blvd
Winter ParkFL32792
Smart Renter's Guide: Calculating Affordable Rent & Housing Costs
Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.
3651 N Goldenrod Rd
Winter ParkFL32792
5214 Josephine St
OrlandoFL32803
2617 Marble Ave
OrlandoFL32803
115 Scottsdale Square
Winter ParkFL32792
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.
7404 Woodburn Ct
Winter ParkFL32792
7404 Woodburn Ct
Winter ParkFL32792
3043 Antique Oaks Cir
Winter ParkFL32792
7417 Wynnewood Square
Winter ParkFL32792
7417 Wynnewood Sq, Unit 174
7417 Wynnewood Sq
Winter ParkFL32792
157 Scottsdale Square
Winter ParkFL32792
1945 Lanier Ct
Winter ParkFL32792
7350 Swallow Run
Winter ParkFL32792
4968 Tangerine Ave
Winter ParkFL32792
4880 Tangerine Ave
Winter ParkFL32792
Winter Park - One of the Best Affordable Neighborhoods in Orlando
Named as one of the Best Affordable Areas to rent in Orlando by our , Local Expert Darla F. See how it ranks!
Showing Results 1-28, Page 1 of 1
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 | $2,051 | $1,500 | $6,800 |
| Winter Park 3 Bedroom Homes for Rent | $2,913 | $1,875 | $5,500 |
| Winter Park 4 Bedroom Homes for Rent | $3,770 | $2,200 | $5,700 |
| Winter Park 5 Bedroom Homes for Rent | $7,672 | $3,695 | $9,500 |
| Winter Park 6 Bedroom Homes for Rent | $7,500 | $7,500 | $7,500 |
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.
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Winter Park, Orlando, FL Local Guide
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Cheapest Available Winter Park Apartments for Rent
The cheapest available apartment rental in the Winter Park area of Orlando, FL is a 2 Beds unit found at GOLDEN OAKS priced from $876. District On Baldwin Park has the second lowest priced unit, which is a Studio apartment currently listed from $1,110. Here are the most affordable Winter Park apartments for rent in Orlando, FL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| GOLDEN OAKS | 2 Bedroom 2 Bathroom | 2BR,2BA | $876 |
| District On Baldwin Park | E235xecutive Studio | Studio,1BA | $1,110 |
| Hillcrest Hampton House | Studio | Studio,1BA | $1,125 |
| Venue At Winter Park | Sable | 1BR,1BA | $1,207 |
| Summerlin at Winter Park Apartments | Aqua | 1BR,1BA | $1,217 |
| Solis at Winter Park | A2 | 1BR,1BA | $1,220 |
| Azure Winter Park | Corrine | Studio,1BA | $1,249 |
| Sovereignty at Winter Park Apartments | A2 | 1BR,1BA | $1,258 |
| Winter Park Woods | A2-1 Bedroom, 1 Bathroom | 1BR,1BA | $1,265 |
| Indigo Winter Park | Harmony | 1BR,1BA | $1,299 |
Best Value Apartments for Rent in Winter Park, FL
As of June 03, 2025 the best value apartment in the Winter Park area is the $1.40 price per square foot The Palms Model at Oasis Club in the in the The Enclave at Lake Jean neighborhood starting from $1,545. The second greatest value Winter Park apartment is the Plan B2B Model at Seabrook starting at $1,737 with a $1.64 price per square foot in the Baldwin Park neighborhood. Here is today’s list of the best values for Winter Park apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| Oasis Club | The Palms | 3BR,2BA | $1.40 |
| Seabrook | Plan B2B | 2BR,2BA | $1.64 |
| Cranes Landing Apartments | Heron | 2BR,2BA | $1.64 |
| The Vista at Winter Park | Town House Renovated | 2BR,2.5BA | $1.61 |
| GOLDEN OAKS | 2 Bedroom 2 Bathroom | 2BR,2BA | $1.03 |
| Bellancia | 1 Bed | 1 Bath | 1BR,1BA | $1.75 |
| Winter Park Woods | A2-1 Bedroom, 1 Bathroom | 1BR,1BA | $1.67 |
| Sovereignty at Winter Park Apartments | A2 | 1BR,1BA | $1.68 |
| Summerlin at Winter Park Apartments | Aqua | 1BR,1BA | $1.66 |
| Venue At Winter Park | Sable | 1BR,1BA | $1.68 |
Quick Rent Budget Calculator
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Frequently Asked Questions about Winter Park
What type of rentals are currently available in Winter Park?
There are currently 123 Apartments for Rent in Winter Park, FL with pricing that ranges from $1,032 to $9,543. There are also 88 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $1,050 to $9,500.
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 $9,500 with an average monthly rent of $4,197.
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 $9,543, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,875 to $5,500. Four Bedroom Single-Family rentals are also available starting from $2,200 and Four Bedroom Apartments start at $3,992.
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 Art of the Rental Viewing: What to look for during a property tour
Written by: Marie Brown
You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.
Know Your Budget: Calculating What You Can Realistically Afford When Renting
Written by: Lauren Harrington
Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.
The Freedom of Short-Term Leases: Exploring the Advantages for Renters
Written by: Bobbi Jackson
If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.