1450 Cavendish Rd
Winter ParkFL32789
Cheap Homes for Rent in Winter Park Neighborhood of Orlando, FL from $800 (26 Rentals)
Search the lowest-cost Homes available for rent right now in the Winter Park area of Orlando.
525 S Lakemont Ave
Winter ParkFL32792
1233 Virginia Dr
OrlandoFL32803
7345 Daniel Webster Dr, Unit D
7345 Daniel Webster Dr
Winter ParkFL32792
1212 Jamajo Blvd
OrlandoFL32803
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.
200 St Andrews Blvd
Winter ParkFL32792
3022 Plaza Terrace Dr
OrlandoFL32803
2929 Antique Oaks Cir
Winter ParkFL32792
614 Grenadine Ct
Winter ParkFL32792
3057 Aaron Burr Ave
Winter ParkFL32792
3054 George Mason Ave
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.
5517 Decatur St
OrlandoFL32807
1000 S Semoran Blvd
Winter ParkFL32792
3651 N Goldenrod Rd
Winter ParkFL32792
115 Scottsdale Square
Winter ParkFL32792
825 N Primrose Dr
OrlandoFL32803
316 Scottsdale Square
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.
3267 Forest Oaks Ct
Winter ParkFL32792
628 Trinidad Ct
Winter ParkFL32792
3045 Aaron Burr Ave
Winter ParkFL32792
3007 George Mason Ave
Winter ParkFL32792
1239 Virginia Dr
OrlandoFL32803
7449 Wynnewood Square
Winter ParkFL32792
1024 Manor Dr
OrlandoFL32807
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.
4968 Tangerine Ave
Winter ParkFL32792
1215 Lake Highland Dr
OrlandoFL32803
Showing Results 1-26, 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 | $1,978 | $800 | $3,850 |
| Winter Park 3 Bedroom Homes for Rent | $3,057 | $1,745 | $6,995 |
| Winter Park 4 Bedroom Homes for Rent | $4,406 | $2,749 | $7,495 |
| Winter Park 5 Bedroom Homes for Rent | $6,200 | $3,750 | $8,650 |
Browse Homes for Rent in this Neighborhood
There are currently 26 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
- Nearby Orlando neighborhoods
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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 1 Bed unit found at Venue At Winter Park priced from $1,072. GOLDEN OAKS has the second lowest priced unit, which is a 3 Beds apartment currently listed from $1,099. Here are the most affordable Winter Park apartments for rent in Orlando, FL:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Venue At Winter Park | Sable | 1BR,1BA | $1,072 |
| GOLDEN OAKS | 3 Bedroom 2 Bathroom | 3BR,2BA | $1,099 |
| District On Baldwin Park | E235xecutive Studio | Studio,1BA | $1,110 |
| Hillcrest Hampton House | Studio | Studio,1BA | $1,125 |
| Sovereignty at Winter Park Apartments | A2 | 1BR,1BA | $1,195 |
| Winter Park Woods | A1-Studio, 1 Bathroom | Studio,1BA | $1,200 |
| Seabrook | Plan A1 | 1BR,1BA | $1,212 |
| Summerlin at Winter Park Apartments | Aqua | 1BR,1BA | $1,216 |
| Solis at Winter Park | A1 | 1BR,1BA | $1,219 |
| The Taylor at Winter Park | S1R | Studio,1BA | $1,290 |
Best Value Apartments for Rent in Winter Park, FL
As of July 29, 2025 the best value apartment in the Winter Park area is the $1.34 price per square foot 2X2 Model at La Aloma in the in the University Commerce Center neighborhood starting from $1,525. The second greatest value Winter Park apartment is the The Palms Model at Oasis Club starting at $1,845 with a $1.68 price per square foot in the The Enclave at Lake Jean 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. |
|---|---|---|---|
| La Aloma | 2X2 | 2BR,2BA | $1.34 |
| Oasis Club | The Palms | 3BR,2BA | $1.68 |
| Bellancia | 2 Bed | 2 Bath | 2BR,2BA | $1.44 |
| GOLDEN OAKS | 3 Bedroom 2 Bathroom | 3BR,2BA | $1.05 |
| Shoreview at Baldwin Park | 1x1C | 1BR,1BA | $1.65 |
| Cranes Landing Apartments | Sandpiper | 1BR,1BA | $1.62 |
| The Avenues of Baldwin Park | Fern | 1BR,1.5BA | $1.65 |
| Sovereignty at Winter Park Apartments | A2 | 1BR,1BA | $1.59 |
| Summerlin at Winter Park Apartments | Aqua | 1BR,1BA | $1.66 |
| Venue At Winter Park | Sable | 1BR,1BA | $1.49 |
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 126 Apartments for Rent in Winter Park, FL with pricing that ranges from $976 to $6,231. There are also 100 Single Family Homes for rent, Condos, and Townhome rentals currently available in Winter Park ranging from $800 to $8,650.
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 $800 to $8,650 with an average monthly rent of $3,059.
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 $6,231, while Three Bedroom Homes, Condos, and Townhomes for rent range from $1,745 to $6,995. Four Bedroom Single-Family rentals are also available starting from $2,749 and Four Bedroom Apartments start at $3,060.
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.
Cash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Written by: Christine Leonard, Esq.
Throughout the day, think about all the times that you have to pay for something. So many of us reach automatically for a credit card or even our phone for a quick payment.
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
Written by: Cheryl Bowman
A fantastic way to save money and enjoy a built-in community is to share an apartment. However, a bad roommate situation can turn your dream rental into a nightmare.
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.