Deals & Discount Filters
Cheap Apartments for Rent in Winter Park, FL
1,853 Rentals
-
-
2 BEDS, 2 BATHS$4,850104 S Interlachen Ave Unit 114
104 S Interlachen Ave, Winter Park, FL 32789 -
4 BEDS, 2.5 BATHS$4,9501580 Oakhurst Ave
1580 Oakhurst Ave, Winter Park, FL 32789 -
4 BEDS, 3.5 BATHS$4,995
438 W Swoope Ave
438 W Swoope Ave, Winter Park, FL 32789 -
4 BEDS, 3 BATHS$4,9951525 Palmer Ave
1525 Palmer Ave, Winter Park, FL 32789 -
4 BEDS, 3.5 BATHS$5,250LUXURY RENTAL In Maitland - Winter Park Area 32751
1610 Lyndale Blvd, Maitland, FL 32751 -
4 BEDS, 3 BATHS$5,4001701 Palmer Ave
1701 Palmer Ave, Winter Park, FL 32789 -
4 BEDS, 3 BATHS$7,0001400 S Pennsylvania Ave
1400 S Pennsylvania Ave, Winter Park, FL 32789 -
4 BEDS, 3.5 BATHS$8,990
2020 Venetian Way
2020 Venetian Way, Winter Park, FL 32789 -
4 BEDS, 3 BATHS$10,950
2220 Vía Tuscany
2220 Vía Tuscany, Winter Park, FL 32789 -
8 BEDS, 6 BATHS$16,5501860 Vía Contessa
1860 Vía Contessa, Winter Park, FL 32789 -
5 BEDS, 5.5 BATHS$19,0001221 Richmond Rd
1221 Richmond Rd, Winter Park, FL 32789 -
5 BEDS, 8 BATHS$22,5003260 Lake Shore Dr
3260 Lake Shore Dr, Orlando, FL 32803 -
-
4 BEDS, 4.25 BATHS$25,000281 Shell Point E
281 Shell Point E, Maitland, FL 32751
Showing 42 of 309 results, Page 8 of 8
Can't find what you are looking for?
Clear All FiltersWinter Park at a Glance
Renting in Winter Park
Average Rental Rates and Apartment Sizes
- Apartment Type Average Sq Ft Average Rent
- Studio 539 Sq Ft $1,347 / mo
- 1 Bedroom 707 Sq Ft $1,448 / mo
- 2 Bedrooms 1,019 Sq Ft $1,734 / mo
- 3 Bedrooms 1,273 Sq Ft $2,021 / mo
- 4 Bedrooms 1,506 Sq Ft $1,540 / mo
Top Budget-Friendly Neighborhoods in Winter Park
(For 1 bedroom apartments)- Neighborhoods Average Sq Ft Average Rent
- Winter Park Woods 761 Sq Ft $1,378/mo
- Four Seasons 606 Sq Ft $1,391/mo
- Winter Park Pines Merrie Oaks 606 Sq Ft $1,391/mo
- Laurel Springs 743 Sq Ft $1,392/mo
- Winter Park Pines 674 Sq Ft $1,427/mo
- Eastbrook 744 Sq Ft $1,442/mo
- Villas of Casselberry 759 Sq Ft $1,511/mo
- Lake Howell 746 Sq Ft $1,512/mo
- Cedarwood Village 654 Sq Ft $1,531/mo
- Windward Square 779 Sq Ft $1,538/mo
Getting Around Winter Park
Education
Data provided by GreatSchools.org 2025 © 2025. All rights reserved.
tooltips
Submitting Request
Thank You
About Our Deals
Apartment Finder utilizes the industry's largest and most complete database of real-time rents and availabilities to help you find an amazing deal on your next rental.
Price Drop
Apartment communities change their rental rates often - sometimes multiple times a day. We track the changes and keep you up to date when a rental rate decreases.
Best Value
"Best value" units are located in buildings rated three stars or higher. We label apartment rentals that are priced significantly less than similar high-quality units nearby.
Rent Specials
Apartment communities regularly advertise deals for new residents. Whether it's a move-in special or a free tv, we locate the rentals that offer a little something extra when you sign your lease.
Note: Based on community-supplied data and independent market research. Subject to change without notice.