2 BEDS, 2 BATHS
$1,590
Deals & Discount Filters
Condos under $2,000 for Rent in Winter Park, FL
1,116 Rentals
-
-
1 BED, 1 BATH$1,275Fantastic 1 /1 x Rent @ Winter Park's Four... Unit 412
200 St Andrews Blvd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,499
Spacious Condo Living in Winter Park – Per...
1000 S Semoran Blvd, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,595115 Scottsdale Square
115 Scottsdale Square, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,8502404 Gallery View Dr Unit 1
2404 Gallery View Dr, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,500
3651 N Goldenrod Rd Unit B109
3651 N Goldenrod Rd, Winter Park, FL 32792 -
1 BED, 1 BATH$1,300
Grdyn House Unit 1
1855 Eastbrook Blvd, Winter Park, FL 32792 -
3 BEDS, 2 BATHS$1,845
7528 University Garden Dr
7528 University Garden Dr, Winter Park, FL 32792 -
2 BEDS, 2.5 BATHS$1,6993007 George Mason Ave Unit H
3007 George Mason Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,700Excellent location Unit 4968
4968 Tangerine Ave, Winter Park, FL 32792 -
2 BEDS, 2 BATHS$1,750
NEWLY RENOVATED 2 BED 2 BATH CONDO NEAR UC...
1165 Paseo De Las Flores Apt C, Casselberry, FL 32707 -
1 BED, 1 BATH$1,599
2307 Formosa Ave Unit A
2307 Formosa Ave, Orlando, FL 32804 -
2 BEDS, 1 BATH$1,350
1820 Rogers Ave Unit B - 1
1820 Rogers Ave, Maitland, FL 32751 -
2 BEDS, 1 BATH$1,150118 Eaton St Unit 2
118 Eaton St, Eatonville, FL 32751 -
2 BEDS, 1 BATH$1,150114 Eaton St Unit 1
114 Eaton St, Eatonville, FL 32751 -
2 BEDS, 2.5 BATHS$1,725
Decatur St Units Unit 5524
5522 Decatur St, Orlando, FL 32807 -
2 BEDS, 1.5 BATHS$1,545
5517 Decatur St Unit 5517 Decatur
5517 Decatur St, Orlando, FL 32807 -
3 BEDS, 2.5 BATHS$1,650
East St N.-230 Unit B
230 East St, Eatonville, FL 32751 -
Discounts| -
Good Value|STUDIO$1,325+1 BED$1,625+2 BEDS$1,715+Onyx Winter Park
100 Reflections Cir, Casselberry, FL 32707 -
|STUDIO$1,750+1 BED$1,800+
The Majestic at Downtown Baldwin Park
4828 New Broad St, Orlando, FL 32814 -
Price Drop. $257 Off
-
Price Drop. $230 Off|
-
Discounts| -
Price Drop. $180 Off|1 BED$1,475+2 BEDS$1,500+Oak Reserve at Winter Park
541 Oak Reserve Ln, Winter Park, FL 32792 -
Price Drop. $225 Off|1 BED$1,293+2 BEDS$1,545+3 BEDS$1,832+
Cranes Landing Apartments
3440 N Goldenrod Rd, Winter Park, FL 32792 -
Rent Special|
-
1 Month Free|
-
| -
Good Value| -
Price Drop. $280 Off1 BED$1,399+2 BEDS$1,599+3 BEDS$1,949+
Sapphire Winter Park
1743 Semoran North Cir, Winter Park, FL 32792 -
Exceptional Value|1 BED$1,350+2 BEDS$1,655+3 BEDS$1,995+
Newport Colony Apartments in Casselberry
1166 Pointe Newport Ter, Casselberry, FL 32707 -
Rent Special|
-
| -
Price Drop. $223 Off|STUDIO$1,754+1 BED$1,609+2 BEDS$1,954+The Ivy Residences at Health Village Apart...
2650 Dade Ave, Orlando, FL 32804 -
|
-
|
-
-
-
STUDIO$1,360+1 BED$1,482+2 BEDS$1,648+3 BEDS$1,932+Westmount at Winter Park
1701 Lee Rd, Winter Park, FL 32789 -
-
1 BED$1,216+2 BEDS$1,329+3 BEDS$1,899+
Summerlin at Winter Park Apartments
3207 Rosebud Ln, Winter Park, FL 32792
Showing 42 of 125 results, Page 2 of 3
Winter Park at a Glance
Renting in Winter Park
Average Rental Rates and Apartment Sizes
- Apartment Type Average Sq Ft Average Rent
- Studio 538 Sq Ft $1,419 / mo
- 1 Bedroom 707 Sq Ft $1,519 / mo
- 2 Bedrooms 1,019 Sq Ft $1,785 / mo
- 3 Bedrooms 1,271 Sq Ft $2,045 / mo
- 4 Bedrooms 1,506 Sq Ft $1,521 / mo
Top Budget-Friendly Neighborhoods in Winter Park
(For 1 bedroom apartments)- Neighborhoods Average Sq Ft Average Rent
- Winter Park Woods 767 Sq Ft $1,406/mo
- Winter Park Pines 722 Sq Ft $1,425/mo
- Cedarwood Village 672 Sq Ft $1,504/mo
- Four Seasons 651 Sq Ft $1,527/mo
- Winter Park Pines Merrie Oaks 651 Sq Ft $1,527/mo
- Eastbrook 740 Sq Ft $1,559/mo
- Lake Howell 733 Sq Ft $1,635/mo
- Winter Park Estates 682 Sq Ft $1,646/mo
- Windward Square 781 Sq Ft $1,657/mo
- Laurel Springs 731 Sq Ft $1,739/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.