Apartments for Rent in Winter Park, FL under $2000
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Studio $1,145+1 bd $1,469+2 bd $1,475+Base rent4.0 (0)1701 Lee Road, Winter Park, FL 32789Apply online • Pet friendly
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1 bd $1,832+Base rent4.0 (0)940 W. Canton Avenue, Winter Park, FL 32789Apply online • Pet friendly
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2 bd $1,995Base rentUnits 1,2,3,4, Winter Park, FL 32792Apply online • Pet friendly
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1 bd $1,3442 bd $1,586Base rent Income restricted550 N. Denning Drive, Winter Park, FL 32789Apply online • Pet friendly
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2 bd $1,800Base rent205 Lewfield Circle, Winter Park, FL 32792Pet friendly
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1 bd $700Base rent2121 N Hastings St, Orlando, FL 32808Apply online • Dog friendly
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More Rentals Near Winter Park, FL
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1 bd $1,717+Base rent4.5 (2)190 Independence Lane, Maitland, FL 32751Apply online • Pet friendly • Parking
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1 bd $1,778+Base rent4.5 (2)955 N Orlando Ave, Maitland, FL 32751Apply online • Pet friendly • Pool
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1 bd $1,295+2 bd $1,590+Total monthly cost3250 Whisper Lake Ln, Winter Park, FL 32792Apply online • Pet friendly • Air conditioner
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1 bd $1,295+2 bd $1,495+Base rent4.5 (2)541 Oak Reserve Lane, Winter Park, FL 32792Apply online • Pet friendly • Parking
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Studio $1,916+Base rent4.0 (0)1305 Morgan Stanley Ave, Winter Park, FL 32789Apply online • Pet friendly
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1 bd $1,300+2 bd $1,4003 bd $1,750+Base rent4.0 (0)3040 Aloma Avenue, WINTER PARK, FL 32792Apply online • Pet friendly
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1 bd $1,854+Base rent4.5 (0)4460 Lower Park Road, Orlando, FL 32814Apply online • Pet friendly
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1 bd $1,300Base rent296 Lewfield Circle, Winter Park, FL 32792Pet friendly
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Studio $1,585+1 bd $1,695+Base rent4.5 (0)741 Clay Street, Winter Park, FL 32789Apply online • Pet friendly
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1 bd $1,393+2 bd $1,655+Base rent4.5 (0)3250 Bishop Park Dr, Winter Park, FL 32792Apply online • Pet friendly
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Studio $1,635+1 bd $1,710+Base rent4.0 (0)1874 Harmon Avenue, Winter Park, FL 32789Apply online • Pet friendly
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1 bd $1,810+Base rent4.0 (0)4688 New Broad Street, Orlando, FL 32814Apply online • Pet friendly
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1 bd $1,2912 bd $1,347+Base rent Income restricted4.0 (0)525 Sybelia Pkwy, Maitland, FL 32751Apply online • Pet friendly
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Studio $1,694+Total monthly cost4.0 (0)2680 North Orange, Orlando, FL 32804Apply online • Pet friendly
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Studio $1,689+1 bd $1,756+Base rent3.5 (0)2650 Dade Avenue, Orlando, FL 32804Apply online • Pet friendly
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Studio $1,695+1 bd $1,770+Base rent4.5 (0)9264 Moss Preserve Pkwy., Orlando, FL 32832Apply online • Pet friendly
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1 bd $1,375+2 bd $1,599+Base rent4.0 (0)1166 Pointe Newport Terrace Drive, Casselberry, FL 32707Apply online • Pet friendly
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1 bd $1,459+2 bd $1,768+Base rent4.5 (0)3935 Sutton Place Blvd, Winter Park, FL 32792Apply online • Pet friendly
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Studio $1,660+1 bd $1,780+Base rent4.5 (0)601 Trelago Way, Maitland, FL 32751Apply online • Pet friendly
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Frequently asked questions
When were prices and availability in Winter Park, FL last updated?
Prices and availability in Winter Park, FL were last updated on 4 May 2026.
What are the best apartments in Winter Park, FL?
The best apartments in Winter Park, FL are: 2029 Taylor Ave Winter Park, FL 32792, Westmount at Winter Park, Paseo at Winter Park Village, 1055 S Kentucky Ave and Village Park Senior Living.
What type of rental buildings are in Winter Park, FL?
In Winter Park, 34% of the residents are renting compared to 66% owning a home, according to data from the U.S. Census Bureau. Large-scale apartment buildings with more than 50 units represent 28% of Winter Park's rentals, 49% are small-scale complexes with under 50 units, and 23% are single-family rentals.