Apartments for Rent in Winter Park, FL under $1400
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1 bd $1,344Base rent Income restricted550 N. Denning Drive, Winter Park, FL 32789Apply online • Pet friendly
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1 bd $1,300Base rent1695 Lee Rd, Winter Park, FL 32789Pet friendly
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More Rentals Near Winter Park, FL
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1 bd $1,195+Base rent4.0 (23)7950 Shoals Drive, Orlando, FL 32817Apply online • Pet friendly • Fitness center
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1 bd $1,295+Total monthly cost3250 Whisper Lake Ln, Winter Park, FL 32792Apply online • Pet friendly • Air conditioner
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1 bd $1,295+Base rent4.5 (5)541 Oak Reserve Lane, Winter Park, FL 32792Apply online • Pet friendly • Parking
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1 bd $1,300+2 bd $1,400Base rent4.0 (110)3040 Aloma Avenue, WINTER PARK, FL 32792Apply online • Pet friendly
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1 bd $1,364+Base rent4.5 (7)3250 Bishop Park Dr, Winter Park, FL 32792Apply online • Pet friendly
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1 bd $1,2912 bd $1,347+Base rent Income restricted4.0 (13)525 Sybelia Pkwy, Maitland, FL 32751Apply online • Pet friendly
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1 bd $1,375+Base rent4.0 (91)1166 Pointe Newport Terrace Drive, Casselberry, FL 32707Apply online • Pet friendly
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1 bd $1,381+Base rent4.5 (22)3935 Sutton Place Blvd, Winter Park, FL 32792Apply online • Pet friendly
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Studio $1,160+1 bd $1,185+2 bd $1,385+Base rent4.0 (13)1001 Shoreview Drive, Orlando, FL 32807Apply online • Pet friendly
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1 bd $1,180Base rent4.0 (11)6031 Old Cheney Hwy, Orlando, FL 32807Apply online • Pet friendly
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1 bd $1,180Base rent5.0 (2)6031 Old Cheney Highway, Orlando, FL 32807Apply online • Pet friendly
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1 bd $1,291Base rent Income restricted3.0 (5)5560 Solidago Drive, Winter Park, FL 32792Apply online
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1 bd $1,139+2 bd $1,369+Base rent Income restricted365 Garden Edge Point, Fern Park, FL 32730Apply online • Pet friendly
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1 bd $1,395+Base rent4.0 (36)3207 Rosebud Lane, Winter Park, FL 32792Apply online • Pet friendly
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Studio $1,1791 bd $1,2092 bd $1,309Base rent4.0 (35)986 Rollingwood Loop, Casselberry, FL 32707Apply online • Pet friendly
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1 bd $1,219Base rent Income restricted3.0 (7)315 W. Concord Street, Orlando, FL 32801Apply online
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1 bd $1,336+Base rent Income restricted315 W. Concord Street, Orlando, FL 32801Apply online
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1 bd $1,100Base rentUnit A, Altamonte Springs, FL 32714Pet friendly -
Studio $1,082+1 bd $1,164+2 bd $1,288+Base rent4.0 (1)828 Orienta Ave, Altamonte Springs, FL 32701Apply online • Pet friendly
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1 bd $1,210Base rent4.5 (22)400 Sandpiper Lane, Casselberry, FL 32707Apply online • Pet friendly
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2 bd $1,316Base rent Income restricted4.5 (15)2201 Weston Point Drive, Orlando, FL 32810Apply online • Pet friendly
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Studio $1,179+Base rent Income restricted4.0 (4)659 W. Amelia Street, Orlando, FL 32801Apply online • Pet friendly
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1 bd $6562 bd $768Base rent Income restricted3.5 (5)659 W. Amelia Street, Orlando, FL 32801Apply 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 15 May 2026.
What are the best apartments in Winter Park, FL?
The best apartments in Winter Park, FL are: Paseo at Winter Park Village, Westmount at Winter Park, 981 Aragon Ave., 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 housing is rented out compared to 66% of homes are owned, according to the most recent Census Bureau estimates. 32% of Winter Park's apartments are found in large buildings of 50 units or more, 45% are located in smaller apartment complexes with less than 50 units, and 23% are single-family rentals.