Apartments for Rent in Winter Park, FL under $2000
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Studio $1,344+1 bd $1,449+2 bd $1,647+Base rent4.0 (21)1701 Lee Road, Winter Park, FL 32789Apply online • Pet friendly • Fitness center
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1 bd $1,997+Base rent4.0 (6)940 W. Canton Avenue, Winter Park, FL 32789Apply online • Pet friendly • Parking
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1 bd $1,3442 bd $1,586Base rent Income restricted550 N. Denning Drive, Winter Park, FL 32789Apply online • Pet friendly • Parking
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Studio $1,300+Base rent801 Virginia Drive, Winter Park, FL 32789Pet friendly -
1 bd $1,650Base rent1512 Indiana Avenue, Winter Park, FL 32789Pet friendly
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2 bd $1,995Base rentUnits 1,2,3,4, Winter Park, FL 32792Pet friendly
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1 bd $1,300Base rent1695 Lee Rd, Winter Park, FL 32789Pet friendly • Pool • Dishwasher
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More Rentals Near Winter Park, FL
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1 bd $1,888+Base rent4.5 (15)4460 Lower Park Road, Orlando, FL 32814Apply online • Pet friendly • Parking
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1 bd $1,997+Base rent4.5 (9)190 Independence Lane, Maitland, FL 32751Apply online • Pet friendly • Parking
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1 bd $1,759+Base rent4.5 (19)955 N Orlando Ave, Maitland, FL 32751Apply online • Pet friendly • Pool
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1 bd $1,325+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 (5)541 Oak Reserve Lane, Winter Park, FL 32792Apply online • Pet friendly • Parking
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Studio $1,844+Base rent4.0 (2)1305 Morgan Stanley Ave, Winter Park, FL 32789Apply online • Pet friendly • Parking
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1 bd $1,3002 bd $1,400+3 bd $1,750Base rent4.0 (113)3040 Aloma Avenue, WINTER PARK, FL 32792Apply online • Pet friendly • Pool
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Studio $1,585+1 bd $1,695+Base rent4.5 (31)741 Clay Street, Winter Park, FL 32789Apply online • Pet friendly • Parking
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1 bd $1,392+2 bd $1,778+Base rent4.5 (7)3250 Bishop Park Dr, Winter Park, FL 32792Apply online • Pet friendly • Fitness center
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Studio $1,530+1 bd $1,739+Base rent4.0 (13)1874 Harmon Avenue, Winter Park, FL 32789Apply online • Pet friendly
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1 bd $1,840+Base rent4.0 (49)4688 New Broad Street, Orlando, FL 32814Apply online • Pet friendly • Parking
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1 bd $1,2912 bd $1,487+Base rent Income restricted4.0 (13)525 Sybelia Pkwy, Maitland, FL 32751Apply online • Pet friendly • Parking
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Studio $1,587+1 bd $1,857+Total monthly cost4.0 (2)2680 North Orange, Orlando, FL 32804Apply online • Pet friendly • Fitness center
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1 bd $1,725+Base rent4.0 (13)2650 Dade Avenue, Orlando, FL 32804Apply online • Pet friendly • Parking
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1 bd $1,745+Base rent4.5 (24)9264 Moss Preserve Pkwy., Orlando, FL 32832Apply online • Pet friendly • Air conditioner
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1 bd $1,299+2 bd $1,599+Base rent4.0 (92)1166 Pointe Newport Terrace Drive, Casselberry, FL 32707Apply online • Pet friendly • Fitness center
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1 bd $1,391+2 bd $1,699+Base rent4.5 (23)3935 Sutton Place Blvd, Winter Park, FL 32792Apply online • Pet friendly • Fitness center
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Studio $1,894+Base rent4.5 (2)295 NE Ivanhoe Blvd., Orlando, FL 32804Apply online • Pet friendly • Parking
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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 8 Jul 2026.
What are the best apartments in Winter Park, FL?
The best apartments in Winter Park, FL are: Westmount at Winter Park, Paseo at Winter Park Village, Village Park Senior Living, 981 Aragon Ave. and 971 Harmon Ave.
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 32% of Winter Park's rentals, 45% are small-scale complexes with under 50 units, and 23% are single-family rentals.
Your search for apartments in Winter Park, FL under $2,000 stops here
Finding apartments for rent in Winter Park, FL for less than $2,000 has never been so easy! At RentCafe nice cheap apartments are just one click away. There are currently 166 available units in Winter Park, FL, renting for under $2,000. On average, $2,096 can get you 1,033 Sqft in this area. Be sure to search for the apartment that is best for you. Under “More”, check the amenities that you consider a must-have, and don’t forget to look at the pet policy. Fitness enthusiasts can even check the Fitness Center box. Whether you are looking for studio apartments, 1 bedroom apartments, 2 bedroom apartments or 3 bedroom apartments, you are sure to find one that will make you want to move in right away.
We’ll help you find the best rental near you
Having to compromise on either price or location can turn your “apartments near me under $2,000” search into a nightmare. At RentCafe we recognize the importance of both. Therefore, we offer a variety of filters that can help you find exactly what you want. Sorting the results by rent, ascending, will make the cheapest units show up first on the list. Try it out! You will find that right now the cheapest apartment under $2,000 in Winter Park, FL goes for $1,291 per month. If some of the results are outside the area of your choice, you can go to the left side of the screen and draw a radius or a polygon around your location. Now you will only see results that are relevant to you.