Apartments for Rent in Winter Park, FL under $2000
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Studio $1,139+1 bd $1,466+2 bd $1,466+Base rent4.0 (20)1701 Lee Road, Winter Park, FL 32789Apply online • Pet friendly • Fitness center
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1 bd $1,911+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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1 bd $1,545+Base rent1512 Indiana 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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Studio $1,300+Base rent801 Virginia Drive, Winter Park, FL 32789Pet friendly -
More Rentals Near Winter Park, FL
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1 bd $1,923+Base rent4.5 (15)4460 Lower Park Road, Orlando, FL 32814Apply online • Pet friendly • Parking
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1 bd $1,783+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 $1,880+Base rent4.0 (2)1305 Morgan Stanley Ave, Winter Park, FL 32789Apply online • Pet friendly • Parking
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1 bd $1,300+2 bd $1,400+3 bd $1,750Base rent4.0 (111)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 (30)741 Clay Street, Winter Park, FL 32789Apply online • Pet friendly • Parking
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1 bd $1,392+2 bd $1,643+Base rent4.5 (7)3250 Bishop Park Dr, Winter Park, FL 32792Apply online • Pet friendly • Fitness center
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2 bd $1,650Base rent625 Trinidad Ct., Winter Park, FL 32792Apply online
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Studio $1,584+1 bd $1,852+Base rent4.0 (13)1874 Harmon Avenue, Winter Park, FL 32789Apply online • Pet friendly
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1 bd $1,710+Base rent4.0 (49)4688 New Broad Street, Orlando, FL 32814Apply online • Pet friendly • Parking
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1 bd $1,2912 bd $1,525Base rent Income restricted4.0 (13)525 Sybelia Pkwy, Maitland, FL 32751Apply online • Pet friendly • Parking
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Studio $1,686+1 bd $1,985+Total monthly cost4.0 (2)2680 North Orange, Orlando, FL 32804Apply online • Pet friendly • Fitness center
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Studio $1,698+1 bd $1,790+Base rent3.5 (12)2650 Dade Avenue, Orlando, FL 32804Apply online • Pet friendly • Parking
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1 bd $1,782+Base rent4.5 (24)9264 Moss Preserve Pkwy., Orlando, FL 32832Apply online • Pet friendly • Air conditioner
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1 bd $1,375+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 $1,291+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 $1,954+Base rent4.5 (2)295 NE Ivanhoe Blvd., Orlando, FL 32804Apply online • Pet friendly • Parking
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Studio $1,840+1 bd $1,905+Base rent4.5 (2)601 Trelago Way, Maitland, FL 32751Apply 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 18 Jun 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, Indiana Ave. Triplex and 1055 S Kentucky 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.
Search for apartments in Winter Park, FL under $2,000
There’s more than one way to spend $2,000 on rent in Winter Park, FL, so the first step is to start thinking about what you really want from your new home. Be mindful of what makes you tick. Look for 2 bedroom apartments for rent for less than $2,000 if you want to share your living space and don’t mind being further away from the city center. Search for 3 bedroom apartments if you’re moving in with family or planning to share part of your life and living expenses with more friends. If city bustle is what you live for, you might want to search for a studio or 1 bedroom apartment closer to the city center.
The perfect $2,000 rental near you
Don’t dismiss the idea of a studio just because it sounds small and featureless: studios come in many shapes and sizes, and it only takes a few strikes of creativity to go from drab to lively. If an all-in-one-room apartment spells total lack of privacy for you, have a look at the 1 bedroom apartments for rent in Winter Park, FL. Customize your search by using more RentCafe filters. Decide what amenities you can’t live without and focus your search on the apartments that offer them. Are you bringing in a pet? Narrow your options to pet-friendly apartments for rent. Want more windows so that natural light floods your home? Hardwood floors or plush carpet in the living area? There are 25 apartments for rent below $2,000 in Winter Park, FL for every taste. Decide what you need, stay focused, and you’re bound to find your perfect apartment in no time.