Apartments for Rent in Winter Park, FL under $1500
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1 bd $1,344Base rent Income restricted550 N. Denning Drive, Winter Park, FL 32789Apply online • Pet friendly • Parking
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Studio $1,344+1 bd $1,449+Base rent4.0 (21)1701 Lee Road, Winter Park, FL 32789Pet friendly • Fitness center • Pool
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1 bd $1,200Base rent1695 Lee Rd, Winter Park, FL 32789Pet friendly • Pool • Dishwasher
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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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2 bd $1,436+Base rent Income restricted5.0 (185)7451 Gatehouse Circle, Orlando, FL 32807Apply online • Pet friendly • Parking
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1 bd $1,325+Total monthly cost3250 Whisper Lake Ln, Winter Park, FL 32792Apply online • Pet friendly • Air conditioner
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1 bd $1,325+2 bd $1,495+Base rent4.5 (5)541 Oak Reserve Lane, Winter Park, FL 32792Apply online • Pet friendly • Parking
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1 bd $1,291Base rent Income restricted4.0 (13)525 Sybelia Pkwy, Maitland, FL 32751Apply online • Pet friendly • Parking
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1 bd $1,299+Base rent4.0 (92)1166 Pointe Newport Terrace Drive, Casselberry, FL 32707Apply online • Pet friendly • Fitness center
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Studio $1,210+1 bd $1,210+2 bd $1,400+Base rent4.0 (13)1001 Shoreview Drive, Orlando, FL 32807Apply online • Pet friendly • Fitness center
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1 bd $1,295+2 bd $1,495+Base rent4.5 (25)7950 Shoals Drive, Orlando, FL 32817Apply online • Pet friendly • Fitness center
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1 bd $1,377Base rent Income restricted315 W. Concord Street, Orlando, FL 32801Apply online • Parking • Fitness center
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1 bd $1,3002 bd $1,400+Base rent4.0 (113)3040 Aloma Avenue, WINTER PARK, FL 32792Pet friendly • Pool • Patio/Balcony
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1 bd $1,276+Base rent4.5 (7)3250 Bishop Park Dr, Winter Park, FL 32792Pet friendly • Fitness center • Pool
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1 bd $1,351+Base rent4.5 (23)3935 Sutton Place Blvd, Winter Park, FL 32792Pet friendly • Fitness center • Pool
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1 bd $1,180Base rent4.0 (11)6031 Old Cheney Hwy, Orlando, FL 32807Pet friendly
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1 bd $1,180Base rent5.0 (2)6031 Old Cheney Highway, Orlando, FL 32807Pet friendly
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1 bd $1,291Base rent Income restricted3.0 (5)5560 Solidago Drive, Winter Park, FL 32792
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1 bd $1,286Base rent Income restricted365 Garden Edge Point, Fern Park, FL 32730Pet friendly • Fitness center • Patio/Balcony
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1 bd $1,361+2 bd $1,446+Base rent4.0 (37)3207 Rosebud Lane, Winter Park, FL 32792Pet friendly • Fitness center • Pool
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2 bd $950+Base rent270 Jasmine Road, Casselberry, FL 32707Pet friendly -
Studio $1,1791 bd $1,2492 bd $1,349Base rent4.0 (37)Spring Tree Village Apartments, Casselberry, FL 32707Pet friendly
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1 bd $1,2192 bd $1,4643 bd $1,419+Base rent Income restricted3.0 (7)315 W. Concord Street, Orlando, FL 32801Parking • Fitness center • Patio/Balcony
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1 bd $1,100Base rentUnit A, Altamonte Springs, FL 32714Pet friendly -
Studio $1,375Base rent715 Palm Dr, Orlando, FL 32803Air conditioner
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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 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 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.
Your search for apartments in Winter Park, FL under $1,500 stops here
Finding apartments for rent in Winter Park, FL for less than $1,500 has never been so easy! At RentCafe nice cheap apartments are just one click away. There are currently 58 available units in Winter Park, FL, renting for under $1,500. On average, $1,439 can get you 834 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.
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Having to compromise on either price or location can turn your “apartments near me under $1,500” 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 $1,500 in Winter Park, FL goes for $950 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.