Apartments for Rent in Winter Park, FL under $1400
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Studio $1,356+Base rent4.0 (21)1701 Lee Road, Winter Park, FL 32789Apply online • Pet friendly • Fitness center
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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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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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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 $1,300+2 bd $1,400+Base rent4.0 (113)3040 Aloma Avenue, WINTER PARK, FL 32792Apply online • Pet friendly • Pool
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1 bd $1,276+Base rent4.5 (7)3250 Bishop Park Dr, Winter Park, FL 32792Apply online • Pet friendly • Fitness center
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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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1 bd $1,351+Base rent4.5 (23)3935 Sutton Place Blvd, Winter Park, FL 32792Apply 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 $1,180Base 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 $1,361+Base rent4.0 (37)3207 Rosebud Lane, Winter Park, FL 32792Apply online • Pet friendly • Fitness center
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1 bd $1,295+Base rent4.5 (25)7950 Shoals Drive, Orlando, FL 32817Apply online • Pet friendly • Fitness center
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Studio $1,1791 bd $1,2492 bd $1,349Base rent4.0 (37)Spring Tree Village Apartments, 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 • Parking • 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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Studio $1,158+1 bd $1,152+2 bd $1,063+Base rent4.5 (2)828 Orienta Ave, Altamonte Springs, FL 32701Apply online • Pet friendly • Parking
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Studio $1,300+Base rent801 Virginia Drive, Orlando, FL 32803Pet friendly -
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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2 bd $950+Base rent270 Jasmine Road, Casselberry, FL 32707Pet friendly -
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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 16 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 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.
Renting apartments in Winter Park, FL under $1,400
Searching for apartments for rent in Winter Park, FL under $1,400 is not an easy task, but luckily you have come to the right place. Whether you are a student on a budget, a young professional on the move, or simply a frugal person, RentCafe can help you find what you are looking for. Just make sure you know what you consider non-negotiable and what you can compromise on. Your new home is just a few clicks away. In Winter Park, FL, where the average rent is $1,385 per month, there are 114 units available for less than $1,400. Click on any of these units to see pictures, floor plans, amenities and more. After you have picked your favorite, you can contact the property to check availability. Considering that you are trying to spend as little as possible, looking at 1 bedroom apartments and studio apartments might be a good idea.
We’ll help you find the cheapest rental near you
Finding a nice cheap apartment is by no means impossible. You just have to be patient. Your “apartments near me under $1,400” search can bear fruit sooner than you think if you look carefully and check our site often. You never know when discount deals and special offers might pop up. Keep in mind that you are not the only one looking for an affordable apartment in Winter Park, FL. Choose “Save Search” to receive the latest apartments available directly to your inbox. This way, you will be able to stay one step ahead of the competition. With the cheapest apartments in Winter Park, FL going for $950 per month, there are great deals waiting to be discovered. Feeling lucky? Expand your search to 2 bedroom apartments and 3 bedroom apartments as well for more space.