Apartments for Rent in Winter Garden, FL under $2000
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1 bd $1,529+Base rent4.5 (18)9005 Solay Road, Winter Garden, FL 34787Apply online • Pet friendly • Dishwasher
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2 bd $1,715+Base rent4.5 (13)1240 Winter Garden Vineland Rd, Winter Garden, FL 34787Apply online • Pet friendly
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1 bd $1,5142 bd $1,599+Base rent Income restricted4.0 (6)15122 West Colonial Drive, Winter Garden, FL 34787Apply online • Pet friendly • Fitness center
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4 bd $1,985Base rent1030 Maxey Drive, Winter Garden, FL 34787Apply online • Pet friendly • Dishwasher
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More Rentals Near Winter Garden, FL
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1 bd $1,708+2 bd $1,975+Base rent4.5 (14)906 Oasis Palm Circle, Ocoee, FL 34761Apply online • Pet friendly • Parking
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Studio $1,864+1 bd $1,904+Total monthly cost4.5 (4)15055 Lake Britt Circle, Winter Garden, FL 34787Apply online • Pet friendly • Fitness center
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1 bd $1,435+2 bd $1,970+Base rent4.0 (133)100 Maguire Park St, Ocoee, FL 34761Apply online • Pet friendly • Parking
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Studio $1,4801 bd $1,685+2 bd $1,965Total monthly cost4.5 (4)2760 Southside Drive, Ocoee, FL 34761Apply online • Pet friendly • Parking
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1 bd $1,366+2 bd $1,739+Base rent4.5 (252)2415 Treasure Landing Pkwy, Ocoee, FL 34761Apply online • Pet friendly • Parking
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1 bd $1,659+2 bd $1,952+Base rent4.5 (60)13644 Tortona Lane, Windermere, FL 34786Apply online • Pet friendly
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1 bd $1,200+2 bd $1,542+Base rent4.0 (17)1024 Vizcaya Lake Road, Ocoee, FL 34761Apply online • Pet friendly • Fitness center
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1 bd $1,7502 bd $1,975Base rent4.5 (103)1236 Arbour Point Way, Ocoee, FL 34761Apply online • Pet friendly • Pool
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2 bd $1,7493 bd $1,590+4 bd $1,931Base rent Income restricted1724 London Crest Drive, Orlando, FL 32818Apply online • Pet friendly • Parking
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3 bd $1,999Base rent Income restricted3.0 (2)1724 London Crest Drive, Orlando, FL 32818Apply online • Pet friendly • Parking
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3 bd $1,965Base rent1836 Columbine Dr, Orlando, FL 32818Apply online • Pet friendly • Dishwasher
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1 bd $1,563+2 bd $1,803+Base rent4.0 (24)11598 Lachlan Lane, Windermere, FL 34786Apply online • Pet friendly • Parking
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1 bd $1,536+2 bd $125+Total monthly cost4.5 (13)6506 San Francesco Way, Windermere, FL 34786Apply online • Pet friendly • Fitness center
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1 bd $1,645+Base rent4.5 (29)7826 Crosswater Trail, Windermere, FL 34786Apply online • Pet friendly • Parking
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1 bd $1,373+2 bd $1,610+Base rent4.0 (23)2207 Lake Debra Drive, Orlando, FL 32835Apply online • Pet friendly • Parking
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Studio $1,719+1 bd $1,772+Base rent2317 Ocoee Apopka Road, Apopka, FL 32703Apply online • Pet friendly • Parking
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1 bd $1,272+2 bd $1,528+Base rent4.5 (1)6315 Westgate Dr., Orlando, FL 32835Apply online • Pet friendly
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4 bd $1,790Base rent5.0 (1)1324 N Powers Dr, Orlando, FL 32818Apply online • Pet friendly • Dishwasher
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Ask for pricingIncome restricted4.0 (4)7200 Woodhill Park Drive, Orlando, FL 32818Apply online • Pet friendly • Fitness center
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1 bd $1,2162 bd $1,4613 bd $1,688Base rent Income restricted4.0 (14)7351 Woodridge Park Drive, Orlando, FL 32818Pet friendly • Parking • Fitness center
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2 bd $2,000Base rent1418 Lamplighter Way, Orlando, FL 32818Dishwasher • Washer/Dryer
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Frequently asked questions
When were prices and availability in Winter Garden, FL last updated?
Prices and availability in Winter Garden, FL were last updated on 25 Jul 2026.
What are the best apartments in Winter Garden, FL?
The best apartments in Winter Garden, FL are: Solay Horizon West, Palm Crossing, Country Gardens, 988 Glenview Circle Winter Garden, FL 34787 and 1030 Maxey Drive Winter Garden, FL 34787.
What type of rental buildings are in Winter Garden, FL?
In Winter Garden 34% of the housing is rented out compared to 66% of homes are owned, according to the most recent Census Bureau estimates. 8% of Winter Garden's apartments are found in large buildings of 50 units or more, 49% are located in smaller apartment complexes with less than 50 units, and 41% are single-family rentals.
Search for apartments in Winter Garden, FL under $2,000
There’s more than one way to spend $2,000 on rent in Winter Garden, 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 Garden, 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 Garden, FL for every taste. Decide what you need, stay focused, and you’re bound to find your perfect apartment in no time.