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  3. Interior Photo - Winterwoods
    1 Month Free
    1 Month Free
    STUDIO
    $1,177+
    1 BED
    $1,349+
    2 BEDS
    $1,600+

    Winterwoods

    15300 W Colonial Dr, Winter Garden, FL 34787
    Call
  4. Building Photo - 726 Regina Cir
    5 BEDS, 4 BATHS
    $3,945

    726 Regina Cir

    726 Regina Cir, Oakland, FL 34787
  21. 3 BEDS, 2.5 BATHS
    $2,295

    Tucker Oaks

    15345 Oak Apple Ct, Winter Garden, FL 34787

Oakland at a Glance

Average Rent

$1,804
(All bedrooms and property types)
Learn more about
Average Rent in Oakland
0

School Rating

out of 10 Rating
Learn more about
Schools in Oakland
2

Some Transit

out of 100 TransitScore® Rating
Learn more about
Transportation in Oakland
43

Somewhat Bikeable

out of 100 BikeScore® Rating
Learn more about
Transportation in Oakland

Oakland, FL Apartments for Rent

Oakland, Florida offers a small-town atmosphere with a rich history dating back to 1887. Those searching for apartments for rent in Oakland will appreciate its location within the Orlando-Kissimmee Metropolitan Area, just 24 miles west of downtown Orlando. The town's 2.36 square miles feature tree-lined streets, historic architecture, and well-maintained parks, creating a distinct identity within western Orange County.

Apartments for rent in Oakland place residents near outdoor recreation destinations like Lake Apopka and the West Orange Trail, which runs through the center of town. The paved, 22-mile West Orange Trail connects Oakland to Winter Garden and Apopka, offering opportunities for walking, cycling, and skating. The town maintains several public parks, including Speer Park and VanderLey Park, while the Oakland Nature Preserve provides boardwalks and educational programs focused on Lake Apopka's ecosystem.

Renting in Oakland

Average Rental Rates and Apartment Sizes

Top Budget-Friendly Neighborhoods in Oakland

(For 1 bedroom apartments)

Average Rent in Nearby Cities

(For 1 bedroom apartments)

Getting Around Oakland

Transportation

20

Car-Dependent

out of 100 WalkScore® Rating
You might be able to get out and walk when living in this area. Some errands can be accomplished on foot, but for others you need a car.
43

Somewhat Bikeable

out of 100 BikeScore® Rating
You might be able to find places to ride your bike in this area, but you'll most likely want your car for most errands.
2

Minimal Transit

out of 100 TransitScore® Rating
You'll likely want a car when living in this area since it has few transit options.
Scores provided by Walk Scoreⓘ

Education

Data provided by GreatSchools.org 2025 © 2025. All rights reserved.

Apartments for Rent Near Oakland

Specialty Housing

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Oakland Apartments for Rent in Your Budget

Frequently asked questions about renting in Oakland, FL

What are the average rent costs in Oakland, FL?

The average rent in Oakland, FL is $1,804.

What are the average rent costs of a studio apartment in Oakland, FL?

The average rent for a studio apartment in Oakland, FL is $1,571.

What are the average rent costs of a one bedroom apartment in Oakland, FL?

The average rent for a 1 bedroom apartment in Oakland, FL is $1,804.

What are the average rent costs of a two bedroom apartment in Oakland, FL?

The average rent for a 2 bedroom apartment in Oakland, FL is $2,027.

What are the average rent costs of a three bedroom apartment in Oakland, FL?

The average rent for a 3 bedroom apartment in Oakland, FL is $2,691.

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