Oakland, FL Houses for Rent

/22
$2,950 Per Month
- 4 Beds
- 2.5 Baths
- 2,094 Sq Ft
- House for Rent
14387 Braemar St, Oakland, FL 34787

Gorgeous Townhome just west of Disney off the 429 located in the Highland Ridge subdivision, offers modern living at its finest! This spacious two-story, 4-bedrooms, 2.5 bathrooms, residence provides ample space for comfortable, energy efficient living under 2,114 sq ft. Enjoy the convenience of a fully equipped kitchen featuring brand new stainless steel appliances. The kitchen boasts beautiful

Eileen Scates SCATES REALTY & INVESTMENT PRO

14387 Braemar St, Oakland, FL 34787
/24
$2,850 Per Month
- 3 Beds
- 2 Baths
- 1,755 Sq Ft
- House for Rent
10672 Words Dr, Winter Garden, FL 34787

Welcome home in the master planned community of Storey Grove! Minutes from Downtown WINTER GARDEN, this stunning 3-Bedroom, 2 1/2 Bath, 2 car garage Townhome property is situated just minutes from world class theme parks and attractions. Enjoying local restaurants and shopping just a short drive away. Love the outdoors? Slow down the pace and explore nearby parks and farmer's markets. Your

10672 Words Dr, Winter Garden, FL 34787
/41
$3,000 Per Month
- 3 Beds
- 2.5 Baths
- 2,014 Sq Ft
- House for Rent
9588 Jacques Aly, Oakland, FL 34787

Welcome to Waterleigh in the desirable area of Horizon West located in Winter Garden, FL. “Come Here and Stay” in this stunning community situated on over 1,400 acres of land with over a dozen lakes and ponds. Check out one of Waterleigh’s most popular bungalow floor-plans the Cordale offering 4 bedrooms, 2.5 bathrooms, and an attached 2 car garage. Enjoy the water view, while sitting on the

Teresa Valdes VALSTAR REALTY LLC

9588 Jacques Aly, Oakland, FL 34787
/50
$6,000 Per Month
- 4 Beds
- 4 Baths
- 3,760 Sq Ft
- House for Rent
705 Largovista Dr, Oakland, FL 34787

Come view this newly built 4 bed/4 bath two-story home in the gated community of John's Landing! Inside, you'll find a bright and airy open layout featuring an impressive vaulted ceiling, large windows, and elegant flooring throughout. The stunning kitchen includes custom built-in Thermador appliances and solid wood cabinetry. The primary suite features vaulted ceilings, a spa-style bath with a

705 Largovista Dr, Oakland, FL 34787
/13
$2,850 Per Month
- 3 Beds
- 2.5 Baths
- 1,770 Sq Ft
- House for Rent
11428 Great Rock St, Oakland, FL 34787

TENANT OCCUPIED – Available August 1, 2026. Welcome to this beautiful 3-bedroom, 2.5-bath home in the sought-after Storey Grove community of Winter Garden. Featuring an open-concept floor plan, 42" cabinets, quartz countertops, and spacious living areas, this home offers both comfort and style. All bedrooms are located upstairs, providing added privacy. Enjoy the fully fenced backyard, perfect

Jackie Yuan JHY REALTY INVESTMENTS, LLC

11428 Great Rock St, Oakland, FL 34787
/29
$2,595 Per Month
- 4 Beds
- 2 Baths
- 1,778 Sq Ft
- House for Rent
17802 Jefferson St, Oakland, FL 34787

Spacious 4 Bedroom, 2 Bath Split Plan Lake View House with Oversized Corner Lot. Owner has recently updated Home. New Paint on Interior. Tile throughout Home. Fireplace has Granite Hearth and Travertine Facing. Newer Custom Kitchen with granite tops, tumbled marble back splash with decorative tiles. Newer Stainless Steel Appliances. Master bath has Frameless Shower Door. No Sewer Bill. No Water

Barry Stephens MAINFRAME REAL ESTATE

17802 Jefferson St, Oakland, FL 34787
/20
$2,800 Per Month
- 4 Beds
- 2.5 Baths
- 2,221 Sq Ft
- House for Rent
2081 Standing Rock Cir, Winter Garden, FL 34787

Move-in ready 4-bedroom, 2.5-bath home located in a desirable Winter Garden/Oakland community. This spacious two-story residence features a functional floor plan with generous living areas, large bedrooms, and ample closet space throughout. Brand-new luxury vinyl flooring was installed on the entire second floor this month, while the main level offers easy-maintenance flooring and no carpet

Andrea Pointon POINTON REALTY INC

2081 Standing Rock Cir, Winter Garden, FL 34787
/76
$5,500 Per Month
- 5 Beds
- 4.5 Baths
- 3,653 Sq Ft
- House for Rent
15511 Shorebird Ln, Oakland, FL 34787

Welcome to this open plan 5 Bedroom, 4 and a half bathroom water front home including a 3 car garage.Flooring includes tile, laminate and carpet. You will never run out of storage with the abundance of cabinets. Chef's kitchen include upgraded appliances and wall oven. Large sliders allow plenty of light and gorgeous water view and open to a covered lanai. Some of the amenities include a

Mark Volchko REALTY WORLD PREFERRED

15511 Shorebird Ln, Oakland, FL 34787

Florida Orange County Oakland

Frequently Asked Questions

How much does it cost to rent a single-family home in Oakland, FL?

The median rent for a single-family home in Oakland, FL is $3,100 per month, though prices vary by neighborhood, size, and property type. As of July 2026, townhouses tend to be the most affordable option while condos and single-family homes are currently more expensive.

How much do you need to make to afford rent in Oakland, FL?

To comfortably afford the median rent in Oakland, FL, a household needs to earn roughly $120,000 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $3,000 per month in Oakland, FL, renters typically need to show $9,000 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.

Is it more affordable to rent or buy in Oakland, FL?

In Oakland, FL, the price-to-rent ratio is 17.6, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.

What neighborhoods in Oakland, FL are best for renting a single-family home?

The best neighborhood for renting in Oakland, FL depends on your priorities: commute, walkability, budget, and lifestyle all play a role. Popular areas for renting a single-family home include Bella Collina, Spring Valley, West Oaks, Prairie Lake and Lake Tibet, each with its own character and price range.

Rental Home Trends in Oakland, FL

There are currently 8 single-family homes available for rent in Oakland, FL. The median rent is $3,100 per month, with 3-bedroom houses renting at $2,825, 4-bedroom houses at $3,200 and 5-bedroom houses at $4,000.

Rental Home Trends

Number of Houses for Rent 8	Median Single Family Home Rent $3,100
Median 3 Bedroom Single Family Home Rent $2,825	Median 4 Bedroom Single Family Home Rent $3,200
Median 5 Bedroom Single Family Home Rent $4,000

How to Rent a Home

Houses for Rent by Price in Oakland

Oakland Houses for Rent under $3,000

Rentals in Oakland

Houses for Rent by Bedrooms in Oakland

More About Living in Oakland

Houses by Amenity in Oakland

Houses for Rent in Nearby Neighborhoods

Houses for Rent in Nearby Cities

Houses for Rent in Nearby Counties

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

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