9

Oakland, FL Houses for Rent

Section Image
  • /46

    $4,800 Per Month

    • 5 Beds
    • 9 Baths
    • 3,575 Sq Ft
    • House for Rent

    5806 Fabry St, Oakland, FL 34787

    Brand new and exceptionally spacious home featuring a modern open-concept floor plan with premium upgrades throughout. This beautifully designed property offers expansive living areas filled with natural light, high ceilings, and elegant finishes that create a luxurious yet comfortable atmosphere. The gourmet kitchen showcases upgraded cabinetry, quartz countertops, a large center island, custom

    Jessyka Dos Santos WRA BUSINESS & REAL ESTATE

    5806 Fabry 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
  • /26

    $3,550 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,489 Sq Ft
    • House for Rent

    15663 Pelican Cay Dr, Oakland, FL 34787

    PRICE REDUCED – Now $3595 for immediate move-in! This well-maintained 2021-built home is located in the Waterleigh community in Winter Garden. The two-story layout includes 4 bedrooms and 3.5 bathrooms, including a private first-floor bedroom with an attached full bath, providing a flexible living arrangement. The open-concept main living area features a kitchen with stainless steel appliances

    Steven Koleno BEYCOME OF FLORIDA LLC

    15663 Pelican Cay Dr, Oakland, FL 34787
  • /17

    $3,800 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,861 Sq Ft
    • House for Rent

    15030 Summer Harvest St, Oakland, FL 34787

    Nestled in the sought-after Harvest at Ovation community in Horizon West/Winter Garden, this beautifully appointed single-family home offers the perfect combination of comfort, style, and location. Featuring 4 bedrooms, 3 full bathrooms, and 1 half bath, the home includes a desirable first-floor suite—ideal for guests or multi-generational living. Enjoy the convenience of being just minutes from

    Cristiane Leon KICANTO REALTY

    15030 Summer Harvest 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
  • /23

    $2,900 Per Month

    • 3 Beds
    • 2 Baths
    • 1,788 Sq Ft
    • House for Rent

    17651 Japonica Bloom Dr, Oakland, FL 34787

    Beautiful, brand-new 3-bedroom, 2-bath single-family home situated on a desirable corner lot, offering 1,788 sq ft of living space. This modern home features an open-concept layout with a contemporary kitchen equipped with stainless steel appliances, granite countertops, and a spacious island. Tile flooring runs throughout the entire home, including all bedrooms, providing a clean and cohesive

    Leidy Sanquiz ROMAN'S PRO REALTY LLC

    17651 Japonica Bloom Dr, Oakland, FL 34787
  • /28

    $2,550 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,451 Sq Ft
    • House for Rent

    13323 Pontoon Rd, Oakland, FL 34787

    Beautiful and well maintained 3bedroom, 2.5 bath townhouse located in the highly sought-after WaterLeigh community in Winter Garden. This property offers an open-concept layout with abundant natural light, a modern kitchen with all appliances included, and spacious living and dining areas ideal for comfortable everyday living. All bedrooms are located upstairs, including a generous primary suite

    Monica Paz LA ROSA REALTY INTERNACIONAL L

    13323 Pontoon Rd, Oakland, 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

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 May 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 $119,000 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 $2,975 per month in Oakland, FL, renters typically need to show $8,925 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 17.8, 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, Greater Hills, Prairie Lake, MetroWest and West Oaks, each with its own character and price range.

Rental Home Trends in Oakland, FL

Rental Home Trends

Number of Houses for Rent
9
Median Single Family Home Rent
$3,100
Median 3 Bedroom Single Family Home Rent
$2,800
Median 4 Bedroom Single Family Home Rent
$3,150
Median 5 Bedroom Single Family Home Rent
$4,000
How to Rent a Home