20

Newest Homes for Rent in Oakland, FL

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    Starting at $1,601

    Total Monthly Price

    • Studio - 3 Beds

    751 W Oakland Ave, Oakland, FL 34787

    Perfectly located in Oakland, Florida with easy access to the West Orange bike trail and minutes from the historic downtown Winter Garden and the Florida Turnpike. The Avenue offers unparalleled amenities and an exquisite collection of studios, one, two- and three-bedroom apartment homes.

    AVENUE ON OAKLAND

    (352) 717-7596

    751 W Oakland Ave, Oakland, FL 34787
  • /36

    $2,750 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,636 Sq Ft
    • Townhouse for Rent

    10768 Rhett Butler Aly, Winter Garden, FL 34787

    Just like new! Designed for modern living, this beautifully maintained 3-bedroom, 2.5-bath townhome is available for rent in the highly desirable Storey Grove community. Built in 2023, this home offers contemporary style, comfort, and convenience near Orlando’s top attractions.The open-concept first floor features tile flooring throughout, a spacious living and dining area, and a modern

    Emilia Faria KARDOSH REALTY

    10768 Rhett Butler Aly, Winter Garden, FL 34787
  • /18

    $2,500 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,873 Sq Ft
    • Townhouse for Rent

    3115 Mindfullness Dr, Oakland, FL 34787

    Stunning brand-new townhome located in the highly sought-after Wellness Ridge community in Clermont. This elegant two-story residence offers 3 spacious bedrooms, 2.5 bathrooms, and a thoughtfully designed open-concept floor plan filled with natural light and modern finishes throughout.The gourmet kitchen features contemporary cabinetry, stainless steel appliances, and a seamless flow into the

    Bruna Sereno SELECTA REALTY LLC

    3115 Mindfullness Dr, Oakland, FL 34787
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    $2,450 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,689 Sq Ft
    • Townhouse for Rent

    6057 Zen Way, Oakland, FL 34787

    Stunning and contemporary townhome located in the highly desirable Wellness Ridge community in Clermont. This beautifully designed residence showcases modern finishes, an open-concept floor plan, and an abundance of natural light throughout.The gourmet kitchen features sleek cabinetry, stainless steel appliances, and a seamless flow into the spacious living and dining areas—perfect for both

    Bruna Sereno SELECTA REALTY LLC

    6057 Zen Way, Oakland, FL 34787
  • /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
  • /37

    $2,900 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,687 Sq Ft
    • Townhouse for Rent

    9109 Legado Dr, Oakland, FL 34787

    Welcome to your new home in one of Central Florida’s most desirable communities! This beautiful residence offers the perfect blend of comfort, convenience, and resort-style living just minutes from the magic of Disney World. Step inside this corner unit, ideally positioned with no neighbors on one side, and discover a spacious, open-concept layout designed for modern living. The gourmet kitchen

    George Berry, III DIAMOND REAL ESTATE GROUP

    9109 Legado Dr, Oakland, FL 34787
  • /22

    $3,149 Per Month

    • 3 Beds
    • 3.5 Baths
    • 1,894 Sq Ft
    • Townhouse for Rent

    6678 Juneberry Way, Oakland, FL 34787

    LIVE WHERE LIFESTYLE MEETS LOCATION • MOVE-IN READY • HEART OF HAMLIN Experience elevated living in this stunning three-story townhome in Parkview at Hamlin featuring 3 BEDROOMS, 2.5 BATHROOMS, and over 1,850 SQ FT of bright, modern space designed to impress. From the moment you walk through the 8’ entry door, you’re welcomed by a versatile FLEX SPACE perfect for a home office or gym, leading

    Marisol Goncalvez De Ayala AGENT TRUST REALTY CORPORATION

    6678 Juneberry Way, Oakland, FL 34787
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    $2,650 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,654 Sq Ft
    • Townhouse for Rent

    12067 Holystone St, Oakland, FL 34787

    Beautiful corner-unit home for rent in the highly sought-after Waterleigh community in Winter Garden. This spacious property features 3 bedrooms, 2.5 bathrooms, and an open, functional layout filled with natural light thanks to its premium corner location.Enjoy the convenience of being short distance to Atwater Bay Elementary, making daily routines effortless for families. Located in a true

    Aura Ruiz LA ROSA REALTY LLC

    12067 Holystone St, Oakland, FL 34787
  • /41

    $3,500 Per Month

    • 4 Beds
    • 3.5 Baths
    • 2,278 Sq Ft
    • House for Rent

    15141 Summer Harvest St, Oakland, FL 34787

    is a newly built single-family home completed in 2024 featuring approximately 2,450 square feet of living space. The property offers 4 bedrooms and around 3.5 to 4 bathrooms, designed with a modern open-concept layout. It includes a spacious gourmet kitchen with a large island, stainless steel appliances, and granite countertops, along with a comfortable living area ideal for entertaining. The

    Agent Photo

    Elaine Garcia

    GARCIA REALTY GROUP

    (321) 252-2876

    15141 Summer Harvest 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
  • /48

    $2,950 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,094 Sq Ft
    • Coming Soon! Gorgeous Townhome For Rent in Horizon West Winter Garden just west of Disney off th...

    14387 Braemar St, Oakland, FL 34787

    Visit the full 360 Video here: Gorgeous Brand-New construction 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

    14387 Braemar St, 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
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    $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
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    $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
  • /50

    $2,650 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,620 Sq Ft
    • Townhouse for Rent

    2208 Gopher Tortoise Terrace, Oakland, FL 34760

    Welcome to this beautifully appointed townhome in the desirable Longleaf at Oakland community. This charming residence features 3 bedrooms and 2.5 bathrooms with a thoughtfully designed open-concept layout. Stylish Vinyl flooring enhances the spacious living and dining areas, creating a warm and inviting atmosphere. The large open kitchen offers a large island with seating for four, granite

    Fred Mansfield ORLANDO PROP MGMNT RLTY LLC

    2208 Gopher Tortoise Terrace, Oakland, FL 34760
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    $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
  • /26

    $3,595 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
  • /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
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    $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 home in Oakland, FL?
The median rent for a home in Oakland, FL is $2,925 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 $117,000 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 $2,925 per month in Oakland, FL, renters typically need to show $8,775 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 18.1, 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 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 home include Bella Collina, Greater Hills, Lost Lake, West Oaks and Indian Hills, each with its own character and price range.

Rental Home Trends in Oakland, FL

Rental Home Trends

Number of Homes for Rent
20
Median Rent
$2,925
Median Single Family Home Rent
$3,100
Median Townhouse Rent
$2,700
Median Condo Rent
$2,775
How to Rent a Home