20

Oakland, FL Homes for Rent

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  • /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
  • /16

    Starting at $1,466

    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
  • /20

    $2,400 Per Month

    • 3 Beds
    • 3 Baths
    • 1,647 Sq Ft
    • House for Rent

    6080 Zen Way, Oakland, FL 34787

    Beatiful home located in a desirable Clermont community. This property offers a functional floor plan with comfortable living spaces, a bright kitchen, and spacious bedrooms, conveniently located near US-27, shopping, dining, and major attractions, with easy access to Orlando and surrounding areas. A mandatory Resident Benefit Package of $50/month is required and includes renters insurance (up to

    Agent Photo

    Juliana Garcia Moraes

    PRISTINE INTERNATIONAL REALTY LLC

    (321) 321-7380

    6080 Zen Way, Oakland, FL 34787
  • /9

    $2,715 Per Month

    • 3 Beds
    • 2 Baths
    • 1,806 Sq Ft
    • House for Rent

    27 Oakland Pointe Cir, Oakland, FL 34760

    Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2859.90. That covers your base rent, $2715.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

    (321) 475-2523

    27 Oakland Pointe Cir, Oakland, FL 34760
  • /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
  • /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
  • /24

    $2,800 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,560 Sq Ft
    • Townhouse for Rent

    6224 Aralia Ivy Ln, Oakland, FL 34787

    Located in the heart of Horizon West and the Highly Desired Hamilton Gardens Community, this spacious open-concept 3-bedroom, 2.5-bath townhome blends modern convenience, smart-home technology, and resort-style community living. Easy access to 429, providing a smooth commute to Disney Parks, Universal, and all major Central Florida destinations also walkable to Hamlin Town Center, this home

    Yesenia Reyes ALL REAL ESTATE & INVESTMENTS

    6224 Aralia Ivy Ln, Oakland, 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
  • /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

    $3,595 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
  • /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
  • /13

    $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

    $2,795 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
  • /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

    $2,600 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
  • /12

    $2,600 Per Month

    • 3 Beds
    • 2 Baths
    • 1,858 Sq Ft
    • House for Rent

    1010 Stationside Dr, Oakland, FL 34787

    Charming 3 bedroom, 2 bath home located in Historic Oakland, just minutes from the Florida Turnpike, West Orange Bike Trail, and Downtown Winter Garden. A split-plan layout includes a formal dining room, formal living room or den that's also perfect for an office space and an open kitchen and dinette that flows seamlessly into a spacious family room, perfect for entertaining. The master bedroom

    Jeffrey Petch GECKO REALTY, INC

    1010 Stationside Dr, Oakland, FL 34787
  • /47

    $2,600 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,568 Sq Ft
    • Townhouse for Rent

    12032 Holystone St, Oakland, FL 34787

    Experience the charm of Waterleigh Community with this stunning 3 bedroom, 2.5 bathroom townhome available for rent. The open-concept main floor features a seamless living room, dining area, and kitchen with stainless steel appliances, including a modern refrigerator. Located in Waterleigh Phase 4 near both the Elementary and Middle School, this home welcomes you with granite countertops, a large

    Marcelo Lopes Santana FLORIDA CONNEXION PROPERTIES

    12032 Holystone St, Oakland, FL 34787
  • /14

    $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
  • /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
  • /35

    $2,550 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,652 Sq Ft
    • Townhouse for Rent

    4576 Maple Waltz, Oakland, FL 34787

    Corner Townhouse for Rent in Clermont, FL. Experience modern living near the highly anticipated Olympus Stadium project! This spacious corner townhome features 3 bedrooms, 2 full bathrooms, and a half bathroom (2.5 total baths), a convenient 2-car rear-facing garage, and a private, fenced rear courtyard perfect for entertaining. The open-concept first floor is ideal, boasting a gourmet kitchen

    Alessandra Oliveira FLORIDA CONNEXION PROPERTIES

    4576 Maple Waltz, Oakland, FL 34787

Why Live in Oakland

Between Lake Apopka and Johns Lake, Oakland, Florida is a small Orange County town with a strong connection to nature and lake access. About 18 miles west of downtown Orlando and 15 miles north of Walt Disney World, it sits close to major attractions while keeping a quiet, low-key feel. Residential streets feature coastal cottages, Colonial Revival homes, and modern traditional builds, many constructed in the 1970s or later, with a large share built in the past decade. Lots are generally a quarter-acre or smaller, shaded by mature oaks and Spanish moss, and many homes include in-ground pools; lakefront properties often add private docks and direct water access. Local students may attend Tildenville Elementary School, which has a high rating, and West Orange High School, also highly rated and known for its dual enrollment options and more than 50 extracurricular activities. Outdoor life centers on the 150-acre Oakland Nature Preserve with wooded trails and regular programs, Speer Park’s playground and sports courts, and the paved West Orange Trail, which runs over 22 miles and links to nearby Winter Garden businesses. The town center along Tubb Street includes the historic Oakland Town Hall and the Healthy West Orange Arts and Heritage Center, which hosts rotating exhibits, classes, and the Oakland Farmers Market, while everyday errands are handled at nearby ALDI and Publix and regional travel relies on Florida’s Turnpike, Route 408, and LYNX bus routes.

Frequently Asked Questions

What are the most popular neighborhoods in Oakland, FL for renters?
The most popular neighborhoods in Oakland, FL for renters are Bella Collina, Greater Hills, Lost Lake, West Oaks and Indian Hills.
What are the most popular zip codes in Oakland, FL for renters?
The most popular zip codes in Oakland, FL for renters include 34787, 34711, 34756, 34786 and 34715.

Rental Home Trends in Oakland, FL

Rental Home Trends

Number of Homes for Rent
20
Median Rent
$2,900
Median Single Family Home Rent
$3,100
Median Townhouse Rent
$2,700
Median Condo Rent
$2,775
How to Rent a Home