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Newest Homes for Rent in Oakland, FL

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  • /16

    Starting at $1,668

    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

    751 W Oakland Ave, Oakland, FL 34787
  • /17

    $1,475 Per Month

    • 1 Bed
    • 1 Bath
    • 500 Sq Ft
    • Apartment for Rent

    12761 Harvest Rain Ave, Oakland, FL 34787

    Beautiful private studio-style apartment located above the garage, offering privacy, comfort, and convenience in a highly desirable location. MONTHLY RENT INCLUDES ELECTRICITY, WATER, GAS, AND INTERNET.This charming open-concept space, and move-in-ready place to call home. It is also an excellent option for corporate housing, relocating professionals, traveling nurses, or anyone looking for a

    Aziz Elbrak LA ROSA REALTY LLC

    12761 Harvest Rain Ave, Oakland, FL 34787
  • /15

    $2,800 Per Month

    • 3 Beds
    • 2 Baths
    • 1,685 Sq Ft
    • House for Rent

    9321 Jaywood Rd, Oakland, FL 34787

    Available NOW! Welcome to this beautiful 3-/2 single-family home located in the highly desirable Waterleigh community of Winter Garden. A charming front porch invites you into a welcoming foyer flanked by two guest bedrooms and a full bathroom. Further inside, the well-appointed kitchen seamlessly overlooks the open-concept family room, dining area, and outdoor lanai. Designed for convenience,

    Valentina Naumenko MILA REALTY

    9321 Jaywood Rd, Oakland, FL 34787
  • /38

    $5,200 Per Month

    • 5 Beds
    • 3.5 Baths
    • 3,910 Sq Ft
    • House for Rent

    9566 Bolero Rd, Oakland, FL 34787

    Welcome to this stunning 5-bedroom, 3.5-bathroom, 3,910 sq. ft. home built in 2021, ideally situated on a quiet cul-de-sac with a 3-car garage, oversized fully fenced yard, and beautiful pond views. This spacious home features a desirable first-floor primary suite, two-story foyer, and a versatile upstairs loft.The gourmet kitchen is designed for both everyday living and entertaining,

    Tina Lopez LEGENDS REALTY

    9566 Bolero Rd, Oakland, FL 34787
  • /79

    $5,500 Per Month

    • 5 Beds
    • 4.5 Baths
    • 3,835 Sq Ft
    • House for Rent

    3324 Buoy Cir, Oakland, FL 34787

    Beautifully furnished and professionally decorated, this luxury residence immediately stands out with extensive upgrades, a PRIVATE POOL and peaceful CONSERVATION VIEWS in the GATED COMMUNITY of Lakeview Preserve. Featuring 5 bedrooms and 4.5 bathrooms, the home was originally showcased as a Taylor Morrison model and offers elevated finishes, generous living spaces and a floor plan designed for

    Gabriella Sadler SERHANT

    3324 Buoy Cir, Oakland, FL 34787
  • /49

    $4,799 Per Month

    • 5 Beds
    • 4 Baths
    • 3,760 Sq Ft
    • House for Rent

    9240 Sylvan Wds St, Oakland, FL 34787

    Spectacular 5/4 with 3 car garage home. This home has all the bells and whistles for your enjoyment, Modern kitchen with open floor plan to family/living room and access to large screened in patio. Fenced backyard. Upstairs has a large Loft and 4 bedrooms including the spacious master bedroom/master bathroom. This home is a must see located in Watermark Sub-division with to many features to

    9240 Sylvan Wds St, Oakland, FL 34787
  • /19

    $3,150 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,534 Sq Ft
    • House for Rent

    1530 Stone Arrow Ct, Winter Garden, FL 34787

    Spacious 4 bedroom, 2.5 bathroom house, no rear neighbors,Oakland Trails community features resort style pool, cabana, dog park, close to West Orange Trail and the Montverde Academy, right off Turnpike and West Colonial Drive. 6 mile away from Winter Garden Village Lawn care included in the rentThis home has open plan family room, dining area and large kitchen with granite

    1530 Stone Arrow Ct, Winter Garden, FL 34787
  • /19

    $2,699 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,628 Sq Ft
    • House for Rent

    16657 Silver Brook Way, Oakland, FL 34787

    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 $2796.90. That covers your base rent, $2699.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Community

    16657 Silver Brook Way, Oakland, FL 34787
  • /20

    $3,399 Per Month

    • 5 Beds
    • 3 Baths
    • 2,231 Sq Ft
    • House for Rent

    16669 Silver Brook Way, Oakland, FL 34787

    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 $3496.90. That covers your base rent, $3399.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Community

    16669 Silver Brook Way, Oakland, FL 34787
  • /15

    $2,949 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,913 Sq Ft
    • House for Rent

    16675 Silver Brook Way, Oakland, FL 34787

    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 $3046.90. That covers your base rent, $2949.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Community

    16675 Silver Brook Way, Oakland, FL 34787
  • /36

    $3,050 Per Month

    • 3 Beds
    • 3.5 Baths
    • 2,332 Sq Ft
    • House for Rent

    15153 Summer Harvest St, Oakland, FL 34787

    Live in the heart of Horizon West, just minutes from Disney! Located in one of Winter Garden’s most desirable areas, this spacious 3-bedroom, 3.5-bath single-family home offers comfort, style, and convenience just down the road from Flamingo Crossings Town Center, shopping, dining, and premier entertainment options. The open-concept main level features a bright great room, dining area, and a

    Carlinhos Fregonezi TALENT REALTY SOLUTIONS

    15153 Summer Harvest St, Oakland, FL 34787
  • /41

    $2,900 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,994 Sq Ft
    • House for Rent

    13075 Spring Grove Way, Oakland, FL 34787

    Welcome to the heart of Horizon West where location, lifestyle, and low-maintenance living come together! This home features an open-concept main floor, which features sleek ceramic plank flooring throughout, giving the space a modern, polished feel that's perfect for everyday living. With a serene pond located in front of the home, you'll love waking up to the peaceful water view right outside

    Rodrigo Barbosa PREMIER FLAT FEE REALTY LLC

    13075 Spring Grove Way, Oakland, FL 34787
  • /38

    $6,000 Per Month

    • 4 Beds
    • 3 Baths
    • 3,038 Sq Ft
    • House for Rent

    15075 Tea Tree Dr, Oakland, FL 34787

    Be the very first to live in this beautifully designed 4 bedroom, 3 bathroom, featuring a versatile flex room that is perfect for a home office, study, playroom, or additional living space. The 20-foot ceiling entryway creates a stunning first impression, leading into a bright and open main living area. The spacious kitchen features contemporary cabinetry, premium appliances, and a large island

    Agent Photo

    Silvia Valebom Fumagalli

    WRA BUSINESS & REAL ESTATE

    15075 Tea Tree Dr, Oakland, FL 34787
  • /30

    $3,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,881 Sq Ft
    • House for Rent

    6162 Glory Bower Dr, Oakland, FL 34787

    Welcome home! NEWLY RENOVATED move in ready 3 bed 2.5 bath in the desirable Horizon West Hamlin area, offering easy access to shopping, restaurants, and amenities nearby. The perfect home fitted with a modern kitchen entailing granite countertops, stainless steel appliances, natural gas burning stove, and large 3-seater island. New updates include laminate floors all throughout, window coverings,

    Ahmad Hassan COMPASS FLORIDA LLC

    6162 Glory Bower Dr, Oakland, FL 34787
  • /20

    $2,500 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,782 Sq Ft
    • House for Rent

    2895 Transformation Way, Oakland, FL 34787

    Brand New 3-Bed, 2.5-Bath Home - Clermont/Winter Garden BorderBe the first to live in this just-completed single-family home located in Wellness Ridge, a vibrant Clermont community designed for healthy, active living. This 3-bedroom, 2.5-bath home offers a spacious open floor plan, a modern kitchen with premium appliances and an oversized island, a 2-car garage, and high-speed internet

    2895 Transformation Way, Oakland, FL 34787
  • /29

    $3,500 Per Month

    • 4 Beds
    • 3 Baths
    • 2,148 Sq Ft
    • House for Rent

    12560 Westhaven Oak Dr, Oakland, FL 34787

    Welcome to your single-family home in the highly sought-after community of Osprey Ranch! Located in the heart of charming Winter Garden, this beautiful 4-bedroom, 3-bath residence with a 2-car garage offers the perfect blend of comfort, convenience, and community — an ideal place to raise a family. Enjoy living just minutes from world-class theme parks, top-rated local schools, major roadways,

    Alexandre Zapparoli LLC WRA BUSINESS & REAL ESTATE

    12560 Westhaven Oak Dr, Oakland, FL 34787
  • /30

    $2,625 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,688 Sq Ft
    • Townhouse for Rent

    15811 Tollington Aly, Oakland, FL 34787

    Make this beautiful townhome YOUR NEXT HOME! Located in Encore at Ovation, in the desirable Horizon West area and just minutes from Disney, this 3-bedroom, 2.5-bath home combines comfort, style, and convenience. The open-concept main level features wood-look tile, quartz countertops, stainless steel appliances, 42-inch cabinets, and plenty of natural light. The detached 2-car garage provides

    Carlinhos Fregonezi TALENT REALTY SOLUTIONS

    15811 Tollington Aly, Oakland, FL 34787
  • /23

    $2,600 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,567 Sq Ft
    • Townhouse for Rent

    9496 Bauer Aly, Oakland, FL 34787

    Waterleigh Subdivision 3/2.5 Town Home For Rent in Winter Garden, Fl. 34787. Range, Refrigerator, D/W, Disposal, Central Heat and A/C, Call to schedule a showing. Brand New Construction, townhouse for rent, energy efficient , 3 bedroom, 2.5 bathrooms. 1 Car Garage and large driveway. Spacious 1,567 SqFt.; Features include laundry room, walk-in closet, linen closet, blinds, ceiling fans, dual sink

    Rick Sein REALSOURCE PROPERTY MANGNT LLC

    9496 Bauer Aly, 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 home

    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
  • /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 home in Oakland, FL?
The median rent for a home in Oakland, FL is $2,900 per month, though prices vary by neighborhood, size, and property type. As of August 2026, townhouses tend to be the most affordable option while 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 $116,000 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 $2,900 per month in Oakland, FL, renters typically need to show $8,700 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 19.6, 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 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, West Oaks, Indian Hills, Waterleigh and Prairie Lake, each with its own character and price range.

Rental Home Trends

Number of Homes for Rent
21
Median Rent
$2,900
Median Single Family Home Rent
$3,150
Median Townhouse Rent
$2,625
How to Rent a Home