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Oakland, FL Homes for Rent

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  • /16

    $1,510 - $2,899 per month

    AVENUE ON OAKLAND

    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.

    751 W Oakland Ave, Oakland, FL 34787
  • /26

    $2,900 per month

    • 4 Beds
    • 2.5 Baths
    • 2,114 Sq Ft
    • House for Rent

    12337 Bracco St, Oakland, FL 34787

    Welcome to this stunning 2023 single-family home, perfectly situated on an oversized lot with no rear neighbors—offering privacy, space, and a serene outdoor area ideal for relaxing, walking, or grilling.Inside, the open-concept layout features a chef’s kitchen designed for entertaining and hosting family gatherings. All four bedrooms are conveniently located on the second floor, along with a

    Janet Quinones MAGNUS REALTY GROUP LLC

    12337 Bracco St, Oakland, FL 34787
  • /35

    $2,950 per month

    • 4 Beds
    • 2.5 Baths
    • 1,992 Sq Ft
    • Townhouse for Rent

    11343 Great Rock St, Oakland, FL 34787

    HOUSE WITH LAKE VIEW!! Welcome to your dream rental! This stunning two-storyhome in the desirable Storey Grove Community provides breathtaking pond views and an impressive layout featuring four spacious bedrooms and three full bathrooms. The modern kitchen with an island seamlessly overlooks the expansive family and dining area, perfect for entertaining. Retreat to the luxurious master suite

    Tiago Ferreira MANAGER PROP

    11343 Great Rock St, Oakland, FL 34787
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    $2,700 per month

    • 3 Beds
    • 2.5 Baths
    • 1,817 Sq Ft
    • Townhouse for Rent

    13118 Bounty Ave, Oakland, FL 34787

    PERFECT Location in PERFECT Waterleigh Community at Winter Garden! CORNER LOT! 3 bedroom + Loft/Office Upstairs + 2.5 baths. Rent includes lawn maintenance and all appliance and ALL 4 community amenities access. Great school district. Waterleigh is an amazing community, tons of amenities, including TWO large resort style clubhouses, TWO resort style pools and 3rd pool amenity, and 4th amenity is

    Jacky Liu YORK MILLS REALTY LLC

    13118 Bounty Ave, Oakland, FL 34787
  • /9

    $1,400 per month

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

    5652 Lemon Grass St Unit B, Oakland, FL 34787

    BRAND NEW HOUSE IN WELLNESS RIDGE!Experience modern living in this beautifully designed private suite, crafted for comfort and convenience. Enjoy your own private entrance, a bright and spacious bedroom, and a luxurious bathroom featuring high-end finishes and a large shower. The well-equipped kitchenette includes a cooktop, refrigerator, microwave, dishwasher, and sink—everything you need

    Tiago Ferreira MANAGER PROP

    5652 Lemon Grass St Unit B, Oakland, FL 34787
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    $4,000 per month

    • 4 Beds
    • 3 Baths
    • 2,170 Sq Ft
    • House for Rent

    14213 Spring Garden Dr, Oakland, FL 34787

    For Rent 14213 Spring Garden Dr, Winter Garden, FL 34787 Brand-New Luxury One-Story Home | 4 Bedrooms | 3 Full Bathrooms | 2-Car Garage | Premium Upgrades Throughout Welcome to this stunning brand-new luxury home located in the highly sought-after Winter Garden area, just 5 minutes from Disney's Western Gate. Built by a top national builder(Toll Brother), this spacious single-story residence

    Qinghe Meng AAA GLOBAL VENTURES PA

    14213 Spring Garden Dr, Oakland, FL 34787
  • /22

    $2,400 per month

    • 3 Beds
    • 2 Baths
    • 1,713 Sq Ft
    • House for Rent

    5652 Lemon Grass St Unit A, Oakland, FL 34787

    BRAND NEW HOME IN WELLNESS RIDGE! Discover modern comfort in this beautifully designed private suite, featuring a spacious bedroom and a luxurious bathroom with premium finishes and a large walk-in shower. The well-appointed kitchenette includes a cooktop, refrigerator, microwave, dishwasher, and sink—perfect for convenient everyday living. Enjoy a bright, open great room that provides a cozy and

    Tiago Ferreira MANAGER PROP

    5652 Lemon Grass St Unit A, Oakland, FL 34787
  • /41

    $3,100 per month

    • 3 Beds
    • 2.5 Baths
    • 2,206 Sq Ft
    • House for Rent

    14111 Frasier St, Oakland, FL 34787

    Be the first to live in this brand new Meritage Home that perfectly combines comfort, style, and energy efficiency. The open concept floor plan features a modern kitchen with a large island overlooking the great room, dining area, and patio, ideal for relaxing or entertaining. Enjoy beautiful finishes throughout, including quartz countertops, stylish tile flooring, and a detached two-car garage

    Denise Batista ALLUX REAL ESTATE LLC

    14111 Frasier St, Oakland, FL 34787
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    $3,500 per month

    • 4 Beds
    • 3.5 Baths
    • 2,807 Sq Ft
    • House for Rent

    12796 Brodlove Ln, Oakland, FL 34787

    Gorgeous 4-bedroom, 3.5-bathroom single-family home located in the sought-after Encore at Ovation Community in Winter Garden. This house offers a spacious and contemporary gourmet kitchen with a large center island and stainless steel appliances. Gas community! There's a convenient guest bedroom suite downstairs, while the master bedroom, two additional bedrooms, and a generous loft are situated

    Agent Photo

    Cui Li

    RATIO REAL ESTATE, LLC

    (321) 321-5962

    12796 Brodlove Ln, Oakland, FL 34787
  • /30

    $2,990 per month

    • 4 Beds
    • 2.5 Baths
    • 1,811 Sq Ft
    • House for Rent

    2684 Bobcat Chase Blvd, Oakland, FL 34787

    LOCATION, LOCATION, LOCATION! Discover this beautifully constructed 4-bedroom, 2.5-bathroom home built in 2021, ideally located just minutes from downtown Winter Garden! The open-concept main floor features a modern kitchen with quartz countertops, solid wood cabinets, tile floors, a breakfast bar, and a closet pantry—perfect for cooking and entertaining. The expansive living room includes a

    Sarah Cohim MCO REALTY GROUP LLC

    2684 Bobcat Chase Blvd, Oakland, FL 34787
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    $2,650 per month

    • 4 Beds
    • 3 Baths
    • 3,259 Sq Ft
    • House for Rent

    225 Largovista Dr, Oakland, FL 34787

    Welcome to this stunning 4-bedroom, 3-bathroom single-family home located in the desirable community of Oakland. This spacious residence features a formal dining room perfect for entertaining, a bright and open living area, and a well-appointed kitchen with plenty of cabinet space and a cozy eat-in nook.Enjoy the split-bedroom floor plan offering comfort and privacy for everyone. The

    Carissa Lawhun FLORIDA REALTY INVESTMENTS

    225 Largovista Dr, Oakland, FL 34787
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    $2,900 per month

    • 3 Beds
    • 2.5 Baths
    • 1,796 Sq Ft
    • House for Rent

    12748 Brodlove Ln, Oakland, FL 34787

    Modern, move-in ready home in a sought-after community minutes from Walt Disney World and Orlando. Bright open-concept living with abundant natural light. Contemporary kitchen with quality cabinetry, quartz counters, and stainless-steel appliances. Spacious primary suite with walk-in closet and private bath. Community amenities: resort-style pool, full fitness center, playgrounds, and open green

    Mayra Rivas Acevedo CASA SOL REALTY LLC

    12748 Brodlove Ln, Oakland, FL 34787
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    $1,995 per month

    • 3 Beds
    • 2 Baths
    • 1,192 Sq Ft
    • House for Rent

    91 N Pollard St, Oakland, FL 34760

    Hard to find Quaint Single Family in the rapidly growing town of Oakland. You cannot find a 3/2 home in downtown Winter Garden for this price. Oakland is rapidly becoming the next Downtown Winter Garden. New Million-dollar homes are being built just behind this subdivision. Minutes from Downtown Winter Garden. This home has been gutted and remodeled throughout. Newer Roof AC, Septic and Plumbing

    Charles Woolley BHHS FLORIDA REALTY

    91 N Pollard St, Oakland, FL 34760
  • /41

    $2,500 per month

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

    4584 Maple Waltz, Oakland, FL 34787

    Welcome to 4584 Maple Waltz Alley, a pristine, never-lived-in new construction home perfectly situated between Clermont and Winter Garden. This thoughtfully designed floorplan offers an open-concept living area where the kitchen, dining, and family spaces flow seamlessly to maximize comfort and natural light. The bedrooms are arranged for privacy, with the primary suite tucked away featuring a

    Ashley Porto GLASSTONE GROUP INC

    4584 Maple Waltz, Oakland, FL 34787
  • /23

    $4,200 per month

    • 3 Beds
    • 2 Baths
    • 1,960 Sq Ft
    • House for Rent

    13673 Fresh Ivy St, Oakland, FL 34787

    Welcome to this fully furnished 3-bedroom, 2-bath single-story home in the highly sought-after 55+ Del Webb Oasis community of Winter Garden. Designed with both comfort and style in mind, this home offers flexible living spaces and access to resort-style amenities just minutes from Orlando’s world-class attractions.Inside, you’ll find a spacious kitchen with a gas stove, ample cabinetry,

    Fernanda Negromonte NOVA REAL ESTATE SERVICES INC

    13673 Fresh Ivy St, Oakland, FL 34787
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    $3,750 per month

    • 5 Beds
    • 4 Baths
    • 2,700 Sq Ft
    • House for Rent

    12887 Westhaven Oak Dr, Oakland, FL 34787

    Amazing Property, Welcome to your Luxury dream home! This stunning 5 bedroom, 4 bathroom property boasts superior quality finishes andtop-of-the-line appliances throughout. From the moment you step inside, you'll be wowed by the open floor plan, 9’4” Ceilings and qualitycraftsmanship that is evident in every detail. The heart of the home is the beautiful gourmet kitchen, complete with

    Maria Elena EXP REALTY LLC

    12887 Westhaven Oak Dr, Oakland, FL 34787
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    $2,500 per month

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

    3027 Mindfullness Dr, Oakland, FL 34787

    Move-in special: Owner offering a $1,000 tenant concession. Amount may be applied toward the first month’s rent or prorated across the lease. End-Unit Townhouse | Clermont – Olympus Area 3 Bedrooms | 2.5 Bathrooms Open-concept floor plan with spacious living & dining Modern kitchen with stainless steel appliances included (refrigerator, range, microwave, dishwasher) Washer & dryer included in the

    Rodrigo Dias de Freitas CELEBRITY GLOBAL REALTY LLC

    3027 Mindfullness Dr, Oakland, FL 34787
  • /41

    $5,500 per month

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

    9849 Lost Creek Dr, Oakland, FL 34787

    ***This home is also available for sale with a unique opportunity for the tenant! Enjoy living in a well-maintained home with the peace of mind that you’ll have the first right of refusal to purchase**Nestled in the heart of Winter Garden’s Waterleigh community, this 5-bedroom, 4-bathroom masterpiece redefines modern luxury and family living. Boasting 3,910 sq. ft. of beautifully designed space,

    Nelson Cruz REAL BROKER, LLC

    9849 Lost Creek Dr, Oakland, FL 34787
  • /9

    $2,700 per month

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

    12028 Holystone St, Oakland, FL 34787

    ATTENTION GOOD RENTERS!! COME TO SHOW THIS WONDERFUL OPORTUNITY FOR RENT YOUR DREAM TOWNHOUSE IN WINTER GARDEN. THE COMMUNITY IS BEAUTIFUL, GREAT SCHOOLS, GREAT AREAS FOR LIVING. ONCE YOU ENTER TO THE PROPERTY, YOU WILL FEEL LIKE YOU ARE AT HOME. THE DISTIBUTION ON FIRST FLOOR IS NICE BECAUSE YOU WILL SEE THE FAMILY ROM, DINING ROOM AND KITCHEN ALL INTEGRATED IN ONE OPEN SPACE. THE SECOND FLOOR

    Maria G Camacho ORLANDO KEY REALTY LLC

    12028 Holystone St, Oakland, FL 34787
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    $2,950 per month

    • 4 Beds
    • 2.5 Baths
    • 1,868 Sq Ft
    • House for Rent

    2435 Standing Rock Cir, Oakland, FL 34787

    Last call to the best deal in Winter Garden region ! PROPERTY WITH STRONG SOLAR SYSTEM FOR ENERGY SUPPORT INCLUDED ! Perfectly situated in Oakland Trails, in a couple of minutes to MONTVERDE ACADEMY. HIGHT QUALITY CONSTRUCTION with 4 bed, 2,5 bath, with luxury 40 thousand upgrades and brand-name appliances. Master suite on second floor in ample and natural light space and dimension with club

    Celestino De Cicco CENTRAL FLORIDA REALTY

    2435 Standing Rock Cir, Oakland, FL 34787
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    $3,200 per month

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

    12832 Lavender Bloom Alley, Oakland, FL 34787

    Welcome to your dream home in the heart of Winter Garden! This beautifully maintained 3-bedroom, 1 office, 2.5-bath residence is nestled in the highly sought-after Waterleigh community, offering a perfect blend of comfort, style, and convenience.Designed for modern living, the open-concept floor plan seamlessly connects the spacious living and dining areas to a gourmet kitchen with

    Agent Photo

    Ursula Garcia Moraes

    PRISTINE INTERNATIONAL REALTY LLC

    (321) 529-1696

    12832 Lavender Bloom Alley, Oakland, FL 34787
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    $3,000 per month

    • 3 Beds
    • 2.5 Baths
    • 2,027 Sq Ft
    • House for Rent

    16190 Harbor Mist Alley, Winter Garden, FL 34787

    Beautiful 3-bedroom, 2.5-bath home in Waterleigh Winter Garden, with a main floor master bedroom! This charming Cordale model by D.R. Horton has a welcoming covered front porch, and an open kitchen complete with a butler's pantry. The modern kitchen has stainless appliances with washer/dryer included . Upstairs, two bedrooms plus a loft make the perfect movie room, play room or office/gym area.

    16190 Harbor Mist Alley, Winter Garden, FL 34787
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    $3,000 per month

    • 3 Beds
    • 2.5 Baths
    • 2,014 Sq Ft
    • House for Rent

    9588 Jacques Alley, 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 Alley, 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

What are the most popular neighborhoods in Oakland, FL for renters?
The most popular neighborhoods in Oakland, FL for renters are Bella Collina, Legends, West Oaks, Indian Hills and Prairie Lake.
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, 34715 and 34786.
How to Rent a Home