24

Oakland, FL Homes for Rent

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  • /19

    $2,500 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
  • /53

    $2,750 per month

    • 3 Beds
    • 2.5 Baths
    • 1,755 Sq Ft
    • Townhouse 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

    Agent Photo

    Bruce Kalin

    JC FLORIDA REALTY LLC

    (321) 483-8669

    10672 Words Dr, Winter Garden, FL 34787
  • /16

    $1,584 - $2,825 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
  • /19

    $3,500 per month

    • 4 Beds
    • 3 Baths
    • 2,100 Sq Ft
    • House for Rent

    17727 Sharp Pummelo Aly, Oakland, FL 34787

    This stunning new home features premium upgrades throughout. The first floor boasts 8-foot exterior and interior doors, a gourmet kitchen, and a private bedroom with a full bathroom featuring an upgraded walk-in shower. The kitchen, family room, and dining area flow seamlessly together and open onto an extended lanai. Upstairs, you'll find the remaining bedrooms, including a primary suite with a

    Angela Magac THE PROPERTY STOP LLC

    17727 Sharp Pummelo Aly, Oakland, FL 34787
  • /15

    $3,185 per month

    • 4 Beds
    • 3 Baths
    • 2,200 Sq Ft
    • House for Rent

    2648 Bobcat Chase Blvd, Oakland, FL 34760

    We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

    2648 Bobcat Chase Blvd, Oakland, FL 34760
  • /16

    $3,200 per month

    • 3 Beds
    • 2.5 Baths
    • 2,103 Sq Ft
    • House for Rent

    17609 Japonica Bloom Dr, Oakland, FL 34787

    Welcome to 17609 Japonica Bloom Drive—a brand new home designed for modern living and effortless entertaining. Soaring 8-foot doors throughout the first floor create an impressive, open atmosphere. The gourmet kitchen flows seamlessly into the dining area, making it easy to host while you cook. Step outside to the extended lanai, perfect for outdoor gatherings and relaxation. Upstairs, you'll

    Angela Magac THE PROPERTY STOP LLC

    17609 Japonica Bloom Dr, Oakland, FL 34787
  • /2

    $3,400 per month

    • 4 Beds
    • 3.5 Baths
    • House for Rent

    15129 Summer Harvest St, Winter Garden, FL 34787

    Property Id: 2341266Welcome to your DREAM RENTAL HOME in the heart of the magical Flamingo Crossings area! This stunning home boasts 4 spacious bedrooms (including TWO ENSUITES!), providing ample space for your family to relax and unwind. With 3 and a half bathrooms, morning routines will be a breeze, and everyone can enjoy their privacy. Spanning over 2300 square feet, this beautiful

    15129 Summer Harvest St, Winter Garden, FL 34787
  • /50

    $6,000 per month

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

    705 Largovista Dr, Oakland, FL 34787

    Come view this newly built 4 bed/4 bath two-story home in the gated community of John’s Landing! Inside, you’ll find a bright and airy open layout featuring an impressive vaulted ceiling, large windows, and elegant flooring throughout. The stunning kitchen includes custom built-in Thermador appliances and solid wood cabinetry. The primary suite features vaulted ceilings, a spa-style bath with a

    Christopher Bright BEST ORLANDO PROPERTY MANAGEMENT LLC

    705 Largovista Dr, Oakland, FL 34787
  • /20

    $2,695 per month

    • 3 Beds
    • 2.5 Baths
    • 1,577 Sq Ft
    • Townhouse for Rent

    17568 Northlake Grv Dr, Oakland, FL 34787

    This property is available. Please inquire on this site to schedule a showing. ? Lakefront Luxury Living in Winter Garden – Brand New 3BR Townhome at Northlake at Ovation ?Discover the perfect blend of comfort, style, and convenience in this brand-new, lakefront townhome located in the highly desirable Northlake at Ovation community. Nestled in the heart of Winter Garden and just a

    17568 Northlake Grv Dr, Oakland, FL 34787
  • /18

    $2,550 per month

    • 3 Beds
    • 2.5 Baths
    • 1,668 Sq Ft
    • Townhouse for Rent

    17604 Northlake Grove Dr, Oakland, FL 34787

    PRIME LOCATION IN HORIZON WEST – WINTER GARDEN | ONLY 10 MINUTES FROM DISNEYEnjoy living in this beautiful corner townhome located in the highly desirable Northlake at Ovation community, right in the heart of Horizon West. Built by Ashton Woods, this stunning townhouse is surrounded by serene lakes and natural conservation areas, offering both comfort and tranquility. This charming home

    Isabel Sirizzotti SUNNY 365 REALTY GROUP

    17604 Northlake Grove Dr, Oakland, FL 34787
  • /26

    $3,750 per month

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

    15663 Pelican Cay Dr, Oakland, FL 34787

    Welcome to this beautifully maintained two-story home located in the heart of Winter Garden, FL, within one of the area’s most sought-after communities. This spacious residence features 4 bedrooms, including a convenient in-law suite, and 3.5 bathrooms, providing a flexible and functional layout.The open-concept kitchen includes stainless steel appliances and granite countertops, flowing

    Steven Koleno BEYCOME OF FLORIDA LLC

    15663 Pelican Cay Dr, Oakland, FL 34787
  • /29

    $3,600 per month

    • 5 Beds
    • 3.5 Baths
    • 2,563 Sq Ft
    • House for Rent

    5816 Dancing Willow St, Oakland, FL 34787

    Step into comfort and convenience in this beautifully designed 2026 5-bedroom, 3.5-bath home located in the desirable Parkside Trails community. With over 2,562 square feet of living space, this home offers a bright, open layout ideal for everyday living, entertaining, and relaxing. Parkside Trails is a growing community with resort-style amenities coming soon, including two pools, a clubhouse,

    Tisa Sa Barreto SELECTA REALTY LLC

    5816 Dancing Willow St, Oakland, FL 34787
  • /80

    $2,700 per month

    • 3 Beds
    • 2.5 Baths
    • 1,635 Sq Ft
    • Townhouse for Rent

    17538 Northlake Grove Dr, Oakland, FL 34787

    Lakefront Luxury Living in Winter Garden - Brand New 3BR Townhome at Northlake at Ovation Discover the perfect blend of comfort, style, and convenience in this brand-new, lakefront townhome located in the highly desirable Northlake at Ovation community. Nestled in the heart of Winter Garden and just a short drive from Downtown Orlando, this beautifully designed residence offers modern living in

    Leo Martins Silva THE FLORIDA LOUNGE REALTY LLC

    17538 Northlake Grove Dr, Oakland, FL 34787
  • /42

    $2,800 per month

    • 4 Beds
    • 3 Baths
    • 1,809 Sq Ft
    • Townhouse for Rent

    2202 Gopher Tortoise Terrace, Oakland, FL 34787

    Welcome to your dream townhome in the heart of Oakland, FL! This spacious 4-bedroom 3-bathroom residence combines comfort, style, and convenience in one beautiful package. Thoughtfully designed with an open layout and ample natural light, this home offers room for everyone-perfect for families, professionals, or anyone looking for space to grow.Enjoy easy living with walking trails just steps

    Johna Jennings Coastal Life Properties LLC

    2202 Gopher Tortoise Terrace, Oakland, FL 34787
  • /41

    $3,700 per month

    • 4 Beds
    • 4.5 Baths
    • 2,931 Sq Ft
    • House for Rent

    15070 Summer Harvest St, Oakland, FL 34787

    Modern Fenced Corner-Lot Home with Multigenerational Suite This spacious single-family home offers a thoughtful layout designed for comfort and flexibility. Located on a desirable fenced corner lot, the property includes 4 bedrooms and 4.5 bathrooms in the main home, PLUS a private multigenerational suite above the garage with its own bedroom, kitchenette, and full bath—ideal for guests, extended

    Robert Benenati 365 REALTY, INC.

    15070 Summer Harvest St, Oakland, FL 34787
  • /14

    $2,149 per month

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

    3075 Mindfullness Dr, Oakland, FL 34787

    ***BRAND NEW TOWNHOME FOR RENT**INTERNET INCLUDED! Enjoy resort-style amenities at Wellness Ridge, including a clubhouse, pool, fitness center, playgrounds, and scenic walking trails. Conveniently located near shopping, dining, top-rated schools, and just minutes from Disney and major highways. Ready for immediate move-in – schedule your showing today!

    Frederico Hexsel KARDOSH REALTY

    3075 Mindfullness Dr, Oakland, FL 34787
  • /20

    $3,380 per month

    • 4 Beds
    • 2.5 Baths
    • 2,441 Sq Ft
    • House for Rent

    12767 Harvest Rain Ave, Oakland, FL 34787

    Be the first to live in this brand-new home just delivered by the builder!Located in one of Winter Garden’s most desirable areas, surrounded by top-rated A schools, this property offers luxury, comfort, and flexibility. This beautiful residence features 4 bedrooms, including one room on the first floor that can serve as a bedroom, office, playroom, or whatever best fits your family’s needs.

    Natalia Romanelli Mourao MS LAND & BUILDING LLC

    12767 Harvest Rain Ave, 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
  • /20

    $2,750 per month

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

    12295 Bracco St, Oakland, FL 34787

    Brand New 3-Bed 2.5-Bath Home For Rent in Winter Garden!Brand new, energy-efficient home for rent in the desirable Highland Ridge community! This stunning 3 bedroom, 2.5 bathroom house offers 1,788 square feet of modern living space. The open kitchen boasts a large island that seamlessly flows into the spacious dining and family room, perfect for entertaining. Upstairs, you'll find a

    Eileen Scates SCATES REALTY & INVESTMENT PRO

    12295 Bracco 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
  • /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
  • /23

    $1,700 per month

    • 2 Beds
    • 1 Bath
    • 572 Sq Ft
    • House for Rent

    665 Lake Apopka Blvd, Winter Garden, FL 34787

    Rental property located in Winter Garden featuring 2 bedrooms, 1 bathroom, and a flex room ideal for a home office or additional living space. Recently renovated with functional layouts and great natural light. No HOA. Prime location near Lake Apopka and just minutes from FL-429 and Hwy-50, offering easy access to major roads, shopping, and recreational areas. Ideal opportunity for those seeking

    Lizandra Troisi Passos MY REALTY GROUP, LLC.

    665 Lake Apopka Blvd, Winter Garden, FL 34787
  • /34

    $4,500 per month

    • 3 Beds
    • 2.5 Baths
    • 2,536 Sq Ft
    • House for Rent

    934 Mckinnon Square, Winter Garden, FL 34787

    Looking for the perfect retinal? Look no further. This beautiful home is located in the sought-after amenity-rich Oakland Park. This community offers the best Winter Garden has to offer, with 2 community pools, playgrounds, a community vegetable garden, numerous parks, and Access to the west Orange Trail. All this with golf cart access to Historic Downtown Winter Garden. better-than-new

    Mauro Costa CORCORAN PREMIER REALTY

    934 Mckinnon Square, Winter Garden, FL 34787

Why Live in Oakland

Between the scenic Lake Apopka and Johns Lake, Oakland is a small, Orange County town with an established, nature-oriented feel. Around 18 miles west of downtown Orlando and 15 miles north of Walt Disney World, the town lies in the heart of ...

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, Spring Valley, Indian Hills and West Oaks.
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.
How to Rent a Home