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Pet-Friendly Homes for Rent in Oakland, FL

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  • /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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    $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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    $2,595 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
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    $2,800 Per Month

    • 4 Beds
    • 3 Baths
    • 1,847 Sq Ft
    • Townhouse for Rent

    4580 Maple Waltz, Oakland, FL 34787

    Welcome to this brand-new 4-bedroom, 3-bathroom townhome located in the highly desirable Parkside Trails community in Clermont. Featuring an open-concept floor plan filled with natural light, this home offers a modern kitchen with quartz countertops, stainless steel appliances, and ample cabinet space. One bedroom and a full bathroom are conveniently located on the first floor, perfect for guests

    Marta Faustino DTB FLORIDA REALTY, INC.

    4580 Maple Waltz, Oakland, FL 34787
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    $3,400 Per Month

    • 4 Beds
    • 3 Baths
    • 2,160 Sq Ft
    • House for Rent

    13007 Tollcross Way, Oakland, FL 34787

    Stunning corner home located directly across from the feature clubhouse, community pool, and playground in the highly desirable Winter Garden area. This spacious two-story property features 4 bedrooms, 3 full bathrooms, and a thoughtfully designed open-concept floor plan with modern finishes throughout. The bright and inviting living area flows seamlessly into the modern kitchen featuring

    Alessandra Oliveira FLORIDA CONNEXION PROPERTIES

    13007 Tollcross Way, Oakland, FL 34787
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    $3,100 Per Month

    • 4 Beds
    • 3 Baths
    • 1,897 Sq Ft
    • Townhouse for Rent

    12851 Westhaven Oak Dr, Oakland, FL 34787

    **AVAILABLE STARTING June 25, 2026** Welcome to this stunning townhome in the highly desirable Winter Garden area. Designed with modern living in mind, this home offers the perfect blend of style, comfort, and convenience. The open-concept floor plan creates a bright and inviting atmosphere, featuring a spacious family room, dining area, and a beautifully appointed kitchen with modern appliances

    Ricardo Molina TALENT REALTY SOLUTIONS

    12851 Westhaven Oak Dr, Oakland, FL 34787
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    $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
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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
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    $2,500 Per Month

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

    6069 Zen Way, Oakland, FL 34787

    Beautiful and brand-new corner-unit townhome in the highly desirable Wellness Ridge community! Ideally located just steps from the clubhouse and resort-style amenities, including a pool, playground, tennis courts, and basketball courts. This 3-bedroom, 2.5-bath home features an open-concept layout, a modern kitchen with stainless steel appliances, a spacious primary suite with a walk-in closet,

    Denise Simoes DELUX MIAMI GROUP, LLC.

    6069 Zen Way, Oakland, FL 34787

Rental Trends in Oakland, FL

Rental Home Trends

Number of Homes for Rent
9
Median Rent
$3,000
Median Single Family Home Rent
$3,100
Median Townhouse Rent
$2,700
Median Condo Rent
$2,775
How to Rent a Home