Starting at $1,751
Total Monthly Price
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
$2,750 Per Month
15769 Tollington Aly, Oakland, FL 34787
Welcome to this beautifully maintained townhome in the highly sought-after Encore at Ovation community in Horizon West. Built in 2024 and occupied for only a short period, this home offers a fresh, like-new feel throughout.The thoughtfully designed floor plan features 3 spacious bedrooms, 2.5 bathrooms, a versatile flex room on the first floor that is ideal for a home office, study, fitness
ORLANDO Davila LA ROSA REALTY KISSIMMEE
$2,850 Per Month
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
$3,049 Per Month
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
$3,390 Per Month
6073 Meditation Dr, Oakland, FL 34787
Spacious and luxurious two-story home available for rent in the highly desirable Wellness Ridge community! This beautiful property offers 6 bedrooms and 3 bathrooms, providing plenty of space for large families or anyone looking for comfort and functionality. The open-concept kitchen connects seamlessly to the dining area, breakfast nook, and family room, creating the perfect environment for
$2,500 Per Month
3115 Mindfullness Dr, Oakland, FL 34787
Stunning brand-new townhome located in the highly sought-after Wellness Ridge community in Clermont. This elegant two-story residence offers 3 spacious bedrooms, 2.5 bathrooms, and a thoughtfully designed open-concept floor plan filled with natural light and modern finishes throughout.The gourmet kitchen features contemporary cabinetry, stainless steel appliances, and a seamless flow into the
Bruna Sereno SELECTA REALTY LLC
$6,000 Per Month
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
$2,950 Per Month
14387 Braemar St, Oakland, FL 34787
Gorgeous 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 featuring brand new stainless steel appliances. The kitchen boasts beautiful
Eileen Scates SCATES REALTY & INVESTMENT PRO
$2,900 Per Month
16461 Prairie School Dr, Oakland, FL 34787
Beautifully Designed Community of Hawksmoor inspired by Frank Lloyd Wright– This Townhouse is Beautiful, Newer, Functional with Top Features and Fixtures. This place checks all boxes. First floor features a Bedroom, Living Room, Kitchen, Dining and Gathering Area, and a Half-Bath - All Stainless-Steel Appliances included in the Kitchen besides Granite Tops, Loaded with Cabinets, Walk-in Pantry,
Jhoana Loyo Urrutia LA ROSA REALTY LLC
$2,700 Per Month
2101 Gopher Tortoise Terrace, Oakland, FL 34760
Beautiful Townhome for rent now available in the sought after community of Longleaf at Oakland. This lovely, like new 3-bedroom, 3 bathroom townhome features one bedroom on the first floor. Open floor plan, overlooking the courtyard. On the second floor you’ll find the spacious Owner’s suite and guest bedroom each equipped with private bathrooms. This end unit open floorplan with an outside patio
Claudia D'Aquino CENTURY 21 CARIOTI
$3,000 Per Month
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
$2,850 Per Month
11428 Great Rock St, Oakland, FL 34787
TENANT OCCUPIED – Available August 1, 2026. Welcome to this beautiful 3-bedroom, 2.5-bath home in the sought-after Storey Grove community of Winter Garden. Featuring an open-concept floor plan, 42" cabinets, quartz countertops, and spacious living areas, this home offers both comfort and style. All bedrooms are located upstairs, providing added privacy. Enjoy the fully fenced backyard, perfect
Jackie Yuan JHY REALTY INVESTMENTS, LLC
$3,800 Per Month
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
$2,595 Per Month
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
$2,800 Per Month
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.
$2,600 Per Month
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
$3,295 Per Month
13227 Spring Grove Way, Oakland, FL 34787
This 4 bedroom, 2 bathroom home in the Encore at Ovation community is located near local shops and restaurants, Hamlin Town Center, theme parks, Orange County National Golf course, SR429, and the Florida Turnpike. The open floor plan features luxury vinyl plank throughout with a large family room and kitchen with stainless steel appliances, quartz counter-tops, breakfast bar, and pantry. The
Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY
$3,100 Per Month
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
$2,900 Per Month
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
$5,500 Per Month
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
$2,500 Per Month
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.
$3,900 Per Month
2501 Sky Stone Ct, Oakland, FL 34787
Beautifully maintained home in the desirable Oakland Trails community, ideally located on a quiet dead-end street withpeaceful preserve views and no rear neighbors. The open layout features natural light, a spacious living area, a modernkitchen, and large, comfortable bedrooms. Enjoy community amenities, including a pool, playground, and walking paths,with direct access to the West
Lisa Reed ENGEL & VOLKERS CLERMONT
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.
There are currently 24 homes available for rent in Oakland, FL. The median rent is $2,925 per month, with single-family homes renting at $3,100, townhouses at $2,700 and condos at $2,775.
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Number of Homes for Rent
24
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Median Rent
$2,925
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Median Single Family Home Rent
$3,100
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Median Townhouse Rent
$2,700
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Median Condo Rent
$2,775
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