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5d+ ago
Studio
1 bath
$800
Apartment for rent
3d ago
House for rent in Winter Garden
181 Zachary Wade St #NA, Winter Garden, FL 34787
Air conditioning | Garage parking | Assigned parking
5 beds
3 baths
$3,200
House for rent
Available Aug 1
5d+ ago
Tucker Oaks condo for rent in Winter Garden
1432 Broken Oak Dr #31A, Winter Garden, FL 34787
In-unit laundry | Garage parking | Swimming pool
2 beds
2 baths
$1,900
Condo for rent
5d+ ago
House for rent in Winter Garden
273 Avalon Rd, Winter Garden, FL 34787
Walk-in closets | Ceiling fan | Storage
4 beds
2 baths
$2,995
House for rent
5d+ ago
Condo for rent in Winter Garden
2 beds
2 baths
$1,750
Condo for rent
Available May 20
5d+ ago
Townhouse for rent in Winter Garden
1000 Dolphin Dr, Winter Garden, FL 34787
In-unit laundry | Dishwasher | Outdoor space
3 beds
2 baths
$2,000
House for rent
4d ago
Townhouse for rent in Winter Garden
968 Stucki Ter, Winter Garden, FL 34787
Outdoor space
3 beds
2 baths
$2,000
House for rent
5d+ ago
House for rent in Winter Garden
4 beds
2 baths
$2,550
House for rent
Available Aug 1
Be the first to hear about new listings matching your search.
2d ago
Studio–2 beds
1 bath
$650–$900
Apartment for rent
5d+ ago
Verified
3 beds
2.5 baths
$2,690
$2,395
Price drop
House for rent
Available Jul 2
2d ago
Verified
2949 Magnolia Blossom Cir, Clermont, FL 34711
Garage parking
4 beds
3.5 baths
$2,995
$2,770
Price drop
House for rent
Available Jul 31
1d ago
Verified
3 beds
1.5 baths
$1,920
House for rent
Available Sep 14
4d ago
Verified
4 beds
2 baths
$3,790
$2,650
Price drop
House for rent
Available Aug 12
1d ago
Verified
397 Regal Downs Cir, Winter Garden, FL 34787
Garage parking | Walk-in closets
3 beds
2 baths
$2,495
House for rent
Available Jul 2
3d ago
Verified
4 beds
2.5 baths
$2,735
House for rent
Available Sep 2
3d ago
Verified
4 beds
1.5 baths
$2,185
$1,900
Price drop
House for rent
Available Jul 27
These rentals are 10%-30% cheaper than the local average price for similar rentals.
3d ago
Verified
3 beds
2.5 baths
$2,935
$2,520
Price drop
House for rent
Available Jul 30
5d+ ago
Verified
3 beds
2 baths
$2,515
$2,355
Price drop
House for rent
Available Jul 24
3d ago
Verified
4 beds
2.5 baths
$2,750
$2,505
Price drop
House for rent
Available Jun 30
3d ago
Verified
4 beds
3 baths
$2,750
$2,530
Price drop
House for rent
Available Jun 16
4d ago
722 S Woodland St, Winter Garden, FL 34787
Air conditioning | Outdoor space | Oven
1 bed
1 bath
$1,050
Apartment for rent
Average rent
The average rent in Oakland, as of August 2026, is up 28.49% compared to last month and up 22.45% year-over-year.Track prices
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1d ago
House for rent in Winter Garden
17392 Bal Harbour Dr #1, Winter Garden, FL 34787
4 beds
3 baths
$3,375
House for rent
Available Aug 1
1d ago
House for rent in Clermont
3524 Banana Shrub Blvd #1, Clermont, FL 34711
4 beds
3 baths
$4,000
House for rent
Available Aug 1
2d ago
Summit Greens house for rent in Clermont
2205 Caledonian St, Clermont, FL 34711
In-unit laundry | Furnished | Garage parking
2 beds
2 baths
$2,500
House for rent
3d ago
House for rent in Clermont
2735 Cedaridge Cir, Clermont, FL 34711
In-unit laundry | Garage parking | Walk-in closets
3 beds
2 baths
$2,500
House for rent
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Locals appreciate the family-friendly vibe of Oakland, FL, highlighting the abundance of outdoor activities and parks that make it easy to enjoy the natural surroundings. Many residents enjoy the community's quaint shops and restaurants, which contribute to a relaxed atmosphere. The city's schools are frequently praised for their quality, making it appealing for families. However, some residents express concerns about traffic issues, particularly during peak hours, which can make commuting challenging. Overall, the balance of amenities and a slower pace attracts many renters to this area.
Oakland maintains a steady rental presence with an average of 16 listings available per month. One-bedroom apartments represent the largest share at 31% of the market, followed by three-bedroom units at 25%. Studios are less common, accounting for 19% of monthly inventory, while two-bedroom apartments are relatively scarce at only 6% of available rentals.
Oakland apartments cater to renters seeking modern conveniences in their urban living experience. Three amenities tie for the most prevalent features, each appearing in 19% of listings: dishwashers, in-unit laundry, and outdoor space. These amenities align well with the practical needs of Oakland's diverse renter base, from young professionals valuing the convenience of in-unit laundry to residents who appreciate outdoor space for relaxation. These averages offer a useful snapshot, though the live market may shift.
Zumper’s proprietary rental data fuels our analysis. Rent and market trends, availability, neighborhood popularity, and lifestyle scores are all calculated using real-time and 2026 rental inventory and prices.
Our Lifestyle Categories ("great for eco-living," "great for social life," "great for pet owners," etc.) are determined by set criteria, against which we score each listing and its available features. At the neighborhood level, we calculate the listing count for each category to determine which lifestyles best fit each area.
Zumper, founded in 2012, is North America’s largest privately-owned rental platform, offering over 1 million listings across the U.S. and Canada. Stay informed on the latest trends and shifts in the rental market with our monthly National Rent Report, your go-to resource for key insights into the evolving rental landscape.
The average size of a 1 bedroom apartment rental in Oakland is 1650 square feet. The average size of a 3 bedroom apartment rental in Oakland is 1898 square feet.
To help you better understand how much rent you can afford, check out Zumper's rent calculator. Our rent calculator can help you learn more about Oakland average rent prices.
| 🔑Available apartment rentals | 25 |
|---|---|
| 💰Best rent deal | Lake Apopka Blvd |
| ✨Popular amenities | , , |
| 🍽With dishwasher | |
| 🏠With photos |