Oakland, FL rental listings

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ABOUT THIS HOME
Oakland, FL Rental Listings
Welcome Home at Avenue on Oakland 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. T

Studio: $1,510

1 bd: $1,694 • 2 bd: $2,000

Avenue on Oakland

| 751 W Oakland Ave, Oakland, FL 34787

22 units available • Car-dependent • Fitness Center

ABOUT THIS HOME
Oakland, FL Rental Listings
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 brigh

$2,650/mo

4 beds3 baths3,259 sq ft

225 Largovista Dr, Oakland, FL 34787

Available 12/13 • Parking • A/C

ABOUT THIS HOME
Oakland, FL Rental Listings
Beautiful 3-bedroom, 2.5-bathroom 2-story home in the highly sought-after Oakland Trails. This amazing floorplan has the best front porch view of the community park and is only a couple of doors down

$2,600/mo

3 beds2.5 baths1,838 sq ft

1775 White Feather Loop, Oakland, FL 34787

Parking • A/C • Dishwasher

ABOUT THIS HOME
Oakland, FL Rental Listings
If you're looking for a no-frills, budget-friendly place to stay in beautiful Winter Garden, this 1 bedroom RV might be just what you need. It's an older model with some character, but it's clean, fun

$985/mo

1 bed1 bath402 sq ft

15992 W Colonial Dr Unit RV08, Oakland, FL 34787

Apartment • 1 unit available

ABOUT THIS HOME
Oakland, FL Rental Listings
2135 Standing Rock Circle is a stunning find in the sought-after Oakland Trails community, blending modern luxury with incredible efficiency. You'll love the freedom of significantly reduced energy co

$2,650/mo

3 beds2.5 baths2,078 sq ft

2135 Standing Rock Cir, Oakland, FL 34787

Parking • Car-dependent

ABOUT THIS HOME
Oakland, FL Rental Listings
Discover modern living at its finest in this beautifully upgraded home located in the desirable community of Oakland Trails. This residence features a contemporary design with no carpet throughout, pr

$2,850/mo

3 beds2.5 baths1,880 sq ft

1943 Standing Rock Cir, Oakland, FL 34787

Pets welcome • Laundry in unit • Parking

Property at 15992 W Colonial Dr, Oakland, FL, 34787, 0 beds, 1 bath, [object Object]

$865/mo

0 beds1 bath450 sq ft

15992 W Colonial Dr, Oakland, FL 34787

Property at 1490 Stone Arrow Ct, Oakland, FL, 34787, 5 beds, 3.5 baths, [object Object]

$3,450/mo

5 beds3.5 baths3,188 sq ft

1490 Stone Arrow Ct, Oakland, FL 34787

Property at 2684 Bobcat Chase Blvd, Oakland, FL, 34787, 4 beds, 2.5 baths, [object Object]

$2,990/mo

4 beds2.5 baths1,811 sq ft

2684 Bobcat Chase Blvd, Oakland, FL 34787

Property at 942 Auction Aly, Winter Garden, FL, 34787, 3 beds, 2.5 baths, [object Object]

$3,000/mo

3 beds2.5 baths1,642 sq ft

942 Auction Aly, Winter Garden, FL 34787

Property at 91 N Pollard St, Oakland, FL, 34760, 3 beds, 2 baths, [object Object]

$1,995/mo

3 beds2 baths1,192 sq ft

91 N Pollard St, Oakland, FL 34760

End of results (Download All)

Here are some rentals close to your search

ABOUT THIS HOME
Oakland, FL Rental Listings
Welcome to Palm Crossing. Located in the historic Winter Garden, FL, Palm Crossing is the perfect community to call home. With a collection of modern floorplans paired with a robust list of resort-sty

1 bd: $1,477

2 bd: $1,727 • 3 bd: $2,088

Palm Crossing

| 1240 Winter Garden Vineland Rd, Winter Garden, FL 34787

12 units match • Pets welcome • Parking

NEW 15 HRS AGO$200 OFF

ABOUT THIS HOME
Oakland, FL Rental Listings
Welcome to Slate Luxury Apartments, where tranquility meets chic living in the heart of downtown Winter Garden, Florida. Nestled in a lush, serene enclave, our boutique community offers townhomes and

1 bd: $1,696

2 bd: $2,198

Slate Luxury Apartments

| 584 W Bay St, Winter Garden, FL 34787

5 units available • Cats welcome • Very walkable

$750 OFF

ABOUT THIS HOME
Oakland, FL Rental Listings
Learn more about our current Move-In Specials and save today! Stylish design at a price that's right! Country Gardens Apartment Homes is located in Winter Garden, Florida, with easy access to Florida

2 bd: $1,729

3 bd: $1,939

Country Gardens

| 15122 W Colonial Dr, Winter Garden, FL 34787

4 units match • Pets welcome • Parking

DEAL

ABOUT THIS HOME
Oakland, FL Rental Listings
Indulge in the epitome of luxury living at Skyline at Westfall Station. Our coach-style, modern farmhouse-themed community offers 1, 2, and 3-bedroom sanctuaries amidst the scenic beauty of Clermont,

1 bd: $1,399

2 bd: $1,699 • 3 bd: $2,149

Skyline at Westfall Station

| 13600 Hilltop Groves Blvd, Clermont, FL 34711

39 units match • Pets welcome • Parking

3D WALKTHROUGH

ABOUT THIS HOME
Oakland, FL Rental Listings
Welcome to Advenir at Castle Hill, a residential community featuring One, Two & Three bedroom apartments in Clermont, FL. Spacious layouts and amenities welcome you home, along with exceptional servic

2 bd: $1,939

3 bd: $2,424

Advenir at Castle Hill

| 13600 Hartle Groves Pl, Clermont, FL 34711

7 units match • Pets welcome • A/C

NEW 35 HRS AGO8 WEEKS FREE

1 bd: $1,749

2 bd: $2,099 • 3 bd: $3,970

Broadstone Overlands

| 5000 Collina Ter, Clermont, FL 34711

10 units available • Car-dependent • Fitness Center

Property at 17424 Chateau Pine Way, Clermont, FL, 34711, 3 beds, 2.5 baths, [object Object]

$3,200/mo

3 beds2.5 baths1,960 sq ft

17424 Chateau Pine Way, Clermont, FL 34711

Property at 502 First Cape Coral Dr, Winter Garden, FL, 34787, 3 beds, 2 baths, [object Object]

$2,650/mo

3 beds2 baths1,923 sq ft

502 First Cape Coral Dr, Winter Garden, FL 34787

Property at 545 First Cape Coral Dr, Winter Garden, FL, 34787, 4 beds, 2.5 baths, [object Object]

$3,500/mo

4 beds2.5 baths2,563 sq ft

545 First Cape Coral Dr, Winter Garden, FL 34787

Property at 611 First Cape Coral Dr, Winter Garden, FL, 34787, 4 beds, 2.5 baths, [object Object]

$2,900/mo

4 beds2.5 baths2,834 sq ft

611 First Cape Coral Dr, Winter Garden, FL 34787

Property at 831 Grande Regal Pt, Winter Garden, FL, 34787, 3 beds, 2 baths, [object Object]

$2,300/mo

3 beds2 baths1,874 sq ft

831 Grande Regal Pt, Winter Garden, FL 34787

Property at 399 Winter Nellis Cir, Winter Garden, FL, 34787, 3 beds, 2.5 baths, [object Object]

$2,400/mo

3 beds2.5 baths1,592 sq ft

399 Winter Nellis Cir, Winter Garden, FL 34787

Property at 1000 Araminta St, Winter Garden, FL, 34787, 4 beds, 2.5 baths, [object Object]

$2,700/mo

4 beds2.5 baths2,880 sq ft

1000 Araminta St, Winter Garden, FL 34787

Property at 316 Southern Pecan Cir #205, Winter Garden, FL, 34787, 3 beds, 2 baths, [object Object]

$2,475/mo

3 beds2 baths1,453 sq ft

316 Southern Pecan Cir #205, Winter Garden, FL 34787

Property at 1030 Bending Oak Trl, Winter Garden, FL, 34787, 5 beds, 3 baths, [object Object]

$3,500/mo

5 beds3 baths2,212 sq ft

1030 Bending Oak Trl, Winter Garden, FL 34787

Property at 207 Black Springs Ln, Winter Garden, FL, 34787, 4 beds, 2.5 baths, [object Object]

$3,350/mo

4 beds2.5 baths3,311 sq ft

207 Black Springs Ln, Winter Garden, FL 34787

Property at 1315 Eastern Pecan Pl #107, Winter Garden, FL, 34787, 1 bed, 1 bath, [object Object]

$1,450/mo

1 bed1 bath838 sq ft

1315 Eastern Pecan Pl #107, Winter Garden, FL 34787

Property at 13145 Moro Ct, Winter Garden, FL, 34787, 5 beds, 3 baths, [object Object]

$3,800/mo

5 beds3 baths3,436 sq ft

13145 Moro Ct, Winter Garden, FL 34787

Property at 14843 Astrolyn St, Winter Garden, FL, 34787, 3 beds, 2 baths, [object Object]

$2,099/mo

3 beds2 baths1,260 sq ft

14843 Astrolyn St, Winter Garden, FL 34787

Property at 874 Bending Oak Trl, Winter Garden, FL, 34787, 5 beds, 2.5 baths, [object Object]

$2,899/mo

5 beds2.5 baths2,212 sq ft

874 Bending Oak Trl, Winter Garden, FL 34787

Based on information submitted to the MLS GRID as of Sun Dec 07 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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