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Houses for Rent in Oakland, FL

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1530 Stone Arrow Ct - Photo 1 of 1

14h ago

House for rent in Oakland

1530 Stone Arrow Ct, Oakland, FL 34787

In-unit laundry | Outdoor space | Swimming pool

4 beds

2.5 baths

$3,150

House for rent

181 Zachary Wade St #NA - Photo 1 of 1

5d+ ago

House for rent in Winter Garden

$3,200 - 5 Bedroom 3 Bathroom House In Winter Garden With Great Amenities close to downtown winter garden

181 Zachary Wade St #NA, Winter Garden, FL 34787

Outdoor space | Garage parking | Air conditioning

5 beds

3 baths

$3,200

House for rent

Available Aug 1

5d+ ago

House for rent in Winter Garden

SINGLE_FAMILY - WINTER GARDEN, FL

273 Avalon Rd, Winter Garden, FL 34787

Outdoor space | Storage | Walk-in closets

4 beds

2 baths

$2,995

House for rent

1000 Dolphin Dr - Photo 1 of 1

5d+ ago

Townhouse for rent in Winter Garden

TOWNHOME - WINTER GARDEN, FL

1000 Dolphin Dr, Winter Garden, FL 34787

In-unit laundry | Outdoor space | Dishwasher

3 beds

2 baths

$2,000

House for rent

968 Stucki Ter - Photo 1 of 1

37m ago

Townhouse for rent in Winter Garden

3 Bedroom 2 Bath Winter Garden Townhome with Remodeled Kitchen and a Fenced Backyard!

968 Stucki Ter, Winter Garden, FL 34787

Outdoor space

3 beds

2 baths

$2,000

$1,900

Price drop

House for rent

23 Zachary Wade St - Photo 1 of 1

5d+ ago

House for rent in Winter Garden

23 Zachary Wade St, Winter Garden, FL 34787

Outdoor space | Garage parking | Carpet

4 beds

2 baths

$2,550

House for rent

Available Aug 1

Nearby rental good for eco-living

$2,495

Winter Garden

Nearby rental good for pet owners

$1,995

Gotha

1198 Maxey Dr - Photo 1 of 1

4d ago

Our team has verified this company

Verified

1198 Maxey Dr, Winter Garden, FL 34787

On-site laundry | Walk-in closets | Ceiling fan

3 beds

1.5 baths

$1,920

House for rent

Available Sep 14

747 Citrus Cove Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

747 Citrus Cove Dr, Winter Garden, FL 34787

Outdoor space | Garage parking | High ceilings

4 beds

2 baths

$3,790

$2,650

Price drop

House for rent

Available Aug 12

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415 Balboa Blvd - Photo 1 of 1

17h ago

Our team has verified this company

Verified

415 Balboa Blvd Clermont, FL 34715

415 Balboa Blvd, Clermont, FL 34715

Garage parking

4 beds

2 baths

$2,545

House for rent

Available Aug 7

1961 Portcastle Cir - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1961 Portcastle Cir, Winter Garden, FL 34787

On-site laundry | Swimming pool | On-site management

4 beds

2.5 baths

$2,735

House for rent

Available Sep 2

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Find sweet deals near Oakland

These rentals are 10%-30% cheaper than the local average price for similar rentals.

$2,000

Winter Garden

$2,550

Winter Garden

$1,920

Winter Garden

$2,650

Winter Garden

1030 Maxey Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1030 Maxey Dr, Winter Garden, FL 34787

On-site laundry | Swimming pool | Balcony

4 beds

1.5 baths

$2,185

$1,900

Price drop

House for rent

Available Jul 27

13509 Laranja St - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

13509 Laranja St, Clermont, FL 34711

On-site laundry | Storage | Swimming pool

3 beds

2.5 baths

$2,935

$2,520

Price drop

House for rent

Available Jul 30

14425 N Greater Hills Blvd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

14425 N Greater Hills Blvd, Clermont, FL 34711

On-site laundry | Swimming pool | On-site management

3 beds

2 baths

$2,515

$2,355

Price drop

House for rent

Available Jul 24

3212 Park Branch Ave - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

3212 Park Branch Ave, Clermont, FL 34711

On-site laundry | Swimming pool | On-site management

4 beds

2.5 baths

$2,750

$2,505

Price drop

House for rent

Available Jun 30

988 Glenview Cir - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

988 Glenview Cir, Winter Garden, FL 34787

On-site laundry | Storage | Swimming pool

4 beds

3 baths

$2,750

$2,530

Price drop

House for rent

Available Jun 16

2949 Magnolia Blossom Cir - Photo 1 of 1

4d ago

Our team has verified this company

Verified

2949 Magnolia Blossom Cir Clermont, FL 34711

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

Average rent

The average rent for houses in Oakland, as of August 2026, is up 19.62% compared to last month but unchanged year-over-year.
$2,950

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397 Regal Downs Cir - Photo 1 of 1

4d ago

Our team has verified this company

Verified

397 Regal Downs Cir Winter Garden, FL 34787

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

419 Home Grove Dr - Photo 1 of 1

13h ago

Our team has verified this company

Verified

419 Home Grove Dr Winter Garden, FL 34787

419 Home Grove Dr, Winter Garden, FL 34787

Outdoor space | Garage parking | Swimming pool

4 beds

3 baths

$3,265

House for rent

Available Aug 10

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14411 Hampshire Bay Cir - Photo 1 of 1

5h ago

House for rent in Winter Garden

14411 Hampshire Bay Cir, Winter Garden, FL 34787

Outdoor space | Storage | Garage parking

4 beds

4 baths

$6,000

House for rent

17392 Bal Harbour Dr #1 - Photo 1 of 1

4d ago

House for rent in Winter Garden

17392 Bal Harbour Drive - 1

17392 Bal Harbour Dr #1, Winter Garden, FL 34787

4 beds

3 baths

$3,375

House for rent

Available Aug 1

3524 Banana Shrub Blvd #1 - Photo 1 of 1

4d ago

House for rent in Clermont

3524 Banana Shrub Boulevard - 1

3524 Banana Shrub Blvd #1, Clermont, FL 34711

4 beds

3 baths

$4,000

House for rent

Available Aug 1

2205 Caledonian St - Photo 1 of 1
Age restricted

5d+ ago

Summit Greens house for rent in Clermont

SINGLE_FAMILY - CLERMONT, FL

2205 Caledonian St, Clermont, FL 34711

In-unit laundry | Outdoor space | Garage parking

2 beds

2 baths

$2,500

House for rent

2735 Cedaridge Cir - Photo 1 of 1

5d+ ago

House for rent in Clermont

SINGLE_FAMILY - CLERMONT, FL

2735 Cedaridge Cir, Clermont, FL 34711

In-unit laundry | Outdoor space | Storage

3 beds

2 baths

$2,500

House for rent

442 Home Grove Dr - Photo 1 of 1

5d+ ago

House for rent in Winter Garden

3 BR / 2 BA Home In Winter Garden

442 Home Grove Dr, Winter Garden, FL 34787

High ceilings | Outdoor space

3 beds

2 baths

$2,795

House for rent

5d+ ago

Stoneybrook West house for rent in Winter Garden

1061 Portmoor Way, Winter Garden, FL 34787

In-unit laundry | Outdoor space | Swimming pool

4 beds

2 baths

$3,200

House for rent

Showing 1 - 25 of 25 results
Home > House Rentals in Oakland
Updated: August 5, 2026

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Discover houses for rent in Oakland, FL

🌇Available house rentals25 houses
💰Best rent deal1030 Maxey Dr
🍃With outdoor space
⭐Popular amenities, ,
🍽With dishwasher
🚗With garage parking
❄️With air conditioning
🏠With photos