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Luxury Apartments for Rent in Oakland, FL

25 rentals

Daniels Landing Cir #13939 - Photo 1 of 1

5d+ ago

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Verified

$2,100 3 Bedroom 2.5 bathroom Townhouse In Winter Garden With Great Amenities

Daniels Landing Cir #13939, Winter Garden, FL 34787

Luxury | Swimming pool | Fitness center

3 beds

2 baths

$2,250

$2,100

Price drop

House for rent

Available Oct 20

Top amenities
Air Conditioning
Assigned Parking
Garage Parking
Hardwood Floor
In-Unit Laundry
Swimming Pool
1317 S Park Ave - Photo 1 of 1

5d+ ago

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Verified

1317 S Park Ave, Winter Garden, FL 34787

Luxury

3 beds

2 baths

$2,980

$2,125

Price drop

House for rent

Available Nov 12

1239 Juniper Hammock St - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1239 Juniper Hammock St, Winter Garden, FL 34787

Luxury | Walk-in closets | Garage parking

5 beds

4 baths

$3,190

House for rent

Available Oct 22

Top amenities
Garage Parking
On-Site Laundry
15261 Harrowgate Way - Photo 1 of 1

1d ago

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Verified

Luxury | Garage parking | On-site laundry

3 beds

2 baths

$2,650

$2,495

Price drop

House for rent

Available Nov 24

Top amenities
On-Site Laundry
744 Westcliffe Dr - Photo 1 of 1

5d+ ago

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Verified

744 Westcliffe Dr, Winter Garden, FL 34787

Luxury | Garage parking | Hardwood floor

4 beds

2 baths

$2,945

House for rent

Available Nov 26

Top amenities
Garage Parking
Hardwood Floor
272 Regal Downs Cir - Photo 1 of 1

2d ago

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Verified

272 Regal Downs Cir, Winter Garden, FL 34787

Luxury | Walk-in closets | Garage parking

4 beds

2 baths

$2,590

House for rent

Available Dec 22

Top amenities
On-Site Laundry

Nearby rental good for eco-living

Nearby rental good for pet owners

$2,100

Winter Garden

15509 Oxley St - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

15509 Oxley St, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

3 beds

2 baths

$2,465

$2,280

Price drop

House for rent

Available Sep 22

Top amenities
Garage Parking
High Ceilings
On-Site Laundry
2925 White Magnolia Loop - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

2925 White Magnolia Loop, Clermont, FL 34711

Luxury | Garage parking | Hardwood floor

3 beds

2 baths

$2,475

House for rent

Available Dec 1

Top amenities
Garage Parking
High Ceilings
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14409 N Greater Hills Blvd - Photo 1 of 1

3d ago

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Verified

14409 N Greater Hills Blvd Clermont, FL 34711

14409 N Greater Hills Blvd, Clermont, FL 34711

Luxury | Garage parking | Outdoor space

3 beds

2 baths

$2,080

House for rent

Available Nov 6

225 Largovista Dr - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

225 Largovista Dr, Oakland, FL 34787

Luxury | Dishwasher

4 beds

3 baths

$2,650

House for rent

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Find sweet deals near Oakland

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

$800

Oakland

$2,100

Winter Garden

$2,125

Winter Garden

$3,190

Winter Garden

1075 Lincoln Ter - Photo 1 of 1

5d+ ago

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Verified

1075 Lincoln Ter, Winter Garden, FL 34787

Luxury | Oven

3 beds

1 bath

$1,450

House for rent

15233 Serenade Dr - Photo 1 of 1

3d ago

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Verified

15233 Serenade Dr Winter Garden, FL 34787

15233 Serenade Dr, Winter Garden, FL 34787

Luxury | Garage parking

4 beds

3 baths

$2,995

House for rent

Available Nov 9

1647 Portcastle Cir - Photo 1 of 1

5d+ ago

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Verified

1647 Portcastle Cir Winter Garden, FL 34787

1647 Portcastle Cir, Winter Garden, FL 34787

Luxury | Walk-in closets | Garage parking

3 beds

2 baths

$2,690

House for rent

Available Oct 30

932 Mcpherson Pl - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

932 McPherson Pl Winter Garden, FL 34787

932 Mcpherson Pl, Winter Garden, FL 34787

Luxury | Walk-in closets | Garage parking

5 beds

4 baths

$3,310

$3,145

Price drop

House for rent

Available Oct 8

705 Sunburst Cove Lane - Photo 1 of 1

2d ago

Luxury house for rent in Winter Garden

705 Sunburst Cove Lane, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

4 beds

2 baths

$3,200

House for rent

Available Nov 1

Top amenities
Air Conditioning
Ceiling Fan
Central Heat
Hardwood Floor
High Ceilings
In-Unit Laundry
13345 Fox Glove St - Photo 1 of 1

1d ago

Luxury Stoneybrook West house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

13345 Fox Glove St, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

5 beds

3 baths

$4,900

House for rent

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
Swimming Pool
214 Woodfall Ln - Photo 1 of 1
New construction

3d ago

Luxury house for rent in Winter Garden

214 Woodfall Ln, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

5 beds

5 baths

$6,500

House for rent

Top amenities
Carpet
Garage Parking
In-Unit Laundry
On-Site Laundry
1563 Priory Cir - Photo 1 of 1

3d ago

Luxury Stoneybrook West townhouse for rent in Winter Garden

Luxury | Swimming pool | In-unit laundry

3 beds

2 baths

$2,400

House for rent

Top amenities
In-Unit Laundry
Swimming Pool
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1490 Stone Arrow Ct - Photo 1 of 1

3d ago

Luxury house for rent in Oakland

Luxury | Swimming pool

5 beds

3 baths

$3,450

House for rent

1712 Portcastle Cir - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Luxury

3 beds

2 baths

$2,500

House for rent

14452 N Greater Hills Blvd - Photo 1 of 1

2d ago

Luxury Greater Hills house for rent in Clermont

Single Family Residence - CLERMONT, FL

14452 N Greater Hills Blvd, Clermont, FL 34711

Luxury | In-unit laundry | Garage parking

3 beds

2 baths

$2,500

$2,300

Price drop

House for rent

Top amenities
Garage Parking
In-Unit Laundry
2521 Sky Stone Ct - Photo 1 of 1

5d+ ago

Luxury house for rent in Oakland

2521 Sky Stone Ct, Oakland, FL 34787

Luxury | Swimming pool | In-unit laundry

4 beds

2 baths

$2,950

House for rent

Top amenities
In-Unit Laundry
992 Stucki Ter - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Garden

992 Stucki Ter, Winter Garden, FL 34787

Luxury | In-unit laundry | Ceiling fan

3 beds

2 baths

$2,175

House for rent

Top amenities
Ceiling Fan
In-Unit Laundry
16300 County Road 455 #205 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Montverde

Condominium - MONTVERDE, FL

16300 County Road 455 #205, Montverde, FL 34756

Luxury | Balcony | Walk-in closets

2 beds

2 baths

$2,800

Condo for rent

Top amenities
Ceiling Fan
Dishwasher
Fitness Center
In-Unit Laundry
1320 Beulah Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

1320 Beulah Rd, Winter Garden, FL 34787

Luxury | In-unit laundry | Air conditioning

2 beds

1 bath

$1,850

$1,650

Price drop

House for rent

Top amenities
Air Conditioning
In-Unit Laundry
Showing 1 - 25 of 25 results
Home > Apartments in Oakland > Oakland Luxury Apartments For Rent
Updated: November 3, 2025

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3 bedrooms for rent in Oakland, FL

Pet friendly apartments in Oakland, FL1 rental

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Looking for luxury apartments in Oakland, FL near you?

🔑Available apartment rentals25
💰Best rent deal1075 Lincoln Ter
✨Popular amenities, ,
🍽With dishwasher
🏠With photos

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