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Luxury Apartments for Rent in Oakland, FL

25 rentals

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

$1,650

$1,550

Price drop

House for rent

1137 Burland Cir - Photo 1 of 1

4d ago

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Verified

1137 Burland Cir Winter Garden, FL 34787

1137 Burland Cir, Winter Garden, FL 34787

Luxury | Garage parking

5 beds

4 baths

$2,845

House for rent

Available Sep 18

2648 Bobcat Chase Blvd - Photo 1 of 1

5d+ ago

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Verified

2648 Bobcat Chase Blvd, Oakland, FL 34787

Luxury | Balcony | Swimming pool

4 beds

3 baths

$3,060

House for rent

Top amenities
On-Site Management
1712 Lindzlu St - Photo 1 of 1

4d ago

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Verified

1712 Lindzlu St Winter Garden, FL 34787

1712 Lindzlu St, Winter Garden, FL 34787

Luxury | Swimming pool | Garage parking

4 beds

3 baths

$2,995

House for rent

Available Sep 12

Top amenities
Garage Parking
619 Grand Royal Cir - Photo 1 of 1

5d+ ago

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Verified

619 Grand Royal Cir Winter Garden, FL 34787

619 Grand Royal Cir, Winter Garden, FL 34787

Luxury | Walk-in closets | Garage parking

3 beds

2 baths

$2,380

$2,275

Price drop

House for rent

Available Aug 29

1239 Juniper Hammock St - Photo 1 of 1

3d ago

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Verified

Luxury | Walk-in closets | Garage parking

5 beds

4 baths

$3,490

$3,345

Price drop

House for rent

Available Nov 3

Top amenities
Carpet
Garage Parking
On-Site Laundry

Nearby rental good for eco-living

Nearby rental good for pet owners

$2,995

Winter Garden

Nearby rental good for social life

$2,275

Winter Garden

15509 Oxley St - Photo 1 of 1

2d ago

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Verified

15509 Oxley St, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

3 beds

2 baths

$3,630

$2,615

Price drop

House for rent

Available Sep 25

Top amenities
Ceiling Fan
Garage Parking
High Ceilings
On-Site Laundry
420 E Cypress St - Photo 1 of 1

1d ago

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Verified

420 E Cypress St, Winter Garden, FL 34787

Luxury | In-unit laundry | Furnished

3 beds

2 baths

$5,170

Apartment for rent

Top amenities
Dishwasher
Furnished
In-Unit Laundry
Oven
TV
Wi-Fi
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1546 Broken Oak Dr #201 - Photo 1 of 1

21h ago

Luxury Tucker Oaks condo for rent in Winter Garden

1546 Broken Oak Dr #201, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

2 beds

2 baths

$1,950

Condo for rent

Top amenities
Carpet
Ceiling Fan
In-Unit Laundry
2628 Balforn Tower Way - Photo 1 of 1

1d ago

Luxury Stoneybrook West house for rent in Winter Garden

2628 Balforn Tower Way, Winter Garden, FL 34787

Luxury | Swimming pool | Fitness center

3 beds

2 baths

$2,900

House for rent

Top amenities
Dishwasher
Fitness Center
In-Unit Laundry
Advertisement

Find sweet deals near Oakland

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

$2,275

Winter Garden

$2,100

Winter Garden

1222 Brandy Lake View Cir - Photo 1 of 1

2d ago

Luxury house for rent in Winter Garden

1222 Brandy Lake View Cir, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

4 beds

2 baths

$2,700

House for rent

Top amenities
Ceiling Fan
Dishwasher
High Ceilings
In-Unit Laundry
15667 Boggy Oak Cir #B - Photo 1 of 1

21h ago

Luxury Tucker Oaks townhouse for rent in Winter Garden

15667 Boggy Oak Cir #B, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

3 beds

2 baths

$2,200

$2,000

Price drop

House for rent

Top amenities
Ceiling Fan
Garage Parking
In-Unit Laundry
On-Site Laundry
14423 Hampshire Bay Cir - Photo 1 of 1

4d ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

14423 Hampshire Bay Cir, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$5,500

House for rent

Top amenities
Ceiling Fan
Dishwasher
Furnished
Garage Parking
High Ceilings
In-Unit Laundry
1532 Broken Oak Dr #22B - Photo 1 of 1

5d+ ago

Luxury Tucker Oaks townhouse for rent in Winter Garden

1532 Broken Oak Dr #22B, Winter Garden, FL 34787

Luxury | Swimming pool | In-unit laundry

3 beds

2 baths

$2,250

House for rent

Top amenities
Controlled Access
Dishwasher
In-Unit Laundry
Swimming Pool
760 Walkers Grove Ln - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

760 Walkers Grove Ln, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

3 beds

2 baths

$3,000

House for rent

Top amenities
Garage Parking
In-Unit Laundry
15404 Thoroughbred Ln - Photo 1 of 1

5d+ ago

Luxury Trails Of Montverde house for rent in Montverde

Single Family Residence - MONTVERDE, FL

15404 Thoroughbred Ln, Montverde, FL 34756

Luxury | Walk-in closets | In-unit laundry

4 beds

3 baths

$3,000

House for rent

Top amenities
Carpet
Fireplace
Garage Parking
High Ceilings
In-Unit Laundry
130 Southern Pecan Cir #108 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Garden

Condominium - WINTER GARDEN, FL

130 Southern Pecan Cir #108, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

3 beds

2 baths

$2,100

Condo for rent

Top amenities
Ceiling Fan
Concierge Service
Dishwasher
Garage Parking
In-Unit Laundry
On-Site Management
14281 Lagoon Cove Ln - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

14281 Lagoon Cove Ln, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

4 beds

2 baths

$3,075

House for rent

Top amenities
Ceiling Fan
High Ceilings
In-Unit Laundry
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13550 Laranja St - Photo 1 of 1

5d+ ago

Luxury house for rent in Clermont

13550 Laranja St, Clermont, FL 34711

Luxury | Walk-in closets | In-unit laundry

3 beds

2 baths

$2,950

House for rent

Top amenities
In-Unit Laundry
16413 Good Hearth Blvd - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Clermont

Luxury | Swimming pool | In-unit laundry

4 beds

3 baths

$3,495

Apartment for rent

Top amenities
Assigned Parking
Ceiling Fan
Central Heat
In-Unit Laundry
Swimming Pool
200 Southern Pecan Cir #101 - Photo 1 of 1

21h ago

Luxury condo for rent in Winter Garden

Condominium - WINTER GARDEN, FL

200 Southern Pecan Cir #101, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

3 beds

2 baths

$2,100

$2,000

Price drop

Condo for rent

Top amenities
Ceiling Fan
Dishwasher
In-Unit Laundry
Swimming Pool
963 Butterfly Blvd - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Garden

963 Butterfly Blvd, Winter Garden, FL 34787

Luxury | Swimming pool | In-unit laundry

3 beds

2 baths

$1,800

House for rent

Top amenities
In-Unit Laundry
694 Brooks Field Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

694 Brooks Field Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

6 beds

4 baths

$6,500

House for rent

Top amenities
Carpet
Dishwasher
High Ceilings
In-Unit Laundry
14416 N Greater Hills Blvd - Photo 1 of 1

4d ago

Luxury Greater Hills house for rent in Clermont

Luxury | Concierge service | Package service

3 beds

2 baths

$2,195

House for rent

Available Sep 1

228 Deepcove Rd - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Garden

Luxury

2 beds

2 baths

$2,250

House for rent

Showing 1 - 25 of 25 results
Home > Apartments in Oakland > Oakland Luxury Apartments For Rent
Updated: September 14, 2025

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3 bedrooms for rent in Oakland, FL2 rentals

2 rentals

Pet friendly apartments in Oakland, FL2 rentals

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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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