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Luxury Apartments for Rent in Oakland, FL

25 rentals

1433 Waverunner Lane #NA - Photo 1 of 1

5d+ ago

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1433 Waverunner Lane #NA, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$3,100

House for rent

Available Dec 8

Top amenities
Assigned Parking
Dishwasher
Garage Parking
1239 Juniper Hammock St - Photo 1 of 1

5d+ ago

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Verified

1239 Juniper Hammock St, Winter Garden, FL 34787

Luxury | Walk-in closets | Garage parking

5 beds

4 baths

$2,945

$2,770

Price drop

House for rent

Available Oct 22

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

3d ago

Our team has verified this company

Verified

744 Westcliffe Dr, Winter Garden, FL 34787

Luxury | Garage parking | Hardwood floor

4 beds

2 baths

$2,970

House for rent

Available Dec 12

Top amenities
Ceiling Fan
Garage Parking
907 Muirwood Way - Photo 1 of 1

3d ago

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Verified

907 Muirwood Way, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

4 beds

2 baths

$2,505

House for rent

Available Feb 2

Top amenities
Garage Parking
On-Site Laundry
Swimming Pool
272 Regal Downs Cir - Photo 1 of 1

19h ago

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Verified

272 Regal Downs Cir, Winter Garden, FL 34787

Luxury | Walk-in closets | Garage parking

4 beds

2 baths

$2,525

House for rent

Available Jan 20

Top amenities
On-Site Laundry
254 Regal Downs Cir - Photo 1 of 1

19h ago

Our team has verified this company

Verified

254 Regal Downs Cir, Winter Garden, FL 34787

Luxury | Walk-in closets | Garage parking

4 beds

2 baths

$3,870

$2,705

Price drop

House for rent

Available Jan 1

Top amenities
Garage Parking
High Ceilings
On-Site Laundry

Nearby rental good for eco-living

$1,095

Winter Garden

Nearby rental good for pet owners

$2,600

Clermont

2925 White Magnolia Loop - Photo 1 of 1

2d ago

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Verified

2925 White Magnolia Loop, Clermont, FL 34711

Luxury | Garage parking | Hardwood floor

3 beds

2 baths

$2,550

$2,175

Price drop

House for rent

Available Nov 18

Top amenities
Garage Parking
High Ceilings
3205 White Blossom Lane - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

3205 White Blossom Ln Clermont, FL 34711

3205 White Blossom Lane, Clermont, FL 34711

Luxury | Walk-in closets | Garage parking

4 beds

2 baths

$2,585

House for rent

Available Dec 21

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924 Woodson Hammock Circle - Photo 1 of 1

4d ago

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Verified

924 Woodson Hammock Cir Winter Garden, FL 34787

924 Woodson Hammock Circle, Winter Garden, FL 34787

Luxury | Garage parking

5 beds

2 baths

$3,045

$2,895

Price drop

House for rent

Available Dec 11

2151 Wintermere Pointe Dr - Photo 1 of 1

7h ago

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Verified

2151 Wintermere Pointe Dr Winter Garden, FL 34787

2151 Wintermere Pointe Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | Garage parking

5 beds

4 baths

$3,230

House for rent

Available Dec 19

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Find sweet deals near Oakland

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

$2,505

Winter Garden

$2,525

Winter Garden

$2,705

Winter Garden

$2,175

Clermont

516 Silverdale Avenue - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

516 Silverdale Ave Winter Garden, FL 34787

516 Silverdale Avenue, Winter Garden, FL 34787

Luxury | Walk-in closets | Garage parking

4 beds

3 baths

$2,549

House for rent

Available Nov 14

1647 Portcastle Circle - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

1647 Portcastle Cir Winter Garden, FL 34787

1647 Portcastle Circle, Winter Garden, FL 34787

Luxury | Walk-in closets | Garage parking

3 beds

2 baths

$2,520

$2,395

Price drop

House for rent

Available Oct 30

705 Sunburst Cove Lane - Photo 1 of 1

5d+ 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

$2,895

House for rent

Available Dec 8

Top amenities
Air Conditioning
Ceiling Fan
Central Heat
Hardwood Floor
High Ceilings
In-Unit Laundry
14843 Astrolyn St - Photo 1 of 1
3D tour

3d ago

Luxury house for rent in Winter Garden

14843 Astrolyn St, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

3 beds

2 baths

$2,099

$1,999

Price drop

House for rent

Available Dec 12

Top amenities
In-Unit Laundry
On-Site Management
Package Service
Brass Ring Apartments - Photo 1 of 1

3d ago

8

Very good

Brass Ring Apartments

722 Woodland Street, Winter Garden, FL 34787

Luxury | Outdoor space | Oven

1 bed

1 bath

$1,095

Apartment for rent

2973 Angelonia Thorn Way - Photo 1 of 1
New construction

22h ago

Luxury townhouse for rent in Clermont

2973 Angelonia Thorn Way, Clermont, FL 34711

Luxury | Balcony | Swimming pool

3 beds

2 baths

$2,400

House for rent

Top amenities
Carpet
Ceiling Fan
Fitness Center
High Ceilings
In-Unit Laundry
Swimming Pool
2435 Standing Rock Cir #1 - Photo 1 of 1

1d ago

Luxury house for rent in Oakland

2435 Standing Rock Cir #1, Oakland, FL 34787

Luxury | Swimming pool | In-unit laundry

4 beds

3 baths

$2,600

House for rent

Available Dec 18

Top amenities
Air Conditioning
Fireplace
In-Unit Laundry
On-Site Laundry
Storage
16940 Apopka Springs Blvd - Photo 1 of 1

2d ago

Luxury house for rent in Montverde

Single Family Residence - MONTVERDE, FL

16940 Apopka Springs Blvd, Montverde, FL 34756

Luxury | Walk-in closets | Swimming pool

4 beds

4 baths

$6,615

House for rent

Top amenities
Carpet
Dishwasher
Garage Parking
In-Unit Laundry
On-Site Laundry
Swimming Pool
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17439 Rain Tree Ct - Photo 1 of 1

3d ago

Luxury house for rent in Montverde

House for rent

3825 Quaint Lane #F - Photo 1 of 1
Age restricted

3d ago

Luxury townhouse for rent in Clermont

Townhouse - CLERMONT, FL

3825 Quaint Lane #F, Clermont, FL 34711

Luxury | Walk-in closets | Swimming pool

2 beds

2 baths

$2,450

House for rent

Top amenities
Carpet
Dishwasher
Fitness Center
In-Unit Laundry
Swimming Pool
1150 Chase Drive - Photo 1 of 1

3d ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

1150 Chase Drive, Winter Garden, FL 34787

Luxury | Swimming pool | In-unit laundry

4 beds

2 baths

$2,375

House for rent

Top amenities
Carpet
Ceiling Fan
In-Unit Laundry
1021 Temple Grove Place #NA - Photo 1 of 1

4d ago

Luxury house for rent in Winter Garden

$9,500 - 4 Bedroom 5 Bathroom Luxury Lake Front House In Winter Garden With Great Amenities

1021 Temple Grove Place #NA, Winter Garden, FL 34787

Luxury | Swimming pool | In-unit laundry

4 beds

5 baths

$9,500

House for rent

Available Feb 1

Top amenities
Assigned Parking
Dishwasher
In-Unit Laundry
Swimming Pool
874 Bending Oak Trail #874 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Garden

5 BR, 3 BA in Winter Garden

874 Bending Oak Trail #874, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

5 beds

3 baths

$2,599

Apartment for rent

Available Nov 26

Top amenities
Carpet
In-Unit Laundry
On-Site Laundry
1500 Broken Oak Drive - Photo 1 of 1

5d+ ago

Luxury Tucker Oaks townhouse for rent in Winter Garden

3 BR, 3 BA in Winter Garden

1500 Broken Oak Drive, Winter Garden, FL 34787

Luxury | Outdoor space

3 beds

3 baths

$2,300

House for rent

Available Dec 2

2489 Chickasaw Plum Loop #2489 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Clermont

4 BR, 3 BA in Clermont

2489 Chickasaw Plum Loop #2489, Clermont, FL 34711

Luxury | Walk-in closets | On-site laundry

4 beds

3 baths

$3,000

Apartment for rent

Available Jan 17

Top amenities
On-Site Laundry
Showing 1 - 25 of 25 results
Home > Apartments in Oakland > Oakland Luxury Apartments For Rent
Updated: December 20, 2025

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3 bedrooms for rent in Oakland, FL1 rental

1 rental

Pet friendly apartments in Oakland, FL4 rentals

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Looking for luxury apartments in Oakland, FL near you?

🔑Available apartment rentals25
💰Best rent deal722 Woodland Street
✨Popular amenities, ,
🍽With dishwasher
🏠With photos

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