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Luxury Apartments for Rent in Oakland, FL

25 rentals

752 Citrus Cove Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

752 Citrus Cove Dr, Winter Garden, FL 34787

Luxury | Dishwasher | Outdoor space

4 beds

3 baths

$2,995

House for rent

14701 Timucua Pl - Photo 1 of 1

20h ago

Luxury Arrowhead house for rent in Orlando

14701 Timucua Pl, Orlando, FL 34711

Luxury | Swimming pool | Dishwasher

4 beds

3 baths

$3,000

$2,850

Price drop

House for rent

1933 Portcastle Cir - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

1933 Portcastle Cir, Winter Garden, FL 34787

Luxury | Air conditioning | Central heat

3 beds

2 baths

$2,450

House for rent

457 Regal Downs Cir - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

457 Regal Downs Cir, Winter Garden, FL 34787

Luxury | Walk-in closets | Garage parking

3 beds

2 baths

$2,570

House for rent

Available Mar 20

Top amenities
High Ceilings
907 Muirwood Way - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

907 Muirwood Way, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

4 beds

2 baths

$2,565

House for rent

Available Jan 22

Top amenities
Garage Parking
On-Site Laundry
Swimming Pool
2648 Bobcat Chase Blvd - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

2648 Bobcat Chase Blvd, Oakland, FL 34787

Luxury | Balcony | Swimming pool

4 beds

3 baths

$3,185

House for rent

Available Mar 13

Top amenities
On-Site Laundry
On-Site Management

Nearby rental good for eco-living

Nearby rental good for pet owners

$2,570

Winter Garden

16000 Arrowhead Trl - Photo 1 of 1

1d ago

Our team has verified this company

Verified

16000 Arrowhead Trl Clermont, FL 34711

16000 Arrowhead Trl, Orlando, FL 34711

Luxury | Garage parking

4 beds

2 baths

$2,775

House for rent

Available Jan 20

15142 Quailmoor St - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

15142 Quailmoor St Winter Garden, FL 34787

15142 Quailmoor St, Winter Garden, FL 34787

Luxury | Walk-in closets | Garage parking

4 beds

2 baths

$2,945

$2,830

Price drop

House for rent

Available Jan 27

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924 Woodson Hammock Cir - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

924 Woodson Hammock Cir Winter Garden, FL 34787

924 Woodson Hammock Cir, Winter Garden, FL 34787

Luxury | Garage parking

5 beds

2 baths

$2,675

$2,520

Price drop

House for rent

Available Dec 11

705 Sunburst Cove Lane - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Garden

705 Sunburst Cove Lane, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

4 beds

2 baths

$2,700

Apartment for rent

Available Jan 17

Top amenities
Air Conditioning
Ceiling Fan
Central Heat
Hardwood Floor
High Ceilings
In-Unit Laundry
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Find sweet deals near Oakland

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

$2,450

Winter Garden

$2,565

Winter Garden

$2,830

Winter Garden

$2,700

Winter Garden

420 E Cypress St - Photo 1 of 1

9h ago

Our team has verified this company

Verified

420 E Cypress St, Winter Garden, FL 34787

Luxury | In-unit laundry | Furnished

3 beds

2 baths

$3,622

Apartment for rent

Top amenities
Dishwasher
In-Unit Laundry
Microwave
Oven
TV
Wi-Fi
Brass Ring Apartments - Photo 1 of 1

23h ago

7.4

Very good

Brass Ring Apartments

722 S Woodland St, Winter Garden, FL 34787

Luxury | Air conditioning | Outdoor space

1 bed

1 bath

$1,000

Apartment for rent

233 Woodfall Ln - Photo 1 of 1
New construction

15h ago

Luxury house for rent in Winter Garden

233 Woodfall Ln, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

5 beds

3 baths

$4,500

House for rent

Top amenities
Carpet
High Ceilings
In-Unit Laundry
430 Southern Pecan Cir #101 - Photo 1 of 1

19h ago

Luxury condo for rent in Winter Garden

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

Luxury | Swimming pool | Fitness center

2 beds

2 baths

$2,100

Condo for rent

Top amenities
Fitness Center
In-Unit Laundry
Swimming Pool
118 Southern Pecan Cir - Photo 1 of 1

1d ago

Luxury condo for rent in Winter Garden

1 BR, 1 BA in Southern Pines Condominiums

118 Southern Pecan Cir, Winter Garden, FL 34787

Luxury

1 bed

1 bath

$1,650

Condo for rent

Available Aug 3

1022 Huntspoint St - Photo 1 of 1

3d ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

1022 Huntspoint St, Winter Garden, FL 34787

Luxury | Swimming pool | In-unit laundry

3 beds

2 baths

$4,800

House for rent

Top amenities
Ceiling Fan
Dishwasher
Garage Parking
In-Unit Laundry
On-Site Laundry
Swimming Pool
2793 Falcon Rdg - Photo 1 of 1
Age restricted

4d ago

Luxury Summit Greens house for rent in Clermont

Single Family Residence - CLERMONT, FL

2793 Falcon Rdg, Clermont, FL 34711

Luxury | In-unit laundry | Garage parking

2 beds

3 baths

$2,700

House for rent

Top amenities
Garage Parking
In-Unit Laundry
17014 Crestmont Blvd #17014 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Clermont

3 BR, 2 BA in Clermont

17014 Crestmont Blvd #17014, Clermont, FL 34711

Luxury | Walk-in closets | In-unit laundry

3 beds

2 baths

$2,985

Apartment for rent

Available Feb 1

Top amenities
In-Unit Laundry
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13931 Daniels Landing Cir #13931 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Garden

2 BR, 3 BA in Daniels Landing

13931 Daniels Landing Cir #13931, Winter Garden, FL 34787

Luxury | Outdoor space

2 beds

3 baths

$2,000

Apartment for rent

Available Jan 22

233 Southern Pecan Cir - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Garden

2 BR, 1 BA in Southern Pines Condominiums

233 Southern Pecan Cir, Winter Garden, FL 34787

Luxury

2 beds

1 bath

$1,795

Condo for rent

Available Feb 1

1182 Orange Season Ln #1182 - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Garden

3 BR, 3 BA in Hickory Hammock

1182 Orange Season Ln #1182, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

3 beds

3 baths

$3,000

Condo for rent

Available Jan 26

Top amenities
Ceiling Fan
In-Unit Laundry
On-Site Laundry
301 S Boyd St - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Garden

2 BR, 1 BA in Winter Garden

301 S Boyd St, Winter Garden, FL 34787

Luxury | On-site laundry | Outdoor space

2 beds

1 bath

$1,800

Apartment for rent

Available Jan 6

Top amenities
On-Site Laundry
39 Windtree Ln - Photo 1 of 1

5d+ ago

Luxury condo for rent in Winter Garden

2 BR, 2 BA in Windtree Gardens Condominiums

39 Windtree Ln, Winter Garden, FL 34787

Luxury | In-unit laundry | Ceiling fan

2 beds

2 baths

$1,750

Condo for rent

Available Feb 1

Top amenities
Ceiling Fan
In-Unit Laundry
15219 Starleigh Rd #15219 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Garden

3 BR, 3 BA in Winter Garden

15219 Starleigh Rd #15219, Winter Garden, FL 34787

Luxury | Outdoor space

3 beds

3 baths

$2,350

Apartment for rent

Available Jan 14

1012 Stucki Ter #1012 - Photo 1 of 1

5d+ ago

Luxury apartment for rent in Winter Garden

2 BR, 2 BA in Winter Garden

1012 Stucki Ter #1012, Winter Garden, FL 34787

Luxury | In-unit laundry | High ceilings

2 beds

2 baths

$1,600

Apartment for rent

Available Feb 1

Top amenities
In-Unit Laundry
Showing 1 - 25 of 25 results
Home > Apartments in Oakland > Oakland Luxury Apartments For Rent
Updated: February 3, 2026

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3 bedrooms for rent in Oakland, FL1 rental

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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 deal722 S Woodland St
✨Popular amenities, ,
🍽With dishwasher
🏠With photos

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