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Luxury Houses for Rent in Winter Garden, FL

31 rentals

5229 Citrus Leaf Blvd - Photo 1 of 1
New construction

1d ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

5229 Citrus Leaf Blvd, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

4 beds

3 baths

$5,600

House for rent

Top amenities
Garage Parking
In-Unit Laundry
On-Site Laundry
Storage
17834 Adrift Rd - Photo 1 of 1
New construction

1d ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

17834 Adrift Rd, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

4 beds

3 baths

$4,500

House for rent

Top amenities
Carpet
Dishwasher
In-Unit Laundry
Storage
15699 Panther Lake Dr - Photo 1 of 1

3d ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

15699 Panther Lake Dr, Winter Garden, FL 34787

Luxury | Balcony | Walk-in closets

5 beds

5 baths

$12,000

House for rent

Top amenities
Carpet
Fitness Center
Furnished
Garage Parking
Hardwood Floor
Storage
7556 John Hancock Dr - Photo 1 of 1
New construction

4d ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

7556 John Hancock Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

5 beds

6 baths

$18,000

House for rent

Top amenities
Furnished
Garage Parking
High Ceilings
In-Unit Laundry
Swimming Pool
1021 Temple Grove Pl - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

1021 Temple Grove Pl, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

4 beds

4 baths

$8,500

House for rent

Top amenities
Ceiling Fan
Furnished
Garage Parking
High Ceilings
In-Unit Laundry
Swimming Pool
8097 Sayings Dr - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

8097 Sayings Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

3 beds

2 baths

$3,000

House for rent

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
Swimming Pool

Nearby rental good for eco-living

$2,550

Winter Garden

Nearby rental good for pet owners

$2,520–$2,761

Ocoee

16055 Silver Brook Way - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

16055 Silver Brook Way, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

3 beds

2 baths

$3,500

House for rent

Top amenities
Dishwasher
In-Unit Laundry
On-Site Laundry
Swimming Pool
15262 Night Heron Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

15262 Night Heron Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

3 beds

2 baths

$3,150

House for rent

Top amenities
Ceiling Fan
Dishwasher
In-Unit Laundry
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1022 Huntspoint St - Photo 1 of 1

5d+ 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
13890 Title Way #13890 - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Garden

3 BR, 3 BA in Hickory Hut

13890 Title Way #13890, Winter Garden, FL 34787

Luxury | Walk-in closets | Outdoor space

3 beds

3 baths

$2,950

House for rent

Available May 1

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Find sweet deals in Winter Garden

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

$2,295

1933 Portcastle Cir

$2,700

12067 Bracco St #NA

$2,450

857 Rivers Crossing St

$2,200

16213 Wilkinson Dr

15523 Bay Bridge St - Photo 1 of 1
New construction

5d+ ago

Luxury townhouse for rent in Winter Garden

15523BBS

15523 Bay Bridge St, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

3 beds

2 baths

$3,100

House for rent

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
On-Site Laundry
Swimming Pool
7054 7054 BROOMSHEDGE TRAIL TRAIL - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

7054 7054 BROOMSHEDGE TRAIL TRAIL, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

2 beds

2 baths

$2,280

House for rent

Top amenities
Dishwasher
High Ceilings
In-Unit Laundry
Residents Lounge
Swimming Pool
9207 Gran Teatro Dr - Photo 1 of 1
New construction

5d+ ago

Luxury townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

9207 Gran Teatro Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

3 beds

2 baths

$3,100

House for rent

Top amenities
Carpet
Dishwasher
Garage Parking
High Ceilings
In-Unit Laundry
On-Site Laundry
11163 Great Rock St - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

11163 Great Rock St, Winter Garden, FL 34787

Luxury | Outdoor space | On-site management

5 beds

3 baths

$5,350

$4,999

Price drop

House for rent

Available Jan 8

Top amenities
On-Site Management
14931 Lebeau Loop - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

14931 Lebeau Loop, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

4 beds

3 baths

$5,400

House for rent

Top amenities
Fitness Center
Garage Parking
In-Unit Laundry
Storage
Swimming Pool
16436 Silver Brook Way - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

16436 Silver Brook Way, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

3 beds

2 baths

$2,950

House for rent

Top amenities
Air Conditioning
Carpet
Dishwasher
In-Unit Laundry
Package Service
Storage
Pixie Mandarin Ct - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

Pixie Mandarin Ct, Winter Garden, FL 34787

Luxury | Swimming pool | In-unit laundry

3 beds

2 baths

$3,200

House for rent

Top amenities
In-Unit Laundry
13357 Harbor Shore Ln - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Garden

13357 Harbor Shore Ln, Winter Garden, FL 34787

Luxury | Swimming pool | In-unit laundry

2 beds

2 baths

$2,100

House for rent

Available Jan 15

Top amenities
Concierge Service
In-Unit Laundry
On-Site Management
Package Service
Swimming Pool
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12615 Clear Sapphire Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

3/2

12615 Clear Sapphire Dr, Winter Garden, FL 34787

Luxury | Air conditioning

3 beds

2 baths

$3,200

House for rent

13241 Tollcross Way - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

13241 Tollcross Way, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

6 beds

5 baths

$6,000

House for rent

Top amenities
Carpet
Garage Parking
In-Unit Laundry
17582 Lake Star Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

17582 Lake Star Rd, Winter Garden, FL 34787

Luxury | In-unit laundry | Outdoor space

4 beds

3 baths

$4,100

House for rent

Top amenities
In-Unit Laundry
7567 Green Mountain Way - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

7567 Green Mountain Way, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

5 beds

4 baths

$10,500

House for rent

Top amenities
Ceiling Fan
Garage Parking
High Ceilings
In-Unit Laundry
Swimming Pool
16324 Silver Grove Blvd #1 - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

16324 Silver Grove Boulevard - 1

16324 Silver Grove Blvd #1, Winter Garden, FL 34787

Luxury | Swimming pool | Outdoor space

5 beds

4 baths

$5,500

House for rent

Available Jan 1

16771 Turtle Hatch Dr #D - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

16771 Turtle Hatch Dr #D, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

4 beds

3 baths

$4,500

House for rent

Top amenities
Ceiling Fan
Garage Parking
In-Unit Laundry
11015 Hollow Bay Dr - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

11015 Hollow Bay Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

4 beds

3 baths

$4,000

House for rent

Top amenities
Garage Parking
In-Unit Laundry
16001 Grafton Way #16001 - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Garden

3 BR, 3 BA in Horizon West-Village I

16001 Grafton Way #16001, Winter Garden, FL 34787

Luxury | Hardwood floor | Ceiling fan

3 beds

3 baths

$2,995

House for rent

Available Oct 30

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11834 Shine View Ln - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

11834 Shine View Ln, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

3 beds

2 baths

$3,300

House for rent

Top amenities
Garage Parking
In-Unit Laundry
On-Site Laundry
5382 Bowman Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

5382 Bowman Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

6 beds

4 baths

$11,000

House for rent

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
Swimming Pool
9849 Lost Creek Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

9849 Lost Creek Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

5 beds

3 baths

$5,500

House for rent

Top amenities
In-Unit Laundry
Swimming Pool
17552 Lake Star Rd - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

17552 Lake Star Rd, Winter Garden, FL 34787

Luxury | In-unit laundry | Outdoor space

4 beds

3 baths

$5,000

House for rent

Top amenities
Carpet
Garage Parking
In-Unit Laundry
14676 Seton Creek Boulevard - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

14676 Seton Creek Boulevard, Winter Garden, FL 34787

Luxury | Swimming pool | In-unit laundry

3 beds

2 baths

$3,000

House for rent

Top amenities
In-Unit Laundry
On-Site Laundry
Showing 1 - 31 of 31 results
Home > House Rentals in Winter Garden > Winter Garden Luxury Houses For Rent
Updated: February 10, 2026

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Pet friendly houses in Winter Garden, FL50 rentals

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Discover luxury Winter Garden, FL houses for rent

🌇Available luxury house rentals31 houses
⭐Popular amenities, ,
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