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Luxury Houses for Rent in Winter Garden, FL

34 rentals

1958 Pantheon Dr - Photo 1 of 1

5d+ ago

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1958 Pantheon Dr, Winter Garden, FL 34787

Luxury | Balcony | Swimming pool

3 beds

2 baths

$3,125

House for rent

Available Jun 22

Top amenities
In-Unit Laundry
On-Site Laundry
On-Site Management
Swimming Pool
1021 Temple Grove Pl - Photo 1 of 1

1d 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

4.5 baths

$8,500

House for rent

Top amenities
Ceiling Fan
Furnished
Hardwood Floor
High Ceilings
In-Unit Laundry
Swimming Pool
17682 Northlake Grove Dr #NA - Photo 1 of 1

1d ago

Luxury house for rent in Winter Garden

$3,400 - 3 Bedroom 2.5 Bathroom House In Winter Garden With Great Amenities

17682 Northlake Grove Dr #NA, Winter Garden, FL 34787

Luxury | Swimming pool | In-unit laundry

3 beds

2.5 baths

$3,350

House for rent

Available May 15

Top amenities
Air Conditioning
Dishwasher
Garage Parking
In-Unit Laundry
Storage
805 Bainbridge Loop - Photo 1 of 1

2d ago

Luxury house for rent in Winter Garden

805 Bainbridge Loop, Winter Garden, FL 34787

Luxury | Swimming pool | Dishwasher

4 beds

4 baths

$3,995

House for rent

17342 Glossy Pomelo Way - Photo 1 of 1
New construction

4d ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

17342 Glossy Pomelo Way, Winter Garden, FL 34787

Luxury | Balcony | Walk-in closets

5 beds

5.5 baths

$6,500

House for rent

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
On-Site Laundry
14154 Shocklach Dr - Photo 1 of 1

4d ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

14154 Shocklach Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

3 beds

2.5 baths

$3,000

House for rent

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
On-Site Laundry
Storage
Swimming Pool

Nearby rental good for eco-living

$2,775

Ocoee

Nearby rental good for pet owners

$2,344–$2,652

Ocoee

455 Winter Grove Blvd - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

455 Winter Grove Blvd, Winter Garden, FL 34787

Luxury | In-unit laundry | Garage parking

5 beds

3.5 baths

$5,690

$5,000

Price drop

House for rent

Top amenities
Dishwasher
In-Unit Laundry
13349 Harbor Shore Ln #1 - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Garden

13349 Harbor Shore Ln #1, Winter Garden, FL 34787

Luxury | Swimming pool | In-unit laundry

2 beds

2.5 baths

$2,159

House for rent

Available May 8

Top amenities
Garage Parking
In-Unit Laundry
On-Site Management
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17822 Adrift Rd - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

17822 Adrift Rd, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

5 beds

4 baths

$5,200

House for rent

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
Swimming Pool
203 S Main St - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

203 S Main St, Winter Garden, FL 34787

Luxury | Outdoor space | On-site management

2 beds

2 baths

$2,699

House for rent

Available Jul 15

Top amenities
On-Site Management
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Find sweet deals in Winter Garden

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

$2,250

326 Daniels Pointe Dr

$2,765

266 Regal Downs Cir

$2,949

6126 Whispering Glen

$3,010

5008 Indian Deer Rd

16710 Point Rock Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

16710 Point Rock Dr, Winter Garden, FL 34787

Luxury | Swimming pool | Fitness center

3 beds

2.5 baths

$3,000

House for rent

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
Microwave
Swimming Pool
15205 Shonan Gold Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

15205 Shonan Gold Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

3 beds

3.5 baths

$3,400

House for rent

Top amenities
Dishwasher
Furnished
Garage Parking
In-Unit Laundry
15532 Sweet Orange Ave - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

15532 Sweet Orange Ave, Winter Garden, FL 34787

Luxury | Swimming pool | In-unit laundry

3 beds

2.5 baths

$3,950

House for rent

Available May 7

Top amenities
Ceiling Fan
In-Unit Laundry
On-Site Management
13344 Harbor Shore Ln - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

13344 Harbor Shore Ln, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

2 beds

2.5 baths

$2,200

House for rent

Top amenities
Ceiling Fan
Fitness Center
Hardwood Floor
In-Unit Laundry
On-Site Laundry
Swimming Pool
16350 Hamlin View St - Photo 1 of 1
New construction

5d+ ago

Luxury townhouse for rent in Winter Garden

16350HVS

16350 Hamlin View St, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

3 beds

2.5 baths

$3,000

House for rent

Top amenities
In-Unit Laundry
On-Site Laundry
216 Deepcove Rd - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

216 Deepcove Rd, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

2 beds

2.5 baths

$2,300

$2,200

Price drop

House for rent

Top amenities
Ceiling Fan
Dishwasher
Garage Parking
In-Unit Laundry
On-Site Laundry
Storage
11153 Green Citron Aly - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

11153 Green Citron Aly, Winter Garden, FL 34787

Luxury | In-unit laundry | Outdoor space

3 beds

2.5 baths

$3,350

$3,100

Price drop

House for rent

Top amenities
Garage Parking
In-Unit Laundry
6460 Makrut Lime Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

6460 Makrut Lime Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

4 beds

3.5 baths

$4,250

House for rent

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
Advertisement
18386 Oliver Twist Way - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Private Pond View Home in Waterleigh - 4BR + Guest Suite, No Rear Neighbors

18386 Oliver Twist Way, Winter Garden, FL 34787

Luxury | Swimming pool | Fitness center

4 beds

3 baths

$4,300

House for rent

Available Jun 1

Top amenities
Dishwasher
Furnished
High Ceilings
In-Unit Laundry
Microwave
Swimming Pool
15363 Hamlin Park Dr - Photo 1 of 1
New construction

5d+ ago

Luxury townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

15363 Hamlin Park Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

3 beds

3.5 baths

$3,500

House for rent

Top amenities
Carpet
Garage Parking
In-Unit Laundry
12506 Westhaven Oak Dr - Photo 1 of 1
New construction

5d+ ago

Luxury townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

12506 Westhaven Oak Dr, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

1 bed

1 bath

$1,600

House for rent

Top amenities
Dishwasher
In-Unit Laundry
238 N Main St - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Spacious 3 Bed/2 Bath Single Family Home in Winter Garden, FL - Available 4/15 - $3100

238 N Main St, Winter Garden, FL 34787

Luxury | Balcony | In-unit laundry

3 beds

2 baths

$3,100

House for rent

Available Apr 15

Top amenities
Dishwasher
In-Unit Laundry
Microwave
149 S Park Ave - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

149 S Park Ave, Winter Garden, FL 34787

Luxury | Balcony | Walk-in closets

3 beds

3.5 baths

$5,200

House for rent

Top amenities
Ceiling Fan
Dishwasher
Garage Parking
High Ceilings
In-Unit Laundry
On-Site Laundry
16242 Outlook Shore Aly - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

16242 Outlook Shore Aly, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

3 beds

2.5 baths

$2,990

House for rent

Top amenities
Carpet
Dishwasher
Fitness Center
High Ceilings
In-Unit Laundry
On-Site Laundry
15060 Andrew Aly - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

15060 Andrew Aly, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

3 beds

3.5 baths

$3,300

House for rent

Top amenities
Garage Parking
In-Unit Laundry
1220 Priory Cir - Photo 1 of 1

5d+ ago

Luxury Stoneybrook West townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

1220 Priory Cir, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

3 beds

2.5 baths

$3,000

House for rent

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
Swimming Pool
Advertisement
9240 Woodcrane Dr - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

9240 Woodcrane Dr, Winter Garden, FL 34787

Luxury | In-unit laundry | Outdoor space

5 beds

4 baths

$5,499

House for rent

Top amenities
Air Conditioning
Ceiling Fan
Central Heat
Garage Parking
In-Unit Laundry
Microwave
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

3.5 baths

$4,500

House for rent

Top amenities
Carpet
Garage Parking
In-Unit Laundry
7556 John Hancock Dr - Photo 1 of 1
New construction

5d+ 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

6.5 baths

$18,000

House for rent

Top amenities
Furnished
Garage Parking
High Ceilings
In-Unit Laundry
Residents Lounge
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

2.5 baths

$2,280

House for rent

Top amenities
Dishwasher
Garage Parking
High Ceilings
In-Unit Laundry
Swimming Pool
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

3.5 baths

$5,400

House for rent

Top amenities
Fitness Center
Garage Parking
In-Unit Laundry
Storage
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

4.5 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

3.5 baths

$4,500

House for rent

Top amenities
Ceiling Fan
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

2.5 baths

$3,000

House for rent

Top amenities
In-Unit Laundry
On-Site Laundry
Advertisement
Showing 1 - 34 of 34 results
Home > House Rentals in Winter Garden > Winter Garden Luxury Houses For Rent
Updated: May 14, 2026

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Pet friendly houses in Winter Garden, FL33 rentals

33 rentals

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