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Luxury Houses for Rent in Winter Garden, FL

33 rentals

11377 Pixie Mandarin Ct - Photo 1 of 1
New construction

7h ago

Luxury house for rent in Winter Garden

11377 Pixie Mandarin Ct, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

3 beds

2 baths

$3,500

House for rent

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

2d 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
40 W Smith St - Photo 1 of 1

3d ago

Luxury house for rent in Winter Garden

House for rent

8503 Tavernier Aly - Photo 1 of 1

3d ago

Luxury house for rent in Winter Garden

Stunning Single Home in Winter Garden | 8503 Tavernier Alley | $3000/mo | Available 1/15/2026

8503 Tavernier Aly, Winter Garden, FL 34787

Luxury | Swimming pool | Fitness center

3 beds

2 baths

$3,000

House for rent

Available Jan 15

Top amenities
Garage Parking
Microwave
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

$9,500

House for rent

Top amenities
Ceiling Fan
Furnished
Garage Parking
High Ceilings
In-Unit Laundry
Swimming Pool
15236 Tribute Ovation Way - Photo 1 of 1
New construction

5d+ ago

Luxury townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

15236 Tribute Ovation Way, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

3 beds

2 baths

$3,250

House for rent

Top amenities
In-Unit Laundry

Nearby rental good for eco-living

$3,000

942 Auction Aly

Nearby rental good for pet owners

$2,489–$2,802

Ocoee

1021 Temple Grove Place #NA - Photo 1 of 1

5d+ 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
16324 Silver Grove Blvd #1 - Photo 1 of 1
New construction

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

$6,000

$5,500

Price drop

House for rent

Available Jan 1

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16771 Turtle Hatch Drive #D - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

16771 Turtle Hatch Drive #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

$4,300

$4,000

Price drop

House for rent

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
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Find sweet deals in Winter Garden

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

$6,500

13241 Tollcross Way

$6,500

694 Brooks Field Drive

$2,955

744 Westcliffe Dr

$2,470

907 Muirwood Way

13357 Harbor Shore Lane - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Garden

13357 Harbor Shore Lane, Winter Garden, FL 34787

Luxury | Swimming pool | In-unit laundry

2 beds

2 baths

$2,100

House for rent

Available Jan 11

Top amenities
Controlled Access
Garage Parking
In-Unit Laundry
On-Site Management
Package Service
Swimming Pool
829 Bainbridge Loop - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

829 Bainbridge Loop, Winter Garden, FL 34787

Luxury | Walk-in closets | Fitness center

3 beds

2 baths

$2,985

House for rent

Top amenities
Fitness Center
Garage Parking
In-Unit Laundry
720 Parkmont Place - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

House for rent

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

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

$6,500

House for rent

Top amenities
Carpet
Garage Parking
In-Unit Laundry
16055 Silver Brook Way - Photo 1 of 1
New construction

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

$3,700

House for rent

Top amenities
Dishwasher
Garage Parking
In-Unit Laundry
On-Site Laundry
16001 Grafton Way - Photo 1 of 1
New construction

5d+ ago

Luxury townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

16001 Grafton Way, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

3 beds

2 baths

$3,250

$2,995

Price drop

House for rent

Top amenities
Ceiling Fan
Dishwasher
Fitness Center
In-Unit Laundry
Swimming Pool
7031 Billie Court - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

7031 Billie Court, Winter Garden, FL 34787

Luxury | Swimming pool | In-unit laundry

4 beds

4 baths

$5,250

House for rent

Top amenities
Carpet
Ceiling Fan
Garage Parking
High Ceilings
In-Unit Laundry
On-Site Laundry
Advertisement
11834 SHINE VIEW LANE - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

11834 SHINE VIEW LANE, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

3 beds

2 baths

$3,300

House for rent

Top amenities
In-Unit Laundry
On-Site Laundry
Package Service
17582 Lake Star Road - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

17582 Lake Star Road, Winter Garden, FL 34787

Luxury | In-unit laundry | Outdoor space

4 beds

3 baths

$4,300

House for rent

Top amenities
In-Unit 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
5229 Citrus Leaf Boulevard - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

5229 Citrus Leaf Boulevard, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

4 beds

3 baths

$5,850

House for rent

Top amenities
Garage Parking
In-Unit Laundry
On-Site Laundry
Storage
12832 Lavender Bloom Aly - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

12832 Lavender Bloom Aly, Winter Garden, FL 34787

Luxury | Dishwasher

3 beds

2 baths

$3,200

House for rent

214 Woodfall Ln - Photo 1 of 1
New construction

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

214 Woodfall Ln, Winter Garden, FL 34787

Luxury | Walk-in closets | In-unit laundry

5 beds

5 baths

$6,500

House for rent

Top amenities
Carpet
Garage Parking
In-Unit Laundry
On-Site Laundry
5885 Chestnut Chase Road - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Garden

5885 Chestnut Chase Road, Winter Garden, FL 34787

Luxury | Swimming pool | Fitness center

2 beds

2 baths

$2,425

House for rent

8884 Bismarck Palm Dr - Photo 1 of 1

5d+ ago

Luxury townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

8884 Bismarck Palm 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
Hardwood Floor
In-Unit Laundry
On-Site Laundry
Swimming Pool
Advertisement
13809 Luna Harvest Avenue - Photo 1 of 1
New construction

5d+ ago

Luxury townhouse for rent in Winter Garden

Townhouse - WINTER GARDEN, FL

13809 Luna Harvest Avenue, Winter Garden, FL 34787

Luxury | Balcony | Walk-in closets

3 beds

3 baths

$3,000

House for rent

Top amenities
Garage Parking
In-Unit Laundry
Swimming Pool
942 Auction Aly - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

942 Auction Alley - 1

942 Auction Aly, Winter Garden, FL 34787

Luxury | Walk-in closets | Swimming pool

3 beds

2 baths

$3,000

House for rent

Available Oct 16

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
Dishwasher
Garage Parking
In-Unit Laundry
694 Brooks Field Drive - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

Single Family Residence - WINTER GARDEN, FL

694 Brooks Field Drive, 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
7984 Wood Sage Drive - Photo 1 of 1

5d+ ago

Luxury house for rent in Winter Garden

7984 Wood Sage Drive, Winter Garden, FL 34787

Luxury | Swimming pool | Fitness center

3 beds

2 baths

$3,100

House for rent

Top amenities
Hardwood Floor
In-Unit Laundry
17552 Lake Star Rd - Photo 1 of 1
New construction

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 - 33 of 33 results
Home > House Rentals in Winter Garden > Winter Garden Luxury Houses For Rent
Updated: December 27, 2025

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Pet friendly houses in Winter Garden, FL47 rentals

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Discover luxury Winter Garden, FL houses for rent

🌇Available luxury house rentals33 houses
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